diff --git a/package.json b/package.json
index 1059177c8..7d7b18216 100644
--- a/package.json
+++ b/package.json
@@ -37,7 +37,7 @@
 		"vite:start:bun": "bun -F @autumn/shared build && bun -F @autumn/vite start:bun",
 
 
-		"dev:bun": "concurrently \"cd server && bun run dev:bun\" \"cd vite && bun run dev:bun\"",
+		"dev:bun": "concurrently \"cd server && bun run dev\" \"cd vite && bun run dev:bun\" \"bun -F @autumn/shared dev:bun\"",
 		"build:all:bun": "bun run -F @autumn/shared build:bun && bun run -F @autumn/server prod:build:bun && bun run -F @autumn/vite build:bun"
 	},
 	"dependencies": {
diff --git a/server/package.json b/server/package.json
index 6d9c81a9b..f9564755b 100644
--- a/server/package.json
+++ b/server/package.json
@@ -7,7 +7,7 @@
   "scripts": {
     "email": "email dev -p 3001",
     "start": "bun src/index.ts",
-    "dev": "NODE_ENV=development bun --watch src/index.ts --ignore scripts --ignore tests",
+    "dev": "NODE_ENV=development bunx --bun nodemon --exec bun src/index.ts --ignore scripts --ignore tests",
     "workers": "bun src/workers.ts",
     "workers:dev": "bun --watch src/workers.ts",
     "cron": "bun src/cron.ts",
diff --git a/server/shell/g4.sh b/server/shell/g4.sh
index b5a362206..647b4702e 100755
--- a/server/shell/g4.sh
+++ b/server/shell/g4.sh
@@ -11,7 +11,8 @@ fi
 $MOCHA_CMD 'tests/advanced/multiFeature/*.ts' \
            'tests/advanced/coupons/*.ts' \
            'tests/attach/updateQuantity/*.ts' \
-           'tests/advanced/referrals/*.ts'
+           'tests/advanced/referrals/*.ts' \
+           'tests/advanced/rollovers/*.ts'
           
 $MOCHA_CMD 'tests/attach/multiProduct/*.ts' \
            'tests/advanced/usageLimit/*.ts' 
diff --git a/server/src/cron.ts b/server/src/cron.ts
index 5b386713b..71be81d6f 100644
--- a/server/src/cron.ts
+++ b/server/src/cron.ts
@@ -1,236 +1,14 @@
-import {
-  AllowanceType,
-  AppEnv,
-  EntInterval,
-  FullCusEntWithProduct,
-  Organization,
-} from "@autumn/shared";
-import { CusEntService } from "./internal/customers/cusProducts/cusEnts/CusEntitlementService.js";
-
 import dotenv from "dotenv";
-import { getEntOptions } from "./internal/products/prices/priceUtils.js";
-import { getNextResetAt } from "./utils/timeUtils.js";
-import chalk from "chalk";
-
-import { format, getDate, getMonth, setDate } from "date-fns";
+import { FullCusEntWithProduct } from "@autumn/shared";
+import { CusEntService } from "./internal/customers/cusProducts/cusEnts/CusEntitlementService.js";
+import { format } from "date-fns";
 import { CronJob } from "cron";
-import {
-  getRelatedCusPrice,
-  getResetBalance,
-} from "./internal/customers/cusProducts/cusEnts/cusEntUtils.js";
-import { getResetBalancesUpdate } from "./internal/customers/cusProducts/cusEnts/groupByUtils.js";
-import { CusProductService } from "./internal/customers/cusProducts/CusProductService.js";
-import { createStripeCli } from "./external/stripe/utils.js";
 import { UTCDate } from "@date-fns/utc";
-import { type DrizzleCli, initDrizzle } from "./db/initDrizzle.js";
-
-import { CusPriceService } from "./internal/customers/cusProducts/cusPrices/CusPriceService.js";
-import { CusService } from "./internal/customers/CusService.js";
-import { refreshCusCache } from "./internal/customers/cusCache/updateCachedCus.js";
+import { initDrizzle } from "./db/initDrizzle.js";
+import { resetCustomerEntitlement } from "./cron/cronUtils.js";
 
 dotenv.config();
 
-const checkSubAnchor = async ({
-  db,
-  cusEnt,
-  nextResetAt,
-}: {
-  db: DrizzleCli;
-  cusEnt: FullCusEntWithProduct;
-  nextResetAt: number;
-}) => {
-  let nextResetAtDate = new UTCDate(nextResetAt);
-
-  // If nextResetAt is on the 28th of March, or Day 30, then do this check.
-  const nextResetAtDay = getDate(nextResetAtDate);
-  const nextResetAtMonth = getMonth(nextResetAtDate);
-
-  const shouldCheck =
-    nextResetAtDay === 30 || (nextResetAtDay === 28 && nextResetAtMonth === 2);
-
-  if (!shouldCheck) {
-    return nextResetAt;
-  }
-
-  // 1. Get the customer product
-  const cusProduct = await CusProductService.getByIdForReset({
-    db,
-    id: cusEnt.customer_product_id,
-  });
-
-  // Get org and env
-  const env = cusProduct.product.env as AppEnv;
-  const org = cusProduct.product.org as Organization;
-
-  const stripeCli = createStripeCli({ org, env });
-  if (!cusProduct.subscription_ids || cusProduct.subscription_ids.length == 0) {
-    return nextResetAt;
-  }
-
-  const subId = cusProduct.subscription_ids[0];
-  const sub = await stripeCli.subscriptions.retrieve(subId);
-
-  const billingCycleAnchor = sub.billing_cycle_anchor * 1000;
-  console.log("Checking billing cycle anchor");
-  console.log(
-    "Next reset at       ",
-    format(new UTCDate(nextResetAt), "dd MMM yyyy HH:mm:ss")
-  );
-  console.log(
-    "Billing cycle anchor",
-    format(new UTCDate(billingCycleAnchor), "dd MMM yyyy HH:mm:ss")
-  );
-
-  const billingCycleDay = getDate(new UTCDate(billingCycleAnchor));
-  const nextResetDay = getDate(nextResetAtDate);
-
-  if (billingCycleDay > nextResetDay) {
-    nextResetAtDate = setDate(nextResetAtDate, billingCycleDay);
-    return nextResetAtDate.getTime();
-  } else {
-    return nextResetAt;
-  }
-};
-
-const resetCustomerEntitlement = async ({
-  db,
-  cusEnt,
-}: {
-  db: DrizzleCli;
-  cusEnt: FullCusEntWithProduct;
-}) => {
-  try {
-    if (cusEnt.usage_allowed) {
-      return;
-    }
-
-    // Fetch related price
-    const cusPrices = await CusPriceService.getByCustomerProductId({
-      db,
-      customerProductId: cusEnt.customer_product_id,
-    });
-
-    // 2. Quantity is from prices...
-    const relatedCusPrice = getRelatedCusPrice(cusEnt, cusPrices);
-    if (relatedCusPrice) {
-      return;
-    }
-
-    const entOptions = getEntOptions(
-      cusEnt.customer_product.options,
-      cusEnt.entitlement
-    );
-
-    const resetBalance = getResetBalance({
-      entitlement: cusEnt.entitlement,
-      options: entOptions,
-      relatedPrice: undefined,
-      // relatedPrice: relatedCusPrice,
-    });
-
-    // Handle if entitlement changed to unlimited...
-    let entitlement = cusEnt.entitlement;
-    if (entitlement.allowance_type === AllowanceType.Unlimited) {
-      await CusEntService.update({
-        db,
-        id: cusEnt.id,
-        updates: {
-          unlimited: true,
-          next_reset_at: null,
-        },
-      });
-
-      console.log(
-        `Reset ${cusEnt.id} | customer: ${chalk.yellow(
-          cusEnt.customer_id
-        )} | feature: ${chalk.yellow(
-          cusEnt.feature_id
-        )} | new balance: unlimited`
-      );
-      return;
-    }
-
-    if (entitlement.interval === EntInterval.Lifetime) {
-      await CusEntService.update({
-        db,
-        id: cusEnt.id,
-        updates: {
-          next_reset_at: null,
-        },
-      });
-
-      console.log(
-        `Reset ${cusEnt.id} | customer: ${chalk.yellow(
-          cusEnt.customer_id
-        )} | feature: ${chalk.yellow(
-          cusEnt.feature_id
-        )} | reset to lifetime (next_reset_at: null)`
-      );
-      return;
-    }
-    let nextResetAt = getNextResetAt(
-      new UTCDate(cusEnt.next_reset_at!),
-      cusEnt.entitlement.interval as EntInterval
-    );
-
-    let resetBalanceUpdate = getResetBalancesUpdate({
-      cusEnt,
-      allowance: resetBalance || undefined,
-    });
-
-    try {
-      nextResetAt = await checkSubAnchor({
-        db,
-        cusEnt,
-        nextResetAt,
-      });
-    } catch (error) {
-      console.log("WARNING: Failed to check sub anchor");
-      console.log(error);
-    }
-
-    await CusEntService.update({
-      db,
-      id: cusEnt.id,
-      updates: {
-        ...resetBalanceUpdate,
-        next_reset_at: nextResetAt,
-        adjustment: 0,
-      },
-    });
-
-    console.log(
-      `Reset ${cusEnt.id} | customer: ${chalk.yellow(
-        cusEnt.customer_id
-      )} | feature: ${chalk.yellow(
-        cusEnt.feature_id
-      )} | new balance: ${chalk.green(
-        resetBalance
-      )} | new next_reset_at: ${chalk.green(
-        format(new UTCDate(nextResetAt), "dd MMM yyyy HH:mm:ss")
-      )}`
-    );
-
-    let customer = await CusService.getByInternalId({
-      db,
-      internalId: cusEnt.internal_customer_id,
-    });
-
-    if (customer) {
-      await refreshCusCache({
-        db,
-        customerId: customer.id!,
-        orgId: customer.org_id,
-        env: customer.env,
-      });
-    }
-  } catch (error: any) {
-    console.log(
-      `Failed to reset ${cusEnt.id} | ${cusEnt.customer_id} | ${cusEnt.feature_id}, error: ${error}`
-    );
-  }
-};
-
 export const cronTask = async () => {
   console.log(
     "\n----------------------------------\nRUNNING RESET CRON:",
diff --git a/server/src/cron/cronUtils.ts b/server/src/cron/cronUtils.ts
new file mode 100644
index 000000000..b2e00dcc1
--- /dev/null
+++ b/server/src/cron/cronUtils.ts
@@ -0,0 +1,260 @@
+import {
+  AllowanceType,
+  AppEnv,
+  EntInterval,
+  FullCusEntWithProduct,
+  Organization,
+  RolloverConfig,
+} from "@autumn/shared";
+import { CusEntService } from "@/internal/customers/cusProducts/cusEnts/CusEntitlementService.js";
+
+import { getEntOptions } from "@/internal/products/prices/priceUtils.js";
+import { getNextResetAt } from "@/utils/timeUtils.js";
+import chalk from "chalk";
+
+import { format, getDate, getMonth, setDate } from "date-fns";
+import {
+  getRelatedCusPrice,
+  getResetBalance,
+} from "@/internal/customers/cusProducts/cusEnts/cusEntUtils.js";
+import { getResetBalancesUpdate } from "@/internal/customers/cusProducts/cusEnts/groupByUtils.js";
+import { getRolloverUpdates } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.js";
+import { CusProductService } from "@/internal/customers/cusProducts/CusProductService.js";
+import { createStripeCli } from "@/external/stripe/utils.js";
+import { UTCDate } from "@date-fns/utc";
+import { type DrizzleCli, initDrizzle } from "../db/initDrizzle.js";
+import { notNullish } from "../utils/genUtils.js";
+
+import { CusPriceService } from "../internal/customers/cusProducts/cusPrices/CusPriceService.js";
+import { RolloverService } from "../internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.js";
+import { CusService } from "@/internal/customers/CusService.js";
+import { refreshCusCache } from "@/internal/customers/cusCache/updateCachedCus.js";
+
+const checkSubAnchor = async ({
+  db,
+  cusEnt,
+  nextResetAt,
+}: {
+  db: DrizzleCli;
+  cusEnt: FullCusEntWithProduct;
+  nextResetAt: number;
+}) => {
+  let nextResetAtDate = new UTCDate(nextResetAt);
+
+  // If nextResetAt is on the 28th of March, or Day 30, then do this check.
+  const nextResetAtDay = getDate(nextResetAtDate);
+  const nextResetAtMonth = getMonth(nextResetAtDate);
+
+  const shouldCheck =
+    nextResetAtDay === 30 || (nextResetAtDay === 28 && nextResetAtMonth === 2);
+
+  if (!shouldCheck) {
+    return nextResetAt;
+  }
+
+  // 1. Get the customer product
+  const cusProduct = await CusProductService.getByIdForReset({
+    db,
+    id: cusEnt.customer_product_id,
+  });
+
+  // Get org and env
+  const env = cusProduct.product.env as AppEnv;
+  const org = cusProduct.product.org as Organization;
+
+  const stripeCli = createStripeCli({ org, env });
+  if (!cusProduct.subscription_ids || cusProduct.subscription_ids.length == 0) {
+    return nextResetAt;
+  }
+
+  const subId = cusProduct.subscription_ids[0];
+  const sub = await stripeCli.subscriptions.retrieve(subId);
+
+  const billingCycleAnchor = sub.billing_cycle_anchor * 1000;
+  console.log("Checking billing cycle anchor");
+  console.log(
+    "Next reset at       ",
+    format(new UTCDate(nextResetAt), "dd MMM yyyy HH:mm:ss")
+  );
+  console.log(
+    "Billing cycle anchor",
+    format(new UTCDate(billingCycleAnchor), "dd MMM yyyy HH:mm:ss")
+  );
+
+  const billingCycleDay = getDate(new UTCDate(billingCycleAnchor));
+  const nextResetDay = getDate(nextResetAtDate);
+
+  if (billingCycleDay > nextResetDay) {
+    nextResetAtDate = setDate(nextResetAtDate, billingCycleDay);
+    return nextResetAtDate.getTime();
+  } else {
+    return nextResetAt;
+  }
+};
+
+export const resetCustomerEntitlement = async ({
+  db,
+  cusEnt,
+}: {
+  db: DrizzleCli;
+  cusEnt: FullCusEntWithProduct;
+}) => {
+  try {
+    if (cusEnt.usage_allowed) {
+      return;
+    }
+
+    // Fetch related price
+    const cusPrices = await CusPriceService.getByCustomerProductId({
+      db,
+      customerProductId: cusEnt.customer_product_id,
+    });
+
+    // 2. Quantity is from prices...
+    const relatedCusPrice = getRelatedCusPrice(cusEnt, cusPrices);
+    if (relatedCusPrice) {
+      return;
+    }
+
+    const entOptions = getEntOptions(
+      cusEnt.customer_product.options,
+      cusEnt.entitlement
+    );
+
+    const resetBalance = getResetBalance({
+      entitlement: cusEnt.entitlement,
+      options: entOptions,
+      relatedPrice: undefined,
+      // relatedPrice: relatedCusPrice,
+    });
+
+    // Handle if entitlement changed to unlimited...
+    let entitlement = cusEnt.entitlement;
+    if (entitlement.allowance_type === AllowanceType.Unlimited) {
+      await CusEntService.update({
+        db,
+        id: cusEnt.id,
+        updates: {
+          unlimited: true,
+          next_reset_at: null,
+        },
+      });
+
+      console.log(
+        `Reset ${cusEnt.id} | customer: ${chalk.yellow(
+          cusEnt.customer_id
+        )} | feature: ${chalk.yellow(
+          cusEnt.feature_id
+        )} | new balance: unlimited`
+      );
+      return;
+    }
+
+    if (entitlement.interval === EntInterval.Lifetime) {
+      await CusEntService.update({
+        db,
+        id: cusEnt.id,
+        updates: {
+          next_reset_at: null,
+        },
+      });
+
+      console.log(
+        `Reset ${cusEnt.id} | customer: ${chalk.yellow(
+          cusEnt.customer_id
+        )} | feature: ${chalk.yellow(
+          cusEnt.feature_id
+        )} | reset to lifetime (next_reset_at: null)`
+      );
+      return;
+    }
+
+    let nextResetAt = getNextResetAt(
+      new UTCDate(cusEnt.next_reset_at!),
+      cusEnt.entitlement.interval as EntInterval
+    );
+
+    let rolloverUpdate = getRolloverUpdates({
+      cusEnt,
+      nextResetAt: cusEnt.next_reset_at! as number,
+    });
+
+    let resetBalanceUpdate = getResetBalancesUpdate({
+      cusEnt,
+      allowance: resetBalance || undefined,
+    });
+
+    try {
+      nextResetAt = await checkSubAnchor({
+        db,
+        cusEnt,
+        nextResetAt,
+      });
+    } catch (error) {
+      console.log("WARNING: Failed to check sub anchor");
+      console.log(error);
+    }
+
+    try {
+      nextResetAt = await checkSubAnchor({
+        db,
+        cusEnt,
+        nextResetAt,
+      });
+    } catch (error) {
+      console.log("WARNING: Failed to check sub anchor");
+      console.log(error);
+    }
+
+    await CusEntService.update({
+      db,
+      id: cusEnt.id,
+      updates: {
+        ...resetBalanceUpdate,
+        next_reset_at: nextResetAt,
+        adjustment: 0,
+      },
+    });
+
+    if (rolloverUpdate?.toInsert && rolloverUpdate.toInsert.length > 0) {
+      await RolloverService.insert({
+        db,
+        rows: rolloverUpdate.toInsert,
+        fullCusEnt: cusEnt,
+        // rolloverConfig: cusEnt.entitlement.rollover as RolloverConfig,
+        // cusEntID: cusEnt.id,
+        // entityMode: notNullish(cusEnt.entitlement.entity_feature_id),
+      });
+    }
+
+    console.log(
+      `Reset ${cusEnt.id} | customer: ${chalk.yellow(
+        cusEnt.customer_id
+      )} | feature: ${chalk.yellow(
+        cusEnt.feature_id
+      )} | new balance: ${chalk.green(
+        resetBalance
+      )} | new next_reset_at: ${chalk.green(
+        format(new UTCDate(nextResetAt), "dd MMM yyyy HH:mm:ss")
+      )}`
+    );
+
+    let customer = await CusService.getByInternalId({
+      db,
+      internalId: cusEnt.internal_customer_id,
+    });
+
+    if (customer) {
+      await refreshCusCache({
+        db,
+        customerId: customer.id!,
+        orgId: customer.org_id,
+        env: customer.env,
+      });
+    }
+  } catch (error: any) {
+    console.log(
+      `Failed to reset ${cusEnt.id} | ${cusEnt.customer_id} | ${cusEnt.feature_id}, error: ${error}`
+    );
+  }
+};
diff --git a/server/src/external/stripe/webhookHandlers/handleCheckoutCompleted.ts b/server/src/external/stripe/webhookHandlers/handleCheckoutCompleted.ts
index 77b5c44c0..52040bdbc 100644
--- a/server/src/external/stripe/webhookHandlers/handleCheckoutCompleted.ts
+++ b/server/src/external/stripe/webhookHandlers/handleCheckoutCompleted.ts
@@ -154,7 +154,7 @@ export const handleCheckoutSessionCompleted = async ({
         product,
         org,
         env: attachParams.customer.env,
-        subId: checkoutSession.subscription as string,
+        subId: checkoutSub?.id as string,
       },
     });
   }
diff --git a/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handlePrepaidPrices.ts b/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handlePrepaidPrices.ts
index f24412676..10c71deca 100644
--- a/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handlePrepaidPrices.ts
+++ b/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handlePrepaidPrices.ts
@@ -1,6 +1,9 @@
 import { DrizzleCli } from "@/db/initDrizzle.js";
 import { CusEntService } from "@/internal/customers/cusProducts/cusEnts/CusEntitlementService.js";
 import { getResetBalance } from "@/internal/customers/cusProducts/cusEnts/cusEntUtils.js";
+import { RolloverService } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.js";
+import { getRolloverUpdates } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.js";
+import { getResetBalancesUpdate } from "@/internal/customers/cusProducts/cusEnts/groupByUtils.js";
 import { getRelatedCusEnt } from "@/internal/customers/cusProducts/cusPrices/cusPriceUtils.js";
 import { CusProductService } from "@/internal/customers/cusProducts/CusProductService.js";
 import { getEntOptions } from "@/internal/products/prices/priceUtils.js";
@@ -11,6 +14,8 @@ import {
   FeatureOptions,
   FullCusProduct,
   FullCustomerPrice,
+  UsagePriceConfig,
+  RolloverConfig,
 } from "@autumn/shared";
 import Stripe from "stripe";
 
@@ -45,26 +50,52 @@ export const handlePrepaidPrices = async ({
 
   if (!cusEnt) {
     logger.error(
-      `Tried to handle prepaid price for ${cusPrice.id} (${cusPrice.price.id}) but no cus ent found`,
+      `Tried to handle prepaid price for ${cusPrice.id} (${cusPrice.price.id}) but no cus ent found`
     );
     return;
   }
 
   const options = getEntOptions(cusProduct.options, cusEnt.entitlement);
 
-  const resetBalance = getResetBalance({
-    entitlement: cusEnt.entitlement,
-    options: notNullish(options?.upcoming_quantity)
-      ? {
-          feature_id: options?.feature_id!,
-          quantity: options?.upcoming_quantity!,
-        }
-      : options,
-    relatedPrice: cusPrice.price,
+  // const resetBalance = getResetBalance({
+  //   entitlement: cusEnt.entitlement,
+  //   options: notNullish(options?.upcoming_quantity)
+  //     ? {
+  //         feature_id: options?.feature_id!,
+  //         quantity: options?.upcoming_quantity!,
+  //       }
+  //     : options,
+  //   relatedPrice: cusPrice.price,
+  // });
+  let resetQuantity = options?.upcoming_quantity || options?.quantity!;
+  let config = cusPrice.price.config as UsagePriceConfig;
+  let billingUnits = config.billing_units || 1;
+  let newAllowance =
+    resetQuantity * billingUnits + (cusEnt.entitlement.allowance || 0);
+
+  const resetUpdate = getResetBalancesUpdate({
+    cusEnt,
+    allowance: newAllowance,
   });
 
   const ent = cusEnt.entitlement;
 
+  let rolloverUpdate = getRolloverUpdates({
+    cusEnt,
+    nextResetAt: usageSub.current_period_end * 1000,
+  });
+  // console.log("🔍 rolloverUpdate", rolloverUpdate);
+
+  // console.log(
+  //   "Rollover update received in handlePrepaidPrices:",
+  //   rolloverUpdate.toInsert.map((rollover) => ({
+  //     id: rollover.id,
+  //     balance: rollover.balance,
+  //     entities: rollover.entities.map((entity) => `${entity.id}: ${entity.balance}`).join(", "),
+  //     expires_at: rollover.expires_at ? new Date(rollover.expires_at).toISOString() : null,
+  //   }))
+  // );
+
   if (notNullish(options?.upcoming_quantity)) {
     const newOptions = cusProduct.options.map((o) => {
       if (o.feature_id == ent.feature_id) {
@@ -100,16 +131,34 @@ export const handlePrepaidPrices = async ({
     return;
   }
 
-  logger.info(
-    `🔥 Resetting balance for ${ent.feature.id}, customer: ${customer.id} (name: ${customer.name})`,
-  );
+  // logger.info(
+  //   `🔥 Resetting balance for ${ent.feature.id}, customer: ${customer.id} (name: ${customer.name})`
+  // );
+
+  if (rolloverUpdate?.toInsert && rolloverUpdate.toInsert.length > 0) {
+    await RolloverService.insert({
+      db,
+      rows: rolloverUpdate.toInsert,
+      fullCusEnt: cusEnt,
+      // rolloverConfig: ent.rollover as RolloverConfig,
+      // cusEntID: cusEnt.id,
+      // entityMode: notNullish(ent.entity_feature_id),
+    });
+  }
+
+  // console.log(
+  //   "Rollover rows",
+  //   Object.values(rolloverRows).map(
+  //     (x) =>
+  //       `${x.id}: ${x.balance} | entities: ${x.entities.map((y: any) => `${y.id}: ${y.balance}`).join(", ")}`
+  //   )
+  // );
 
   await CusEntService.update({
     db,
     id: cusEnt.id,
     updates: {
-      balance: resetBalance,
-      adjustment: 0,
+      ...resetUpdate,
       next_reset_at: usageSub.current_period_end * 1000,
     },
   });
diff --git a/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handleUsagePrices.ts b/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handleUsagePrices.ts
index 559e09544..40701d969 100644
--- a/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handleUsagePrices.ts
+++ b/server/src/external/stripe/webhookHandlers/handleInvoiceCreated/handleUsagePrices.ts
@@ -10,12 +10,16 @@ import {
   EntInterval,
   Customer,
   APIVersion,
+  RolloverConfig,
 } from "@autumn/shared";
 import { differenceInMinutes, subDays } from "date-fns";
 import { submitUsageToStripe } from "../../stripeMeterUtils.js";
 import { getInvoiceItemForUsage } from "../../stripePriceUtils.js";
 import { getCusPriceUsage } from "@/internal/customers/cusProducts/cusPrices/cusPriceUtils.js";
 import { findStripeItemForPrice } from "../../stripeSubUtils/stripeSubItemUtils.js";
+import { getRolloverUpdates } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.js";
+import { RolloverService } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.js";
+import { notNullish } from "@/utils/genUtils.js";
 
 export const handleUsagePrices = async ({
   db,
@@ -42,8 +46,8 @@ export const handleUsagePrices = async ({
     Math.abs(
       differenceInMinutes(
         new Date(activeProduct.created_at),
-        new Date(invoice.created * 1000),
-      ),
+        new Date(invoice.created * 1000)
+      )
     ) < 10;
 
   let invoiceFromUpgrade = invoice.billing_reason == "subscription_update";
@@ -93,7 +97,7 @@ export const handleUsagePrices = async ({
   } else {
     if (!config.stripe_meter_id) {
       logger.warn(
-        `Price ${price.id} has no stripe meter id, skipping invoice.created for usage in arrear`,
+        `Price ${price.id} has no stripe meter id, skipping invoice.created for usage in arrear`
       );
       return;
     }
@@ -105,7 +109,7 @@ export const handleUsagePrices = async ({
     });
 
     const usageTimestamp = Math.round(
-      subDays(new Date(invoice.created * 1000), 1).getTime() / 1000,
+      subDays(new Date(invoice.created * 1000), 1).getTime() / 1000
     );
 
     await submitUsageToStripe({
@@ -124,6 +128,7 @@ export const handleUsagePrices = async ({
   }
 
   let ent = relatedCusEnt.entitlement;
+
   let resetBalancesUpdate = getResetBalancesUpdate({
     cusEnt: relatedCusEnt,
     allowance: ent.interval == EntInterval.Lifetime ? 0 : ent.allowance!,
@@ -141,5 +146,21 @@ export const handleUsagePrices = async ({
     },
   });
 
+  let rolloverUpdate = getRolloverUpdates({
+    cusEnt: relatedCusEnt,
+    nextResetAt: usageSub.current_period_end * 1000,
+  });
+
+  if (rolloverUpdate?.toInsert && rolloverUpdate.toInsert.length > 0) {
+    await RolloverService.insert({
+      db,
+      rows: rolloverUpdate.toInsert,
+      fullCusEnt: relatedCusEnt,
+      // rolloverConfig: ent.rollover as RolloverConfig,
+      // cusEntID: ent.id,
+      // entityMode: notNullish(ent.entity_feature_id),
+    });
+  }
+
   logger.info("✅ Successfully reset balance");
 };
diff --git a/server/src/external/stripe/webhookHandlers/handleSubUpdated.ts b/server/src/external/stripe/webhookHandlers/handleSubUpdated.ts
index 173ec87f4..20df69153 100644
--- a/server/src/external/stripe/webhookHandlers/handleSubUpdated.ts
+++ b/server/src/external/stripe/webhookHandlers/handleSubUpdated.ts
@@ -74,14 +74,7 @@ export const handleSubscriptionUpdated = async ({
 
   if (updatedCusProducts.length > 0) {
     logger.info(
-      `subscription.updated: updated ${updatedCusProducts.length} customer products`,
-      {
-        data: {
-          ids: updatedCusProducts.map((cp) => cp.id),
-          status: updatedCusProducts[0].status,
-          canceled_at: updatedCusProducts[0].canceled_at,
-        },
-      },
+      `✅ Updated ${updatedCusProducts.length} customer product${updatedCusProducts.length === 1 ? '' : 's'} (${updatedCusProducts.map(cp => cp.id).join(', ')}) - Status: ${updatedCusProducts[0].status}${updatedCusProducts[0].canceled_at ? `, Canceled: ${new Date(updatedCusProducts[0].canceled_at).toISOString()}` : ''}`
     );
   }
 
diff --git a/server/src/internal/customers/add-product/createFullCusProduct.ts b/server/src/internal/customers/add-product/createFullCusProduct.ts
index 6790a8f3f..40f2cd434 100644
--- a/server/src/internal/customers/add-product/createFullCusProduct.ts
+++ b/server/src/internal/customers/add-product/createFullCusProduct.ts
@@ -33,6 +33,8 @@ import { CusEntService } from "../cusProducts/cusEnts/CusEntitlementService.js";
 import { CusPriceService } from "../cusProducts/cusPrices/CusPriceService.js";
 import { addExistingUsagesToCusEnts } from "../cusProducts/cusEnts/cusEntUtils/getExistingUsage.js";
 import { RepService } from "../cusProducts/cusEnts/RepService.js";
+import { getNewProductRollovers } from "../cusProducts/cusEnts/cusRollovers/getNewProductRollovers.js";
+import { RolloverService } from "../cusProducts/cusEnts/cusRollovers/RolloverService.js";
 
 export const initCusPrice = ({
   price,
@@ -197,7 +199,7 @@ export const expireOrDeleteCusProduct = async ({
         cp.status === CusProductStatus.Scheduled &&
         (internalEntityId
           ? cp.internal_entity_id === internalEntityId
-          : nullish(cp.internal_entity_id)),
+          : nullish(cp.internal_entity_id))
     );
 
     if (curScheduledProduct) {
@@ -350,7 +352,7 @@ export const createFullCusProduct = async ({
 
   const cusProdId = generateId("cus_prod");
   logger.info(
-    `Inserting cus product ${product.id} for ${customer.name}, cus product ID: ${cusProdId}`,
+    `Inserting cus product ${product.id} for ${customer.name}, cus product ID: ${cusProdId}`
   );
 
   // 1. create customer entitlements
@@ -403,6 +405,15 @@ export const createFullCusProduct = async ({
     features: attachParams.features,
   });
 
+  // 4. Get new rollovers
+  let rolloverOps = await getNewProductRollovers({
+    db,
+    curCusProduct: curCusProduct as FullCusProduct,
+    cusEnts,
+    entitlements,
+    logger,
+  });
+
   // 4. create customer prices
   const cusPrices: CustomerPrice[] = [];
 
@@ -458,10 +469,23 @@ export const createFullCusProduct = async ({
     replaceables: newReplaceables,
   });
 
-  let fullCusProduct = {
-    ...cusProd,
-    product,
-    customer_entitlements: cusEnts.map((ce) => ({
+  let rolloverInserts: any = [];
+
+  for (const operation of rolloverOps) {
+    rolloverInserts.push(
+      RolloverService.insert({
+        db,
+        rows: operation.toInsert,
+        fullCusEnt: operation.cusEnt,
+      })
+    );
+  }
+
+  let finalRollovers = (await Promise.all(rolloverInserts)).flatMap((r) => r);
+
+  // Get rollovers for each entitlement
+  const cusEntsWithRollovers = await Promise.all(
+    cusEnts.map(async (ce) => ({
       ...ce,
       entitlement: entitlements.find((e) => e.id === ce.entitlement_id)!,
       replaceables: newReplaceables
@@ -470,7 +494,18 @@ export const createFullCusProduct = async ({
           ...r,
           delete_next_cycle: r.delete_next_cycle || false,
         })),
-    })),
+      rollovers: finalRollovers.filter((r) => r.cus_ent_id === ce.id),
+      // await RolloverService.getCurrentRollovers({
+      //   db,
+      //   cusEntID: ce.id,
+      // }),
+    }))
+  );
+
+  let fullCusProduct = {
+    ...cusProd,
+    product,
+    customer_entitlements: cusEntsWithRollovers,
     customer_prices: cusPrices.map((cp) => ({
       ...cp,
       price: prices.find((p) => p.id === cp.price_id)!,
diff --git a/server/src/internal/customers/attach/attachUtils/getAttachFunction.ts b/server/src/internal/customers/attach/attachUtils/getAttachFunction.ts
index 1272054b0..015c58f81 100644
--- a/server/src/internal/customers/attach/attachUtils/getAttachFunction.ts
+++ b/server/src/internal/customers/attach/attachUtils/getAttachFunction.ts
@@ -142,15 +142,18 @@ export const runAttachFunction = async ({
     logger.info(`Entity: ${customer.entity.name} (${customer.entity.id})`);
   }
   logger.info(
-    `Branch: ${chalk.yellow(branch)}, Function: ${chalk.yellow(attachFunction)}`,
-    {
-      data: {
-        curMainProduct: curMainProduct?.product.id,
-        curSameProduct: curSameProduct?.product.id,
-        curScheduledProduct: curScheduledProduct?.product.id,
-      },
-    }
+    `Branch: ${chalk.yellow(branch)}, Function: ${chalk.yellow(attachFunction)}`
   );
+  
+  if (curMainProduct) {
+    logger.info(`→ Current Main Product: ${curMainProduct.product.id}`);
+  }
+  if (curSameProduct) {
+    logger.info(`→ Current Same Product: ${curSameProduct.product.id}`);
+  }
+  if (curScheduledProduct) {
+    logger.info(`→ Current Scheduled Product: ${curScheduledProduct.product.id}`);
+  }
 
   // config.proration = ProrationBehavior.None;
   // attachParams.billingAnchor = 1781702400000;
diff --git a/server/src/internal/customers/cusProducts/CusProductService.ts b/server/src/internal/customers/cusProducts/CusProductService.ts
index 61ff6a7e2..fa5660d50 100644
--- a/server/src/internal/customers/cusProducts/CusProductService.ts
+++ b/server/src/internal/customers/cusProducts/CusProductService.ts
@@ -85,6 +85,7 @@ const getFullCusProdRelations = () => {
           },
         },
         replaceables: true,
+        rollovers: true,
       },
     },
     customer_prices: {
@@ -147,6 +148,7 @@ export class CusProductService {
               },
             },
             replaceables: true,
+            rollovers: true,
           },
         },
         customer_prices: {
@@ -197,7 +199,7 @@ export class CusProductService {
     let cusProducts = await db.query.customerProducts.findMany({
       where: and(
         eq(customerProducts.internal_customer_id, internalCustomerId),
-        inStatuses ? inArray(customerProducts.status, inStatuses) : undefined,
+        inStatuses ? inArray(customerProducts.status, inStatuses) : undefined
       ),
       with: {
         customer: withCustomer ? true : undefined,
@@ -210,6 +212,7 @@ export class CusProductService {
               },
             },
             replaceables: true,
+            rollovers: true,
           },
         },
         customer_prices: {
@@ -259,14 +262,14 @@ export class CusProductService {
       .from(customerProducts)
       .innerJoin(
         products,
-        eq(customerProducts.internal_product_id, products.internal_id),
+        eq(customerProducts.internal_product_id, products.internal_id)
       )
       .where(
         and(
           eq(products.id, productId),
           eq(products.org_id, orgId),
-          eq(products.env, env),
-        ),
+          eq(products.env, env)
+        )
       )
       .limit(1);
 
@@ -294,7 +297,7 @@ export class CusProductService {
       where: (table, { and, or, inArray }) =>
         and(
           or(arrayContains(customerProducts.subscription_ids, [stripeSubId])),
-          inStatuses ? inArray(customerProducts.status, inStatuses) : undefined,
+          inStatuses ? inArray(customerProducts.status, inStatuses) : undefined
         ),
 
       with: {
@@ -308,6 +311,7 @@ export class CusProductService {
               },
             },
             replaceables: true,
+            rollovers: true,
           },
         },
         customer_prices: {
@@ -345,10 +349,10 @@ export class CusProductService {
           or(
             eq(
               sql`${customerProducts.processor}->>'subscription_schedule_id'`,
-              stripeScheduledId,
+              stripeScheduledId
             ),
-            sql`${customerProducts.scheduled_ids} @> ${sql`ARRAY[${stripeScheduledId}]`}`,
-          ),
+            sql`${customerProducts.scheduled_ids} @> ${sql`ARRAY[${stripeScheduledId}]`}`
+          )
         ),
 
       with: {
@@ -362,6 +366,7 @@ export class CusProductService {
               },
             },
             replaceables: true,
+            rollovers: true,
           },
         },
         customer_prices: {
@@ -402,6 +407,7 @@ export class CusProductService {
             },
           },
           replaceables: true,
+          rollovers: true,
         },
       },
       customer_prices: {
@@ -462,9 +468,9 @@ export class CusProductService {
           or(
             eq(customerProducts.status, CusProductStatus.Active),
             eq(customerProducts.status, CusProductStatus.PastDue),
-            eq(customerProducts.status, CusProductStatus.Scheduled),
-          ),
-        ),
+            eq(customerProducts.status, CusProductStatus.Scheduled)
+          )
+        )
       )
       .returning({
         id: customerProducts.id,
@@ -473,7 +479,7 @@ export class CusProductService {
     let fullUpdated = (await db.query.customerProducts.findMany({
       where: inArray(
         customerProducts.id,
-        updated.map((u) => u.id),
+        updated.map((u) => u.id)
       ),
       with: {
         product: true,
@@ -514,21 +520,21 @@ export class CusProductService {
       .from(customerProducts)
       .innerJoin(
         customers,
-        eq(customerProducts.internal_customer_id, customers.internal_id),
+        eq(customerProducts.internal_customer_id, customers.internal_id)
       )
       .innerJoin(
         products,
-        eq(customerProducts.internal_product_id, products.internal_id),
+        eq(customerProducts.internal_product_id, products.internal_id)
       )
       .where(
         and(
           or(
             fingerprint ? eq(customers.fingerprint, fingerprint) : undefined,
-            eq(customers.internal_id, internalCustomerId),
+            eq(customers.internal_id, internalCustomerId)
           ),
           eq(products.id, productId),
-          isNotNull(customerProducts.free_trial_id),
-        ),
+          isNotNull(customerProducts.free_trial_id)
+        )
       );
 
     return data;
@@ -546,7 +552,7 @@ export class CusProductService {
     let data = await db.query.customerProducts.findMany({
       where: and(
         eq(customerProducts.free_trial_id, freeTrialId),
-        eq(customerProducts.internal_customer_id, internalCustomerId),
+        eq(customerProducts.internal_customer_id, internalCustomerId)
       ),
       with: {
         customer: true,
diff --git a/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.ts b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.ts
new file mode 100644
index 000000000..573dc1eb6
--- /dev/null
+++ b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/RolloverService.ts
@@ -0,0 +1,133 @@
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import {
+  FullCustomerEntitlement,
+  Rollover,
+  RolloverConfig,
+  rollovers,
+} from "@autumn/shared";
+import { and, eq, gte, inArray } from "drizzle-orm";
+import { performMaximumClearing } from "./rolloverUtils.js";
+import { buildConflictUpdateColumns } from "@/db/dbUtils.js";
+
+export class RolloverService {
+  static async update({
+    db,
+    id,
+    updates,
+  }: {
+    db: DrizzleCli;
+    id: string;
+    updates: Partial<Rollover>;
+  }) {
+    if (!updates.balance && !updates.entities) return [];
+
+    const data = await db
+      .update(rollovers)
+      .set(updates as any)
+      .where(eq(rollovers.id, id))
+      .returning();
+
+    return data;
+  }
+
+  static async upsert({ db, rows }: { db: DrizzleCli; rows: Rollover[] }) {
+    if (Array.isArray(rows) && rows.length == 0) return;
+
+    const updateColumns = buildConflictUpdateColumns(rollovers, ["id"]);
+    await db
+      .insert(rollovers)
+      .values(rows as any)
+      .onConflictDoUpdate({
+        target: rollovers.id,
+        set: updateColumns,
+      });
+  }
+
+  // static async bulkUpdate({ db, rows }: { db: DrizzleCli; rows: Rollover[] }) {
+  //   if (rows.length === 0) return [];
+
+  //   const results = [];
+  //   for (const row of rows) {
+  //     const result = await this.update({
+  //       db,
+  //       id: row.id,
+  //       updates: row,
+  //     });
+  //     results.push(...result);
+  //   }
+  //   return results;
+  // }
+
+  static async getCurrentRollovers({
+    db,
+    cusEntID,
+  }: {
+    db: DrizzleCli;
+    cusEntID: string;
+  }) {
+    return await db
+      .select()
+      .from(rollovers)
+      .where(
+        and(
+          eq(rollovers.cus_ent_id, cusEntID),
+          gte(rollovers.expires_at, new Date().getTime())
+        )
+      );
+  }
+
+  static async insert({
+    db,
+    rows,
+    // rolloverConfig,
+    fullCusEnt,
+    // cusEntID,
+    // entityMode,
+  }: {
+    db: DrizzleCli;
+    rows: Rollover[];
+    // rolloverConfig: RolloverConfig;
+    fullCusEnt: FullCustomerEntitlement;
+    // cusEntID: string;
+    // entityMode: boolean;
+  }) {
+    if (rows.length === 0) return {};
+
+    await db
+      .insert(rollovers)
+      .values(rows as any)
+      .returning();
+
+    let curRollovers = [...fullCusEnt.rollovers, ...rows];
+
+    let { toDelete, toUpdate } = performMaximumClearing({
+      rows: curRollovers as Rollover[],
+      cusEnt: fullCusEnt,
+    });
+
+    if (toDelete.length > 0) {
+      await RolloverService.delete({ db, ids: toDelete });
+    }
+
+    if (toUpdate.length > 0) {
+      await RolloverService.upsert({ db, rows: toUpdate });
+    }
+
+    // Return latest rollovers...?
+    curRollovers = curRollovers.filter((r) => toDelete.includes(r.id));
+    curRollovers = curRollovers.map((r) => {
+      let updatedRow = toUpdate.find((u) => u.id === r.id);
+      if (updatedRow) {
+        return updatedRow;
+      }
+      return r;
+    });
+
+    return curRollovers;
+  }
+
+  static async delete({ db, ids }: { db: DrizzleCli; ids: string[] }) {
+    if (ids.length === 0) return;
+    const data = await db.delete(rollovers).where(inArray(rollovers.id, ids));
+  }
+}
diff --git a/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/getNewProductRollovers.ts b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/getNewProductRollovers.ts
new file mode 100644
index 000000000..92fce5265
--- /dev/null
+++ b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/getNewProductRollovers.ts
@@ -0,0 +1,138 @@
+import { generateId, nullish } from "@/utils/genUtils.js";
+import {
+  CustomerEntitlement,
+  EntitlementWithFeature,
+  FullCusProduct,
+  FullCustomerEntitlement,
+  Rollover,
+  RolloverConfig,
+} from "@autumn/shared";
+import { RolloverService } from "./RolloverService.js";
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { calculateNextExpiry } from "./rolloverUtils.js";
+
+export const getNewProductRollovers = async ({
+  curCusProduct,
+  cusEnts: newCusEnts,
+  entitlements,
+  db,
+  logger,
+}: {
+  curCusProduct: FullCusProduct;
+  cusEnts: CustomerEntitlement[];
+  entitlements: EntitlementWithFeature[];
+  db: DrizzleCli;
+  logger: any;
+}) => {
+  if (!curCusProduct) return [];
+  if (!curCusProduct.id) return [];
+  try {
+    let rolloverOperations: {
+      // rolloverConfig: RolloverConfig;
+      toInsert: Rollover[];
+      cusEnt: FullCustomerEntitlement;
+      // cusEntId: string;
+      // toUpdate: Rollover[];
+      // entityMode: boolean;
+    }[] = [];
+
+    // let newRollovers: Rollover[] = [];
+
+    let oldCusEnts = curCusProduct.customer_entitlements;
+
+    for (const newCusEnt of newCusEnts) {
+      let newRollovers: Rollover[] = [];
+      let newEnt = entitlements.find((e) => e.id === newCusEnt.entitlement_id);
+      let oldCusEnt = oldCusEnts.find(
+        (e) => e.entitlement.internal_feature_id === newEnt?.internal_feature_id
+      );
+      let oldEnt = oldCusEnt?.entitlement;
+
+      if (!oldCusEnt || !newEnt?.rollover) continue;
+
+      // Do not handle case where user is upgrading from non-entity to entity or vice versa
+      if (newEnt?.entity_feature_id && !oldEnt?.entity_feature_id) {
+        continue;
+      }
+      if (!newEnt?.entity_feature_id && oldEnt?.entity_feature_id) {
+        continue;
+      }
+
+      // Bring over current balance (if greater > 0), and any existing rollover
+      // if (
+      //   oldCusEnt.balance &&
+      //   oldCusEnt.balance > 0 &&
+      //   !oldCusEnt.entitlement.entity_feature_id &&
+      //   rollover
+      // ) {
+      //   newRollovers.push({
+      //     id: generateId("roll"),
+      //     cus_ent_id: newCusEnt.id,
+      //     balance: oldCusEnt.balance,
+      //     entities: {},
+      //     usage: 0,
+      //     expires_at: calculateNextExpiry(Date.now(), rollover),
+      //   });
+      // } else if (
+      //   oldCusEnt.entitlement.entity_feature_id &&
+      //   oldCusEnt.entities
+      // ) {
+      //   const entityRollovers = Object.keys(oldCusEnt.entities || {}).reduce(
+      //     (acc, entityId) => {
+      //       const entityBalance = oldCusEnt.entities?.[entityId];
+      //       if (entityBalance && entityBalance.balance > 0) {
+      //         acc[entityId] = {
+      //           id: entityId,
+      //           balance: entityBalance.balance || 0,
+      //           usage: 0,
+      //         };
+      //       }
+      //       return acc;
+      //     },
+      //     {} as Record<string, { id: string; balance: number; usage: number }>
+      //   );
+
+      //   if (Object.keys(entityRollovers).length > 0) {
+      //     newRollovers.push({
+      //       id: generateId("roll"),
+      //       cus_ent_id: newCusEnt.id,
+      //       balance: 0,
+      //       entities: entityRollovers,
+      //       usage: 0,
+      //       expires_at: calculateNextExpiry(Date.now(), rollover),
+      //     });
+      //   }
+      // }
+
+      let curRollovers = oldCusEnt.rollovers;
+
+      for (const curRollover of curRollovers) {
+        newRollovers.push({
+          ...curRollover,
+          id: generateId("roll"),
+          cus_ent_id: newCusEnt.id,
+        });
+      }
+
+      console.log(`Feature ${newEnt?.feature_id} rollovers:`, newRollovers);
+
+      // // Add this entitlement's rollover operations
+      rolloverOperations.push({
+        toInsert: newRollovers,
+        cusEnt: {
+          ...newCusEnt,
+          entitlement: newEnt,
+          rollovers: [],
+          replaceables: [],
+        },
+      });
+    }
+
+    return rolloverOperations;
+  } catch (error) {
+    logger.error(`Failed to handle new product rollovers:`, {
+      error,
+    });
+    return [];
+  }
+};
diff --git a/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverDeductionUtils.ts b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverDeductionUtils.ts
new file mode 100644
index 000000000..a7c923b8f
--- /dev/null
+++ b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverDeductionUtils.ts
@@ -0,0 +1,130 @@
+import { RolloverDeductParams } from "@/trigger/updateBalanceTask.js";
+import { FullCusEntWithFullCusProduct, Rollover } from "@autumn/shared";
+import { RolloverService } from "./RolloverService.js";
+
+export const deductFromCusRollovers = async ({
+  toDeduct,
+  deductParams,
+  cusEnt,
+}: {
+  toDeduct: number;
+  deductParams: RolloverDeductParams;
+  cusEnt: FullCusEntWithFullCusProduct;
+}) => {
+  if (toDeduct == 0) {
+    return toDeduct;
+  }
+
+  let updates = {
+    toInsert: [] as Rollover[],
+    toUpdate: [] as Rollover[],
+  };
+  let rollovers = getSortedRollovers({
+    cusEnts: [cusEnt],
+    featureId: deductParams.feature.id,
+    entityId: deductParams.entity?.id,
+  });
+
+  if (deductParams.entity) {
+    for (let rollover of rollovers) {
+      let entityRollover = rollover.entities[deductParams.entity.id];
+      if (entityRollover) {
+        if (entityRollover.balance >= toDeduct) {
+          entityRollover.balance -= toDeduct;
+          entityRollover.usage += toDeduct;
+
+          updates.toUpdate.push(rollover);
+          toDeduct = 0;
+          break;
+        } else {
+          if (entityRollover.balance > 0) {
+            let deductedAmount = entityRollover.balance;
+            toDeduct -= entityRollover.balance;
+            entityRollover.balance = 0;
+            entityRollover.usage += deductedAmount;
+            updates.toUpdate.push(rollover);
+          }
+        }
+      }
+    }
+  } else {
+    for (let rollover of rollovers) {
+      if (rollover.balance >= toDeduct) {
+        rollover = {
+          ...rollover,
+          balance: rollover.balance - toDeduct,
+          usage: rollover.usage + toDeduct,
+        };
+
+        updates.toUpdate.push(rollover);
+        toDeduct = 0;
+
+        break;
+      } else {
+        if (rollover.balance > 0) {
+          toDeduct -= rollover.balance;
+          rollover = {
+            ...rollover,
+            usage: rollover.usage + rollover.balance,
+            balance: 0,
+          };
+
+          updates.toUpdate.push(rollover);
+        }
+      }
+    }
+  }
+
+  await RolloverService.upsert({
+    db: deductParams.db,
+    rows: updates.toUpdate,
+  });
+
+  return toDeduct;
+};
+
+export const getSortedRollovers = ({
+  cusEnts,
+  featureId,
+  entityId,
+}: {
+  cusEnts: FullCusEntWithFullCusProduct[];
+  featureId: string;
+  entityId?: string;
+}) => {
+  if (!entityId)
+    return cusEnts
+      .filter((cusEnt) => {
+        return cusEnt.feature_id === featureId;
+      })
+      .flatMap((cusEnt) => {
+        return cusEnt.rollovers;
+      })
+      .sort((a, b) => {
+        if (a.expires_at && b.expires_at) return a.expires_at - b.expires_at;
+        if (a.expires_at && !b.expires_at) return -1;
+        if (!a.expires_at && b.expires_at) return 1;
+        return 0;
+      });
+  else {
+    return cusEnts
+      .filter((cusEnt) => {
+        return (
+          cusEnt.feature_id === featureId &&
+          cusEnt.entities &&
+          cusEnt.entities[entityId]
+        );
+      })
+      .flatMap((cusEnt) => {
+        return cusEnt.rollovers.filter((x) => {
+          return x.entities[entityId];
+        });
+      })
+      .sort((a, b) => {
+        if (a.expires_at && b.expires_at) return a.expires_at - b.expires_at;
+        if (a.expires_at && !b.expires_at) return -1;
+        if (!a.expires_at && b.expires_at) return 1;
+        return 0;
+      });
+  }
+};
diff --git a/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.ts b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.ts
new file mode 100644
index 000000000..01b326b62
--- /dev/null
+++ b/server/src/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverUtils.ts
@@ -0,0 +1,394 @@
+import {
+  FullCustomerEntitlement,
+  RolloverConfig,
+  EntityRolloverBalance,
+  RolloverDuration,
+  Rollover,
+} from "@autumn/shared";
+import { generateId, notNullish, nullish } from "@/utils/genUtils.js";
+import { addMonths } from "date-fns";
+import { Decimal } from "decimal.js";
+
+export const getRolloverUpdates = ({
+  cusEnt,
+  nextResetAt,
+}: {
+  cusEnt: FullCustomerEntitlement;
+  nextResetAt: number;
+}) => {
+  let update: {
+    toDelete: string[];
+    toInsert: Rollover[];
+    toUpdate: Rollover[];
+  } = {
+    toDelete: [],
+    toInsert: [],
+    toUpdate: [],
+  };
+  let ent = cusEnt.entitlement;
+  let shouldRollover =
+    cusEnt.balance && cusEnt.balance > 0 && notNullish(ent.rollover);
+
+  if (!shouldRollover) return update;
+
+  let nextExpiry = calculateNextExpiry(nextResetAt, ent.rollover!);
+
+  let newRollover: Rollover = {
+    id: generateId("roll"),
+    cus_ent_id: cusEnt.id,
+    balance: 0,
+    usage: 0,
+    expires_at: nextExpiry,
+    entities: {},
+  };
+
+  if (notNullish(ent.entity_feature_id)) {
+    for (const entityId in cusEnt.entities) {
+      let entRollover = cusEnt.entities[entityId].balance;
+
+      if (entRollover > 0) {
+        newRollover.entities[entityId] = {
+          id: entityId,
+          balance: entRollover,
+          usage: 0,
+        };
+      }
+    }
+
+    update.toInsert.push(newRollover);
+  } else {
+    let balance = cusEnt.balance!;
+    if (balance > 0) {
+      newRollover.balance = balance;
+      update.toInsert.push(newRollover);
+    }
+  }
+
+  return update;
+};
+
+export const calculateNextExpiry = (
+  nextResetAt: number,
+  config: RolloverConfig
+) => {
+  if (nullish(config)) {
+    return null;
+  }
+
+  if (config.duration == RolloverDuration.Forever) return null;
+
+  return addMonths(nextResetAt, config.length).getTime();
+};
+
+export function performMaximumClearing({
+  rows,
+  // rolloverConfig,
+  cusEnt,
+  // cusEntID,
+  // entityMode,
+}: {
+  rows: Rollover[];
+  // rolloverConfig: RolloverConfig;
+  cusEnt: FullCustomerEntitlement;
+  // cusEntID: string;
+  // entityMode: boolean;
+}) {
+  let rolloverConfig = cusEnt.entitlement.rollover;
+
+  if (!rolloverConfig) {
+    return { toDelete: [], toUpdate: [] };
+  }
+
+  if (rolloverConfig.max == null) {
+    return { toDelete: [], toUpdate: [] };
+  }
+
+  let total = 0;
+  let toDelete: string[] = [];
+  let toUpdate: Rollover[] = [];
+
+  // look through each row
+  // if entityMode is true, then look through each entity
+  // otherwise look at balance
+
+  // sort by the oldest first
+  // add the balance of the oldest to the total
+  // if the total is greater than or equal to the max, then:
+  // subtract the max from the total, if theres a difference then instantiate the updated row object and push to toUpdate
+  // if theres no difference, then push to toDelete
+  // move to the next row
+  // if the total is less than the max, then
+  // move to the next row
+
+  rows.sort((a, b) => {
+    if (a.expires_at && b.expires_at) return a.expires_at - b.expires_at;
+    if (a.expires_at && !b.expires_at) return -1;
+    if (!a.expires_at && b.expires_at) return 1;
+    return 0;
+  });
+
+  let ent = cusEnt.entitlement;
+  let entityMode = !!ent.entity_feature_id;
+
+  if (!entityMode) {
+    let totalRolloverBalance = rows.reduce((acc, row) => acc + row.balance, 0);
+    let toDeduct = new Decimal(totalRolloverBalance).sub(rolloverConfig.max);
+
+    if (toDeduct.lt(0)) return { toDelete: [], toUpdate: [] };
+
+    let toUpdate: Rollover[] = [];
+    let toDelete: string[] = [];
+
+    for (const row of rows) {
+      let curBalance = new Decimal(row.balance);
+      let newBalance = curBalance;
+      if (curBalance.gte(toDeduct)) {
+        newBalance = newBalance.sub(toDeduct);
+        toDeduct = new Decimal(0);
+
+        toUpdate.push({ ...row, balance: newBalance.toNumber() });
+      } else {
+        newBalance = new Decimal(0);
+        toDeduct = toDeduct.sub(curBalance);
+
+        toDelete.push(row.id);
+      }
+
+      if (toDeduct.lte(0)) break;
+    }
+
+    return { toDelete, toUpdate };
+  } else {
+    const allEntityIds = new Set<string>();
+    rows.forEach((row) => {
+      if (row.entities && Array.isArray(row.entities)) {
+        row.entities.forEach((entity: any) => {
+          if (entity.id) {
+            allEntityIds.add(entity.id);
+          }
+        });
+      }
+    });
+
+    const entityTotals = new Map<string, number>();
+    allEntityIds.forEach((id) => entityTotals.set(id, 0));
+    let entityIdToTotal: Record<string, number> = {};
+    rows.forEach((row) => {
+      for (const entityId in row.entities) {
+        entityIdToTotal[entityId] =
+          (entityIdToTotal[entityId] || 0) + row.entities[entityId].balance;
+      }
+    });
+
+    // console.log(`id to total:`, entityIdToTotal);
+
+    let toUpdate: Rollover[] = [];
+    let toDelete: string[] = [];
+
+    // Non entity mode
+    for (const row of rows) {
+      let update = structuredClone(row);
+      let shouldUpdate = false;
+
+      for (const entityId in entityIdToTotal) {
+        let entityTotal = entityIdToTotal[entityId];
+        let toDeduct = new Decimal(entityTotal).sub(rolloverConfig.max);
+
+        if (toDeduct.lte(0) || !row.entities[entityId]) continue;
+        // console.log(`Entity ${entityId}, deducting ${toDeduct.toNumber()}`);
+
+        let curBalance = new Decimal(row.entities[entityId].balance);
+        let newBalance = curBalance;
+
+        if (curBalance.gte(toDeduct)) {
+          newBalance = newBalance.sub(toDeduct);
+          entityIdToTotal[entityId] = 0;
+          shouldUpdate = true;
+          update.entities[entityId] = {
+            id: entityId,
+            balance: newBalance.toNumber(),
+            usage: 0,
+          };
+        } else {
+          newBalance = new Decimal(0);
+          entityIdToTotal[entityId] = toDeduct.sub(curBalance).toNumber();
+          shouldUpdate = true;
+          update.entities[entityId] = {
+            id: entityId,
+            balance: 0,
+            usage: 0,
+          };
+        }
+      }
+      // console.log(`Max clearing for row ${row.id}`);
+      // console.log(`Update:`, update.entities);
+
+      // If all keys are 0, then delete the row
+      if (
+        Object.values(update.entities).every(
+          (entity: EntityRolloverBalance) => entity.balance === 0
+        )
+      ) {
+        toDelete.push(row.id);
+      } else if (shouldUpdate) {
+        toUpdate.push(update);
+      }
+    }
+
+    return { toDelete, toUpdate };
+  }
+}
+
+// For each entity ID, perform maximum clearing...
+
+// console.log(
+//   `🔍 Found ${allEntityIds.size} unique entity IDs: ${Array.from(allEntityIds).join(", ")}`
+// );
+
+// Sort rows by expiry date (oldest first)
+// rows.sort((a, b) => a.expires_at - b.expires_at);
+// console.log(`📅 Sorted rows by expiry date (oldest first)`);
+
+// Track totals per entity ID
+
+//   for (let i = 0; i < rows.length; i++) {
+//     let row = rows[i];
+//     // console.log(`\n🔍 Processing row ${i + 1}/${rows.length}:`);
+//     // console.log(`  - Row ID: ${row.id}`);
+//     // console.log(`  - Expires at: ${new Date(row.expires_at).toISOString()}`);
+
+//     if (!row.entities || !Array.isArray(row.entities)) {
+//       console.log(`  - ⚠️ Row has no entities array, skipping`);
+//       continue;
+//     }
+
+//     let rowNeedsUpdate = false;
+//     let updatedEntities = [...row.entities];
+
+//     // Process each entity in this row
+//     for (let j = 0; j < updatedEntities.length; j++) {
+//       const entity = updatedEntities[j];
+//       if (!entity.id || !entity.balance) {
+//         // console.log(`    - ⚠️ Entity missing id or balance, skipping`);
+//         continue;
+//       }
+
+//       const currentTotal = entityTotals.get(entity.id) || 0;
+//       const newTotal = currentTotal + entity.balance;
+
+//       console.log(
+//         `    - Entity ${entity.id}: balance=${entity.balance}, currentTotal=${currentTotal}, newTotal=${newTotal}`
+//       );
+
+//       if (newTotal > rolloverConfig.max) {
+//         const excess = newTotal - rolloverConfig.max;
+//         const newBalance = entity.balance - excess;
+
+//         console.log(
+//           `      - ⚠️ Total exceeds maximum (${rolloverConfig.max})`
+//         );
+//         console.log(`      - Excess to remove: ${excess}`);
+//         console.log(
+//           `      - Updating entity balance from ${entity.balance} to ${newBalance}`
+//         );
+
+//         if (newBalance > 0) {
+//           updatedEntities[j] = { ...entity, balance: newBalance };
+//           entityTotals.set(entity.id, rolloverConfig.max);
+//           rowNeedsUpdate = true;
+//         } else {
+//           console.log(`      - 🗑️ Removing entity (no remaining balance)`);
+//           updatedEntities.splice(j, 1);
+//           j--; // Adjust index after removal
+//           entityTotals.set(entity.id, rolloverConfig.max);
+//           rowNeedsUpdate = true;
+//         }
+//       } else {
+//         entityTotals.set(entity.id, newTotal);
+//         console.log(`      - ✅ Total still under maximum, continuing`);
+//       }
+//     }
+
+//     // Determine what to do with this row
+//     if (updatedEntities.length === 0) {
+//       console.log(`  - 🗑️ Marking row for deletion (no entities remaining)`);
+//       toDelete.push(row.id);
+//     } else if (rowNeedsUpdate) {
+//       console.log(`  - ✏️ Marking row for update (entities modified)`);
+//       toUpdate.push({
+//         ...row,
+//         entities: updatedEntities,
+//       });
+//     } else {
+//       console.log(`  - ✅ Row unchanged`);
+//     }
+//   }
+
+//   console.log(
+//     `\n📋 Maximum clearing summary for cusEnt ${cusEntID} (entity mode):`
+//   );
+//   console.log(`  - Rows to update: ${toUpdate.length}`);
+//   console.log(`  - Rows to delete: ${toDelete.length}`);
+//   console.log(`  - Final entity totals:`);
+//   entityTotals.forEach((total, entityId) => {
+//     console.log(`    - ${entityId}: ${total}`);
+//   });
+//   if (toUpdate.length > 0) {
+//     console.log(
+//       `  - Updated row IDs: ${toUpdate.map((r) => r.id).join(", ")}`
+//     );
+//   }
+//   if (toDelete.length > 0) {
+//     console.log(`  - Deleted row IDs: ${toDelete.join(", ")}`);
+//   }
+// }
+
+// return the rows that were cleared
+
+// for (let i = 0; i < rows.length; i++) {
+//   let row = rows[i];
+//   // console.log(`\n🔍 Processing row ${i + 1}/${rows.length}:`);
+//   // console.log(`  - Row ID: ${row.id}`);
+//   // console.log(`  - Row balance: ${row.balance}`);
+//   // console.log(`  - Expires at: ${new Date(row.expires_at).toISOString()}`);
+//   // console.log(`  - Total before adding this row: ${total}`);
+
+//   total += row.balance;
+//   // console.log(`  - Total after adding this row: ${total}`);
+
+//   if (total > rolloverConfig.max) {
+//     let diff = total - rolloverConfig.max;
+//     // console.log(`  - ⚠️ Total exceeds maximum (${rolloverConfig.max})`);
+//     // console.log(`  - Difference to remove: ${diff}`);
+
+//     let newBalance = row.balance - diff;
+//     if (newBalance > 0) {
+//       // console.log(
+//       //   `  - ✏️ Updating row balance from ${row.balance} to ${newBalance}`
+//       // );
+//       toUpdate.push({
+//         ...row,
+//         balance: newBalance,
+//       });
+//     } else {
+//       // console.log(`  - 🗑️ Marking row for deletion (no remaining balance)`);
+//       toDelete.push(row.id);
+//     }
+//   } else {
+//     // console.log(`  - ✅ Total still under maximum, continuing to next row`);
+//     continue;
+//   }
+// }
+
+// console.log(`\n📋 Maximum clearing summary for cusEnt ${cusEntID}:`);
+// console.log(`  - Final total: ${total}`);
+// console.log(`  - Rows to update: ${toUpdate.length}`);
+// console.log(`  - Rows to delete: ${toDelete.length}`);
+// if (toUpdate.length > 0) {
+//   console.log(
+//     `  - Updated balances: ${toUpdate.map((r) => `${r.id}: ${r.balance}`).join(", ")}`
+//   );
+// }
+// if (toDelete.length > 0) {
+//   console.log(`  - Deleted row IDs: ${toDelete.join(", ")}`);
+// }
diff --git a/server/src/internal/customers/cusProducts/cusEnts/groupByUtils.ts b/server/src/internal/customers/cusProducts/cusEnts/groupByUtils.ts
index 0d672433a..6c04a904a 100644
--- a/server/src/internal/customers/cusProducts/cusEnts/groupByUtils.ts
+++ b/server/src/internal/customers/cusProducts/cusEnts/groupByUtils.ts
@@ -1,30 +1,32 @@
-import { FullCustomerEntitlement } from "@autumn/shared";
+import {
+	FullCustomerEntitlement,
+} from "@autumn/shared";
 import { notNullish } from "@/utils/genUtils.js";
 
 export const getResetBalancesUpdate = ({
-  cusEnt,
-  allowance,
+	cusEnt,
+	allowance,
 }: {
-  cusEnt: FullCustomerEntitlement;
-  allowance?: number;
+	cusEnt: FullCustomerEntitlement;
+	allowance?: number;
 }) => {
-  let update = {};
-  let newBalance = notNullish(allowance)
-    ? allowance!
-    : cusEnt.entitlement.allowance || 0;
+	let update = {};
+	let newBalance = notNullish(allowance)
+		? allowance!
+		: cusEnt.entitlement.allowance || 0;
 
-  let entitlement = cusEnt.entitlement;
+	let entitlement = cusEnt.entitlement;
 
-  if (notNullish(entitlement.entity_feature_id)) {
-    let newEntities = { ...cusEnt.entities };
-    for (const entityId in newEntities) {
-      newEntities[entityId].balance = newBalance;
-      newEntities[entityId].adjustment = 0;
-    }
-    update = { entities: newEntities };
-  } else {
-    update = { balance: newBalance };
-  }
+	if (notNullish(entitlement.entity_feature_id)) {
+		let newEntities = { ...cusEnt.entities };
+		for (const entityId in newEntities) {
+			newEntities[entityId].balance = newBalance;
+			newEntities[entityId].adjustment = 0;
+		}
+		update = { entities: newEntities };
+	} else {
+		update = { balance: newBalance };
+	}
 
-  return update;
-};
+	return update;
+};
\ No newline at end of file
diff --git a/server/src/internal/customers/cusProducts/cusProductUtils.ts b/server/src/internal/customers/cusProducts/cusProductUtils.ts
index 68dcd1edf..166d708e8 100644
--- a/server/src/internal/customers/cusProducts/cusProductUtils.ts
+++ b/server/src/internal/customers/cusProducts/cusProductUtils.ts
@@ -20,7 +20,7 @@ import {
   getUsageTier,
 } from "@/internal/products/prices/priceUtils.js";
 import { ProductService } from "@/internal/products/ProductService.js";
-import { CusProductService } from "./CusProductService.js";
+import { CusProductService, RELEVANT_STATUSES } from "./CusProductService.js";
 import { createStripeCli } from "@/external/stripe/utils.js";
 import { createFullCusProduct } from "../add-product/createFullCusProduct.js";
 import Stripe from "stripe";
@@ -514,11 +514,7 @@ export const getMainCusProduct = async ({
   let cusProducts = await CusProductService.list({
     db,
     internalCustomerId,
-    inStatuses: [
-      CusProductStatus.Active,
-      CusProductStatus.PastDue,
-      CusProductStatus.Scheduled,
-    ],
+    inStatuses: RELEVANT_STATUSES,
   });
 
   let mainCusProduct = cusProducts.find(
@@ -527,7 +523,7 @@ export const getMainCusProduct = async ({
       (productGroup ? cusProduct.product.group === productGroup : true)
   );
 
-  return mainCusProduct;
+  return mainCusProduct as FullCusProduct;
 };
 
 export const getCusProductsWithStripeSubId = ({
diff --git a/server/src/internal/customers/cusProducts/cusProductUtils/convertCusProduct.ts b/server/src/internal/customers/cusProducts/cusProductUtils/convertCusProduct.ts
index 56c3b603b..8117bc74f 100644
--- a/server/src/internal/customers/cusProducts/cusProductUtils/convertCusProduct.ts
+++ b/server/src/internal/customers/cusProducts/cusProductUtils/convertCusProduct.ts
@@ -36,7 +36,7 @@ export const cusProductsToCusPrices = ({
     let prices = cusProduct.customer_prices;
     if (billingType) {
       prices = prices.filter(
-        (cp) => getBillingType(cp.price.config) === billingType,
+        (cp) => getBillingType(cp.price.config) === billingType
       );
     }
 
@@ -68,13 +68,13 @@ export const cusProductsToCusEnts = ({
       ...cusProduct.customer_entitlements.map((cusEnt) => ({
         ...cusEnt,
         customer_product: cusProduct,
-      })),
+      }))
     );
   }
 
   if (featureId) {
     cusEnts = cusEnts.filter(
-      (cusEnt) => cusEnt.entitlement.feature_id === featureId,
+      (cusEnt) => cusEnt.entitlement.feature_id === featureId
     );
   }
 
@@ -153,3 +153,26 @@ export const cusProductsToStripeSubs = ({
     subIds: cusProducts.flatMap((p: any) => p.subscription_ids || []),
   });
 };
+
+export const cusProductToCusEnt = ({
+  cusProduct,
+  featureId,
+}: {
+  cusProduct: FullCusProduct;
+  featureId: string;
+}) => {
+  let cusEnts = cusProduct.customer_entitlements;
+
+  let fullCusEnt = cusEnts.find(
+    (ce) => ce.entitlement.feature_id === featureId
+  );
+
+  if (fullCusEnt) {
+    return {
+      ...fullCusEnt,
+      customer_product: cusProduct,
+    } as FullCusEntWithFullCusProduct;
+  }
+
+  return undefined;
+};
diff --git a/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/balancesToFeatureResponse.ts b/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/balancesToFeatureResponse.ts
index 3e66e2360..be62a6a41 100644
--- a/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/balancesToFeatureResponse.ts
+++ b/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/balancesToFeatureResponse.ts
@@ -3,6 +3,7 @@ import {
   CusEntResponse,
   CusEntResponseSchema,
   CusEntResponseV2,
+  CusRollover,
   Feature,
   FeatureType,
   FullCustomerEntitlement,
@@ -16,7 +17,7 @@ import { notNullish } from "@/utils/genUtils.js";
 
 export const sumValues = (
   entList: CusEntResponse[],
-  key: keyof CusEntResponse,
+  key: keyof CusEntResponse
 ) => {
   return entList.reduce((acc, curr) => {
     if (curr[key]) {
@@ -66,7 +67,9 @@ export const featuresToObject = ({
       usageLimit = undefined;
     }
 
-    featureObject[featureId] = {
+    // console.log(`Feature ${featureId} list:`, relatedEnts);
+
+    let cusFeature: CusEntResponseV2 = {
       id: featureId,
       name: feature.name,
       type: featureType,
@@ -95,7 +98,13 @@ export const featuresToObject = ({
             credit_amount: s.credit_amount,
           }))
         : undefined,
+
+      rollovers: relatedEnts
+        .flatMap((e) => e.rollovers)
+        .filter(notNullish) as CusRollover[],
     };
+
+    featureObject[featureId] = cusFeature;
   }
 
   return featureObject;
diff --git a/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/getCusBalances.ts b/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/getCusBalances.ts
index f6b9075f2..4e7c94645 100644
--- a/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/getCusBalances.ts
+++ b/server/src/internal/customers/cusUtils/cusFeatureResponseUtils/getCusBalances.ts
@@ -69,6 +69,100 @@ export const getV1EntitlementsRes = ({
   return res;
 };
 
+export const getRolloverFields = ({
+  cusEnt,
+  entityId,
+}: {
+  cusEnt: FullCustomerEntitlement;
+  entityId?: string;
+}) => {
+  let hasRollover = notNullish(cusEnt.entitlement.rollover);
+  if (!hasRollover) {
+    return null;
+  }
+
+  if (cusEnt.entitlement.entity_feature_id) {
+    if (entityId) {
+      return cusEnt.rollovers.reduce(
+        (acc, rollover) => {
+          if (rollover.entities[entityId]) {
+            return {
+              balance: acc.balance + rollover.entities[entityId].balance,
+              usage: acc.usage + rollover.entities[entityId].usage,
+              rollovers: [
+                ...acc.rollovers,
+                {
+                  balance: rollover.entities[entityId].balance,
+                  usage: rollover.entities[entityId].usage,
+                  expires_at: rollover.expires_at,
+                },
+              ],
+            };
+          }
+          return acc;
+        },
+        {
+          balance: 0,
+          usage: 0,
+          rollovers: [] as any[],
+        }
+      );
+    } else {
+      return cusEnt.rollovers.reduce(
+        (acc, rollover) => {
+          let newBalance = 0;
+          let newUsage = 0;
+
+          for (const entityId in rollover.entities) {
+            newBalance += rollover.entities[entityId].balance;
+            newUsage += rollover.entities[entityId].usage;
+          }
+
+          return {
+            balance: acc.balance + newBalance,
+            usage: acc.usage + newUsage,
+            rollovers: [
+              ...acc.rollovers,
+              {
+                balance: newBalance,
+                usage: newUsage,
+                expires_at: rollover.expires_at,
+              },
+            ],
+          };
+        },
+        {
+          balance: 0,
+          usage: 0,
+          rollovers: [] as any[],
+        }
+      );
+    }
+  } else {
+    return cusEnt.rollovers.reduce(
+      (acc, rollover) => {
+        return {
+          balance: acc.balance + rollover.balance,
+          usage: acc.usage + rollover.usage,
+          rollovers: [
+            ...acc.rollovers,
+            {
+              balance: rollover.balance,
+              usage: rollover.usage,
+              expires_at: rollover.expires_at,
+            },
+          ],
+        };
+      },
+      {
+        balance: 0,
+        usage: 0,
+        rollovers: [] as any[],
+      }
+    );
+  }
+};
+
 // IMPORTANT FUNCTION
 export const getCusBalances = async ({
   cusEntsWithCusProduct,
@@ -87,7 +181,7 @@ export const getCusBalances = async ({
 }) => {
   const data: Record<string, any> = {};
   const features = cusEntsWithCusProduct.map(
-    (cusEnt) => cusEnt.entitlement.feature,
+    (cusEnt) => cusEnt.entitlement.feature
   );
   const cusEntsFiltered = cusEntsWithCusProduct.filter((cusEnt) => {
     const ent: EntitlementWithFeature = cusEnt.entitlement;
@@ -183,6 +277,17 @@ export const getCusBalances = async ({
     data[key].total += total;
     data[key].unused += unused || 0;
 
+    let rollover = getRolloverFields({
+      cusEnt,
+      entityId: entity?.id,
+    });
+
+    if (rollover) {
+      data[key].balance += rollover.balance;
+      data[key].total += rollover.balance + rollover.usage;
+      data[key].rollovers = rollover.rollovers;
+    }
+
     if (org.config.api_version >= BREAK_API_VERSION) {
       if (
         !data[key].next_reset_at ||
@@ -256,5 +361,9 @@ export const getCusBalances = async ({
     });
   }
 
+  // if (org.api_version == APIVersion.v1) {
+
+  // }
+
   return balances as CusFeatureBalance[];
 };
diff --git a/server/src/internal/customers/getFullCusQuery.ts b/server/src/internal/customers/getFullCusQuery.ts
index 41fe031bf..a00650e54 100644
--- a/server/src/internal/customers/getFullCusQuery.ts
+++ b/server/src/internal/customers/getFullCusQuery.ts
@@ -7,7 +7,7 @@ const buildOptimizedCusProductsCTE = (inStatuses?: CusProductStatus[]) => {
     return inStatuses
       ? sql`AND cp.status = ANY(ARRAY[${sql.join(
           inStatuses.map((status) => sql`${status}`),
-          sql`, `,
+          sql`, `
         )}])`
       : sql``;
   };
@@ -26,7 +26,7 @@ const buildOptimizedCusProductsCTE = (inStatuses?: CusProductStatus[]) => {
           '[]'::json
         ) AS customer_prices,
         
-        -- Spread customer_entitlements fields + add entitlement and replaceables
+        -- Spread customer_entitlements fields + add entitlement, replaceables, and rollovers
         COALESCE(
           json_agg(DISTINCT (
             to_jsonb(ce.*) || jsonb_build_object(
@@ -46,6 +46,14 @@ const buildOptimizedCusProductsCTE = (inStatuses?: CusProductStatus[]) => {
                 )
                 FROM replaceables r
                 WHERE r.cus_ent_id = ce.id
+              ),
+              'rollovers', (
+                SELECT COALESCE(
+                  json_agg(row_to_json(ro) ORDER BY ro.expires_at ASC) FILTER (WHERE ro.expires_at > EXTRACT(EPOCH FROM now()) * 1000),
+                  '[]'::json
+                )
+                FROM rollovers ro
+                WHERE ro.cus_ent_id = ce.id
               )
             )
           )) FILTER (WHERE ce.id IS NOT NULL),
@@ -110,7 +118,7 @@ const buildEntityCTE = (entityId?: string) => {
 const buildTrialsUsedCTE = (
   withTrialsUsed: boolean,
   orgId: string,
-  env: AppEnv,
+  env: AppEnv
 ) => {
   if (!withTrialsUsed) {
     return sql``;
@@ -140,7 +148,7 @@ const buildTrialsUsedCTE = (
 
 const buildSubscriptionsCTE = (
   withSubs: boolean,
-  inStatuses?: CusProductStatus[],
+  inStatuses?: CusProductStatus[]
 ) => {
   if (!withSubs) {
     return sql``;
@@ -194,7 +202,7 @@ export const getFullCusQuery = (
   withEntities: boolean,
   withTrialsUsed: boolean,
   withSubs: boolean,
-  entityId?: string,
+  entityId?: string
 ) => {
   const sqlChunks: SQL[] = [];
 
diff --git a/server/src/internal/products/entitlements/EntitlementService.ts b/server/src/internal/products/entitlements/EntitlementService.ts
index 5b3bce4a7..c95ff0401 100644
--- a/server/src/internal/products/entitlements/EntitlementService.ts
+++ b/server/src/internal/products/entitlements/EntitlementService.ts
@@ -81,7 +81,6 @@ export class EntitlementService {
     if (Array.isArray(data) && data.length == 0) return;
 
     const updateColumns = buildConflictUpdateColumns(entitlements, ["id"]);
-
     await db
       .insert(entitlements)
       .values(data as any)
diff --git a/server/src/internal/products/entitlements/entitlementUtils.ts b/server/src/internal/products/entitlements/entitlementUtils.ts
index 33e89fe10..d7caa27c8 100644
--- a/server/src/internal/products/entitlements/entitlementUtils.ts
+++ b/server/src/internal/products/entitlements/entitlementUtils.ts
@@ -112,6 +112,10 @@ export const entsAreSame = (ent1: Entitlement, ent2: Entitlement) => {
       condition: ent1.usage_limit !== ent2.usage_limit,
       message: `Usage limit different: ${ent1.usage_limit} !== ${ent2.usage_limit}`,
     },
+    rollover: {
+      condition: JSON.stringify(ent1.rollover) !== JSON.stringify(ent2.rollover),
+      message: `Rollover different: ${ent1.rollover} !== ${ent2.rollover}`,
+    },
   };
 
   let entsAreDiff = Object.values(diffs).some((d) => d.condition);
diff --git a/server/src/internal/products/handlers/handleUpdateProduct/updateProductDetails.ts b/server/src/internal/products/handlers/handleUpdateProduct/updateProductDetails.ts
index 66eb86c63..9f60a95ef 100644
--- a/server/src/internal/products/handlers/handleUpdateProduct/updateProductDetails.ts
+++ b/server/src/internal/products/handlers/handleUpdateProduct/updateProductDetails.ts
@@ -14,7 +14,6 @@ import {
 } from "@autumn/shared";
 import { ProductService } from "../../ProductService.js";
 import { createStripeCli } from "@/external/stripe/utils.js";
-import { priceToFeature } from "../../prices/priceUtils/convertPrice.js";
 import { usagePriceToProductName } from "../../prices/priceUtils/usagePriceUtils/convertUsagePrice.js";
 import {
   isFeaturePriceItem,
diff --git a/server/src/internal/products/product-items/compareItemUtils.ts b/server/src/internal/products/product-items/compareItemUtils.ts
index 0ec162bcf..c2c8129f3 100644
--- a/server/src/internal/products/product-items/compareItemUtils.ts
+++ b/server/src/internal/products/product-items/compareItemUtils.ts
@@ -67,16 +67,17 @@ export const featureItemsAreSame = ({
   item1: FeatureItem;
   item2: FeatureItem;
 }) => {
-  const same =
+  // Compare config objects (including rollover)
+  const configsAreSame = JSON.stringify(item1.config) === JSON.stringify(item2.config);
+  
+  const same = (
     item1.feature_id === item2.feature_id &&
     item1.included_usage == item2.included_usage &&
     item1.interval == item2.interval &&
     item1.entity_feature_id == item2.entity_feature_id &&
-    item1.reset_usage_when_enabled == item2.reset_usage_when_enabled;
-
-  if (!same) {
-    console.log(`Feature items different: ${item1.feature_id}`);
-  }
+    item1.reset_usage_when_enabled == item2.reset_usage_when_enabled &&
+    configsAreSame
+  );
 
   return same;
 };
@@ -118,6 +119,10 @@ export const featurePriceItemsAreSame = ({
         item1.reset_usage_when_enabled == item2.reset_usage_when_enabled,
       message: `Reset usage when enabled different: ${item1.reset_usage_when_enabled} !== ${item2.reset_usage_when_enabled}`,
     },
+    config: {
+      condition: JSON.stringify(item1.config) === JSON.stringify(item2.config),
+      message: `Config different: ${JSON.stringify(item1.config)} !== ${JSON.stringify(item2.config)}`,
+    },
   };
 
   const pricesSame = {
@@ -189,6 +194,8 @@ export const itemsAreSame = ({
   let same = false;
   let pricesChanged = false;
 
+
+
   if (isFeatureItem(item1)) {
     if (!isFeatureItem(item2)) {
       return {
diff --git a/server/src/internal/products/product-items/mapToItem.ts b/server/src/internal/products/product-items/mapToItem.ts
index 95bcca4d3..9f439e8b7 100644
--- a/server/src/internal/products/product-items/mapToItem.ts
+++ b/server/src/internal/products/product-items/mapToItem.ts
@@ -41,7 +41,9 @@ export const toFeatureItem = ({ ent }: { ent: EntitlementWithFeature }) => {
     };
   }
 
-  return {
+  const itemConfig = ent.rollover ? { rollover: ent.rollover } : undefined;
+
+  const item = {
     feature_id: ent.feature.id,
     included_usage:
       ent.allowance_type == AllowanceType.Unlimited ? Infinite : ent.allowance,
@@ -50,10 +52,15 @@ export const toFeatureItem = ({ ent }: { ent: EntitlementWithFeature }) => {
     entity_feature_id: ent.entity_feature_id,
     reset_usage_when_enabled: !ent.carry_from_previous,
 
+    // Include rollover config
+    config: itemConfig,
+
     // Stored in backend
     entitlement_id: ent.id,
     created_at: ent.created_at,
   };
+
+  return item;
 };
 
 export const toFeaturePriceItem = ({
@@ -71,6 +78,15 @@ export const toFeaturePriceItem = ({
     };
   });
 
+  // Build the item config from both price proration config and entitlement rollover
+  let itemConfig: any = {};
+  if (price.proration_config) {
+    itemConfig = { ...price.proration_config };
+  }
+  if (ent.rollover) {
+    itemConfig.rollover = ent.rollover;
+  }
+
   let item: ProductItem = {
     feature_id: ent.feature.id,
     feature_type:
@@ -98,7 +114,7 @@ export const toFeaturePriceItem = ({
     price_id: price.id,
 
     price_config: price.config,
-    config: price.proration_config || undefined,
+    config: Object.keys(itemConfig).length > 0 ? itemConfig : undefined,
     usage_limit: ent.usage_limit,
   };
 
diff --git a/server/src/internal/products/product-items/productItemUtils/itemToPriceAndEnt.ts b/server/src/internal/products/product-items/productItemUtils/itemToPriceAndEnt.ts
index aa78e5e3f..07ab6b936 100644
--- a/server/src/internal/products/product-items/productItemUtils/itemToPriceAndEnt.ts
+++ b/server/src/internal/products/product-items/productItemUtils/itemToPriceAndEnt.ts
@@ -141,6 +141,8 @@ export const toFeature = ({
     carry_from_previous: !resetUsage,
     entity_feature_id: item.entity_feature_id,
     usage_limit: null,
+
+    rollover: item.config?.rollover,
   };
 
   if (isCustom || newVersion) {
@@ -196,6 +198,8 @@ export const toFeatureAndPrice = ({
     carry_from_previous: !resetUsage,
     entity_feature_id: item.entity_feature_id,
     usage_limit: item.usage_limit || null,
+
+    rollover: item.config?.rollover,
   };
 
   // Will only create new ent id if
diff --git a/server/src/internal/products/product-items/validateProductItems.ts b/server/src/internal/products/product-items/validateProductItems.ts
index 0677bd3c0..f60e08685 100644
--- a/server/src/internal/products/product-items/validateProductItems.ts
+++ b/server/src/internal/products/product-items/validateProductItems.ts
@@ -12,7 +12,7 @@ import {
   AppEnv,
   OnIncrease,
   UsageModel,
-  FeatureUsageType,
+  RolloverDuration,
 } from "@autumn/shared";
 import { StatusCodes } from "http-status-codes";
 import { notNullish, nullish } from "@/utils/genUtils.js";
@@ -160,6 +160,14 @@ const validateProductItem = ({
       statusCode: StatusCodes.BAD_REQUEST,
     });
   }
+
+  // Rollover
+  // if (item.config?.rollover) {
+  //   let rollover = item.config.rollover;
+
+  //   if (rollover.duration == RolloverDuration.Month) {
+  //   }
+  // }
 };
 export const validateProductItems = ({
   newItems,
diff --git a/server/src/trigger/updateBalanceTask.ts b/server/src/trigger/updateBalanceTask.ts
index 87cf80d2c..989c36b54 100644
--- a/server/src/trigger/updateBalanceTask.ts
+++ b/server/src/trigger/updateBalanceTask.ts
@@ -42,11 +42,12 @@ import {
   getBillingType,
   getEntOptions,
 } from "@/internal/products/prices/priceUtils.js";
+import { deductFromCusRollovers } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverDeductionUtils.js";
 import { refreshCusCache } from "@/internal/customers/cusCache/updateCachedCus.js";
 
 // Decimal.set({ precision: 12 }); // 12 DP precision
 
-type DeductParams = {
+export type DeductParams = {
   db: DrizzleCli;
   env: AppEnv;
   org: Organization;
@@ -57,6 +58,13 @@ type DeductParams = {
   entity?: Entity;
 };
 
+export type RolloverDeductParams = {
+  db: DrizzleCli;
+  env: AppEnv;
+  feature: Feature;
+  entity?: Entity;
+};
+
 // 2. Get deductions for each feature
 const getFeatureDeductions = ({
   cusEnts,
@@ -603,6 +611,21 @@ export const updateCustomerBalance = async ({
         continue;
       }
 
+      toDeduct = await deductFromCusRollovers({
+        toDeduct,
+        cusEnt,
+        deductParams: {
+          db,
+          feature,
+          env,
+          entity: customer.entity ? customer.entity : undefined,
+        },
+      });
+
+      if (toDeduct == 0) {
+        continue;
+      }
+
       toDeduct = await deductAllowanceFromCusEnt({
         toDeduct,
         cusEnt,
diff --git a/server/src/trigger/updateUsageTask.ts b/server/src/trigger/updateUsageTask.ts
index 8eea77faf..ac86c9e66 100644
--- a/server/src/trigger/updateUsageTask.ts
+++ b/server/src/trigger/updateUsageTask.ts
@@ -20,6 +20,7 @@ import {
 } from "./updateBalanceTask.js";
 import { CusService } from "@/internal/customers/CusService.js";
 import { DrizzleCli } from "@/db/initDrizzle.js";
+import { deductFromCusRollovers } from "@/internal/customers/cusProducts/cusEnts/cusRollovers/rolloverDeductionUtils.js";
 import { refreshCusCache } from "@/internal/customers/cusCache/updateCachedCus.js";
 
 // 2. Get deductions for each feature
@@ -230,6 +231,20 @@ export const updateUsage = async ({
         continue;
       }
 
+      toDeduct = await deductFromCusRollovers({
+        toDeduct,
+        cusEnt,
+        deductParams: {
+          db,
+          feature,
+          env,
+          entity: customer.entity ? customer.entity : undefined,
+        },
+      });
+
+      if (toDeduct == 0) {
+        continue;
+      }
       toDeduct = await deductAllowanceFromCusEnt({
         toDeduct,
         cusEnt,
diff --git a/server/src/utils/scriptUtils/constructItem.ts b/server/src/utils/scriptUtils/constructItem.ts
index 81809f55e..199fad396 100644
--- a/server/src/utils/scriptUtils/constructItem.ts
+++ b/server/src/utils/scriptUtils/constructItem.ts
@@ -5,6 +5,7 @@ import {
   ProductItem,
   ProductItemConfig,
   ProductItemInterval,
+  RolloverConfig,
   UsageModel,
 } from "@autumn/shared";
 
@@ -14,12 +15,14 @@ export const constructFeatureItem = ({
   interval = ProductItemInterval.Month,
   entityFeatureId,
   isBoolean = false,
+  rolloverConfig,
 }: {
   featureId: string;
   includedUsage?: number;
   interval?: ProductItemInterval | null;
   entityFeatureId?: string;
   isBoolean?: boolean;
+  rolloverConfig?: RolloverConfig;
 }) => {
   if (isBoolean) {
     return {
@@ -34,6 +37,12 @@ export const constructFeatureItem = ({
     interval: interval,
   };
 
+  if (rolloverConfig) {
+    item.config = {
+      rollover: rolloverConfig,
+    };
+  }
+
   return item;
 };
 
@@ -47,6 +56,7 @@ export const constructPrepaidItem = ({
     on_increase: OnIncrease.ProrateImmediately,
     on_decrease: OnDecrease.ProrateImmediately,
   },
+  rolloverConfig,
   usageLimit,
 }: {
   featureId: string;
@@ -55,6 +65,7 @@ export const constructPrepaidItem = ({
   includedUsage?: number;
   isOneOff?: boolean;
   config?: ProductItemConfig;
+  rolloverConfig?: RolloverConfig;
   usageLimit?: number;
 }) => {
   let item: ProductItem = {
@@ -67,7 +78,10 @@ export const constructPrepaidItem = ({
     interval: isOneOff ? null : ProductItemInterval.Month,
     included_usage: includedUsage,
 
-    config,
+    config: {
+      ...config,
+      ...(rolloverConfig ? { rollover: rolloverConfig } : {}),
+    },
     usage_limit: usageLimit,
   };
 
@@ -119,12 +133,14 @@ export const constructArrearProratedItem = ({
     on_decrease: OnDecrease.None,
   },
   usageLimit,
+  rolloverConfig,
 }: {
   featureId: string;
   pricePerUnit?: number;
   includedUsage?: number;
   config?: ProductItemConfig;
   usageLimit?: number;
+  rolloverConfig?: RolloverConfig;
 }) => {
   let item: ProductItem = {
     feature_id: featureId,
@@ -133,7 +149,10 @@ export const constructArrearProratedItem = ({
     price: pricePerUnit,
     billing_units: 1,
     interval: ProductItemInterval.Month,
-    config,
+    config: {
+      ...config,
+      ...(rolloverConfig ? { rollover: rolloverConfig } : {}),
+    },
     usage_limit: usageLimit,
   };
 
diff --git a/server/tests/advanced/rollovers/rollover1.ts b/server/tests/advanced/rollovers/rollover1.ts
new file mode 100644
index 000000000..09cfaaece
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover1.ts
@@ -0,0 +1,197 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  ProductItemInterval,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructFeatureItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { timeout } from "@/utils/genUtils.js";
+import { resetAndGetCusEnt } from "./rolloverTestUtils.js";
+
+let rolloverConfig = { max: 500, length: 1, duration: RolloverDuration.Month };
+const messagesItem = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 400,
+  interval: ProductItemInterval.Month,
+  rolloverConfig,
+}) as LimitedItem;
+
+export let free = constructProduct({
+  items: [messagesItem],
+  type: "free",
+  isDefault: false,
+});
+
+const testCase = "rollover1";
+// , per entity and regular
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for feature item`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [free],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [free],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  it("should attach free product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: free.id,
+    });
+  });
+
+  let messageUsage = 250;
+  let curBalance = messagesItem.included_usage;
+
+  it("should create track messages, reset, and have correct rollover", async function () {
+    await autumn.track({
+      customer_id: customerId,
+      feature_id: TestFeature.Messages,
+      value: messageUsage,
+    });
+
+    await timeout(3000);
+
+    await resetAndGetCusEnt({
+      db,
+      customer,
+      productGroup: free.group,
+      featureId: TestFeature.Messages,
+    });
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    let expectedRollover = Math.min(
+      messagesItem.included_usage - messageUsage,
+      rolloverConfig.max
+    );
+
+    let expectedBalance = messagesItem.included_usage + expectedRollover;
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(expectedBalance);
+    // @ts-ignore
+    expect(msgesFeature?.rollovers[0].balance).to.equal(expectedRollover);
+    curBalance = expectedBalance;
+  });
+
+  // let usage2 = 50;
+  it("should reset again and have correct rollover", async function () {
+    await resetAndGetCusEnt({
+      db,
+      customer,
+      productGroup: free.group,
+      featureId: TestFeature.Messages,
+    });
+
+    let expectedRollover = Math.min(curBalance, rolloverConfig.max);
+    let expectedBalance = messagesItem.included_usage + expectedRollover;
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(expectedBalance);
+
+    // @ts-ignore (oldest rollover should be 100 (150 - 50))
+    expect(msgesFeature?.rollovers[0].balance).to.equal(100);
+    // @ts-ignore (newest rollover should be 400 (msges.included_usage))
+    expect(msgesFeature?.rollovers[1].balance).to.equal(400);
+  });
+
+  it("should track messages and deduct from rollovers first", async function () {
+    await autumn.track({
+      customer_id: customerId,
+      feature_id: TestFeature.Messages,
+      value: 150,
+    });
+
+    await timeout(3000);
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    // @ts-ignore
+    let rollover1 = msgesFeature?.rollovers[0];
+    // @ts-ignore
+    let rollover2 = msgesFeature?.rollovers[1];
+
+    expect(rollover1.balance).to.equal(0);
+    expect(rollover2.balance).to.equal(350);
+  });
+
+  it("should track and deduct from rollover + original balance", async function () {
+    await autumn.track({
+      customer_id: customerId,
+      feature_id: TestFeature.Messages,
+      value: 400,
+    });
+
+    await timeout(3000);
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    // @ts-ignore
+    let rollovers = msgesFeature.rollovers;
+    expect(rollovers[0].balance).to.equal(0);
+    expect(rollovers[1].balance).to.equal(0);
+    expect(msgesFeature.balance).to.equal(messagesItem.included_usage - 50);
+  });
+});
diff --git a/server/tests/advanced/rollovers/rollover2.ts b/server/tests/advanced/rollovers/rollover2.ts
new file mode 100644
index 000000000..f02cd2100
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover2.ts
@@ -0,0 +1,227 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  ProductItemInterval,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructFeatureItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { getMainCusProduct } from "@/internal/customers/cusProducts/cusProductUtils.js";
+import { cusProductToCusEnt } from "@/internal/customers/cusProducts/cusProductUtils/convertCusProduct.js";
+import { timeout } from "@/utils/genUtils.js";
+import { resetCustomerEntitlement } from "@/cron/cronUtils.js";
+import { resetAndGetCusEnt } from "./rolloverTestUtils.js";
+
+let rolloverConfig = { max: 500, length: 1, duration: RolloverDuration.Month };
+
+const msgesItem = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 400,
+  interval: ProductItemInterval.Month,
+  rolloverConfig,
+  entityFeatureId: TestFeature.Users,
+}) as LimitedItem;
+
+export let free = constructProduct({
+  items: [msgesItem],
+  type: "free",
+  isDefault: false,
+});
+
+const testCase = "rollover2";
+// , per entity and regular
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for feature item (per entity)`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [free],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [free],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  const entities: any[] = [
+    {
+      id: "1",
+      name: "Entity 1",
+      feature_id: TestFeature.Users,
+    },
+    {
+      id: "2",
+      name: "Entity 2",
+      feature_id: TestFeature.Users,
+    },
+  ];
+
+  it("should attach pro product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: free.id,
+    });
+
+    await autumn.entities.create(customerId, entities);
+  });
+
+  let entity1Id = entities[0].id;
+  let entity2Id = entities[1].id;
+  let newEntity1Balance = 300;
+  let newEntity2Balance = 200;
+  let includedUsage = msgesItem.included_usage;
+  let usages = [
+    {
+      entityId: entity1Id,
+      usage: includedUsage - newEntity1Balance,
+      rollover: newEntity1Balance,
+    },
+    {
+      entityId: entity2Id,
+      usage: includedUsage - newEntity2Balance,
+      rollover: newEntity2Balance,
+    },
+  ];
+
+  it("should create track messages, reset, and have correct rollover", async function () {
+    for (const usage of usages) {
+      await autumn.track({
+        customer_id: customerId,
+        feature_id: TestFeature.Messages,
+        value: usage.usage,
+        entity_id: usage.entityId,
+      });
+    }
+
+    await timeout(3000);
+
+    // Run reset cusEnt on ...
+    await resetAndGetCusEnt({
+      db,
+      customer,
+      productGroup: free.group,
+      featureId: TestFeature.Messages,
+    });
+
+    for (const usage of usages) {
+      let entity = await autumn.entities.get(customerId, usage.entityId);
+      let msgesFeature = entity.features[TestFeature.Messages];
+      let expectedRollover = Math.min(usage.rollover, rolloverConfig.max);
+
+      expect(msgesFeature.rollovers.length).to.equal(1);
+      expect(msgesFeature.balance).to.equal(includedUsage + expectedRollover);
+      expect(msgesFeature.rollovers[0].balance).to.equal(expectedRollover);
+    }
+  });
+
+  it("should reset again and have correct rollovers", async function () {
+    await resetAndGetCusEnt({
+      db,
+      customer,
+      productGroup: free.group,
+      featureId: TestFeature.Messages,
+    });
+
+    let entity1 = await autumn.entities.get(customerId, entity1Id);
+    let entity1Msges = entity1.features[TestFeature.Messages];
+    // 400, 300 -> 400, 100 (max is 500)
+    let rollovers = entity1Msges.rollovers;
+    expect(rollovers[0].balance).to.equal(100);
+    expect(rollovers[1].balance).to.equal(400);
+
+    let entity2 = await autumn.entities.get(customerId, entity2Id);
+    let entity2Msges = entity2.features[TestFeature.Messages];
+    // 400, 200 -> 400, 0 (max is 500)
+    let rollovers2 = entity2Msges.rollovers;
+    expect(rollovers2[0].balance).to.equal(100);
+    expect(rollovers2[1].balance).to.equal(400);
+  });
+
+  it("should track and deduct from oldest rollovers first", async function () {
+    for (const entity of entities) {
+      await autumn.track({
+        customer_id: customerId,
+        feature_id: TestFeature.Messages,
+        value: 150,
+        entity_id: entity.id,
+      });
+
+      await timeout(2000);
+      let entRes = await autumn.entities.get(customerId, entity.id);
+      let msgesFeature = entRes.features[TestFeature.Messages];
+      let rollovers = msgesFeature.rollovers;
+      expect(rollovers[0].balance).to.equal(0);
+      expect(rollovers[1].balance).to.equal(350);
+      expect(msgesFeature.balance).to.equal(includedUsage + 350);
+    }
+  });
+
+  it("should track past rollovers and deduct from original balance", async function () {
+    for (const entity of entities) {
+      await autumn.track({
+        customer_id: customerId,
+        feature_id: TestFeature.Messages,
+        value: 400,
+        entity_id: entity.id,
+      });
+      await timeout(2000);
+
+      let entRes = await autumn.entities.get(customerId, entity.id);
+      let msgesFeature = entRes.features[TestFeature.Messages];
+      let rollovers = msgesFeature.rollovers;
+      expect(rollovers[0].balance).to.equal(0);
+      expect(rollovers[1].balance).to.equal(0);
+      expect(msgesFeature.balance).to.equal(includedUsage - 50);
+    }
+  });
+});
diff --git a/server/tests/advanced/rollovers/rollover3.ts b/server/tests/advanced/rollovers/rollover3.ts
new file mode 100644
index 000000000..b4a34c996
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover3.ts
@@ -0,0 +1,126 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructArrearProratedItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { timeout } from "@/utils/genUtils.js";
+import { advanceTestClock } from "@/utils/scriptUtils/testClockUtils.js";
+import { addMonths } from "date-fns";
+
+let rolloverConfig = { max: 500, length: 1, duration: RolloverDuration.Month };
+const messagesItem = constructArrearProratedItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 400,
+  rolloverConfig,
+}) as LimitedItem;
+
+export let pro = constructProduct({
+  items: [messagesItem],
+  type: "pro",
+  isDefault: false,
+});
+
+const testCase = "rollover3";
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for usage price feature`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [pro],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [pro],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  it("should attach pro product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: pro.id,
+    });
+  });
+
+  let rollover = 250;
+  let curBalance = messagesItem.included_usage;
+
+  it("should create track messages, reset, and have correct rollover", async function () {
+    await autumn.track({
+      customer_id: customerId,
+      feature_id: TestFeature.Messages,
+      value: messagesItem.included_usage - rollover,
+    });
+
+    await timeout(3000);
+
+    await advanceTestClock({
+      stripeCli,
+      testClockId,
+      advanceTo: addMonths(new Date(), 1).getTime(),
+      waitForSeconds: 20,
+    });
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    let expectedBalance = messagesItem.included_usage + rollover;
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(expectedBalance);
+    // @ts-ignore
+    expect(msgesFeature?.rollovers[0].balance).to.equal(rollover);
+    curBalance = expectedBalance;
+  });
+});
diff --git a/server/tests/advanced/rollovers/rollover4.ts b/server/tests/advanced/rollovers/rollover4.ts
new file mode 100644
index 000000000..7e191a047
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover4.ts
@@ -0,0 +1,157 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructPrepaidItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { timeout } from "@/utils/genUtils.js";
+import { advanceTestClock } from "@/utils/scriptUtils/testClockUtils.js";
+import { addMonths } from "date-fns";
+import { resetAndGetCusEnt } from "./rolloverTestUtils.js";
+
+let rolloverConfig = { max: 400, length: 1, duration: RolloverDuration.Month };
+const messagesItem = constructPrepaidItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 100,
+  billingUnits: 300,
+  price: 10,
+  rolloverConfig,
+}) as LimitedItem;
+
+export let pro = constructProduct({
+  items: [messagesItem],
+  type: "pro",
+  isDefault: false,
+});
+
+const testCase = "rollover4";
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for usage price feature`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [pro],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [pro],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  let paidQuantity = 300;
+  let balance = paidQuantity + messagesItem.included_usage;
+  const options = [
+    {
+      feature_id: TestFeature.Messages,
+      quantity: paidQuantity,
+    },
+  ];
+
+  it("should attach pro product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: pro.id,
+      options,
+    });
+  });
+
+  let rollover = 50;
+  it("should create track messages, reset, and have correct rollover", async function () {
+    await autumn.track({
+      customer_id: customerId,
+      feature_id: TestFeature.Messages,
+      value: balance - rollover,
+    });
+
+    await timeout(3000);
+
+    curUnix = await advanceTestClock({
+      stripeCli,
+      testClockId,
+      advanceTo: addMonths(new Date(), 1).getTime(),
+      waitForSeconds: 20,
+    });
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+
+    // @ts-ignore
+    let rollovers = msgesFeature?.rollovers;
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(balance + rollover);
+    expect(rollovers[0].balance).to.equal(rollover);
+  });
+
+  // let usage2 = 50;
+  it("should  reset again and have correct rollover", async function () {
+    await advanceTestClock({
+      stripeCli,
+      testClockId,
+      advanceTo: addMonths(curUnix, 1).getTime(),
+      waitForSeconds: 20,
+    });
+
+    let newRollover = Math.min(balance + rollover, rolloverConfig.max);
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+    // @ts-ignore
+    let rollovers = msgesFeature?.rollovers;
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(balance + newRollover);
+    expect(rollovers[0].balance).to.equal(0);
+    expect(rollovers[1].balance).to.equal(400);
+  });
+});
diff --git a/server/tests/advanced/rollovers/rollover5.ts b/server/tests/advanced/rollovers/rollover5.ts
new file mode 100644
index 000000000..54162e863
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover5.ts
@@ -0,0 +1,140 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructFeatureItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { resetAndGetCusEnt } from "./rolloverTestUtils.js";
+
+let freeRollover = { max: 1000, length: 1, duration: RolloverDuration.Month };
+let proRollover = { max: 600, length: 1, duration: RolloverDuration.Month };
+
+const freeMsges = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 500,
+  rolloverConfig: freeRollover,
+}) as LimitedItem;
+
+const proMsges = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 500,
+  rolloverConfig: proRollover,
+}) as LimitedItem;
+
+const free = constructProduct({
+  items: [freeMsges],
+  type: "free",
+  isDefault: false,
+});
+
+const pro = constructProduct({
+  items: [proMsges],
+  type: "pro",
+});
+
+const testCase = "rollover5";
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for upgrade`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [free, pro],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [free, pro],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  it("should attach free product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: free.id,
+    });
+  });
+
+  it("should create rollovers", async function () {
+    await resetAndGetCusEnt({
+      customer,
+      db,
+      productGroup: testCase,
+      featureId: TestFeature.Messages,
+    });
+    await resetAndGetCusEnt({
+      customer,
+      db,
+      productGroup: testCase,
+      featureId: TestFeature.Messages,
+    });
+
+    // Attach pro
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: pro.id,
+    });
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+    let freeRolloverBalance = freeMsges.included_usage * 2;
+    let proRolloverBalance = Math.min(proRollover.max, freeRolloverBalance);
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(
+      proMsges.included_usage + proRolloverBalance
+    );
+    // @ts-ignore
+    let rollovers = msgesFeature?.rollovers;
+    expect(rollovers[0].balance).to.equal(100);
+    expect(rollovers[1].balance).to.equal(500);
+  });
+});
diff --git a/server/tests/advanced/rollovers/rollover6.ts b/server/tests/advanced/rollovers/rollover6.ts
new file mode 100644
index 000000000..c9dc16ffa
--- /dev/null
+++ b/server/tests/advanced/rollovers/rollover6.ts
@@ -0,0 +1,154 @@
+import chalk from "chalk";
+import Stripe from "stripe";
+import { AutumnInt } from "@/external/autumn/autumnCli.js";
+import { initCustomer } from "@/utils/scriptUtils/initCustomer.js";
+
+import {
+  APIVersion,
+  AppEnv,
+  Customer,
+  LimitedItem,
+  Organization,
+  RolloverDuration,
+} from "@autumn/shared";
+
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { setupBefore } from "tests/before.js";
+import { createProducts } from "tests/utils/productUtils.js";
+import { constructProduct } from "@/utils/scriptUtils/createTestProducts.js";
+import { constructFeatureItem } from "@/utils/scriptUtils/constructItem.js";
+import { TestFeature } from "tests/setup/v2Features.js";
+import { addPrefixToProducts } from "tests/attach/utils.js";
+
+import { expect } from "chai";
+import { resetAndGetCusEnt } from "./rolloverTestUtils.js";
+import { advanceTestClock } from "@/utils/scriptUtils/testClockUtils.js";
+import { addHours, addMonths } from "date-fns";
+import { hoursToFinalizeInvoice } from "tests/utils/constants.js";
+
+let freeRollover = { max: 600, length: 1, duration: RolloverDuration.Month };
+let proRollover = { max: 1000, length: 1, duration: RolloverDuration.Month };
+
+const freeMsges = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 500,
+  rolloverConfig: freeRollover,
+}) as LimitedItem;
+
+const proMsges = constructFeatureItem({
+  featureId: TestFeature.Messages,
+  includedUsage: 500,
+  rolloverConfig: proRollover,
+}) as LimitedItem;
+
+const free = constructProduct({
+  items: [freeMsges],
+  type: "free",
+  isDefault: false,
+});
+
+const pro = constructProduct({
+  items: [proMsges],
+  type: "pro",
+});
+
+const testCase = "rollover6";
+
+describe(`${chalk.yellowBright(`${testCase}: Testing rollovers for upgrade`)}`, () => {
+  let customerId = testCase;
+  let autumn: AutumnInt = new AutumnInt({ version: APIVersion.v1_4 });
+  let testClockId: string;
+  let db: DrizzleCli, org: Organization, env: AppEnv;
+  let customer: Customer;
+  let stripeCli: Stripe;
+  let curUnix = new Date().getTime();
+
+  before(async function () {
+    await setupBefore(this);
+    const { autumnJs } = this;
+    db = this.db;
+    org = this.org;
+    env = this.env;
+
+    stripeCli = this.stripeCli;
+
+    addPrefixToProducts({
+      products: [free, pro],
+      prefix: testCase,
+    });
+
+    await createProducts({
+      autumn,
+      products: [free, pro],
+      customerId,
+      db,
+      orgId: org.id,
+      env,
+    });
+
+    const res = await initCustomer({
+      autumn: autumnJs,
+      customerId,
+      db,
+      org,
+      env,
+      attachPm: "success",
+    });
+
+    testClockId = res.testClockId!;
+    customer = res.customer;
+  });
+
+  it("should attach free product", async function () {
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: pro.id,
+    });
+  });
+
+  it("should create rollovers", async function () {
+    await resetAndGetCusEnt({
+      customer,
+      db,
+      productGroup: testCase,
+      featureId: TestFeature.Messages,
+    });
+    await resetAndGetCusEnt({
+      customer,
+      db,
+      productGroup: testCase,
+      featureId: TestFeature.Messages,
+    });
+
+    // Attach pro
+    await autumn.attach({
+      customer_id: customerId,
+      product_id: free.id,
+    });
+
+    await advanceTestClock({
+      stripeCli,
+      testClockId,
+      advanceTo: addHours(
+        addMonths(curUnix, 1),
+        hoursToFinalizeInvoice
+      ).getTime(),
+      waitForSeconds: 20,
+    });
+
+    let cus = await autumn.customers.get(customerId);
+    let msgesFeature = cus.features[TestFeature.Messages];
+    let proRolloverBalance = proMsges.included_usage * 2;
+    let freeRolloverBalance = Math.min(freeRollover.max, proRolloverBalance);
+
+    expect(msgesFeature).to.exist;
+    expect(msgesFeature?.balance).to.equal(
+      freeMsges.included_usage + freeRolloverBalance
+    );
+
+    // @ts-ignore
+    let rollovers = msgesFeature?.rollovers;
+    expect(rollovers[0].balance).to.equal(100);
+    expect(rollovers[1].balance).to.equal(500);
+  });
+});
diff --git a/server/tests/advanced/rollovers/rolloverTestUtils.ts b/server/tests/advanced/rollovers/rolloverTestUtils.ts
new file mode 100644
index 000000000..f038160f4
--- /dev/null
+++ b/server/tests/advanced/rollovers/rolloverTestUtils.ts
@@ -0,0 +1,48 @@
+import { resetCustomerEntitlement } from "@/cron/cronUtils.js";
+import { DrizzleCli } from "@/db/initDrizzle.js";
+import { getMainCusProduct } from "@/internal/customers/cusProducts/cusProductUtils.js";
+import { cusProductToCusEnt } from "@/internal/customers/cusProducts/cusProductUtils/convertCusProduct.js";
+import { Customer } from "@autumn/shared";
+import { TestFeature } from "tests/setup/v2Features.js";
+
+export const resetAndGetCusEnt = async ({
+  db,
+  customer,
+  productGroup,
+  featureId,
+}: {
+  db: DrizzleCli;
+  customer: Customer;
+  productGroup: string;
+  featureId: string;
+}) => {
+  // Run reset cusEnt on ...
+  let mainCusProduct = await getMainCusProduct({
+    db,
+    internalCustomerId: customer.internal_id,
+    productGroup,
+  });
+
+  let cusEnt = cusProductToCusEnt({
+    cusProduct: mainCusProduct!,
+    featureId,
+  });
+
+  await resetCustomerEntitlement({
+    db,
+    cusEnt: cusEnt!,
+  });
+
+  mainCusProduct = await getMainCusProduct({
+    db,
+    internalCustomerId: customer.internal_id,
+    productGroup,
+  });
+
+  cusEnt = cusProductToCusEnt({
+    cusProduct: mainCusProduct!,
+    featureId,
+  });
+
+  return cusEnt;
+};
diff --git a/server/tests/attach/utils.ts b/server/tests/attach/utils.ts
index ae36b286d..1a1238c2d 100644
--- a/server/tests/attach/utils.ts
+++ b/server/tests/attach/utils.ts
@@ -91,7 +91,7 @@ export const runAttachTest = async ({
 
   expect(
     productCount,
-    `customer should only have 1 product (from this group: ${product.group})`,
+    `customer should only have 1 product (from this group: ${product.group})`
   ).to.equal(1);
 
   expectProductAttached({
@@ -101,7 +101,7 @@ export const runAttachTest = async ({
   });
 
   let intervals = Array.from(
-    new Set(product.items.map((item) => item.interval)),
+    new Set(product.items.map((item) => item.interval))
   ).filter(notNullish);
   const multiInterval = intervals.length > 1;
 
@@ -150,7 +150,7 @@ export const runAttachTest = async ({
   } else {
     expect(stripeSubs.data.length).to.equal(
       1,
-      "should only have 1 subscription",
+      "should only have 1 subscription"
     );
   }
 };
@@ -191,7 +191,7 @@ export const replaceItems = ({
 
   if (interval) {
     index = newItems.findIndex(
-      (item) => item.interval == (interval as any) && nullish(item.feature_id),
+      (item) => item.interval == (interval as any) && nullish(item.feature_id)
     );
   }
 
diff --git a/shared/db/schema.ts b/shared/db/schema.ts
index b5fb36227..6ce6d4e4e 100644
--- a/shared/db/schema.ts
+++ b/shared/db/schema.ts
@@ -12,6 +12,8 @@ import { products } from "../models/productModels/productTable.js";
 import { prices } from "../models/productModels/priceModels/priceTable.js";
 import { entitlements } from "../models/productModels/entModels/entTable.js";
 import { freeTrials } from "../models/productModels/freeTrialModels/freeTrialTable.js";
+import { rollovers } from "../models/cusProductModels/cusEntModels/rolloverModels/rolloverTable.js";
+import { rolloverRelations } from "../models/cusProductModels/cusEntModels/rolloverModels/rolloverRelations.js";
 
 // CusProduct Tables
 import { customerProducts } from "../models/cusProductModels/cusProductTable.js";
@@ -106,6 +108,7 @@ export {
   actions,
   events,
   replaceables,
+  rollovers,
 
   // Auth
   user,
@@ -134,7 +137,7 @@ export {
   migrationErrorRelations,
   replaceableRelations,
   invoiceRelations,
-
+  rolloverRelations,
   // Auth Relations
   userRelations,
 };
diff --git a/shared/index.ts b/shared/index.ts
index 9b78e0d8f..623798664 100644
--- a/shared/index.ts
+++ b/shared/index.ts
@@ -67,6 +67,7 @@ export * from "./models/cusProductModels/cusEntModels/cusEntWithProduct.js";
 export * from "./models/cusProductModels/cusEntModels/cusEntTable.js";
 export * from "./models/cusProductModels/cusEntModels/replaceableTable.js";
 export * from "./models/cusProductModels/cusEntModels/replaceableSchema.js";
+export * from "./models/cusProductModels/cusEntModels/rolloverModels/rolloverTable.js";
 
 // 8. Customer Models
 export * from "./models/cusModels/cusModels.js";
diff --git a/shared/models/cusModels/cusResModels/cusFeatureResponse.ts b/shared/models/cusModels/cusResModels/cusFeatureResponse.ts
index eeaaaea08..1caae1a8c 100644
--- a/shared/models/cusModels/cusResModels/cusFeatureResponse.ts
+++ b/shared/models/cusModels/cusResModels/cusFeatureResponse.ts
@@ -2,6 +2,11 @@ import { z } from "zod";
 import { EntInterval } from "../../productModels/entModels/entEnums.js";
 import { ProductItemFeatureType } from "../../productV2Models/productItemModels/productItemModels.js";
 
+export const CusRolloverSchema = z.object({
+  balance: z.number(),
+  expires_at: z.number(),
+});
+
 export const CusEntResponseSchema = z.object({
   feature_id: z.string(),
   interval: z.nativeEnum(EntInterval).nullish(),
@@ -12,6 +17,7 @@ export const CusEntResponseSchema = z.object({
   next_reset_at: z.number().nullish(),
   overage_allowed: z.boolean().nullish(),
   usage_limit: z.number().nullish(),
+  rollovers: z.array(CusRolloverSchema).nullish(),
 });
 
 export const CoreCusFeatureResponseSchema = z.object({
@@ -31,7 +37,7 @@ export const CoreCusFeatureResponseSchema = z.object({
         usage: z.number().nullish(),
         included_usage: z.number().nullish(),
         next_reset_at: z.number().nullish(),
-      }),
+      })
     )
     .nullish(),
   credit_schema: z
@@ -39,11 +45,12 @@ export const CoreCusFeatureResponseSchema = z.object({
       z.object({
         feature_id: z.string(),
         credit_amount: z.number(),
-      }),
+      })
     )
     .nullish(),
 
   usage_limit: z.number().nullish(),
+  rollovers: z.array(CusRolloverSchema).nullish(),
 });
 
 export const CusEntResponseV2Schema = z
@@ -68,3 +75,4 @@ export const CheckResponseSchema = z
 export type CusEntResponse = z.infer<typeof CusEntResponseSchema>;
 export type CusEntResponseV2 = z.infer<typeof CusEntResponseV2Schema>;
 export type CheckResponse = z.infer<typeof CheckResponseSchema>;
+export type CusRollover = z.infer<typeof CusRolloverSchema>;
diff --git a/shared/models/cusProductModels/cusEntModels/cusEntModels.ts b/shared/models/cusProductModels/cusEntModels/cusEntModels.ts
index d675122f8..3b8665d30 100644
--- a/shared/models/cusProductModels/cusEntModels/cusEntModels.ts
+++ b/shared/models/cusProductModels/cusEntModels/cusEntModels.ts
@@ -2,6 +2,7 @@ import { z } from "zod";
 import { EntitlementWithFeatureSchema } from "../../productModels/entModels/entModels.js";
 import { Replaceable } from "./replaceableTable.js";
 import { ReplaceableSchema } from "./replaceableSchema.js";
+import { RolloverSchema } from "./rolloverModels/rolloverTable.js";
 
 export const EntityBalanceSchema = z.object({
   id: z.string(),
@@ -36,9 +37,11 @@ export const CustomerEntitlementSchema = z.object({
 export const FullCustomerEntitlementSchema = CustomerEntitlementSchema.extend({
   entitlement: EntitlementWithFeatureSchema,
   replaceables: z.array(ReplaceableSchema),
+  rollovers: z.array(RolloverSchema),
 });
 
 export type EntityBalance = z.infer<typeof EntityBalanceSchema>;
+
 export type CustomerEntitlement = z.infer<typeof CustomerEntitlementSchema>;
 export type FullCustomerEntitlement = z.infer<
   typeof FullCustomerEntitlementSchema
diff --git a/shared/models/cusProductModels/cusEntModels/cusEntRelations.ts b/shared/models/cusProductModels/cusEntModels/cusEntRelations.ts
index 8dd3d61ba..8453f23c9 100644
--- a/shared/models/cusProductModels/cusEntModels/cusEntRelations.ts
+++ b/shared/models/cusProductModels/cusEntModels/cusEntRelations.ts
@@ -6,6 +6,7 @@ import { features } from "../../featureModels/featureTable.js";
 import { customerEntitlements } from "./cusEntTable.js";
 import { customerProducts } from "../cusProductTable.js";
 import { replaceables } from "./replaceableTable.js";
+import { rollovers } from "./rolloverModels/rolloverTable.js";
 
 export const customerEntitlementsRelations = relations(
   customerEntitlements,
@@ -27,5 +28,6 @@ export const customerEntitlementsRelations = relations(
       references: [features.internal_id],
     }),
     replaceables: many(replaceables),
-  }),
+    rollovers: many(rollovers),
+  })
 );
diff --git a/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverModels.ts b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverModels.ts
new file mode 100644
index 000000000..b4428dbf6
--- /dev/null
+++ b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverModels.ts
@@ -0,0 +1,13 @@
+// import { z } from "zod";
+// import { EntityBalance, EntityBalanceSchema } from "../../../index.js";
+// import { jsonb } from "drizzle-orm/pg-core";
+
+// export const RolloverModelSchema = z.object({
+//   id: z.string(),
+//   cus_ent_id: z.string(),
+//   balance: z.number(),
+//   entities: z.record(z.string(), EntityBalanceSchema),
+//   expires_at: z.number().nullable(),
+// });
+
+// export type RolloverModel = z.infer<typeof RolloverModelSchema>;
diff --git a/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverRelations.ts b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverRelations.ts
new file mode 100644
index 000000000..35cf54c76
--- /dev/null
+++ b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverRelations.ts
@@ -0,0 +1,10 @@
+import { relations } from "drizzle-orm";
+import { rollovers } from "./rolloverTable.js";
+import { customerEntitlements } from "../cusEntTable.js";
+
+export const rolloverRelations = relations(rollovers, ({ one }) => ({
+  customer_entitlement: one(customerEntitlements, {
+    fields: [rollovers.cus_ent_id],
+    references: [customerEntitlements.id],
+  }),
+}));
diff --git a/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverTable.ts b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverTable.ts
new file mode 100644
index 000000000..3da143aba
--- /dev/null
+++ b/shared/models/cusProductModels/cusEntModels/rolloverModels/rolloverTable.ts
@@ -0,0 +1,55 @@
+import { z } from "zod";
+import { customerEntitlements } from "../cusEntTable.js";
+import {
+  foreignKey,
+  pgTable,
+  numeric,
+  jsonb,
+  text,
+  index,
+} from "drizzle-orm/pg-core";
+
+export const EntityRolloverBalanceSchema = z.object({
+  id: z.string(),
+  balance: z.number(),
+  usage: z.number(),
+});
+
+export const RolloverSchema = z.object({
+  id: z.string(),
+  cus_ent_id: z.string(),
+  balance: z.number(),
+  usage: z.number().default(0),
+  expires_at: z.number().nullable(),
+  entities: z.record(z.string(), EntityRolloverBalanceSchema),
+});
+
+export const rollovers = pgTable(
+  "rollovers",
+  {
+    id: text("id").primaryKey().notNull(),
+    cus_ent_id: text("cus_ent_id").notNull(),
+    balance: numeric({ mode: "number" }).notNull(),
+    expires_at: numeric({ mode: "number" }),
+    usage: numeric({ mode: "number" }).default(0).notNull(),
+    entities: jsonb("entities")
+      .$type<Record<string, EntityRolloverBalance>>()
+      .notNull()
+      .default({}),
+  },
+  (table) => [
+    foreignKey({
+      columns: [table.cus_ent_id],
+      foreignColumns: [customerEntitlements.id],
+      name: "rollover_cus_ent_id_fkey",
+    })
+      .onUpdate("cascade")
+      .onDelete("cascade"),
+
+    index("idx_rollovers_cus_ent_id").on(table.cus_ent_id),
+  ]
+).enableRLS();
+
+export type Rollover = z.infer<typeof RolloverSchema>;
+export type InsertRollover = typeof rollovers.$inferInsert;
+export type EntityRolloverBalance = z.infer<typeof EntityRolloverBalanceSchema>;
diff --git a/shared/models/productModels/entModels/entModels.ts b/shared/models/productModels/entModels/entModels.ts
index 36c10d3b1..383e85fd1 100644
--- a/shared/models/productModels/entModels/entModels.ts
+++ b/shared/models/productModels/entModels/entModels.ts
@@ -1,6 +1,7 @@
 import { z } from "zod";
 import { FeatureSchema } from "../../featureModels/featureModels.js";
 import { EntInterval } from "./entEnums.js";
+import { RolloverConfigSchema } from "../../productV2Models/productItemModels/productItemModels.js";
 
 export enum AllowanceType {
   Fixed = "fixed",
@@ -27,6 +28,8 @@ export const EntitlementSchema = z.object({
   org_id: z.string().optional(),
   feature_id: z.string().optional(),
   usage_limit: z.number().nullable().optional().default(null),
+
+  rollover: RolloverConfigSchema.nullish(),
 });
 
 export const CreateEntitlementSchema = z.object({
@@ -39,6 +42,7 @@ export const CreateEntitlementSchema = z.object({
   carry_from_previous: z.boolean().default(false),
   entity_feature_id: z.string().nullish(),
   usage_limit: z.number().nullish().default(null),
+  rollover: RolloverConfigSchema.nullish(),
 });
 
 export type CreateEntitlement = z.infer<typeof CreateEntitlementSchema>;
diff --git a/shared/models/productModels/entModels/entTable.ts b/shared/models/productModels/entModels/entTable.ts
index 5ad8dd2fc..26718ba01 100644
--- a/shared/models/productModels/entModels/entTable.ts
+++ b/shared/models/productModels/entModels/entTable.ts
@@ -6,6 +6,7 @@ import {
   unique,
   text,
   index,
+  jsonb,
 } from "drizzle-orm/pg-core";
 
 import { features } from "../../featureModels/featureTable.js";
@@ -13,6 +14,7 @@ import { products } from "../productTable.js";
 import { createInsertSchema } from "drizzle-zod";
 import { sql } from "drizzle-orm";
 import { collatePgColumn } from "../../../db/utils.js";
+import { RolloverConfig } from "../../../index.js";
 
 export const entitlements = pgTable(
   "entitlements",
@@ -34,6 +36,8 @@ export const entitlements = pgTable(
     org_id: text("org_id"),
     feature_id: text("feature_id"),
     usage_limit: numeric({ mode: "number" }),
+
+    rollover: jsonb().$type<RolloverConfig>(),
   },
   (table) => [
     foreignKey({
@@ -50,7 +54,7 @@ export const entitlements = pgTable(
       .onDelete("cascade"),
     unique("entitlements_id_key").on(table.id),
     index("idx_entitlements_internal_product_id").on(table.internal_product_id),
-  ],
+  ]
 );
 
 export const EntInsertSchema = createInsertSchema(entitlements);
diff --git a/shared/models/productV2Models/productItemModels/featureItem.ts b/shared/models/productV2Models/productItemModels/featureItem.ts
index 82d40796f..3ce838cba 100644
--- a/shared/models/productV2Models/productItemModels/featureItem.ts
+++ b/shared/models/productV2Models/productItemModels/featureItem.ts
@@ -9,6 +9,7 @@ export const FeatureItemSchema = ProductItemSchema.pick({
   interval: true,
   entity_feature_id: true,
   reset_usage_when_enabled: true,
+  config: true,
 }).extend({
   feature_id: z.string().nonempty(),
   included_usage: z
diff --git a/shared/models/productV2Models/productItemModels/featurePriceItem.ts b/shared/models/productV2Models/productItemModels/featurePriceItem.ts
index a54b92035..63eb4a780 100644
--- a/shared/models/productV2Models/productItemModels/featurePriceItem.ts
+++ b/shared/models/productV2Models/productItemModels/featurePriceItem.ts
@@ -14,6 +14,7 @@ export const FeaturePriceItemSchema = ProductItemSchema.pick({
 
   reset_usage_when_enabled: true,
   usage_limit: true,
+  config: true,
 }).extend({
   feature_id: z.string().nonempty(),
   included_usage: z.number().nonnegative().nullish(),
diff --git a/shared/models/productV2Models/productItemModels/productItemModels.ts b/shared/models/productV2Models/productItemModels/productItemModels.ts
index efd9aa01d..910cfe787 100644
--- a/shared/models/productV2Models/productItemModels/productItemModels.ts
+++ b/shared/models/productV2Models/productItemModels/productItemModels.ts
@@ -43,15 +43,21 @@ export enum ProductItemFeatureType {
   Static = "static",
 }
 
+export enum RolloverDuration {
+  Month = "month",
+  Forever = "forever",
+}
+
+export const RolloverConfigSchema = z.object({
+  max: z.number().nullable(),
+  duration: z.nativeEnum(RolloverDuration).default(RolloverDuration.Month),
+  length: z.number(),
+});
+
 const ProductItemConfigSchema = z.object({
-  on_increase: z
-    .nativeEnum(OnIncrease)
-    .optional()
-    .default(OnIncrease.BillImmediately),
-  on_decrease: z
-    .nativeEnum(OnDecrease)
-    .optional()
-    .default(OnDecrease.ProrateImmediately),
+  on_increase: z.nativeEnum(OnIncrease).nullish(),
+  on_decrease: z.nativeEnum(OnDecrease).nullish(),
+  rollover: RolloverConfigSchema.nullish(),
 });
 
 export const ProductItemSchema = z.object({
@@ -90,3 +96,4 @@ export type ProductItem = z.infer<typeof ProductItemSchema>;
 export type LimitedItem = z.infer<typeof LimitedItemSchema>;
 export type ProductItemConfig = z.infer<typeof ProductItemConfigSchema>;
 export type PriceTier = z.infer<typeof PriceTierSchema>;
+export type RolloverConfig = z.infer<typeof RolloverConfigSchema>;
diff --git a/shared/package.json b/shared/package.json
index 396cc0ac6..d4a4fd5a6 100644
--- a/shared/package.json
+++ b/shared/package.json
@@ -13,8 +13,10 @@
   "author": "Recase Inc.",
   "license": "Apache-2.0",
   "scripts": {
+    "build:tsc": "tsc",
     "build": "bun build ./index.ts --outdir dist --target bun --external zod",
     "dev": "bunx nodemon --ext ts --ignore dist --exec \"bun run build\"",
+    "dev:bun": "bun ./index.ts --outdir dist --target bun --external zod --watch",
 
     "db:push": "cross-env NODE_OPTIONS=\"--import tsx\" pnpm exec drizzle-kit push --config drizzle.config.ts",
     "db:generate": "cross-env NODE_OPTIONS=\"--import tsx\" pnpm exec drizzle-kit generate --config drizzle.config.ts",
diff --git a/vite/src/components/general/CustomToaster.tsx b/vite/src/components/general/CustomToaster.tsx
index 0f88bc060..d266a3abc 100644
--- a/vite/src/components/general/CustomToaster.tsx
+++ b/vite/src/components/general/CustomToaster.tsx
@@ -13,6 +13,8 @@ export const CustomToaster = () => {
         gap-2 bg-white/70 backdrop-blur-sm border border-red-400 rounded-sm p-2 text-sm shadow-md`,
           success: `w-[350px] text-green-600 flex items-start
         gap-2 bg-white/90 backdrop-blur-sm border border-green-500 rounded-sm p-2 text-sm shadow-md`,
+          warning: `w-[350px] text-yellow-600 flex items-start
+        gap-2 bg-white/90 backdrop-blur-sm border border-yellow-500 rounded-sm p-2 text-sm shadow-md`,
         },
       }}
     />
diff --git a/vite/src/utils/product/entitlementUtils.ts b/vite/src/utils/product/entitlementUtils.ts
index 29dcb0523..21d9d5bb1 100644
--- a/vite/src/utils/product/entitlementUtils.ts
+++ b/vite/src/utils/product/entitlementUtils.ts
@@ -1,24 +1,37 @@
-import { Feature, ProductItem } from "@autumn/shared";
+import { Feature, FeatureType, ProductItem } from "@autumn/shared";
 
 export const getFeature = (
-  featureId: string | undefined,
-  features: Feature[],
+	featureId: string | undefined,
+	features: Feature[]
 ) => {
-  const foundFeature = features?.find(
-    (feature: Feature) => feature.id === featureId,
-  );
-  return foundFeature || null;
+	const foundFeature = features?.find(
+		(feature: Feature) => feature.id === featureId
+	);
+	return foundFeature || null;
 };
 
 export const getFeatureUsageType = ({
-  item,
-  features,
+	item,
+	features,
 }: {
-  item: ProductItem;
-  features: Feature[];
+	item: ProductItem;
+	features: Feature[];
 }) => {
-  if (!item.feature_id) return null;
-  const feature = getFeature(item.feature_id, features);
+	if (!item.feature_id) return null;
+	const feature = getFeature(item.feature_id, features);
 
-  return feature?.config?.usage_type;
+	return feature?.config?.usage_type;
+};
+
+export const getFeatureCreditSystem = ({
+  item,
+  features
+}: {
+	item: ProductItem;
+	features: Feature[];
+}) => {
+	if (!item.feature_id) return null;
+	const feature = getFeature(item.feature_id, features);
+
+	return feature?.type === FeatureType.CreditSystem;
 };
diff --git a/vite/src/utils/product/product-item/validateProductItem.ts b/vite/src/utils/product/product-item/validateProductItem.ts
index 05bac1b65..5dffaf5a6 100644
--- a/vite/src/utils/product/product-item/validateProductItem.ts
+++ b/vite/src/utils/product/product-item/validateProductItem.ts
@@ -1,7 +1,16 @@
-import { invalidNumber, notNullish } from "@/utils/genUtils";
-import { Feature, FeatureUsageType, ProductItem } from "@autumn/shared";
+import { invalidNumber, notNullish, nullish } from "@/utils/genUtils";
+import {
+  Feature,
+  FeatureUsageType,
+  Infinite,
+  ProductItem,
+  ProductItemInterval,
+  RolloverConfig,
+  RolloverDuration,
+} from "@autumn/shared";
 import { toast } from "sonner";
 import { isFeatureItem, isFeaturePriceItem } from "../getItemType";
+import { isOneOffProduct } from "../priceUtils";
 
 export const validateProductItem = ({
   item,
@@ -100,5 +109,57 @@ export const validateProductItem = ({
     }
   }
 
+  if (item.config?.rollover) {
+    const rollover = item.config?.rollover as RolloverConfig;
+
+    if (rollover.max && rollover.max !== null) {
+      rollover.max = parseFloat(rollover.max.toString());
+    }
+
+    if (rollover.duration !== RolloverDuration.Forever) {
+      rollover.length = parseFloat(rollover.length.toString());
+    } else {
+      rollover.length = 0;
+    }
+
+    if (
+      item.interval === null ||
+      nullish(item.included_usage) ||
+      item.included_usage === 0
+    ) {
+      item.config!.rollover = null;
+      return item;
+    }
+
+    if (rollover.max !== null && invalidNumber(rollover.max)) {
+      toast.error("Please enter a valid maximum rollover amount");
+      return null;
+    }
+
+    if (invalidNumber(rollover.length)) {
+      toast.error("Please enter a valid rollover duration");
+      item.config.rollover = undefined;
+      return null;
+    }
+
+    // if (rollover.duration != RolloverDuration.Month) {
+    //   toast.error("Rollovers currently only support monthly cycles.");
+    //   item.config.rollover = undefined;
+    //   return null;
+    // }
+
+    if (typeof rollover.max == "number" && rollover.max < 0) {
+      toast.error("Please enter a positive rollover max amount");
+      item.config.rollover = undefined;
+      return null;
+    }
+
+    if (rollover.duration == RolloverDuration.Month && rollover.length < 0) {
+      toast.error("Please enter a positive rollover length");
+      item.config.rollover = undefined;
+      return null;
+    }
+  }
+
   return item;
 };
diff --git a/vite/src/views/customers/customer/entitlements/CusEntBalance.tsx b/vite/src/views/customers/customer/entitlements/CusEntBalance.tsx
new file mode 100644
index 000000000..93001873c
--- /dev/null
+++ b/vite/src/views/customers/customer/entitlements/CusEntBalance.tsx
@@ -0,0 +1,109 @@
+import {
+  AllowanceType,
+  FeatureType,
+  FullCusEntWithFullCusProduct,
+} from "@autumn/shared";
+import { useCustomerContext } from "../CustomerContext";
+
+const BalanceWrapper = ({ children }: { children: React.ReactNode }) => {
+  return (
+    <div className="flex items-center font-mono font-medium rounded-md border-b border-stone-300 border-dashed ">
+      {children}
+    </div>
+  );
+};
+
+export const CusEntBalance = ({
+  cusEnt,
+}: {
+  cusEnt: FullCusEntWithFullCusProduct;
+}) => {
+  const { entityId } = useCustomerContext();
+  const ent = cusEnt.entitlement;
+  const feature = ent.feature;
+  const rollovers = cusEnt.rollovers;
+
+  if (feature.type == FeatureType.Boolean) {
+    return <></>;
+  }
+
+  if (ent.allowance_type == AllowanceType.Unlimited) {
+    return <BalanceWrapper>Unlimited</BalanceWrapper>;
+  }
+
+  if (entityId && cusEnt.entities?.[entityId]) {
+    const entityBalance = cusEnt.entities?.[entityId]?.balance;
+    const rolloverAmount = rollovers
+      .filter((x) => x.entities && x.entities[entityId])
+      .reduce(
+        (sum, rollover) => sum + (rollover.entities?.[entityId]?.balance || 0),
+        0
+      );
+
+    return (
+      <BalanceWrapper>
+        <p>
+          {entityBalance}
+          {rolloverAmount > 0 && (
+            <span className="text-t3">
+              {" + "}
+              {rolloverAmount} (rolled over)
+            </span>
+          )}
+        </p>
+      </BalanceWrapper>
+    );
+  }
+
+  if (cusEnt.entities) {
+    const totalBalance = Object.values(cusEnt.entities).reduce(
+      (sum, entity) => sum + (entity.balance || 0),
+      0
+    );
+
+    const rolloverAmount = cusEnt.rollovers.reduce((sum, rollover) => {
+      // Add global rollover balance
+      return (
+        sum +
+        Object.values(rollover.entities).reduce(
+          (entitySum: number, entity: any) => entitySum + (entity.balance || 0),
+          0
+        )
+      );
+    }, 0);
+
+    return (
+      <BalanceWrapper>
+        <p>
+          {totalBalance}
+          {rolloverAmount > 0 && (
+            <span className="text-t3">
+              {" + "}
+              {rolloverAmount} (rolled over)
+            </span>
+          )}
+        </p>
+      </BalanceWrapper>
+    );
+  }
+
+  const rolloverAmount = cusEnt.rollovers.reduce((sum, rollover) => {
+    return sum + (rollover.balance || 0);
+  }, 0);
+
+  return (
+    <BalanceWrapper>
+      <p>
+        {cusEnt.balance}
+        {rolloverAmount > 0 && (
+          <span className="text-t3"> + {rolloverAmount} (rolled over)</span>
+        )}
+        {cusEnt.replaceables.length > 0 && (
+          <span className="text-t3">
+            {` (${cusEnt.replaceables.length} free)`}
+          </span>
+        )}
+      </p>
+    </BalanceWrapper>
+  );
+};
diff --git a/vite/src/views/customers/customer/entitlements/CustomerEntitlementsList.tsx b/vite/src/views/customers/customer/entitlements/CustomerEntitlementsList.tsx
index 74e1a3f9c..fbd337d66 100644
--- a/vite/src/views/customers/customer/entitlements/CustomerEntitlementsList.tsx
+++ b/vite/src/views/customers/customer/entitlements/CustomerEntitlementsList.tsx
@@ -6,7 +6,10 @@ import {
 } from "@autumn/shared";
 
 import { useCustomerContext } from "../CustomerContext";
-import { formatUnixToDateTime } from "@/utils/formatUtils/formatDateUtils";
+import {
+  formatUnixToDate,
+  formatUnixToDateTime,
+} from "@/utils/formatUtils/formatDateUtils";
 
 import { useState } from "react";
 
@@ -18,6 +21,7 @@ import { Tabs, TabsList, TabsTrigger } from "@/components/ui/tabs";
 import { Button } from "@/components/ui/button";
 import { cn } from "@/lib/utils";
 import { CusProductEntityItem } from "../components/CusProductEntityItem";
+import { CusEntBalance } from "./CusEntBalance";
 
 export const CustomerEntitlementsList = () => {
   const [featureType, setFeatureType] = useState<FeatureType>(
@@ -125,6 +129,26 @@ export const CustomerEntitlementsList = () => {
       });
     }
 
+    if (cusEnt.rollovers.length > 0) {
+      hoverTexts.push({
+        key: "Rollovers",
+        value: cusEnt.rollovers
+          .map((r: any) => {
+            if (Object.values(r.entities).length > 0) {
+              return (
+                Object.values(r.entities)
+                  .map((e: any) => `${e.balance} (${e.id})`)
+                  .join(", ") +
+                ` (expires: ${r.expires_at ? formatUnixToDate(r.expires_at) : "N/A"})`
+              );
+            } else {
+              return `${r.balance} (ex: ${r.expires_at ? formatUnixToDate(r.expires_at) : "N/A"})`;
+            }
+          })
+          .join("\n"),
+      });
+    }
+
     return hoverTexts;
   };
 
@@ -234,26 +258,7 @@ export const CustomerEntitlementsList = () => {
               </Item>
             )}
             <Item className="col-span-3">
-              <div className="flex items-center font-mono font-medium rounded-md px-1 border-b border-stone-300 border-dashed ">
-                {entitlement.feature.type == FeatureType.Boolean ? (
-                  <></>
-                ) : allowanceType == AllowanceType.Unlimited ? (
-                  "Unlimited"
-                ) : entityId && cusEnt.entities?.[entityId] ? (
-                  <div className="flex items-center gap-2">
-                    {cusEnt.entities?.[entityId]?.balance}{" "}
-                  </div>
-                ) : (
-                  <>
-                    {cusEnt.balance}{" "}
-                    <span className="text-t3">
-                      {cusEnt.replaceables.length > 0
-                        ? ` (${cusEnt.replaceables.length} free)`
-                        : ""}
-                    </span>
-                  </>
-                )}
-              </div>
+              <CusEntBalance cusEnt={cusEnt} />
             </Item>
 
             <Item className="col-span-3">
diff --git a/vite/src/views/products/product/hooks/useProductData.tsx b/vite/src/views/products/product/hooks/useProductData.tsx
index eea9ffc28..ff0b4887e 100644
--- a/vite/src/views/products/product/hooks/useProductData.tsx
+++ b/vite/src/views/products/product/hooks/useProductData.tsx
@@ -27,6 +27,7 @@ export const useProductData = ({ data }: { data: any }) => {
         ...data.product,
         items: sortProductItems(data.product.items),
       };
+
       initialProductRef.current = structuredClone(sortedProduct);
       setEntityFeatureIds(initEntityFeatureIds(sortedProduct));
       setProduct(sortedProduct);
diff --git a/vite/src/views/products/product/product-item/ProductItemConfig.tsx b/vite/src/views/products/product/product-item/ProductItemConfig.tsx
index 4c88deeeb..27b4d8ceb 100644
--- a/vite/src/views/products/product/product-item/ProductItemConfig.tsx
+++ b/vite/src/views/products/product/product-item/ProductItemConfig.tsx
@@ -63,13 +63,21 @@ export const ProductItemConfig = () => {
           reset_usage_when_enabled: resetUsageWhenEnabled,
         };
 
-        const newConfig = !showProration ? undefined : item.config;
+        // Only manage proration config if this item should show proration
+        if (showProration) {
+          // Preserve existing config and manage proration parts
+          const existingConfig = item.config || {};
+          const newConfig = {
+            ...existingConfig,
+            on_increase: existingConfig.on_increase,
+            on_decrease: existingConfig.on_decrease,
+          };
 
-        if (newConfig) {
-          newItem.config = newConfig;
-        } else {
-          delete newItem.config;
+          if (Object.keys(newConfig).length > 0) {
+            newItem.config = newConfig;
+          }
         }
+        // If showProration is false, don't touch the config at all - preserve whatever is there
 
         setItem(newItem);
       }
@@ -84,7 +92,7 @@ export const ProductItemConfig = () => {
         "flex flex-col gap-6 w-md transition-all ease-in-out duration-300 !overflow-visible", //modal animations
         isPriceItem(item) && "w-xs",
         isFeaturePriceItem(item) && "w-md",
-        isFeaturePriceItem(item) && item.tiers?.length > 1 && "w-md",
+        isFeaturePriceItem(item) && item.tiers?.length > 1 && "w-md"
       )}
     >
       {isPrice ? (
diff --git a/vite/src/views/products/product/product-item/product-item-config/advanced-config/AdvancedItemConfig.tsx b/vite/src/views/products/product/product-item/product-item-config/advanced-config/AdvancedItemConfig.tsx
index ce0643331..2d306a126 100644
--- a/vite/src/views/products/product/product-item/product-item-config/advanced-config/AdvancedItemConfig.tsx
+++ b/vite/src/views/products/product/product-item/product-item-config/advanced-config/AdvancedItemConfig.tsx
@@ -7,19 +7,30 @@ import { OnDecreaseSelect } from "./proration-config/OnDecreaseSelect";
 import { OnIncreaseSelect } from "./proration-config/OnIncreaseSelect";
 import { shouldShowProrationConfig } from "@/utils/product/productItemUtils";
 import {
-  getFeature,
+  getFeatureCreditSystem,
   getFeatureUsageType,
 } from "@/utils/product/entitlementUtils";
 import { FeatureUsageType } from "@autumn/shared";
 import { Input } from "@/components/ui/input";
 
+import { RolloverConfigView } from "./RolloverConfig";
+import { notNullish } from "@/utils/genUtils";
+
 export const AdvancedItemConfig = () => {
   const { features } = useProductContext();
   const { item, setItem } = useProductItemContext();
+
   const [isOpen, setIsOpen] = useState(item.usage_limit != null);
 
   const showProrationConfig = shouldShowProrationConfig({ item, features });
+
   const usageType = getFeatureUsageType({ item, features });
+  const hasCreditSystem = getFeatureCreditSystem({ item, features });
+  const showRolloverConfig =
+    (hasCreditSystem || usageType === FeatureUsageType.Single) &&
+    item.interval !== null &&
+    item.included_usage &&
+    item.included_usage > 0;
 
   return (
     <div className="w-full h-fit">
@@ -37,10 +48,10 @@ export const AdvancedItemConfig = () => {
 
       <div
         className={`overflow-hidden transition-all duration-150 ease-out ${
-          isOpen ? "max-h-72 opacity-100 mt-2" : "max-h-0 opacity-0"
+          isOpen ? "max-h-80 opacity-100 mt-2" : "max-h-0 opacity-0"
         }`}
       >
-        <div className="flex flex-col gap-4 p-4 bg-stone-100">
+        <div className="flex flex-col gap-4 p-4 bg-stone-100 ">
           <ToggleButton
             value={item.reset_usage_when_enabled}
             setValue={() => {
@@ -52,10 +63,13 @@ export const AdvancedItemConfig = () => {
             infoContent="A customer has used 20/100 credits on a free plan. Then they upgrade to a Pro plan with 500 credits. If this flag is enabled, they’ll get 500 credits on upgrade. If false, they’ll have 480."
             buttonText="Reset existing usage when product is enabled"
             className="text-t3 h-fit"
-            disabled={usageType === FeatureUsageType.Continuous}
+            disabled={
+              usageType === FeatureUsageType.Continuous ||
+              notNullish(item.config?.rollover)
+            }
           />
 
-          <div className="relative flex flex-row items-center gap-3 min-h-[35px]">
+          <div className="relative flex flex-row items-center gap-3">
             <ToggleButton
               value={item.usage_limit != null}
               setValue={() => {
@@ -98,6 +112,14 @@ export const AdvancedItemConfig = () => {
           )}
           {/* <div className="flex flex-col gap-2"></div>
           <div className="flex gap-2"></div> */}
+
+          {showRolloverConfig && (
+            <RolloverConfigView
+              item={item}
+              setItem={setItem}
+              showRolloverConfig={showRolloverConfig}
+            />
+          )}
         </div>
       </div>
     </div>
diff --git a/vite/src/views/products/product/product-item/product-item-config/advanced-config/RolloverConfig.tsx b/vite/src/views/products/product/product-item/product-item-config/advanced-config/RolloverConfig.tsx
new file mode 100644
index 000000000..0da2d1e19
--- /dev/null
+++ b/vite/src/views/products/product/product-item/product-item-config/advanced-config/RolloverConfig.tsx
@@ -0,0 +1,137 @@
+import { ToggleButton } from "@/components/general/ToggleButton";
+import { ToggleDisplayButton } from "@/components/general/ToggleDisplayButton";
+import { Input } from "@/components/ui/input";
+import { ProductItem, RolloverConfig, RolloverDuration } from "@autumn/shared";
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from "@/components/ui/select";
+
+export const RolloverConfigView = ({
+  item,
+  setItem,
+  showRolloverConfig,
+}: {
+  item: ProductItem;
+  setItem: (item: any) => void;
+  showRolloverConfig: boolean;
+}) => {
+  const defaultRollover: RolloverConfig = {
+    duration: RolloverDuration.Month,
+    length: 1,
+    max: null,
+  };
+
+  const setRolloverConfigKey = (key: keyof RolloverConfig, value: any) => {
+    setItem({
+      ...item,
+      config: {
+        ...(item.config || {}),
+        rollover: {
+          ...(item.config?.rollover || {}),
+          [key]: value,
+        },
+      },
+    });
+  };
+
+  const setRolloverConfig = (rollover: RolloverConfig | null) => {
+    setItem({
+      ...item,
+      config: {
+        ...(item.config || {}),
+        rollover: rollover,
+      },
+    });
+  };
+
+  const rollover = item.config?.rollover as RolloverConfig;
+
+  return (
+    <div className="relative flex flex-col gap-3">
+      <ToggleButton
+        value={item.config?.rollover != null}
+        setValue={() => {
+          if (item.config?.rollover != null) {
+            setRolloverConfig(null);
+          } else {
+            setItem({
+              ...item,
+              reset_usage_when_enabled: true,
+              config: {
+                ...(item.config || {}),
+                rollover: defaultRollover,
+              },
+            });
+          }
+        }}
+        buttonText="Enable rollovers"
+        infoContent="Rollovers carry unused credits to the next billing cycle. Set a maximum rollover amount and specify how many cycles before resetting."
+        className="text-t3 h-fit"
+        disabled={!showRolloverConfig}
+      />
+
+      {item.config?.rollover && showRolloverConfig && (
+        <div className="flex gap-3 w-full">
+          <div className="w-6/12 flex gap-1">
+            <Input
+              value={rollover.max === null ? "Unlimited" : rollover.max}
+              className="w-full"
+              placeholder="Max"
+              disabled={rollover.max === null}
+              onChange={(e) => {
+                setRolloverConfigKey("max", e.target.value);
+              }}
+            />
+            <ToggleDisplayButton
+              label="Unlimited"
+              show={rollover.max === null}
+              className="h-8"
+              onClick={() => {
+                if (rollover.max === null) {
+                  setRolloverConfigKey("max", 0);
+                } else {
+                  setRolloverConfigKey("max", null);
+                }
+              }}
+            >
+              ♾️
+            </ToggleDisplayButton>
+          </div>
+
+          <div className="w-6/12 flex gap-1">
+            {rollover.duration === RolloverDuration.Month && (
+              <Input
+                value={rollover.length || ""}
+                onChange={(e) => {
+                  setRolloverConfigKey("length", e.target.value);
+                }}
+                className="w-14"
+              />
+            )}
+            <Select
+              value={rollover.duration}
+              onValueChange={(value) => {
+                setRolloverConfigKey("duration", value as RolloverDuration);
+              }}
+            >
+              <SelectTrigger>
+                <SelectValue placeholder="Select a duration" />
+              </SelectTrigger>
+              <SelectContent>
+                {Object.values(RolloverDuration).map((duration) => (
+                  <SelectItem key={duration} value={duration}>
+                    {duration}
+                  </SelectItem>
+                ))}
+              </SelectContent>
+            </Select>
+          </div>
+        </div>
+      )}
+    </div>
+  );
+};
diff --git a/vite/src/views/products/product/product-item/product-item-config/components/feature-price/FeaturePrice.tsx b/vite/src/views/products/product/product-item/product-item-config/components/feature-price/FeaturePrice.tsx
index 07c518804..c667e8c47 100644
--- a/vite/src/views/products/product/product-item/product-item-config/components/feature-price/FeaturePrice.tsx
+++ b/vite/src/views/products/product/product-item/product-item-config/components/feature-price/FeaturePrice.tsx
@@ -38,12 +38,14 @@ export default function FeaturePrice() {
   };
 
   const handlePriceRemoved = () => {
-    setItem(
-      FeatureItemSchema.parse({
-        ...item,
-        included_usage: item.included_usage || 0,
-      }),
-    );
+    setItem({
+      feature_id: item.feature_id,
+      included_usage: item.included_usage || 0,
+      interval: item.interval,
+      entity_feature_id: item.entity_feature_id,
+      reset_usage_when_enabled: item.reset_usage_when_enabled,
+      config: item.config,
+    });
   };
   const handleRemoveTier = (index: number) => {
     const newTiers = [...item.tiers];
@@ -88,7 +90,7 @@ export default function FeaturePrice() {
                   <div
                     className={cn(
                       "flex w-full text-sm",
-                      tier.to == -1 && "bg-transparent",
+                      tier.to == -1 && "bg-transparent"
                     )}
                   >
                     <UsageTierInput
@@ -104,7 +106,7 @@ export default function FeaturePrice() {
               <div
                 className={cn(
                   "flex text-sm",
-                  item.tiers?.length == 1 ? "w-full" : "w-32",
+                  item.tiers?.length == 1 ? "w-full" : "w-32"
                 )}
               >
                 <UsageTierInput