diff --git a/server/src/external/stripe/webhookHandlers/common/eventContextToArrearLineItems.ts b/server/src/external/stripe/webhookHandlers/common/eventContextToArrearLineItems.ts
index bf2662467..55a9a2826 100644
--- a/server/src/external/stripe/webhookHandlers/common/eventContextToArrearLineItems.ts
+++ b/server/src/external/stripe/webhookHandlers/common/eventContextToArrearLineItems.ts
@@ -17,16 +17,21 @@ import { logWebhookArrearLineItems } from "./logs/logWebhookArrearLineItems";
 /**
  * Generates arrear (usage-in-arrear) line items from webhook event context.
  *
- * This function is used by both:
+ * Used by:
  * - `invoice.created` webhook: adds consumable usage line items to renewal invoice
  * - `subscription.deleted` webhook: creates final arrear invoice for usage
  *
- * @param ctx - Autumn context (for org currency, etc.)
- * @param eventContext - Common webhook context (stripeSubscription, stripeCustomer, fullCustomer, customerProducts, nowMs, paymentMethod)
- * @param periodEndMs - End of billing period (optional, falls back to nowMs)
- * @param cusEntFilter - Optional filter for multi-interval billing (invoice.created uses this)
+ * ## Discount handling
  *
- * @returns Object with line items and the billing context used
+ * Line items are created with `discountable: true`, which tells Stripe to auto-apply
+ * subscription/customer discounts when adding these items to an invoice.
+ *
+ * We also call `applyStripeDiscountsToLineItems` locally to calculate the discounted
+ * amounts for our own records (stored in `amountAfterDiscounts`). This is purely for
+ * audit/tracking purposes - Stripe handles the actual discount application.
+ *
+ * We use `skipDescriptionTag: true` so the description doesn't include "[inc. discount]"
+ * since we're not pre-deducting the discount from the amount sent to Stripe.
  */
 export const eventContextToArrearLineItems = ({
 	ctx,
@@ -60,20 +65,26 @@ export const eventContextToArrearLineItems = ({
 			customerProduct,
 			billingContext,
 			filters: { cusEntFilter },
-			options: { updateNextResetAt: true },
+			options: { updateNextResetAt: true, discountable: true },
 		});
 		lineItems.push(...productLineItems);
 		updateCustomerEntitlements.push(...productUpdates);
 	}
 
-	// Apply discounts to line items
+	// Apply discounts to line items (for our DB records)
+	// Note: discountable: true lets Stripe auto-apply discounts, but we still
+	// need to track discounts on our side for accurate DB storage
 	const discounts = extractStripeDiscounts({
 		stripeSubscription: eventContext.stripeSubscription,
 		stripeCustomer: eventContext.stripeCustomer,
 	});
 
 	if (discounts.length > 0) {
-		lineItems = applyStripeDiscountsToLineItems({ lineItems, discounts });
+		lineItems = applyStripeDiscountsToLineItems({
+			lineItems,
+			discounts,
+			options: { skipDescriptionTag: true },
+		});
 	}
 
 	// Log the arrear line items and customer entitlement updates
diff --git a/server/src/external/stripe/webhookHandlers/common/logCustomerProductUpdates.ts b/server/src/external/stripe/webhookHandlers/common/logCustomerProductUpdates.ts
index 70fd171ab..295b200bc 100644
--- a/server/src/external/stripe/webhookHandlers/common/logCustomerProductUpdates.ts
+++ b/server/src/external/stripe/webhookHandlers/common/logCustomerProductUpdates.ts
@@ -48,11 +48,7 @@ export const logCustomerProductUpdates = ({
 		status: customerProduct.status,
 	}));
 
-	if (
-		updates.length === 0 &&
-		deletions.length === 0 &&
-		insertions.length === 0
-	)
+	if (updates.length === 0 && deletions.length === 0 && insertions.length === 0)
 		return;
 
 	addToExtraLogs({
diff --git a/server/src/external/stripe/webhookHandlers/common/logs/logWebhookArrearLineItems.ts b/server/src/external/stripe/webhookHandlers/common/logs/logWebhookArrearLineItems.ts
index ac8c2fe7a..205b6722e 100644
--- a/server/src/external/stripe/webhookHandlers/common/logs/logWebhookArrearLineItems.ts
+++ b/server/src/external/stripe/webhookHandlers/common/logs/logWebhookArrearLineItems.ts
@@ -1,6 +1,6 @@
+import type { UpdateCustomerEntitlement } from "@autumn/shared";
 import { formatMs, type LineItem } from "@autumn/shared";
 import type { StripeWebhookContext } from "@/external/stripe/webhookMiddlewares/stripeWebhookContext";
-import type { UpdateCustomerEntitlement } from "@autumn/shared";
 import { addToExtraLogs } from "@/utils/logging/addToExtraLogs";
 
 export const logWebhookArrearLineItems = ({
@@ -16,13 +16,12 @@ export const logWebhookArrearLineItems = ({
 		ctx,
 		extras: {
 			arrearLineItems: {
-				lineItems: lineItems.map((item) => {
-					const hasDiscount =
-						item.finalAmount !== undefined && item.finalAmount !== item.amount;
-					return hasDiscount
-						? `${item.description}: ${item.amount} → ${item.finalAmount} (discounted)`
-						: `${item.description}: ${item.amount}`;
-				}),
+				lineItems: lineItems.map((item) => ({
+					description: item.description,
+					amount: item.amount,
+					amountAfterDiscounts: item.amountAfterDiscounts,
+					discountable: item.context.discountable ?? false,
+				})),
 				updateCustomerEntitlements: updateCustomerEntitlements.map(
 					(update) => ({
 						featureId: update.customerEntitlement.entitlement.feature?.id,
diff --git a/server/src/internal/billing/v2/actions/updateSubscription/compute/updateQuantity/computeUpdateQuantityLineItems.ts b/server/src/internal/billing/v2/actions/updateSubscription/compute/updateQuantity/computeUpdateQuantityLineItems.ts
index 5fce3111b..6468ba78e 100644
--- a/server/src/internal/billing/v2/actions/updateSubscription/compute/updateQuantity/computeUpdateQuantityLineItems.ts
+++ b/server/src/internal/billing/v2/actions/updateSubscription/compute/updateQuantity/computeUpdateQuantityLineItems.ts
@@ -111,8 +111,8 @@ export const computeUpdateQuantityLineItems = ({
 	// Don't return line items if they sum to 0
 	if (
 		sumValues([
-			refundLineItem?.finalAmount ?? 0,
-			chargeLineItem?.finalAmount ?? 0,
+			refundLineItem?.amountAfterDiscounts ?? 0,
+			chargeLineItem?.amountAfterDiscounts ?? 0,
 		]) === 0
 	) {
 		return [];
diff --git a/server/src/internal/billing/v2/compute/computeAutumnUtils/buildSharedSubscriptionTrialLineItems.ts b/server/src/internal/billing/v2/compute/computeAutumnUtils/buildSharedSubscriptionTrialLineItems.ts
index 4d4796c8e..ae5297fb3 100644
--- a/server/src/internal/billing/v2/compute/computeAutumnUtils/buildSharedSubscriptionTrialLineItems.ts
+++ b/server/src/internal/billing/v2/compute/computeAutumnUtils/buildSharedSubscriptionTrialLineItems.ts
@@ -15,7 +15,7 @@ import { customerProductToLineItems } from "@/internal/billing/v2/utils/lineItem
 const formatLineItem = (item: LineItem) => ({
 	description: item.description,
 	amount: item.amount,
-	finalAmount: item.finalAmount,
+	amountAfterDiscounts: item.amountAfterDiscounts,
 });
 
 const logSharedSubscriptionTrialLineItems = ({
@@ -30,7 +30,7 @@ const logSharedSubscriptionTrialLineItems = ({
 	lineItems: LineItem[];
 }) => {
 	const formatLineItemCompact = (item: LineItem) =>
-		`  ${item.description}: ${chalk.yellow(item.finalAmount.toFixed(2))}`;
+		`  ${item.description}: ${chalk.yellow(item.amountAfterDiscounts.toFixed(2))}`;
 
 	// Structured info log
 	// logger.info(`buildSharedSubscriptionTrialLineItems data`, {
diff --git a/server/src/internal/billing/v2/compute/computeAutumnUtils/logBuildAutumnLineItems.ts b/server/src/internal/billing/v2/compute/computeAutumnUtils/logBuildAutumnLineItems.ts
index eced1a24d..12d402cb6 100644
--- a/server/src/internal/billing/v2/compute/computeAutumnUtils/logBuildAutumnLineItems.ts
+++ b/server/src/internal/billing/v2/compute/computeAutumnUtils/logBuildAutumnLineItems.ts
@@ -5,7 +5,7 @@ import type { Logger } from "@/external/logtail/logtailUtils";
 const formatLineItem = (item: LineItem) => ({
 	description: item.description,
 	amount: item.amount,
-	finalAmount: item.finalAmount,
+	amountAfterDiscounts: item.amountAfterDiscounts,
 });
 
 export const logBuildAutumnLineItems = ({
@@ -19,7 +19,7 @@ export const logBuildAutumnLineItems = ({
 }) => {
 	// Debug output (compact table format)
 	const formatLineItemCompact = (item: LineItem) =>
-		`  ${item.description}: ${chalk.yellow(item.finalAmount.toFixed(2))}`;
+		`  ${item.description}: ${chalk.yellow(item.amountAfterDiscounts.toFixed(2))}`;
 
 	logger.debug("========== [buildAutumnLineItems] ==========");
 
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyAmountOffDiscountToLineItems.ts b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyAmountOffDiscountToLineItems.ts
index ef1e12f1f..b47077836 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyAmountOffDiscountToLineItems.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyAmountOffDiscountToLineItems.ts
@@ -16,9 +16,13 @@ import { discountAppliesToLineItem } from "./discountAppliesToLineItem";
 export const applyAmountOffDiscountToLineItems = ({
 	lineItems,
 	discount,
+	options = {},
 }: {
 	lineItems: LineItem[];
 	discount: StripeDiscountWithCoupon;
+	options?: {
+		skipDescriptionTag?: boolean;
+	};
 }): LineItem[] => {
 	const coupon = discount.source.coupon;
 	const amountOffCents = coupon.amount_off;
@@ -75,18 +79,20 @@ export const applyAmountOffDiscountToLineItems = ({
 
 		// Discounts only apply to charges (refunds filtered by discountAppliesToLineItem)
 		// Cap at 0 to prevent negative charges
-		const finalAmount = Math.max(
+		const amountAfterDiscounts = Math.max(
 			new Decimal(item.amount).minus(totalDiscount).toNumber(),
 			0,
 		);
 
+		const description = options.skipDescriptionTag
+			? item.description
+			: addDiscountTagToDescription({ description: item.description });
+
 		return {
 			...item,
-			description: addDiscountTagToDescription({
-				description: item.description,
-			}),
+			description,
 			discounts: [...existingDiscounts, newDiscount],
-			finalAmount,
+			amountAfterDiscounts,
 		};
 	});
 };
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyPercentOffDiscountToLineItems.ts b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyPercentOffDiscountToLineItems.ts
index dabd27d8e..53b9e2e6e 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyPercentOffDiscountToLineItems.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyPercentOffDiscountToLineItems.ts
@@ -14,9 +14,13 @@ import { discountAppliesToLineItem } from "./discountAppliesToLineItem";
 export const applyPercentOffDiscountToLineItems = ({
 	lineItems,
 	discount,
+	options = {},
 }: {
 	lineItems: LineItem[];
 	discount: StripeDiscountWithCoupon;
+	options?: {
+		skipDescriptionTag?: boolean;
+	};
 }): LineItem[] => {
 	const coupon = discount.source.coupon;
 	const percentOff = coupon.percent_off;
@@ -31,9 +35,9 @@ export const applyPercentOffDiscountToLineItems = ({
 			return item;
 		}
 
-		// Use current finalAmount as base for multiplicative stacking
-		// If no previous discounts, finalAmount equals amount
-		const currentAmount = item.finalAmount ?? item.amount;
+		// Use current amountAfterDiscounts as base for multiplicative stacking
+		// If no previous discounts, amountAfterDiscounts equals amount
+		const currentAmount = item.amountAfterDiscounts ?? item.amount;
 
 		// Calculate discount amount: |currentAmount| * (percentOff / 100)
 		const itemDiscount = new Decimal(Math.abs(currentAmount))
@@ -55,18 +59,20 @@ export const applyPercentOffDiscountToLineItems = ({
 
 		// Discounts only apply to charges (refunds filtered by discountAppliesToLineItem)
 		// Cap at 0 to prevent negative charges
-		const finalAmount = Math.max(
+		const amountAfterDiscounts = Math.max(
 			new Decimal(currentAmount).minus(itemDiscount).toNumber(),
 			0,
 		);
 
+		const description = options.skipDescriptionTag
+			? item.description
+			: addDiscountTagToDescription({ description: item.description });
+
 		return {
 			...item,
-			description: addDiscountTagToDescription({
-				description: item.description,
-			}),
+			description,
 			discounts: [...existingDiscounts, newDiscount],
-			finalAmount,
+			amountAfterDiscounts,
 		};
 	});
 };
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyStripeDiscountsToLineItems.ts b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyStripeDiscountsToLineItems.ts
index eb19bdb9d..98341fb7b 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyStripeDiscountsToLineItems.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/discounts/applyStripeDiscountsToLineItems.ts
@@ -5,9 +5,13 @@ import { applyPercentOffDiscountToLineItems } from "./applyPercentOffDiscountToL
 export const applyStripeDiscountsToLineItems = ({
 	lineItems,
 	discounts,
+	options = {},
 }: {
 	lineItems: LineItem[];
 	discounts: StripeDiscountWithCoupon[];
+	options?: {
+		skipDescriptionTag?: boolean;
+	};
 }): LineItem[] => {
 	const percentOffDiscounts = discounts.filter(
 		(d) => d.source.coupon.percent_off,
@@ -20,11 +24,16 @@ export const applyStripeDiscountsToLineItems = ({
 		lineItems = applyPercentOffDiscountToLineItems({
 			lineItems,
 			discount,
+			options,
 		});
 	}
 
 	for (const discount of amountOffDiscounts) {
-		lineItems = applyAmountOffDiscountToLineItems({ lineItems, discount });
+		lineItems = applyAmountOffDiscountToLineItems({
+			lineItems,
+			discount,
+			options,
+		});
 	}
 
 	return lineItems;
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemToMetadata.ts b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemToMetadata.ts
new file mode 100644
index 000000000..1dd69720d
--- /dev/null
+++ b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemToMetadata.ts
@@ -0,0 +1,42 @@
+import type { LineItem } from "@autumn/shared";
+import type Stripe from "stripe";
+
+/**
+ * Converts a LineItem to Stripe metadata for invoice line items.
+ *
+ * Metadata includes:
+ * - autumn_product_id: The Autumn product ID
+ * - autumn_price_id: The Autumn price ID
+ * - stripe_product_id: The Stripe product ID (if available)
+ * - coupon_ids: Comma-separated list of coupon IDs (if discounts applied)
+ */
+export const lineItemToMetadata = ({
+	lineItem,
+}: {
+	lineItem: LineItem;
+}): Stripe.MetadataParam => {
+	const { context, discounts } = lineItem;
+	const { product, price } = context;
+
+	const metadata: Stripe.MetadataParam = {
+		autumn_product_id: product.id,
+		autumn_price_id: price.id,
+	};
+
+	const stripeProductId = product.processor?.id;
+	if (stripeProductId) {
+		metadata.stripe_product_id = stripeProductId;
+	}
+
+	if (discounts.length > 0) {
+		const couponIds = discounts
+			.map((d) => d.stripeCouponId)
+			.filter(Boolean)
+			.join(",");
+		if (couponIds) {
+			metadata.coupon_ids = couponIds;
+		}
+	}
+
+	return metadata;
+};
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToCreateInvoiceItemsParams.ts b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToCreateInvoiceItemsParams.ts
index 8de819802..06678c3da 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToCreateInvoiceItemsParams.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToCreateInvoiceItemsParams.ts
@@ -1,11 +1,9 @@
 import { atmnToStripeAmount, type LineItem, msToSeconds } from "@autumn/shared";
 import type Stripe from "stripe";
+import { lineItemToMetadata } from "./lineItemToMetadata";
 
 /**
  * Converts a single LineItem to Stripe.InvoiceItemCreateParams
- *
- * Uses effectivePeriod (the actual period being charged/refunded) for Stripe,
- * which accounts for mid-cycle changes.
  */
 const toStripeCreateInvoiceItemParams = ({
 	stripeCustomerId,
@@ -18,17 +16,35 @@ const toStripeCreateInvoiceItemParams = ({
 	stripeInvoiceId?: string;
 	lineItem: LineItem;
 }): Stripe.InvoiceItemCreateParams => {
-	const { finalAmount, description, context } = lineItem;
-	const { effectivePeriod, currency } = context;
+	const { amount, amountAfterDiscounts, description, context } = lineItem;
+	const { effectivePeriod, currency, discountable } = context;
+
+	// If discountable, use amount (let Stripe apply discounts), otherwise use amountAfterDiscounts
+	const lineAmount = discountable ? amount : amountAfterDiscounts;
+	const isNegative = lineAmount < 0;
+	const stripeProductId = context.product.processor?.id ?? "";
+	const shouldUsePriceData = !isNegative && stripeProductId;
 
 	return {
 		customer: stripeCustomerId,
 		subscription: stripeSubscriptionId,
 		invoice: stripeInvoiceId,
-		amount: atmnToStripeAmount({ amount: finalAmount }),
+
+		amount: shouldUsePriceData
+			? undefined
+			: atmnToStripeAmount({ amount: lineAmount }),
+
+		price_data: shouldUsePriceData
+			? {
+					unit_amount: atmnToStripeAmount({ amount: lineAmount }),
+					currency,
+					product: stripeProductId,
+				}
+			: undefined,
+		metadata: lineItemToMetadata({ lineItem }),
 		currency,
 		description,
-		discountable: false,
+		discountable: discountable ?? false,
 		period: effectivePeriod
 			? {
 					start: msToSeconds(effectivePeriod.start),
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToInvoiceAddLinesParams.ts b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToInvoiceAddLinesParams.ts
index e56725280..e46f37694 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToInvoiceAddLinesParams.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/invoiceLines/lineItemsToInvoiceAddLinesParams.ts
@@ -1,5 +1,6 @@
 import { atmnToStripeAmount, type LineItem, msToSeconds } from "@autumn/shared";
 import type Stripe from "stripe";
+import { lineItemToMetadata } from "./lineItemToMetadata";
 
 /**
  * Converts a single LineItem to Stripe.InvoiceAddLinesParams.Line
@@ -12,13 +13,29 @@ const toStripeAddLineParams = ({
 }: {
 	lineItem: LineItem;
 }): Stripe.InvoiceAddLinesParams.Line => {
-	const { finalAmount, description, context } = lineItem;
-	const { effectivePeriod } = context;
+	const { amount, amountAfterDiscounts, description, context } = lineItem;
+	const { effectivePeriod, currency, discountable } = context;
+
+	// If discountable, use amount (let Stripe apply discounts), otherwise use amountAfterDiscounts
+	const lineAmount = discountable ? amount : amountAfterDiscounts;
+	const isNegative = lineAmount < 0;
+	const stripeProductId = context.product.processor?.id ?? "";
+	const shouldUsePriceData = !isNegative && stripeProductId;
 
 	return {
 		description,
-		amount: atmnToStripeAmount({ amount: finalAmount }),
-		discountable: false,
+		amount: shouldUsePriceData
+			? undefined
+			: atmnToStripeAmount({ amount: lineAmount }),
+		price_data: shouldUsePriceData
+			? {
+					unit_amount: atmnToStripeAmount({ amount: lineAmount }),
+					currency,
+					product: stripeProductId,
+				}
+			: undefined,
+		metadata: lineItemToMetadata({ lineItem }),
+		discountable: discountable ?? false,
 		period: effectivePeriod
 			? {
 					start: msToSeconds(effectivePeriod.start),
diff --git a/server/src/internal/billing/v2/providers/stripe/utils/invoices/shouldCreateManualStripeInvoice.ts b/server/src/internal/billing/v2/providers/stripe/utils/invoices/shouldCreateManualStripeInvoice.ts
index 6876c3745..a0581eea8 100644
--- a/server/src/internal/billing/v2/providers/stripe/utils/invoices/shouldCreateManualStripeInvoice.ts
+++ b/server/src/internal/billing/v2/providers/stripe/utils/invoices/shouldCreateManualStripeInvoice.ts
@@ -21,7 +21,10 @@ export const shouldCreateManualStripeInvoice = ({
 	if (!stripeSubscription) {
 		const lineItems = autumnBillingPlan.lineItems;
 		const totalAmount =
-			lineItems?.reduce((acc, lineItem) => acc + lineItem.finalAmount, 0) ?? 0;
+			lineItems?.reduce(
+				(acc, lineItem) => acc + lineItem.amountAfterDiscounts,
+				0,
+			) ?? 0;
 
 		return totalAmount !== 0;
 	}
diff --git a/server/src/internal/billing/v2/utils/billingContextToCheckoutResponse.ts b/server/src/internal/billing/v2/utils/billingContextToCheckoutResponse.ts
index fafe74e2b..6c59de502 100644
--- a/server/src/internal/billing/v2/utils/billingContextToCheckoutResponse.ts
+++ b/server/src/internal/billing/v2/utils/billingContextToCheckoutResponse.ts
@@ -63,7 +63,7 @@ export const billingContextToCheckoutResponse = async ({
 
 			return {
 				description: line.description,
-				amount: line.finalAmount,
+				amount: line.amountAfterDiscounts,
 				item: getProductItemResponse({
 					item: productItem,
 					features,
diff --git a/server/src/internal/billing/v2/utils/billingPlan/billingPlanToNextCyclePreview.ts b/server/src/internal/billing/v2/utils/billingPlan/billingPlanToNextCyclePreview.ts
index bc402efc8..9da4ef643 100644
--- a/server/src/internal/billing/v2/utils/billingPlan/billingPlanToNextCyclePreview.ts
+++ b/server/src/internal/billing/v2/utils/billingPlan/billingPlanToNextCyclePreview.ts
@@ -143,7 +143,9 @@ export const billingPlanToNextCyclePreview = ({
 	);
 
 	const previewLineItems = autumnLineItems.map(lineItemToPreviewLineItem);
-	const total = sumValues(autumnLineItems.map((line) => line.finalAmount));
+	const total = sumValues(
+		autumnLineItems.map((line) => line.amountAfterDiscounts),
+	);
 
 	return {
 		nextCycle: {
diff --git a/server/src/internal/billing/v2/utils/lineItems/customerProductToArrearLineItems.ts b/server/src/internal/billing/v2/utils/lineItems/customerProductToArrearLineItems.ts
index 896e52ca4..0035c3781 100644
--- a/server/src/internal/billing/v2/utils/lineItems/customerProductToArrearLineItems.ts
+++ b/server/src/internal/billing/v2/utils/lineItems/customerProductToArrearLineItems.ts
@@ -25,6 +25,7 @@ export const customerProductToArrearLineItems = ({
 	options = {
 		includePeriodDescription: false,
 		updateNextResetAt: true,
+		discountable: false,
 	},
 }: {
 	ctx: AutumnContext;
@@ -38,6 +39,7 @@ export const customerProductToArrearLineItems = ({
 	options?: {
 		includePeriodDescription?: boolean;
 		updateNextResetAt?: boolean;
+		discountable?: boolean;
 	};
 }): {
 	lineItems: LineItem[];
@@ -98,7 +100,10 @@ export const customerProductToArrearLineItems = ({
 		const lineItem = usagePriceToLineItem({
 			cusEnt,
 			context,
-			options: { includePeriodDescription: options.includePeriodDescription },
+			options: {
+				includePeriodDescription: options.includePeriodDescription,
+				discountable: options.discountable,
+			},
 		});
 
 		// Only include line items with non-zero amounts
diff --git a/server/src/internal/billing/v2/utils/lineItems/lineItemToPreviewLineItem.ts b/server/src/internal/billing/v2/utils/lineItems/lineItemToPreviewLineItem.ts
index 110170c5e..292a7a80b 100644
--- a/server/src/internal/billing/v2/utils/lineItems/lineItemToPreviewLineItem.ts
+++ b/server/src/internal/billing/v2/utils/lineItems/lineItemToPreviewLineItem.ts
@@ -12,7 +12,7 @@ export const lineItemToPreviewLineItem = (line: LineItem): PreviewLineItem => {
 	return {
 		title,
 		description: line.description,
-		amount: line.finalAmount,
+		amount: line.amountAfterDiscounts,
 		discounts: line.discounts,
 		is_base: isBase,
 		total_quantity: line.total_quantity ?? 1,
diff --git a/server/src/internal/billing/v2/utils/logs/logAutumnBillingPlan.ts b/server/src/internal/billing/v2/utils/logs/logAutumnBillingPlan.ts
index adb16d03d..88cee9dc7 100644
--- a/server/src/internal/billing/v2/utils/logs/logAutumnBillingPlan.ts
+++ b/server/src/internal/billing/v2/utils/logs/logAutumnBillingPlan.ts
@@ -57,7 +57,7 @@ export const logAutumnBillingPlan = ({
 
 				lineItems:
 					plan.lineItems?.map(
-						(item) => `${item.description}: ${item.finalAmount}`,
+						(item) => `${item.description}: ${item.amountAfterDiscounts}`,
 					) ?? "none",
 			},
 		},
diff --git a/server/src/internal/billing/v2/utils/logs/logBillingPreview.ts b/server/src/internal/billing/v2/utils/logs/logBillingPreview.ts
index bda6fbece..0066c6a9f 100644
--- a/server/src/internal/billing/v2/utils/logs/logBillingPreview.ts
+++ b/server/src/internal/billing/v2/utils/logs/logBillingPreview.ts
@@ -12,7 +12,7 @@ const formatCustomerProduct = (customerProduct: FullCusProduct) =>
 	`${customerProduct.product.name} (${customerProduct.product_id}) [${customerProduct.status}]`;
 
 const formatLineItem = (item: LineItem) =>
-	`${item.description}: ${item.finalAmount} (charge: ${item.chargeImmediately})`;
+	`${item.description}: ${item.amountAfterDiscounts} (charge: ${item.chargeImmediately})`;
 
 export const logBillingPreview = ({
 	ctx,
diff --git a/server/src/internal/billing/v2/utils/logs/logNextCyclePreview.ts b/server/src/internal/billing/v2/utils/logs/logNextCyclePreview.ts
index ec4f56c06..28315b397 100644
--- a/server/src/internal/billing/v2/utils/logs/logNextCyclePreview.ts
+++ b/server/src/internal/billing/v2/utils/logs/logNextCyclePreview.ts
@@ -12,7 +12,7 @@ const formatCustomerProduct = (customerProduct: FullCusProduct) =>
 	`${customerProduct.product.name} (${customerProduct.product_id}) [${customerProduct.status}]`;
 
 const formatLineItem = (item: LineItem) =>
-	`${item.description}: ${item.finalAmount} (charge: ${item.chargeImmediately})`;
+	`${item.description}: ${item.amountAfterDiscounts} (charge: ${item.chargeImmediately})`;
 
 export const logBillingPreview = ({
 	ctx,
diff --git a/server/tests/_groups/core/coreUpdateSubscription.ts b/server/tests/_groups/core/coreUpdateSubscription.ts
index 4bc9eb421..de2a68cd7 100644
--- a/server/tests/_groups/core/coreUpdateSubscription.ts
+++ b/server/tests/_groups/core/coreUpdateSubscription.ts
@@ -25,6 +25,7 @@ export const coreUpdateSubscription: TestGroup = {
 		"billing/update-subscription/invoice/update-with-invoice-basic.test.ts",
 		"billing/update-subscription/errors/update-errors-basic.test.ts",
 		"billing/update-subscription/discounts/percent-off-discount.test.ts",
+		"billing/update-subscription/discounts/discount-applies-to.test.ts",
 		"billing/update-subscription/billing-behavior/next-cycle-only.test.ts",
 		"billing/update-subscription/billing-behavior/next-cycle-only-cancel.test.ts",
 	],
diff --git a/server/tests/integration/billing/attach/immediate-switch/immediate-switch-basic.test.ts b/server/tests/integration/billing/attach/immediate-switch/immediate-switch-basic.test.ts
index 1a700787b..529024c33 100644
--- a/server/tests/integration/billing/attach/immediate-switch/immediate-switch-basic.test.ts
+++ b/server/tests/integration/billing/attach/immediate-switch/immediate-switch-basic.test.ts
@@ -10,7 +10,7 @@
  */
 
 import { expect, test } from "bun:test";
-import type { ApiCustomerV3 } from "@autumn/shared";
+import { type ApiCustomerV3, atmnToStripeAmount } from "@autumn/shared";
 import { expectCustomerFeatureCorrect } from "@tests/integration/billing/utils/expectCustomerFeatureCorrect";
 import { expectCustomerInvoiceCorrect } from "@tests/integration/billing/utils/expectCustomerInvoiceCorrect";
 import {
@@ -23,6 +23,7 @@ import { expectSubToBeCorrect } from "@tests/merged/mergeUtils/expectSubCorrect"
 import { TestFeature } from "@tests/setup/v2Features";
 import { items } from "@tests/utils/fixtures/items";
 import { products } from "@tests/utils/fixtures/products";
+import ctx from "@tests/utils/testInitUtils/createTestContext";
 import { initScenario, s } from "@tests/utils/testInitUtils/initScenario";
 import chalk from "chalk";
 
@@ -452,3 +453,102 @@ test.concurrent(`${chalk.yellowBright("immediate-switch-basic 5: premium to pro
 		usage: 0,
 	});
 });
+
+// ═══════════════════════════════════════════════════════════════════════════════
+// TEST 6: Invoice line item metadata and price_data
+// ═══════════════════════════════════════════════════════════════════════════════
+
+/**
+ * Scenario:
+ * - Customer has free product
+ * - Upgrade to pro with invoice mode
+ *
+ * Expected Result:
+ * - Invoice line items have correct metadata:
+ *   - autumn_product_id
+ *   - autumn_price_id
+ *   - stripe_product_id (when available)
+ * - Line items with positive amounts use price_data (when stripe_product_id exists)
+ */
+test.concurrent(`${chalk.yellowBright("immediate-switch-basic 6: invoice line item metadata and price_data")}`, async () => {
+	const customerId = "imm-switch-metadata-price-data";
+
+	const proMessagesItem = items.monthlyMessages({ includedUsage: 500 });
+	const pro = products.pro({
+		id: "pro",
+		items: [proMessagesItem],
+	});
+
+	const premiumMessagesItem = items.monthlyMessages({ includedUsage: 1000 });
+	const premium = products.premium({
+		id: "premium",
+		items: [premiumMessagesItem],
+	});
+
+	const { autumnV1 } = await initScenario({
+		customerId,
+		setup: [
+			s.customer({ paymentMethod: "success" }),
+			s.products({ list: [pro, premium] }),
+		],
+		actions: [s.billing.attach({ productId: pro.id })],
+	});
+
+	// Upgrade from pro to premium with invoice mode to get invoice response
+	const result = await autumnV1.billing.attach({
+		customer_id: customerId,
+		product_id: premium.id,
+		// invoice: true,
+		// finalize_invoice: true,
+		// enable_product_immediately: true,
+		redirect_mode: "if_required",
+	});
+
+	// Verify invoice was created
+	expect(result.invoice).toBeDefined();
+	expect(result.invoice!.stripe_id).toBeDefined();
+
+	// Retrieve the Stripe invoice with line items expanded
+	const stripeInvoice = await ctx.stripeCli.invoices.retrieve(
+		result.invoice!.stripe_id,
+		{ expand: ["lines.data"] },
+	);
+
+	// Verify invoice has line items (charge for premium, refund for pro)
+	expect(stripeInvoice.lines.data.length).toBeGreaterThan(0);
+
+	// Check each line item for metadata and price_data
+	for (const lineItem of stripeInvoice.lines.data) {
+		const metadata = lineItem.metadata;
+
+		// Verify autumn metadata is present
+		expect(metadata).toBeDefined();
+		expect(metadata?.autumn_product_id).toBeDefined();
+		expect(metadata?.autumn_price_id).toBeDefined();
+
+		// Verify shouldUsePriceData logic:
+		// - Positive amounts with stripe_product_id should use price_data
+		// - This manifests as the line having pricing.price_details with product reference
+		// - Negative amounts (refunds) should NOT have price_data
+		if (lineItem.amount > 0 && metadata?.stripe_product_id) {
+			expect(lineItem.pricing?.price_details).toBeDefined();
+			expect(lineItem.pricing?.price_details?.product).toBe(
+				metadata.stripe_product_id,
+			);
+		}
+	}
+
+	// Verify the total is correct (upgrade from $20 to $50 = $30 difference)
+	expect(stripeInvoice.total).toBe(
+		atmnToStripeAmount({ amount: 30, currency: "usd" }),
+	);
+
+	const customer = await autumnV1.customers.get<ApiCustomerV3>(customerId);
+
+	// Verify product states
+	await expectCustomerProducts({
+		customer,
+		active: [premium.id],
+		notPresent: [pro.id],
+	});
+});
diff --git a/server/tests/unit/billing/stripe/discounts/apply-amount-off-discount-to-line-items.spec.ts b/server/tests/unit/billing/stripe/discounts/apply-amount-off-discount-to-line-items.spec.ts
index e52ac49ea..af069e1d8 100644
--- a/server/tests/unit/billing/stripe/discounts/apply-amount-off-discount-to-line-items.spec.ts
+++ b/server/tests/unit/billing/stripe/discounts/apply-amount-off-discount-to-line-items.spec.ts
@@ -30,7 +30,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(40); // 50 - 10
+			expect(result[0].amountAfterDiscounts).toBe(40); // 50 - 10
 			expect(result[0].discounts).toHaveLength(1);
 			expect(result[0].discounts[0].amountOff).toBe(10);
 		});
@@ -44,9 +44,9 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			// The discount amount is still recorded as $50, but finalAmount caps at 0
+			// The discount amount is still recorded as $50, but amountAfterDiscounts caps at 0
 			expect(result[0].discounts[0].amountOff).toBe(50);
-			expect(result[0].finalAmount).toBe(0);
+			expect(result[0].amountAfterDiscounts).toBe(0);
 		});
 
 		test("zero amount_off returns unchanged items", () => {
@@ -58,7 +58,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
@@ -80,9 +80,9 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 
 				// Each item is 50% of total, so each gets $5
 				expect(result[0].discounts[0].amountOff).toBe(5);
-				expect(result[0].finalAmount).toBe(45);
+				expect(result[0].amountAfterDiscounts).toBe(45);
 				expect(result[1].discounts[0].amountOff).toBe(5);
-				expect(result[1].finalAmount).toBe(45);
+				expect(result[1].amountAfterDiscounts).toBe(45);
 			});
 
 			test("distributes $30 proportionally across unequal items", () => {
@@ -100,9 +100,9 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 				// First item: 75/100 * 30 = 22.5 → 23 (rounded)
 				// Second item: 25/100 * 30 = 7.5 → 8 (rounded)
 				expect(result[0].discounts[0].amountOff).toBe(23);
-				expect(result[0].finalAmount).toBe(52); // 75 - 23
+				expect(result[0].amountAfterDiscounts).toBe(52); // 75 - 23
 				expect(result[1].discounts[0].amountOff).toBe(8);
-				expect(result[1].finalAmount).toBe(17); // 25 - 8
+				expect(result[1].amountAfterDiscounts).toBe(17); // 25 - 8
 			});
 		},
 	);
@@ -122,11 +122,11 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 
 			// Charge item gets full $20 (only applicable item)
 			expect(result[0].discounts[0].amountOff).toBe(20);
-			expect(result[0].finalAmount).toBe(80); // 100 - 20
+			expect(result[0].amountAfterDiscounts).toBe(80); // 100 - 20
 
 			// Refund item is skipped - discounts don't apply to refunds
 			expect(result[1].discounts).toHaveLength(0);
-			expect(result[1].finalAmount).toBe(-50);
+			expect(result[1].amountAfterDiscounts).toBe(-50);
 		});
 
 		test("distributes within charge group only (multiple charges)", () => {
@@ -143,10 +143,10 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 
 			// First item: 60/100 * 10 = 6
 			expect(result[0].discounts[0].amountOff).toBe(6);
-			expect(result[0].finalAmount).toBe(54);
+			expect(result[0].amountAfterDiscounts).toBe(54);
 			// Second item: 40/100 * 10 = 4
 			expect(result[1].discounts[0].amountOff).toBe(4);
-			expect(result[1].finalAmount).toBe(36);
+			expect(result[1].amountAfterDiscounts).toBe(36);
 		});
 	});
 
@@ -174,11 +174,11 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			// Only prod_a gets the discount
 			expect(result[0].discounts).toHaveLength(1);
 			expect(result[0].discounts[0].amountOff).toBe(20);
-			expect(result[0].finalAmount).toBe(80);
+			expect(result[0].amountAfterDiscounts).toBe(80);
 
 			// prod_b unchanged
 			expect(result[1].discounts).toHaveLength(0);
-			expect(result[1].finalAmount).toBe(100);
+			expect(result[1].amountAfterDiscounts).toBe(100);
 		});
 
 		test("skips items without stripeProductId when applies_to exists", () => {
@@ -193,7 +193,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			});
 
 			expect(result[0].discounts).toHaveLength(0);
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 		});
 	});
 
@@ -211,7 +211,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			});
 
 			expect(result[0].discounts[0].amountOff).toBe(25);
-			expect(result[0].finalAmount).toBe(75);
+			expect(result[0].amountAfterDiscounts).toBe(75);
 		});
 	});
 
@@ -231,11 +231,11 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			});
 
 			// Total discount: 10 + 15 = 25
-			// finalAmount: 100 - 25 = 75
+			// amountAfterDiscounts: 100 - 25 = 75
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(10);
 			expect(result[0].discounts[1].amountOff).toBe(15);
-			expect(result[0].finalAmount).toBe(75);
+			expect(result[0].amountAfterDiscounts).toBe(75);
 		});
 	});
 
@@ -269,7 +269,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			});
 
 			expect(result[0].discounts).toHaveLength(0);
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 		});
 
 		test("zero amount line items are skipped in distribution", () => {
@@ -288,7 +288,7 @@ describe(chalk.yellowBright("applyAmountOffDiscountToLineItems"), () => {
 			expect(result[0].discounts).toHaveLength(0);
 			// Second item gets full $10
 			expect(result[1].discounts[0].amountOff).toBe(10);
-			expect(result[1].finalAmount).toBe(90);
+			expect(result[1].amountAfterDiscounts).toBe(90);
 		});
 	});
 });
diff --git a/server/tests/unit/billing/stripe/discounts/apply-percent-off-discount-to-line-items.spec.ts b/server/tests/unit/billing/stripe/discounts/apply-percent-off-discount-to-line-items.spec.ts
index 5b3fa316e..3d19abe3c 100644
--- a/server/tests/unit/billing/stripe/discounts/apply-percent-off-discount-to-line-items.spec.ts
+++ b/server/tests/unit/billing/stripe/discounts/apply-percent-off-discount-to-line-items.spec.ts
@@ -30,7 +30,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(90); // 100 - 10
+			expect(result[0].amountAfterDiscounts).toBe(90); // 100 - 10
 			expect(result[0].discounts).toHaveLength(1);
 			expect(result[0].discounts[0].amountOff).toBe(10);
 			expect(result[0].discounts[0].percentOff).toBe(10);
@@ -46,12 +46,12 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(100); // 200 - 100
+			expect(result[0].amountAfterDiscounts).toBe(100); // 200 - 100
 			expect(result[0].discounts[0].amountOff).toBe(100);
 			expect(result[0].discounts[0].percentOff).toBe(50);
 		});
 
-		test("100% discount results in zero finalAmount", () => {
+		test("100% discount results in zero amountAfterDiscounts", () => {
 			const lineItems = [lineItemFixtures.charge({ amount: 50 })];
 			const discount = discounts.hundredPercentOff();
 
@@ -61,7 +61,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(0);
+			expect(result[0].amountAfterDiscounts).toBe(0);
 			expect(result[0].discounts[0].amountOff).toBe(50);
 		});
 
@@ -75,7 +75,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
@@ -90,8 +90,8 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			// Charge: finalAmount = amount - discount = 100 - 20 = 80
-			expect(result[0].finalAmount).toBe(80);
+			// Charge: amountAfterDiscounts = amount - discount = 100 - 20 = 80
+			expect(result[0].amountAfterDiscounts).toBe(80);
 		});
 
 		test("refund direction: discounts do not apply to refunds", () => {
@@ -104,8 +104,8 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			// Refunds are skipped by discountAppliesToLineItem
-			// finalAmount stays at -100, no discounts applied
-			expect(result[0].finalAmount).toBe(-100);
+			// amountAfterDiscounts stays at -100, no discounts applied
+			expect(result[0].amountAfterDiscounts).toBe(-100);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
@@ -131,9 +131,9 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			expect(result[0].finalAmount).toBe(50); // Discounted
+			expect(result[0].amountAfterDiscounts).toBe(50); // Discounted
 			expect(result[0].discounts).toHaveLength(1);
-			expect(result[1].finalAmount).toBe(100); // Not discounted
+			expect(result[1].amountAfterDiscounts).toBe(100); // Not discounted
 			expect(result[1].discounts).toHaveLength(0);
 		});
 
@@ -148,7 +148,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
@@ -167,9 +167,9 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			expect(result[0].finalAmount).toBe(90); // 100 - 10
-			expect(result[1].finalAmount).toBe(180); // 200 - 20
-			expect(result[2].finalAmount).toBe(45); // 50 - 5
+			expect(result[0].amountAfterDiscounts).toBe(90); // 100 - 10
+			expect(result[1].amountAfterDiscounts).toBe(180); // 200 - 20
+			expect(result[2].amountAfterDiscounts).toBe(45); // 50 - 5
 		});
 	});
 
@@ -188,10 +188,10 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 				discount,
 			});
 
-			// Existing discount already reduced finalAmount from 100 to 90
+			// Existing discount already reduced amountAfterDiscounts from 100 to 90
 			// New discount: 90 * 20% = 18 (multiplicative stacking)
-			// finalAmount: 90 - 18 = 72
-			expect(result[0].finalAmount).toBe(72);
+			// amountAfterDiscounts: 90 - 18 = 72
+			expect(result[0].amountAfterDiscounts).toBe(72);
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(10);
 			expect(result[0].discounts[1].amountOff).toBe(18);
@@ -222,7 +222,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			expect(result[0].discounts[0].amountOff).toBe(3);
-			expect(result[0].finalAmount).toBe(30);
+			expect(result[0].amountAfterDiscounts).toBe(30);
 		});
 
 		test("zero amount line item is skipped", () => {
@@ -235,7 +235,7 @@ describe(chalk.yellowBright("applyPercentOffDiscountToLineItems"), () => {
 			});
 
 			// 0 * 50% = 0, so itemDiscount is 0 and item is returned unchanged
-			expect(result[0].finalAmount).toBe(0);
+			expect(result[0].amountAfterDiscounts).toBe(0);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
diff --git a/server/tests/unit/billing/stripe/discounts/apply-stripe-discounts-to-line-items.spec.ts b/server/tests/unit/billing/stripe/discounts/apply-stripe-discounts-to-line-items.spec.ts
index 4fe7f2a57..4a95ce686 100644
--- a/server/tests/unit/billing/stripe/discounts/apply-stripe-discounts-to-line-items.spec.ts
+++ b/server/tests/unit/billing/stripe/discounts/apply-stripe-discounts-to-line-items.spec.ts
@@ -38,7 +38,7 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 			});
 
 			expect(result).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(100);
+			expect(result[0].amountAfterDiscounts).toBe(100);
 			expect(result[0].discounts).toHaveLength(0);
 		});
 	});
@@ -55,7 +55,7 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			expect(result[0].finalAmount).toBe(75); // 100 - 25
+			expect(result[0].amountAfterDiscounts).toBe(75); // 100 - 25
 			expect(result[0].discounts).toHaveLength(1);
 			expect(result[0].discounts[0].amountOff).toBe(25);
 			expect(result[0].discounts[0].percentOff).toBe(25);
@@ -70,7 +70,7 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			expect(result[0].finalAmount).toBe(85); // 100 - 15
+			expect(result[0].amountAfterDiscounts).toBe(85); // 100 - 15
 			expect(result[0].discounts).toHaveLength(1);
 			expect(result[0].discounts[0].amountOff).toBe(15);
 		});
@@ -90,12 +90,12 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 			});
 
 			// Multiplicative stacking:
-			// First discount: 100 * 10% = 10, finalAmount = 90
-			// Second discount: 90 * 20% = 18, finalAmount = 72
+			// First discount: 100 * 10% = 10, amountAfterDiscounts = 90
+			// Second discount: 90 * 20% = 18, amountAfterDiscounts = 72
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(10);
 			expect(result[0].discounts[1].amountOff).toBe(18);
-			expect(result[0].finalAmount).toBe(72);
+			expect(result[0].amountAfterDiscounts).toBe(72);
 		});
 
 		test("percent then amount discounts stack correctly", () => {
@@ -110,12 +110,12 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			// First: 100 * 20% = 20, finalAmount = 80
-			// Second: + $10, total = 30, finalAmount = 70
+			// First: 100 * 20% = 20, amountAfterDiscounts = 80
+			// Second: + $10, total = 30, amountAfterDiscounts = 70
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(20);
 			expect(result[0].discounts[1].amountOff).toBe(10);
-			expect(result[0].finalAmount).toBe(70);
+			expect(result[0].amountAfterDiscounts).toBe(70);
 		});
 
 		test("percent applied before amount regardless of input order", () => {
@@ -130,14 +130,14 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			// Percent always applied first: 100 * 20% = 20, finalAmount = 80
-			// Amount applied second: + $10, total = 30, finalAmount = 70
+			// Percent always applied first: 100 * 20% = 20, amountAfterDiscounts = 80
+			// Amount applied second: + $10, total = 30, amountAfterDiscounts = 70
 			// Discounts array order: percent first, then amount
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(20); // percent discount
 			expect(result[0].discounts[0].percentOff).toBe(20);
 			expect(result[0].discounts[1].amountOff).toBe(10); // amount discount
-			expect(result[0].finalAmount).toBe(70);
+			expect(result[0].amountAfterDiscounts).toBe(70);
 		});
 	});
 
@@ -162,12 +162,12 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 			expect(result[0].discounts).toHaveLength(2);
 			expect(result[0].discounts[0].amountOff).toBe(8); // 10%
 			expect(result[0].discounts[1].amountOff).toBe(8); // $10 * 80%
-			expect(result[0].finalAmount).toBe(64);
+			expect(result[0].amountAfterDiscounts).toBe(64);
 
 			expect(result[1].discounts).toHaveLength(2);
 			expect(result[1].discounts[0].amountOff).toBe(2); // 10%
 			expect(result[1].discounts[1].amountOff).toBe(2); // $10 * 20%
-			expect(result[1].finalAmount).toBe(16);
+			expect(result[1].amountAfterDiscounts).toBe(16);
 		});
 	});
 
@@ -194,8 +194,8 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			expect(result[0].finalAmount).toBe(50); // Discounted
-			expect(result[1].finalAmount).toBe(100); // Not discounted
+			expect(result[0].amountAfterDiscounts).toBe(50); // Discounted
+			expect(result[1].amountAfterDiscounts).toBe(100); // Not discounted
 		});
 
 		test("amount discount applies to restricted products only", () => {
@@ -220,8 +220,8 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 				discounts: discountList,
 			});
 
-			expect(result[0].finalAmount).toBe(100); // Not discounted
-			expect(result[1].finalAmount).toBe(80); // Discounted
+			expect(result[0].amountAfterDiscounts).toBe(100); // Not discounted
+			expect(result[1].amountAfterDiscounts).toBe(80); // Discounted
 		});
 
 		test("mixed discounts with different applies_to", () => {
@@ -251,11 +251,11 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 
 			// prod_a: 20% off = $20, final = 80
 			expect(result[0].discounts).toHaveLength(1);
-			expect(result[0].finalAmount).toBe(80);
+			expect(result[0].amountAfterDiscounts).toBe(80);
 
 			// prod_b: $10 off, final = 90
 			expect(result[1].discounts).toHaveLength(1);
-			expect(result[1].finalAmount).toBe(90);
+			expect(result[1].amountAfterDiscounts).toBe(90);
 		});
 	});
 
@@ -273,9 +273,9 @@ describe(chalk.yellowBright("applyStripeDiscountsToLineItems"), () => {
 			});
 
 			// Refunds are skipped by discountAppliesToLineItem
-			// finalAmount stays at -100, no discounts applied
+			// amountAfterDiscounts stays at -100, no discounts applied
 			expect(result[0].discounts).toHaveLength(0);
-			expect(result[0].finalAmount).toBe(-100);
+			expect(result[0].amountAfterDiscounts).toBe(-100);
 		});
 	});
 });
diff --git a/server/tests/utils/fixtures/db/lineItems.ts b/server/tests/utils/fixtures/db/lineItems.ts
index 5fd8f2d06..2bc997bf8 100644
--- a/server/tests/utils/fixtures/db/lineItems.ts
+++ b/server/tests/utils/fixtures/db/lineItems.ts
@@ -10,14 +10,14 @@ import type { LineItem } from "@autumn/shared";
  * @param direction - "charge" or "refund" (default: inferred from amount sign)
  * @param stripeProductId - Optional Stripe product ID for applies_to matching
  * @param discounts - Existing discounts on this line item
- * @param finalAmount - Override finalAmount (default: same as amount)
+ * @param amountAfterDiscounts - Override amountAfterDiscounts (default: same as amount)
  */
 const create = ({
 	amount,
 	direction,
 	stripeProductId,
 	discounts = [],
-	finalAmount,
+	amountAfterDiscounts,
 	description = "Test line item",
 	chargeImmediately = true,
 }: {
@@ -25,12 +25,12 @@ const create = ({
 	direction?: "charge" | "refund";
 	stripeProductId?: string;
 	discounts?: LineItem["discounts"];
-	finalAmount?: number;
+	amountAfterDiscounts?: number;
 	description?: string;
 	chargeImmediately?: boolean;
 }): LineItem => ({
 	amount,
-	finalAmount: finalAmount ?? amount,
+	amountAfterDiscounts: amountAfterDiscounts ?? amount,
 	description,
 	discounts,
 	chargeImmediately,
@@ -53,19 +53,19 @@ const charge = ({
 	amount = 100,
 	stripeProductId,
 	discounts = [],
-	finalAmount,
+	amountAfterDiscounts,
 }: {
 	amount?: number;
 	stripeProductId?: string;
 	discounts?: LineItem["discounts"];
-	finalAmount?: number;
+	amountAfterDiscounts?: number;
 } = {}): LineItem =>
 	create({
 		amount: Math.abs(amount),
 		direction: "charge",
 		stripeProductId,
 		discounts,
-		finalAmount,
+		amountAfterDiscounts,
 	});
 
 /**
@@ -76,19 +76,19 @@ const refund = ({
 	amount = 100,
 	stripeProductId,
 	discounts = [],
-	finalAmount,
+	amountAfterDiscounts,
 }: {
 	amount?: number;
 	stripeProductId?: string;
 	discounts?: LineItem["discounts"];
-	finalAmount?: number;
+	amountAfterDiscounts?: number;
 } = {}): LineItem =>
 	create({
 		amount: -Math.abs(amount),
 		direction: "refund",
 		stripeProductId,
 		discounts,
-		finalAmount,
+		amountAfterDiscounts,
 	});
 
 /**
@@ -128,7 +128,7 @@ const withExistingDiscount = ({
 	stripeProductId?: string;
 }): LineItem => {
 	const existingDiscount = { amountOff: existingDiscountAmount };
-	const adjustedFinalAmount =
+	const adjustedAmountAfterDiscounts =
 		direction === "charge"
 			? amount - existingDiscountAmount
 			: amount + existingDiscountAmount;
@@ -138,7 +138,7 @@ const withExistingDiscount = ({
 		direction,
 		stripeProductId,
 		discounts: [existingDiscount],
-		finalAmount: adjustedFinalAmount,
+		amountAfterDiscounts: adjustedAmountAfterDiscounts,
 	});
 };
 
diff --git a/shared/models/billingModels/lineItem/lineItem.ts b/shared/models/billingModels/lineItem/lineItem.ts
index 05bb84339..1e7aad19a 100644
--- a/shared/models/billingModels/lineItem/lineItem.ts
+++ b/shared/models/billingModels/lineItem/lineItem.ts
@@ -13,7 +13,7 @@ export const LineItemSchema = z
 		amount: z.number(),
 
 		discounts: z.array(LineItemDiscountSchema).default([]),
-		finalAmount: z.number().default(0),
+		amountAfterDiscounts: z.number().default(0),
 
 		description: z.string(),
 
@@ -35,7 +35,7 @@ export const LineItemSchema = z
 	.transform((data) => {
 		return {
 			...data,
-			finalAmount: data.amount,
+			amountAfterDiscounts: data.amount,
 		};
 	});
 
diff --git a/shared/models/billingModels/lineItem/lineItemContext.ts b/shared/models/billingModels/lineItem/lineItemContext.ts
index 4636cf748..7e769d49b 100644
--- a/shared/models/billingModels/lineItem/lineItemContext.ts
+++ b/shared/models/billingModels/lineItem/lineItemContext.ts
@@ -19,6 +19,7 @@ export const LineItemContextSchema = z.object({
 	direction: z.enum(["charge", "refund"]),
 	now: z.number(),
 	billingTiming: z.enum(["in_arrear", "in_advance"]),
+	discountable: z.boolean().optional(), // If true, let Stripe auto-apply discounts to this line item
 });
 
 export type BillingPeriod = z.infer<typeof BillingPeriodSchema>;
diff --git a/shared/utils/billingUtils/invoicingUtils/lineItemBuilders/usagePriceToLineItem.ts b/shared/utils/billingUtils/invoicingUtils/lineItemBuilders/usagePriceToLineItem.ts
index aa5e9304c..b8360e3a4 100644
--- a/shared/utils/billingUtils/invoicingUtils/lineItemBuilders/usagePriceToLineItem.ts
+++ b/shared/utils/billingUtils/invoicingUtils/lineItemBuilders/usagePriceToLineItem.ts
@@ -27,6 +27,7 @@ export const usagePriceToLineItem = ({
 		shouldProrateOverride?: boolean;
 		chargeImmediatelyOverride?: boolean;
 		includePeriodDescription?: boolean;
+		discountable?: boolean;
 	};
 }) => {
 	const cusPrice = cusEntToCusPrice({ cusEnt });
@@ -75,6 +76,7 @@ export const usagePriceToLineItem = ({
 		...context,
 		price: cusPrice.price,
 		feature: cusEnt.entitlement.feature,
+		discountable: options.discountable ?? false,
 	};
 
 	// 3. Generate description
@@ -98,7 +100,7 @@ export const usagePriceToLineItem = ({
 		options.shouldProrateOverride ?? !isConsumablePrice(price);
 
 	return buildLineItem({
-		context,
+		context: lineItemContext,
 		amount,
 		description,