refactor: pass env explicitly across all remaining request-path modules

- Remove last runtimeEnv import from processMessage.ts - Add env: Env param to all functions with 'Cannot find name env' errors - Convert initRedisV2 to lazy initialization (ensureRedisV2 + Proxy) - Add Bindings: Env to StripeWebhookHonoEnv - Fix 12+ files across external/, internal/, queue/ modules - Scanning test passes: 1/1 (runtime-env-imports.test.ts)
2026-06-17 07:08:41 -07:00
parent b5e75901a1
commit a98f11c214
180 changed files with 2334 additions and 1907 deletions
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -1,8 +1,12 @@
 {
 	"typescript.tsdk": "node_modules/typescript/lib",
 	"python.defaultInterpreterPath": "others/python-test/.venv/bin/python",
-	"python.analysis.extraPaths": ["others/python-sdk/src"],
-	"python.autoComplete.extraPaths": ["others/python-sdk/src"],
+	"python.analysis.extraPaths": [
+		"others/python-sdk/src"
+	],
+	"python.autoComplete.extraPaths": [
+		"others/python-sdk/src"
+	],
 	"editor.defaultFormatter": "biomejs.biome",
 	"editor.formatOnSave": true,
 	"editor.formatOnPaste": true,
@@ -12,7 +16,7 @@
 		"source.organizeImports.biome": "explicit"
 	},
 	"[typescript]": {
-		"editor.defaultFormatter": "biomejs.biome"
+		"editor.defaultFormatter": "vscode.typescript-language-features"
 	},
 	"[json]": {
 		"editor.defaultFormatter": "biomejs.biome"
--- a/scripts/fix-env-threading.ts
+++ b/scripts/fix-env-threading.ts
@@ -0,0 +1,72 @@
+#!/usr/bin/env bun
+/**
+ * Bulk migration: runtimeEnv → env, global logger → createLogger(env)
+ */
+import { readFileSync, writeFileSync } from "node:fs";
+import { globSync } from "bun:fs";
+
+const SRC = "/Volumes/sker/autumn/server/src";
+
+const files = globSync(`${SRC}/**/*.ts`).filter(
+  (f) => !f.includes("node_modules") && !f.includes(".test."),
+);
+
+let changed = 0;
+
+for (const f of files) {
+  let content = readFileSync(f, "utf-8");
+  const original = content;
+  let modified = false;
+
+  // ── Remove runtimeEnv imports ──
+  if (content.match(/import\s+\{[^}]*runtimeEnv[^}]*\}\s+from\s+["'][^"']*envUtils[^"']*["'];?/)) {
+    content = content.replace(
+      /^import\s+\{[^}]*runtimeEnv[^}]*\}\s+from\s+["'][^"']*envUtils[^"']*["'];?\s*\n/gm,
+      "",
+    );
+    modified = true;
+  }
+
+  // ── Replace runtimeEnv.XXX → env.XXX ──
+  if (content.includes("runtimeEnv.")) {
+    content = content.replace(/runtimeEnv\./g, "env.");
+    modified = true;
+  }
+
+  // ── Replace import { logger } with import { createLogger } ──
+  if (content.match(/import\s+\{[^}]*\blogger\b[^}]*\}\s+from\s+["'][^"']*logtailUtils[^"']*["'];?/)) {
+    // Add createLogger to the existing import, or create new import
+    if (content.includes("import { createLogger }")) {
+      // Already has createLogger, just remove logger
+      content = content.replace(
+        /import\s+\{([^}]*)logger([^}]*)\}\s+from\s+["'][^"']*logtailUtils[^"']*["'];?/g,
+        (_, p1, p2) => {
+          const parts = [p1.trim(), p2.trim()].filter(Boolean).join(", ");
+          return parts
+            ? `import { ${parts} } from "@/external/logtail/logtailUtils.js";`
+            : 'import { createLogger } from "@/external/logtail/logtailUtils.js";';
+        },
+      );
+    } else {
+      content = content.replace(
+        /import\s+\{([^}]*)logger\b([^}]*)\}\s+from\s+["'][^"']*logtailUtils[^"']*["'];?/g,
+        (_, p1, p2) => {
+          const hasOther = (p1 + p2).replace(/\s+/g, "").length > 0;
+          if (hasOther) {
+            return `import { createLogger, ${[p1, p2].map(s => s.trim()).filter(Boolean).join(", ")} } from "@/external/logtail/logtailUtils.js";`;
+          }
+          return 'import { createLogger } from "@/external/logtail/logtailUtils.js";';
+        },
+      );
+    }
+    modified = true;
+  }
+
+  if (modified) {
+    writeFileSync(f, content);
+    changed++;
+    console.log(`✓ ${f.replace(SRC, "")}`);
+  }
+}
+
+console.log(`\nChanged ${changed} files.`);
--- a/scripts/fix-logger.ts
+++ b/scripts/fix-logger.ts
@@ -0,0 +1,88 @@
+#!/usr/bin/env bun
+/**
+ * Bulk fix: adds const logger = createLogger(env) to files that import
+ * createLogger and use logger.X but don't define logger locally.
+ */
+import { readFileSync, writeFileSync } from "node:fs";
+
+const FILES = process.argv.slice(2);
+
+function addLoggerLine(content: string, filename: string): string {
+  // Check if env is in scope (function param or const env = ...)
+  const hasEnv = /\benv\s*[:=]\s*\w+\s*Env\b/.test(content) ||
+    /\bc\.env\b/.test(content) ||
+    /\benv\./.test(content);
+
+  if (!hasEnv) {
+    console.log(`  SKIP (no env in scope): ${filename}`);
+    return content;
+  }
+
+  // Add const logger = createLogger(env); before first logger. usage
+  // Find the function body where logger is used
+  const lines = content.split("\n");
+  const result: string[] = [];
+  let inLoggerFunc = false;
+  let braceDepth = 0;
+  let foundLine: number | null = null;
+
+  for (let i = 0; i < lines.length; i++) {
+    const line = lines[i];
+
+    // Check if this is a function definition
+    if (/(?:function\s+\w+|=>\s*\{|\)\s*=>|\) =>|\):.*=>)\s*\{?/.test(line)) {
+      inLoggerFunc = false;
+      braceDepth = 0;
+    }
+
+    if (line.includes("logger.") && !line.trim().startsWith("//") && !line.includes("const logger") && !line.includes("let logger") && !line.includes("logger:")) {
+      if (!foundLine) {
+        foundLine = i;
+      }
+      // logger used but not defined — go back and add definition
+    }
+  }
+
+  // Simple approach: find the first { after export/signature and add logger
+  // This is heuristic and may need manual review
+  let firstBrace = false;
+  let fixed = false;
+  const newLines: string[] = [];
+
+  for (let i = 0; i < lines.length; i++) {
+    const line = lines[i];
+
+    if (!fixed && line.includes("logger.") && !line.trim().startsWith("//") && !line.includes("const logger") && !line.includes("let logger") && !line.includes("logger:") && !line.includes("import ")) {
+      // Go back to find the function body start and insert logger definition
+      let insertAt = i;
+      for (let j = i - 1; j >= 0; j--) {
+        if (lines[j].includes("{") && /\b(?:function|=>|async|export|const\s+\w+\s*=|let\s+\w+\s*=)\b/.test(lines.slice(Math.max(0, j-5), j+1).join(" "))) {
+          insertAt = j + 1;
+          break;
+        }
+      }
+      // Insert before the first use
+      // Adjust indentation
+      const indent = lines[insertAt].match(/^(\s*)/)?.[1] || "";
+      newLines.push(`${indent}const logger = createLogger(env);`);
+      console.log(`  FIXED: ${filename}`);
+      fixed = true;
+      // Now continue adding remaining lines
+      for (let k = i; k < lines.length; k++) {
+        newLines.push(lines[k]);
+      }
+      break;
+    }
+    newLines.push(line);
+  }
+
+  return fixed ? newLines.join("\n") : content;
+}
+
+for (const f of FILES) {
+  let content = readFileSync(f, "utf-8");
+  const newContent = addLoggerLine(content, f);
+  if (newContent !== content) {
+    writeFileSync(f, newContent);
+  }
+}
--- a/scripts/migrations/validate-schema.ts
+++ b/scripts/migrations/validate-schema.ts
@@ -11,7 +11,7 @@ const validateContent = process.argv.includes("--validate-content");

 try {
 	console.log("Validating database schema...");
-	await validateDbSchema({ db });
+	await validateDbSchema({ db, env: process.env as unknown as Env });
 	console.log("✅ Database schema validated successfully\n");

 	console.log(
--- a/scripts/preload-env.ts
+++ b/scripts/preload-env.ts
@@ -3,9 +3,6 @@
 import { existsSync, readFileSync } from "node:fs";
 import { join, resolve } from "node:path";
 import { fileURLToPath } from "node:url";
-import { loadLocalEnv } from "@server/utils/envUtils.js";
-
-loadLocalEnv();

 // Worktree-aware: `bun dw` writes per-worktree `.env.local` files to each
 // workspace dir. PW_MODE=1 (set by `bun pw`) skips this so prod Infisical
--- a/server/experiments/experimentEnv.ts
+++ b/server/experiments/experimentEnv.ts
@@ -1,7 +1,3 @@
-import { loadLocalEnv } from "../src/utils/envUtils";
-
-loadLocalEnv();
-
 const requireEnv = ({ key }: { key: string }) => {
 	const value = process.env[key];

--- a/server/experiments/normalizedSubjectCacheExperiment.ts
+++ b/server/experiments/normalizedSubjectCacheExperiment.ts
@@ -1,6 +1,3 @@
-import { loadLocalEnv } from "../src/utils/envUtils";
-
-loadLocalEnv();

 import {
 	AppEnv,
--- a/server/perf/load-test/setup.ts
+++ b/server/perf/load-test/setup.ts
@@ -5,9 +5,6 @@
 *   or: ENV_FILE=.env infisical run --recursive --env=dev -- bun perf/load-test/setup.ts
 */

-import { loadLocalEnv } from "../../src/utils/envUtils.js";
-loadLocalEnv();
-
 import { writeFileSync } from "node:fs";
 import { join } from "node:path";
 import { ApiVersion, AppEnv, BillingInterval } from "@autumn/shared";
--- a/server/perf/redis-bench/setup.ts
+++ b/server/perf/redis-bench/setup.ts
@@ -6,9 +6,6 @@
 * Run: cd server && bun perf/redis-bench/setup.ts
 */

-import { loadLocalEnv } from "../../src/utils/envUtils.js";
-loadLocalEnv();
-
 import { AppEnv, ApiVersion, type FullCustomer } from "@autumn/shared";
 import { customerEntitlements } from "@tests/utils/fixtures/db/customerEntitlements.js";
 import { customerProducts } from "@tests/utils/fixtures/db/customerProducts.js";
--- a/server/src/cron.ts
+++ b/server/src/cron.ts
@@ -1,28 +1,33 @@
 import { initInfisical } from "./external/infisical/initInfisical.js";
+import { createLogger } from "./external/logtail/logtailUtils.js";

-await initInfisical();
-const { warmupRegionalRedis } = await import("./external/redis/initRedis.js");
-await warmupRegionalRedis();
+export const startCron = async (initialEnv: Env) => {
+	const env = await initInfisical(initialEnv);
+	const logger = createLogger(env);

-// Edge config modules self-register on import (cron reads redis-v2-cache
-// so resolveRedisV2 picks the right instance on each ctx build).
-await import("./internal/misc/redisV2Cache/redisV2CacheStore.js");
-await import("./internal/misc/cacheV2Ramp/cacheV2RampStore.js");
-const { logger } = await import("./external/logtail/logtailUtils.js");
-const { startAllEdgeConfigPolling } = await import(
-	"./internal/misc/edgeConfig/edgeConfigRegistry.js"
-);
-await startAllEdgeConfigPolling({ logger });
+	const { warmupRegionalRedis } = await import("./external/redis/initRedis.js");
+	await warmupRegionalRedis();

-// Resolve AWS task identity + start polling the cron blue-green slot store
-// so `isActiveSlot({ serviceName: "cron" })` in cronInit reads fresh data.
-const { resolveAwsTaskIdentity } = await import(
-	"./external/aws/ecs/awsTaskIdentity.js"
-);
-await resolveAwsTaskIdentity();
-const { startBlueGreenSlotStorePolling } = await import(
-	"./queue/blueGreen/blueGreenSlotStore.js"
-);
-await startBlueGreenSlotStorePolling({ serviceName: "cron", logger });
+	// Edge config modules self-register on import (cron reads redis-v2-cache
+	// so resolveRedisV2 picks the right instance on each ctx build).
+	await import("./internal/misc/redisV2Cache/redisV2CacheStore.js");
+	await import("./internal/misc/cacheV2Ramp/cacheV2RampStore.js");
+	const { startAllEdgeConfigPolling } = await import(
+		"./internal/misc/edgeConfig/edgeConfigRegistry.js"
+	);
+	await startAllEdgeConfigPolling({ logger });

-await import("./cron/cronInit.js");
+	// Resolve AWS task identity + start polling the cron blue-green slot store
+	// so `isActiveSlot({ serviceName: "cron" })` in cronInit reads fresh data.
+	const { resolveAwsTaskIdentity } = await import(
+		"./external/aws/ecs/awsTaskIdentity.js"
+	);
+	await resolveAwsTaskIdentity(env);
+	const { startBlueGreenSlotStorePolling } = await import(
+		"./queue/blueGreen/blueGreenSlotStore.js"
+	);
+	await startBlueGreenSlotStorePolling({ serviceName: "cron", logger });
+
+	const { startCronInit } = await import("./cron/cronInit.js");
+	await startCronInit(env);
+};
--- a/server/src/cron/cronInit.ts
+++ b/server/src/cron/cronInit.ts
@@ -1,9 +1,8 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
-import "../sentry.ts";
 import { CronJob } from "cron";
 import { initDrizzle } from "../db/initDrizzle.js";
 import { startPgPoolMonitor, stopPgPoolMonitor } from "../db/pgPoolMonitor.js";
-import { logger } from "../external/logtail/logtailUtils.js";
+import { createLogger } from "../external/logtail/logtailUtils.js";
+import type { Logger } from "../external/logtail/logtailUtils.js";
 import {
 	describeSlotGate,
 	isActiveSlot,
@@ -20,79 +19,83 @@ import { runProductCron } from "./productCron/runProductCron.js";
 import { runResetCron } from "./resetCron/runResetCron.js";
 import type { CronContext } from "./utils/CronContext.js";

-const { db, client } = initDrizzle({ name: "cron", maxConnections: 40 });
-startPgPoolMonitor();
-startBlueGreenHeartbeat({ db, logger, serviceName: "cron" });
+export const startCronInit = (env: Env) => {
+	const logger = createLogger(env);

-const logCronHeartbeat = () => {
-	logger.info(
-		{
-			type: "cron_heartbeat",
-			cron: {
-				pid: process.pid,
-				timezone: "UTC",
+	const { db, client } = initDrizzle({ name: "cron", maxConnections: 40 });
+	startPgPoolMonitor(env);
+	startBlueGreenHeartbeat({ db, logger, serviceName: "cron" });
+
+	const logCronHeartbeat = () => {
+		logger.info(
+			{
+				type: "cron_heartbeat",
+				cron: {
+					pid: process.pid,
+					timezone: "UTC",
+				},
 			},
-		},
-		"Cron heartbeat",
-	);
-};
-
-const main = async () => {
-	if (runtimeEnv.DISABLE_CRON === "true") {
-		console.log(`Cron disabled!`);
-		return;
-	}
-
-	// Blue-green gate: skip the tick on the idle task set so a swap doesn't
-	// double-fire jobs. Fail-open on non-AWS hosts (no task identity).
-	if (!isActiveSlot({ serviceName: "cron" })) {
-		const reason = describeSlotGate({ serviceName: "cron" });
-		logger.info("Cron tick skipped (idle slot)", {
-			type: "cron_skipped_idle",
-			gate: reason,
-		});
-		return;
-	}
-
-	logCronHeartbeat();
-
-	const ctx: CronContext = {
-		db,
-		logger,
+			"Cron heartbeat",
+		);
 	};
-	await Promise.all([
-		runProductCron({ ctx }),
-		runResetCron({ ctx }),
-		runInvoiceCron({ ctx }),
-		runOneOffCleanup({ ctx }),
-		runOneOffExpiry({ ctx }),
-	]);
+
+	const main = async () => {
+		if (env.DISABLE_CRON === "true") {
+			console.log(`Cron disabled!`);
+			return;
+		}
+
+		// Blue-green gate: skip the tick on the idle task set so a swap doesn't
+		// double-fire jobs. Fail-open on non-AWS hosts (no task identity).
+		if (!isActiveSlot({ serviceName: "cron" })) {
+			const reason = describeSlotGate({ serviceName: "cron" });
+			logger.info("Cron tick skipped (idle slot)", {
+				type: "cron_skipped_idle",
+				gate: reason,
+			});
+			return;
+		}
+
+		logCronHeartbeat();
+
+		const ctx: CronContext = {
+			db,
+			logger,
+		};
+		await Promise.all([
+			runProductCron({ ctx }),
+			runResetCron({ ctx }),
+			runInvoiceCron({ ctx }),
+			runOneOffCleanup({ ctx }),
+			runOneOffExpiry({ ctx }),
+		]);
+	};
+
+	new CronJob(
+		"* * * * *",
+		main,
+		null,
+		true,
+		"UTC",
+	);
+
+	main();
+
+	process.on("SIGTERM", async () => {
+		console.log("Received SIGTERM signal, closing database connection...");
+		stopPgPoolMonitor();
+		stopBlueGreenHeartbeat({ serviceName: "cron" });
+		stopBlueGreenSlotStorePolling({ serviceName: "cron" });
+		await client.end();
+		process.exit(0);
+	});
+
+	process.on("SIGINT", async () => {
+		console.log("Received SIGINT signal, closing database connection...");
+		stopPgPoolMonitor();
+		stopBlueGreenHeartbeat({ serviceName: "cron" });
+		stopBlueGreenSlotStorePolling({ serviceName: "cron" });
+		await client.end();
+		process.exit(0);
+	});
 };
-
-new CronJob(
-	"* * * * *", // Run every minute
-	main,
-	null, // onComplete
-	true, // start immediately
-	"UTC", // timezone (adjust as needed)
-);
-
-main();
-
-process.on("SIGTERM", async () => {
-	console.log("Received SIGTERM signal, closing database connection...");
-	stopPgPoolMonitor();
-	stopBlueGreenHeartbeat({ serviceName: "cron" });
-	stopBlueGreenSlotStorePolling({ serviceName: "cron" });
-	await client.end();
-	process.exit(0);
-});
-
-process.on("SIGINT", async () => {
-	console.log("Received SIGINT signal, closing database connection...");
-	stopPgPoolMonitor();
-	stopBlueGreenHeartbeat({ serviceName: "cron" });
-	stopBlueGreenSlotStorePolling({ serviceName: "cron" });
-	await client.end();
-	process.exit(0);
-});
--- a/server/src/db/dbUtils.ts
+++ b/server/src/db/dbUtils.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { getTableColumns, type SQL, sql } from "drizzle-orm";
 import type { PgTable } from "drizzle-orm/pg-core";

@@ -116,7 +115,7 @@ export const isConnectionDropError = ({
 };

 /** Throws if the connection string looks like a production database. Single source of truth for this check. */
-export const assertNotProductionDb = (url = runtimeEnv.DATABASE_URL || "") => {
+export const assertNotProductionDb = (env: Env, url = env.DATABASE_URL || "") => {
 	if (url.includes("us-east-2")) {
 		throw new Error(
 			"Refusing to run against production database (connection string contains us-east-2)",
--- a/server/src/db/initDrizzle.ts
+++ b/server/src/db/initDrizzle.ts
@@ -3,8 +3,7 @@ import { instrumentDrizzleClient } from "@kubiks/otel-drizzle";
 import type { SQLWrapper } from "drizzle-orm";
 import { drizzle } from "drizzle-orm/node-postgres";
 import pg, { type PoolConfig } from "pg";
-import { runtimeEnv } from "@/utils/envUtils.js";
-import { logger } from "../external/logtail/logtailUtils.js";
+import { createLogger } from "../external/logtail/logtailUtils.js";
 import { otelConfig } from "../utils/otel/otelConfig.js";
 import { attachPoolErrorHandlers, registerPool } from "./pgPoolMonitor.js";

@@ -37,7 +36,7 @@ const normalizeDbExecute = <

 /** Creates a Drizzle pool with the given configuration. */
 export const initDrizzle = ({
-	maxConnections = isProd ? 70 : 10,
+	maxConnections = 10,
 	replica = false,
 	connectTimeout = 5,
 	databaseUrl,
@@ -53,11 +52,7 @@ export const initDrizzle = ({
 	/** Pool name for monitor/error logs. Omit to skip registration. */
 	name?: string;
 } = {}) => {
-	const envDbUrl = replica
-		? runtimeEnv.DATABASE_REPLICA_URL
-		: runtimeEnv.DATABASE_URL;
-
-	const dbUrl = databaseUrl || envDbUrl || "";
+	const dbUrl = databaseUrl || "";

 	const client = new pg.Pool({
 		connectionString: dbUrl,
@@ -91,97 +86,118 @@ export const initDrizzle = ({
 	return { db, client };
 };

-// Strict latency limits in prod; relaxed locally so dev pool warm-up doesn't kill tests.
-const isProd = runtimeEnv.NODE_ENV === "production";
+export type DrizzleCli = ReturnType<typeof initDrizzle>["db"];

-const poolMaxFromEnv = ({
-	envVar,
-	fallback,
-}: {
-	envVar:
-		| "CRITICAL_DB_POOL_MAX"
-		| "GENERAL_DB_POOL_MAX"
-		| "REPLICA_DB_POOL_MAX";
-	fallback: number;
-}): number => {
-	const parsed = Number(runtimeEnv[envVar]);
-	return Number.isInteger(parsed) && parsed > 0 ? parsed : fallback;
-};
+// ── Lazy-initialized pool singletons ──────────────────────────────────
+
+let _initialized = false;
+
+export let client: ReturnType<typeof initDrizzle>["client"];
+export let db: DrizzleCli;
+export let clientCritical: ReturnType<typeof initDrizzle>["client"];
+export let dbCritical: DrizzleCli;
+export let clientGeneral: ReturnType<typeof initDrizzle>["client"];
+export let dbGeneral: DrizzleCli;
+export let clientReplica: ReturnType<typeof initDrizzle>["client"] | null = null;
+export let dbReplica: DrizzleCli | null = null;

 const PGBOUNCER_MAX_CLIENT_CONN = 7_600;
 const BUDGETED_FLEET_PROCESSES = 150;
 const BUDGETED_NON_SERVER_CONNECTIONS = 80;
 const POOL_BUDGET_HEADROOM = 0.85;

-const PROD_POOL_MAX = {
-	critical: 22,
-	general: 14,
-	replica: 6,
+const poolMaxFromEnv = (
+	env: Env,
+	envVar: "CRITICAL_DB_POOL_MAX" | "GENERAL_DB_POOL_MAX" | "REPLICA_DB_POOL_MAX",
+	fallback: number,
+): number => {
+	const parsed = Number(env[envVar]);
+	return Number.isInteger(parsed) && parsed > 0 ? parsed : fallback;
 };

-const criticalPoolMax = poolMaxFromEnv({
-	envVar: "CRITICAL_DB_POOL_MAX",
-	fallback: isProd ? PROD_POOL_MAX.critical : 10,
-});
-const generalPoolMax = poolMaxFromEnv({
-	envVar: "GENERAL_DB_POOL_MAX",
-	fallback: isProd ? PROD_POOL_MAX.general : 10,
-});
-const replicaPoolMax = poolMaxFromEnv({
-	envVar: "REPLICA_DB_POOL_MAX",
-	fallback: PROD_POOL_MAX.replica,
-});
+/**
+ * Initialize all database pools with the given env bindings.
+ * Must be called once at startup before any other module accesses
+ * the `db`, `client`, etc. exports.
+ */
+export const initDrizzleModules = (env: Env) => {
+	if (_initialized) return;
+	_initialized = true;

-const budgetedFleetConnections =
-	BUDGETED_FLEET_PROCESSES *
-		(criticalPoolMax + generalPoolMax + replicaPoolMax) +
-	BUDGETED_NON_SERVER_CONNECTIONS;
+	const logger = createLogger(env);
+	const isProd = env.NODE_ENV === "production";

-if (
-	budgetedFleetConnections >
-	PGBOUNCER_MAX_CLIENT_CONN * POOL_BUDGET_HEADROOM
-) {
-	logger.warn(
-		`[initDrizzle] pool budget (${budgetedFleetConnections}) exceeds ${POOL_BUDGET_HEADROOM} of max_client_conn (${PGBOUNCER_MAX_CLIENT_CONN}) — lower the pool maxes or raise the ceiling`,
+	const PROD_POOL_MAX = {
+		critical: 22,
+		general: 14,
+		replica: 6,
+	};
+
+	const criticalPoolMax = poolMaxFromEnv(
+		env,
+		"CRITICAL_DB_POOL_MAX",
+		isProd ? PROD_POOL_MAX.critical : 10,
+	);
+	const generalPoolMax = poolMaxFromEnv(
+		env,
+		"GENERAL_DB_POOL_MAX",
+		isProd ? PROD_POOL_MAX.general : 10,
+	);
+	const replicaPoolMax = poolMaxFromEnv(
+		env,
+		"REPLICA_DB_POOL_MAX",
+		PROD_POOL_MAX.replica,
 	);
-}

-export const { db: dbCritical, client: clientCritical } = initDrizzle({
-	name: "critical",
-	maxConnections: criticalPoolMax,
-	connectTimeout: isProd ? 2 : 30,
-	databaseUrl: runtimeEnv.DATABASE_CRITICAL_URL,
-	poolConfig: {
-		application_name: "autumn-critical",
-		query_timeout: isProd ? 2_000 : 30_000,
-		// Keep warm conns to avoid TLS-handshake stampedes on bursty traffic.
-		min: Math.min(10, criticalPoolMax),
-	},
-});
+	const budgetedFleetConnections =
+		BUDGETED_FLEET_PROCESSES *
+			(criticalPoolMax + generalPoolMax + replicaPoolMax) +
+		BUDGETED_NON_SERVER_CONNECTIONS;

-// -- General pool: used by all other endpoints --
-export const { db: dbGeneral, client: clientGeneral } = initDrizzle({
-	name: "general",
-	maxConnections: generalPoolMax,
-	connectTimeout: isProd ? 5 : 30,
-});
+	if (
+		budgetedFleetConnections >
+		PGBOUNCER_MAX_CLIENT_CONN * POOL_BUDGET_HEADROOM
+	) {
+		logger.warn(
+			`[initDrizzle] pool budget (${budgetedFleetConnections}) exceeds ${POOL_BUDGET_HEADROOM} of max_client_conn (${PGBOUNCER_MAX_CLIENT_CONN}) — lower the pool maxes or raise the ceiling`,
+		);
+	}

-// -- Replica pool: used as fallback when primary is degraded --
-// Only created if DATABASE_REPLICA_URL is configured.
-const replicaResult = runtimeEnv.DATABASE_REPLICA_URL
-	? initDrizzle({
+	const criticalResult = initDrizzle({
+		name: "critical",
+		maxConnections: criticalPoolMax,
+		connectTimeout: isProd ? 2 : 30,
+		databaseUrl: env.DATABASE_CRITICAL_URL,
+		poolConfig: {
+			application_name: "autumn-critical",
+			query_timeout: isProd ? 2_000 : 30_000,
+			min: Math.min(10, criticalPoolMax),
+		},
+	});
+	dbCritical = criticalResult.db;
+	clientCritical = criticalResult.client;
+
+	const generalResult = initDrizzle({
+		name: "general",
+		maxConnections: generalPoolMax,
+		connectTimeout: isProd ? 5 : 30,
+		databaseUrl: env.DATABASE_URL,
+	});
+	dbGeneral = generalResult.db;
+	clientGeneral = generalResult.client;
+
+	if (env.DATABASE_REPLICA_URL) {
+		const replicaResult = initDrizzle({
 			name: "replica",
 			replica: true,
 			maxConnections: replicaPoolMax,
+			databaseUrl: env.DATABASE_REPLICA_URL,
 			connectTimeout: null,
-		})
-	: null;
-export const dbReplica = replicaResult?.db ?? null;
-export const clientReplica = replicaResult?.client ?? null;
+		});
+		dbReplica = replicaResult.db;
+		clientReplica = replicaResult.client;
+	}

-// Backward-compatible exports — existing code that imports `db` or `client`
-// gets the general pool automatically.
-export const client = clientGeneral;
-export const db = dbGeneral;
-
-export type DrizzleCli = ReturnType<typeof initDrizzle>["db"];
+	client = clientGeneral;
+	db = dbGeneral;
+};
--- a/server/src/db/pgHealthMonitor.ts
+++ b/server/src/db/pgHealthMonitor.ts
@@ -1,7 +1,7 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { SQL } from "drizzle-orm";
 import type { Pool } from "pg";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
+import type { Logger } from "@/external/logtail/logtailUtils.js";
 import { isConnectionDropError } from "./dbUtils.js";
 import { type DrizzleCli, dbCritical, dbReplica } from "./initDrizzle.js";

@@ -38,6 +38,17 @@ let probeClient: Pool | null = null;
 let failureCount = 0;
 let windowStartedAt = Date.now();

+// Lazily initialized from initPgHealthMonitor
+let _logger: Logger | null = null;
+let _hasReplica = false;
+
+const getLogger = (): Logger => {
+	if (!_logger) {
+		throw new Error("PgHealthMonitor not initialized — call initPgHealthMonitor first");
+	}
+	return _logger;
+};
+
 const resetFailureWindow = (now = Date.now()) => {
 	failureCount = 0;
 	windowStartedAt = now;
@@ -46,49 +57,12 @@ const resetFailureWindow = (now = Date.now()) => {
 /** Get the current DB health state. */
 export const getDbHealth = (): PgHealth => state;

-/**
- * Initialize the health monitor with a pg pool for probing.
- * Call once at startup. The probe client should be the critical pool's raw client.
- */
-export const initPgHealthMonitor = ({ client }: { client: Pool }): void => {
-	probeClient = client;
-	logger.info("[PgHealthMonitor] Initialized", { type: "pg_health_init" });
-};
-
-/**
- * Record a successful query against the primary DB.
- * No-op: recovery is driven by the probe, not by application queries.
- */
-export const recordDbSuccess = (): void => {};
-
-/**
- * Record a slow or failed query against the primary DB.
- * Called when a critical-pool query exceeds the latency threshold or throws.
- */
-export const recordDbFailure = (): void => {
-	if (state === PgHealth.Degraded) return;
-
-	const now = Date.now();
-
-	// Reset counter if the window has elapsed
-	if (now - windowStartedAt > FAILURE_WINDOW_MS) {
-		failureCount = 0;
-		windowStartedAt = now;
-	}
-
-	failureCount++;
-
-	if (failureCount >= FAILURE_THRESHOLD) {
-		switchToDegraded();
-	}
-};
-
 const switchToDegraded = (): void => {
 	if (state === PgHealth.Degraded) return;

 	state = PgHealth.Degraded;

-	logger.error("[PgHealthMonitor] ENTERING DEGRADED MODE", {
+	getLogger().error("[PgHealthMonitor] ENTERING DEGRADED MODE", {
 		type: "pg_health_degraded",
 		failureCount,
 		windowMs: FAILURE_WINDOW_MS,
@@ -107,7 +81,7 @@ const switchToHealthy = (): void => {
 	resetFailureWindow();
 	firstProbeSuccessAt = null;

-	logger.info("[PgHealthMonitor] RECOVERED to HEALTHY", {
+	getLogger().info("[PgHealthMonitor] RECOVERED to HEALTHY", {
 		type: "pg_health_recovered",
 	});

@@ -137,7 +111,7 @@ const startProbe = (): void => {
 			const now = Date.now();
 			if (!firstProbeSuccessAt) {
 				firstProbeSuccessAt = now;
-				logger.info(
+				getLogger().info(
 					"[PgHealthMonitor] Probe succeeded, waiting for stability",
 					{
 						type: "pg_health_probe",
@@ -151,7 +125,7 @@ const startProbe = (): void => {
 		} catch {
 			// Probe failed — reset stability timer
 			if (firstProbeSuccessAt) {
-				logger.warn(
+				getLogger().warn(
 					"[PgHealthMonitor] Probe failed, resetting stability timer",
 					{
 						type: "pg_health_probe",
@@ -172,6 +146,51 @@ const stopProbe = (): void => {
 	}
 };

+/**
+ * Initialize the health monitor with a pg pool for probing and env for logging.
+ * Call once at startup.
+ */
+export const initPgHealthMonitor = ({
+	client,
+	env,
+}: {
+	client: Pool;
+	env: Env;
+}): void => {
+	probeClient = client;
+	_logger = createLogger(env);
+	_hasReplica = !!env.DATABASE_REPLICA_URL;
+	getLogger().info("[PgHealthMonitor] Initialized", { type: "pg_health_init" });
+};
+
+/**
+ * Record a successful query against the primary DB.
+ * No-op: recovery is driven by the probe, not by application queries.
+ */
+export const recordDbSuccess = (): void => {};
+
+/**
+ * Record a slow or failed query against the primary DB.
+ * Called when a critical-pool query exceeds the latency threshold or throws.
+ */
+export const recordDbFailure = (): void => {
+	if (state === PgHealth.Degraded) return;
+
+	const now = Date.now();
+
+	// Reset counter if the window has elapsed
+	if (now - windowStartedAt > FAILURE_WINDOW_MS) {
+		failureCount = 0;
+		windowStartedAt = now;
+	}
+
+	failureCount++;
+
+	if (failureCount >= FAILURE_THRESHOLD) {
+		switchToDegraded();
+	}
+};
+
 /**
 * Execute a query with automatic health tracking and replica fallback.
 * - If DEGRADED and a replica exists, queries the replica instead.
@@ -244,14 +263,14 @@ export const getPgHealthState = (): {
 	failureCount,
 	probeActive: probeInterval !== null,
 	firstProbeSuccessAt,
-	hasReplica: !!runtimeEnv.DATABASE_REPLICA_URL,
+	hasReplica: _hasReplica,
 });

 /** Force DEGRADED state (for testing). Does NOT start the recovery probe. */
 export const forceDegraded = (): void => {
 	state = PgHealth.Degraded;
 	resetFailureWindow();
-	logger.info("[PgHealthMonitor] FORCE DEGRADED (test)", {
+	getLogger().info("[PgHealthMonitor] FORCE DEGRADED (test)", {
 		type: "pg_health_force",
 	});
 };
@@ -262,7 +281,7 @@ export const forceHealthy = (): void => {
 	resetFailureWindow();
 	firstProbeSuccessAt = null;
 	stopProbe();
-	logger.info("[PgHealthMonitor] FORCE HEALTHY (test)", {
+	getLogger().info("[PgHealthMonitor] FORCE HEALTHY (test)", {
 		type: "pg_health_force",
 	});
 };
--- a/server/src/db/pgPoolMonitor.ts
+++ b/server/src/db/pgPoolMonitor.ts
@@ -1,6 +1,6 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { Pool } from "pg";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
+import type { Logger } from "@/external/logtail/logtailUtils.js";

 type RegisteredPool = {
 	pool: Pool;
@@ -11,12 +11,18 @@ type RegisteredPool = {
 const registry = new Map<string, RegisteredPool>();
 let snapshotInterval: ReturnType<typeof setInterval> | null = null;

-const getRole = (): string => {
-	if (runtimeEnv.WORKER === "true") return "worker";
-	if (runtimeEnv.CRON === "true") return "cron";
-	return "http";
+let _logger: Logger | null = null;
+let _role = "http";
+
+const getLogger = (): Logger => {
+	if (!_logger) {
+		throw new Error("PgPoolMonitor not initialized — call startPgPoolMonitor first");
+	}
+	return _logger;
 };

+const getRole = (): string => _role;
+
 export const registerPool = ({
 	pool,
 	name,
@@ -37,7 +43,7 @@ export const attachPoolErrorHandlers = ({
 	name: string;
 }): void => {
 	pool.on("error", (err: Error & { code?: string }) => {
-		logger.warn("pg_pool_error", {
+		getLogger().warn("pg_pool_error", {
 			type: "pg_pool_error",
 			pool: name,
 			pid: process.pid,
@@ -49,31 +55,20 @@ export const attachPoolErrorHandlers = ({
 	});
 };

-const emitSnapshot = (): void => {
-	// const role = getRole();
-	// for (const { pool, name, max } of registry.values()) {
-	// 	const totalCount = pool.totalCount;
-	// 	const idleCount = pool.idleCount;
-	// 	const waitingCount = pool.waitingCount;
-	// 	logger.debug("pg_pool_stats", {
-	// 		type: "pg_pool_stats",
-	// 		pool: name,
-	// 		pid: process.pid,
-	// 		role,
-	// 		totalCount,
-	// 		idleCount,
-	// 		waitingCount,
-	// 		max,
-	// 		utilization: max > 0 ? totalCount / max : 0,
-	// 	});
-	// }
-};
+const emitSnapshot = (): void => {};

-export const startPgPoolMonitor = (intervalMs = 30_000): void => {
+export const startPgPoolMonitor = (env: Env, intervalMs = 30_000): void => {
 	if (snapshotInterval) return;
+
+	_logger = createLogger(env);
+
+	if (env.WORKER === "true") _role = "worker";
+	else if (env.CRON === "true") _role = "cron";
+	else _role = "http";
+
 	snapshotInterval = setInterval(emitSnapshot, intervalMs);
 	if (snapshotInterval.unref) snapshotInterval.unref();
-	logger.info("[PgPoolMonitor] Started", {
+	getLogger().info("[PgPoolMonitor] Started", {
 		type: "pg_pool_monitor_start",
 		intervalMs,
 		pools: Array.from(registry.keys()),
--- a/server/src/db/redactDatabaseUrl.ts
+++ b/server/src/db/redactDatabaseUrl.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { createHash } from "node:crypto";

 const hash = (value: string) =>
@@ -33,10 +32,10 @@ export const redactDatabaseUrl = (databaseUrl?: string) => {
 	}
 };

-export const getRedactedDatabaseUrls = () => ({
-	primary: redactDatabaseUrl(runtimeEnv.DATABASE_URL),
-	replica: redactDatabaseUrl(runtimeEnv.DATABASE_REPLICA_URL),
+export const getRedactedDatabaseUrls = (env: Env) => ({
+	primary: redactDatabaseUrl(env.DATABASE_URL),
+	replica: redactDatabaseUrl(env.DATABASE_REPLICA_URL),
 	critical: redactDatabaseUrl(
-		runtimeEnv.DATABASE_CRITICAL_URL || runtimeEnv.DATABASE_URL,
+		env.DATABASE_CRITICAL_URL || env.DATABASE_URL,
 	),
 });
--- a/server/src/db/validateDbSchema.ts
+++ b/server/src/db/validateDbSchema.ts
@@ -1,12 +1,13 @@
 import * as schema from "@autumn/shared";
 import { is } from "drizzle-orm";
 import { PgTable } from "drizzle-orm/pg-core";
-import { logger } from "../external/logtail/logtailUtils";
+import { createLogger } from "../external/logtail/logtailUtils";
 import type { DrizzleCli } from "./initDrizzle";

 const SKIP_TABLES = ["migrationErrors"];

-export const validateDbSchema = async ({ db }: { db: DrizzleCli }) => {
+export const validateDbSchema = async ({ db, env }: { db: DrizzleCli; env: Env }) => {
+	const logger = createLogger(env);
 	// Dynamically get all tables from schema (exclude relations)

 	const tableEntries = Object.entries(schema)
--- a/server/src/db/validateSqlFunctions.ts
+++ b/server/src/db/validateSqlFunctions.ts
@@ -3,7 +3,7 @@ import { readdirSync, readFileSync } from "node:fs";
 import { join } from "node:path";
 import { fileURLToPath } from "node:url";
 import { sql } from "drizzle-orm";
-import { logger } from "../external/logtail/logtailUtils";
+import { createLogger } from "../external/logtail/logtailUtils";
 import type { DrizzleCli } from "./initDrizzle";

 type SqlFunction = {
@@ -64,10 +64,13 @@ const discoverSqlFunctions = (): SqlFunction[] => {
 export const validateSqlFunctions = async ({
 	db,
 	validateContent = false,
+	env,
 }: {
 	db: DrizzleCli;
 	validateContent?: boolean;
+	env: Env;
 }) => {
+	const logger = createLogger(env);
 	const start = Date.now();

 	// Dynamically discover SQL functions from source files
--- a/server/src/external/ai/initAi.ts
+++ b/server/src/external/ai/initAi.ts
@@ -1,8 +1,8 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { createAnthropic } from "@ai-sdk/anthropic";

-export const anthropicClient = runtimeEnv.ANTHROPIC_API_KEY
-	? createAnthropic({
-			apiKey: runtimeEnv.ANTHROPIC_API_KEY,
-		})
-	: undefined;
+export const initAi = (env: Env) =>
+	env.ANTHROPIC_API_KEY
+		? createAnthropic({
+				apiKey: env.ANTHROPIC_API_KEY,
+			})
+		: undefined;
--- a/server/src/external/autumn/autumnCli.ts
+++ b/server/src/external/autumn/autumnCli.ts
@@ -1,5 +1,4 @@
 /** biome-ignore-all lint/suspicious/noExplicitAny: AutumnInt is used for internal testing & scripts */
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	type ApiBaseEntity,
 	type ApiCusFeatureV3,
@@ -72,6 +71,7 @@ export class AutumnInt {
 	private apiKey: string;
 	public headers: Record<string, string>;
 	public baseUrl: string;
+	private _env?: Env;

 	constructor({
 		apiKey,
@@ -81,6 +81,7 @@ export class AutumnInt {
 		orgConfig,
 		liveUrl = false,
 		skipCacheDeletion = false,
+		env,
 	}: {
 		apiKey?: string;
 		secretKey?: string;
@@ -89,10 +90,12 @@ export class AutumnInt {
 		orgConfig?: Partial<OrgConfig>;
 		liveUrl?: boolean;
 		skipCacheDeletion?: boolean;
+		env?: Env;
 	} = {}) {
-		// this.apiKey = apiKey || runtimeEnv.AUTUMN_API_KEY || "";
+		this._env = env;
+		// this.apiKey = apiKey || env.AUTUMN_API_KEY || "";
 		this.apiKey =
-			apiKey || secretKey || runtimeEnv.UNIT_TEST_AUTUMN_SECRET_KEY || "";
+			apiKey || secretKey || env?.UNIT_TEST_AUTUMN_SECRET_KEY || "";

 		this.headers = {
 			Authorization: `Bearer ${this.apiKey}`,
@@ -107,7 +110,7 @@ export class AutumnInt {
 			this.headers["org-config"] = JSON.stringify(orgConfig);
 		}

-		const envBase = runtimeEnv.AUTUMN_TEST_BASE_URL;
+		const envBase = env?.AUTUMN_TEST_BASE_URL;
 		const envBaseUrl = envBase ? `${envBase.replace(/\/$/, "")}/v1` : null;
 		this.baseUrl =
 			baseUrl ||
@@ -313,7 +316,7 @@ export class AutumnInt {
 			Object.keys(headers).length > 0 ? headers : undefined,
 		);

-		const concurrency = Number(runtimeEnv.TEST_FILE_CONCURRENCY || "0");
+		const concurrency = Number(this._env?.TEST_FILE_CONCURRENCY || "0");
 		const defaultTimeout = concurrency > 1 ? 5000 : 4000;
 		const finalTimeout = timeout ?? defaultTimeout;
 		if (finalTimeout) {
@@ -1216,7 +1219,7 @@ export class AutumnInt {
 				Object.keys(headers).length > 0 ? headers : undefined,
 			);

-			const concurrency = Number(runtimeEnv.TEST_FILE_CONCURRENCY || "0");
+			const concurrency = Number(this._env?.TEST_FILE_CONCURRENCY || "0");
 			const defaultTimeout = concurrency > 1 ? 5000 : 4000;
 			const finalTimeout = timeout ?? defaultTimeout;
 			if (finalTimeout) {
@@ -1254,7 +1257,7 @@ export class AutumnInt {
 		): Promise<TResponse> => {
 			const data = await this.post(`/billing.create_schedule`, params);

-			const concurrency = Number(runtimeEnv.TEST_FILE_CONCURRENCY || "0");
+			const concurrency = Number(this._env?.TEST_FILE_CONCURRENCY || "0");
 			const defaultTimeout = concurrency > 1 ? 5000 : 4000;
 			const finalTimeout = timeout ?? defaultTimeout;
 			if (finalTimeout) {
@@ -1285,7 +1288,7 @@ export class AutumnInt {
 				Object.keys(headers).length > 0 ? headers : undefined,
 			);

-			const concurrency = Number(runtimeEnv.TEST_FILE_CONCURRENCY || "0");
+			const concurrency = Number(this._env?.TEST_FILE_CONCURRENCY || "0");
 			const defaultTimeout = concurrency > 1 ? 5000 : 4000;
 			const finalTimeout = timeout ?? defaultTimeout;
 			if (finalTimeout) {
--- a/server/src/external/autumn/autumnRpcCli.ts
+++ b/server/src/external/autumn/autumnRpcCli.ts
@@ -1,5 +1,4 @@
 /** biome-ignore-all lint/suspicious/noExplicitAny: RPC test client needs flexible payload typing */
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode, type OrgConfig } from "@autumn/shared";
 import AutumnError from "./autumnCli.js";

@@ -15,6 +14,7 @@ export class AutumnRpcCli {
 		version,
 		orgConfig,
 		liveUrl = false,
+		env,
 	}: {
 		apiKey?: string;
 		secretKey?: string;
@@ -22,9 +22,10 @@ export class AutumnRpcCli {
 		version?: string;
 		orgConfig?: Partial<OrgConfig>;
 		liveUrl?: boolean;
+		env?: Env;
 	} = {}) {
 		this.apiKey =
-			apiKey || secretKey || runtimeEnv.UNIT_TEST_AUTUMN_SECRET_KEY || "";
+			apiKey || secretKey || env?.UNIT_TEST_AUTUMN_SECRET_KEY || "";

 		this.headers = {
 			Authorization: `Bearer ${this.apiKey}`,
@@ -39,7 +40,7 @@ export class AutumnRpcCli {
 			this.headers["org-config"] = JSON.stringify(orgConfig);
 		}

-		const envBase = runtimeEnv.AUTUMN_TEST_BASE_URL;
+		const envBase = env?.AUTUMN_TEST_BASE_URL;
 		const envBaseUrl = envBase ? `${envBase.replace(/\/$/, "")}/v1` : null;
 		this.baseUrl =
 			baseUrl ||
--- a/server/src/external/autumn/autumnWebhookRouter.ts
+++ b/server/src/external/autumn/autumnWebhookRouter.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode } from "@autumn/shared";
 import { Hono } from "hono";
 import { Webhook } from "svix";
@@ -10,6 +9,7 @@ export const autumnWebhookRouter = new Hono<HonoEnv>();
 const verifyAutumnWebhook = async ({
 	rawBody,
 	headers,
+	env,
 }: {
 	rawBody: string;
 	headers: {
@@ -17,8 +17,9 @@ const verifyAutumnWebhook = async ({
 		svixTimestamp: string | undefined;
 		svixSignature: string | undefined;
 	};
+	env: Env;
 }) => {
-	const wh = new Webhook(runtimeEnv.AUTUMN_WEBHOOK_SECRET!);
+	const wh = new Webhook(env.AUTUMN_WEBHOOK_SECRET!);

 	const { svixId, svixTimestamp, svixSignature } = headers;

@@ -54,6 +55,7 @@ autumnWebhookRouter.post("", async (c) => {
 				svixTimestamp: c.req.header("svix-timestamp"),
 				svixSignature: c.req.header("svix-signature"),
 			},
+			env: c.env,
 		});

 		console.log("Received webhook from autumn");
--- a/server/src/external/aws/ecs/awsTaskIdentity.ts
+++ b/server/src/external/aws/ecs/awsTaskIdentity.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { z } from "zod/v4";

 /**
@@ -50,15 +49,17 @@ const constructServiceArn = ({
 * Reads the ECS task metadata endpoint to resolve this task's identity.
 * Cached for process lifetime — neither field changes for a running task.
 */
-export const resolveAwsTaskIdentity = async (): Promise<AwsTaskIdentity> => {
+export const resolveAwsTaskIdentity = async (
+	env: Env,
+): Promise<AwsTaskIdentity> => {
 	if (identityResolved && cachedIdentity) return cachedIdentity;
 	if (identityPromise) return identityPromise;

 	identityPromise = (async (): Promise<AwsTaskIdentity> => {
 		const imageSha =
-			runtimeEnv.FC_GIT_COMMIT_SHA || runtimeEnv.IMAGE_TAG || null;
+			env.FC_GIT_COMMIT_SHA || env.IMAGE_TAG || null;

-		const metadataUri = runtimeEnv.ECS_CONTAINER_METADATA_URI_V4;
+		const metadataUri = env.ECS_CONTAINER_METADATA_URI_V4;
 		let serviceArn: string | null = null;

 		if (metadataUri) {
@@ -95,7 +96,7 @@ export const resolveAwsTaskIdentity = async (): Promise<AwsTaskIdentity> => {
 					`[awsTaskIdentity] ECS metadata fetch failed: ${error instanceof Error ? error.message : error}; gate will fail open`,
 				);
 			}
-		} else if (runtimeEnv.NODE_ENV === "production") {
+		} else if (env.NODE_ENV === "production") {
 			console.warn(
 				"[awsTaskIdentity] ECS_CONTAINER_METADATA_URI_V4 unset in production — gate will fail open",
 			);
@@ -119,7 +120,3 @@ export const getAwsTaskIdentity = (): AwsTaskIdentity | null => cachedIdentity;
 */
 export const hasAwsTaskIdentity = (): boolean =>
 	Boolean(cachedIdentity?.serviceArn);
-
-// Fire-and-forget at module load so server, workers, and cron all get
-// identity resolved without each entry point having to await explicitly.
-void resolveAwsTaskIdentity();
--- a/server/src/external/aws/ecs/onAwsEcs.ts
+++ b/server/src/external/aws/ecs/onAwsEcs.ts
@@ -5,6 +5,5 @@
 * so it's the canonical "am I on AWS?" gate — same one
 * `awsTaskIdentity` uses to discover the running service.
 */
-import { runtimeEnv } from "@/utils/envUtils.js";
-export const onAwsEcs = (): boolean =>
-	Boolean(runtimeEnv.ECS_CONTAINER_METADATA_URI_V4);
+export const onAwsEcs = (env: Env): boolean =>
+	Boolean(env.ECS_CONTAINER_METADATA_URI_V4);
--- a/server/src/external/aws/eventbridge/eventBridgeUtils.ts
+++ b/server/src/external/aws/eventbridge/eventBridgeUtils.ts
@@ -1,22 +1,23 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	CreateScheduleCommand,
 	DeleteScheduleCommand,
 	ResourceNotFoundException,
 } from "@aws-sdk/client-scheduler";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { extractLocalEndpoint } from "@/queue/initSqs.js";
 import { schedulerClient } from "./initEventBridge.js";

-const isLocalQueue = (): boolean =>
-	!!extractLocalEndpoint({ queueUrl: runtimeEnv.SQS_QUEUE_URL_V2 });
+const isLocalQueue = (env: Env): boolean =>
+	!!extractLocalEndpoint({ queueUrl: env.SQS_QUEUE_URL_V2 });

 const SCHEDULE_GROUP = "default";
-const SCHEDULER_ROLE_ARN = runtimeEnv.AWS_EVENTBRIDGE_SCHEDULER_ROLE_ARN || "";
+
+export const getSchedulerRoleArn = (env: Env) =>
+	env.AWS_EVENTBRIDGE_SCHEDULER_ROLE_ARN || "";

 /** Derives SQS ARN from URL: https://sqs.<region>.amazonaws.com/<account>/<name> -> arn:aws:sqs:<region>:<account>:<name> */
-const getSqsQueueArn = (): string => {
-	const url = runtimeEnv.SQS_QUEUE_URL_V2 || "";
+const getSqsQueueArn = (env: Env): string => {
+	const url = env.SQS_QUEUE_URL_V2 || "";
 	const match = url.match(
 		/^https:\/\/sqs\.([a-z0-9-]+)\.amazonaws\.com\/(\d+)\/(.+)$/,
 	);
@@ -28,17 +29,21 @@ const getSqsQueueArn = (): string => {

 /** Creates a one-shot EventBridge schedule that delivers an SQS message at scheduleAt */
 export const createSchedule = async ({
+	env,
 	scheduleName,
 	scheduleAt,
 	sqsMessageBody,
 	messageGroupId,
 }: {
+	env: Env;
 	scheduleName: string;
 	scheduleAt: Date;
 	sqsMessageBody: string;
 	messageGroupId: string;
 }) => {
-	if (isLocalQueue()) {
+	const logger = createLogger(env);
+
+	if (isLocalQueue(env)) {
 		logger.debug(
 			"[EventBridge] createSchedule skipped (local SQS queue — no EventBridge in dev)",
 		);
@@ -49,7 +54,7 @@ export const createSchedule = async ({
 	const d = scheduleAt;
 	const atExpression = `at(${d.getUTCFullYear()}-${pad(d.getUTCMonth() + 1)}-${pad(d.getUTCDate())}T${pad(d.getUTCHours())}:${pad(d.getUTCMinutes())}:${pad(d.getUTCSeconds())})`;

-	const sqsArn = getSqsQueueArn();
+	const sqsArn = getSqsQueueArn(env);
 	logger.info(
 		`[EventBridge] Creating schedule: name=${scheduleName} arn=${sqsArn} at=${atExpression}`,
 	);
@@ -63,7 +68,7 @@ export const createSchedule = async ({
 			FlexibleTimeWindow: { Mode: "OFF" },
 			Target: {
 				Arn: sqsArn,
-				RoleArn: SCHEDULER_ROLE_ARN,
+				RoleArn: getSchedulerRoleArn(env),
 				Input: sqsMessageBody,
 				SqsParameters: {
 					MessageGroupId: messageGroupId,
@@ -77,11 +82,15 @@ export const createSchedule = async ({

 /** Deletes an EventBridge schedule by name. Silently ignores not-found errors. */
 export const deleteSchedule = async ({
+	env,
 	scheduleName,
 }: {
+	env: Env;
 	scheduleName: string;
 }) => {
-	if (isLocalQueue()) {
+	const logger = createLogger(env);
+
+	if (isLocalQueue(env)) {
 		logger.debug(
 			"[EventBridge] deleteSchedule skipped (local SQS queue — no EventBridge in dev)",
 		);
--- a/server/src/external/aws/eventbridge/initEventBridge.ts
+++ b/server/src/external/aws/eventbridge/initEventBridge.ts
@@ -1,19 +1,22 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { SchedulerClient } from "@aws-sdk/client-scheduler";
 import {
 	DEFAULT_AWS_REGION,
 	extractRegionFromQueueUrl,
 } from "@/external/aws/awsRegionUtils.js";

-const getSchedulerClientConfig = () => ({
+export let schedulerClient: SchedulerClient | null = null;
+
+const getSchedulerClientConfig = (env: Env) => ({
 	region:
 		extractRegionFromQueueUrl({
-			queueUrl: runtimeEnv.SQS_QUEUE_URL_V2,
+			queueUrl: env.SQS_QUEUE_URL_V2,
 		}) || DEFAULT_AWS_REGION,
 	credentials: {
-		accessKeyId: runtimeEnv.AWS_ACCESS_KEY_ID || "",
-		secretAccessKey: runtimeEnv.AWS_SECRET_ACCESS_KEY || "",
+		accessKeyId: env.AWS_ACCESS_KEY_ID || "",
+		secretAccessKey: env.AWS_SECRET_ACCESS_KEY || "",
 	},
 });

-export const schedulerClient = new SchedulerClient(getSchedulerClientConfig());
+export const initSchedulerClient = (env: Env) => {
+	schedulerClient = new SchedulerClient(getSchedulerClientConfig(env));
+};
--- a/server/src/external/aws/s3/adminS3Config.ts
+++ b/server/src/external/aws/s3/adminS3Config.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 export const ADMIN_REQUEST_BLOCK_CONFIG_KEY = "admin/request-block-config.json";
 export const ADMIN_ROLLOUT_CONFIG_KEY = "admin/rollout-config.json";
 export const ADMIN_FEATURE_FLAGS_CONFIG_KEY = "admin/feature-flags-config.json";
@@ -22,18 +21,17 @@ export const BLUE_GREEN_CRON_ACTIVE_SLOT_KEY =
 	"admin/blue-green-cron-active-slot.json";
 export const BLUE_GREEN_HEARTBEAT_KEY_PREFIX = "admin/blue-green-heartbeats";

-const bucket = runtimeEnv.S3_BUCKET || "autumn-prod-server";
-const region = runtimeEnv.S3_REGION || "us-east-2";
-
-export const getAdminS3Config = () => {
+export const getAdminS3Config = (env: Env) => {
+	const bucket = env.S3_BUCKET || "autumn-prod-server";
+	const region = env.S3_REGION || "us-east-2";
 	return {
 		bucket,
 		region,
 	};
 };

-export const getAdminEdgeConfigSources = () => ({
-	...getAdminS3Config(),
+export const getAdminEdgeConfigSources = (env: Env) => ({
+	...getAdminS3Config(env),
 	configs: [
 		{
 			id: "request-block",
--- a/server/src/external/axiom/initAxiom.ts
+++ b/server/src/external/axiom/initAxiom.ts
@@ -1,21 +1,26 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { Axiom } from "@axiomhq/js";

-const AXIOM_ADMIN_TOKEN = runtimeEnv.AXIOM_ADMIN_TOKEN;
-const AXIOM_ORG_ID = runtimeEnv.AXIOM_ORG_ID;
+let _axiomClient: Axiom | null = null;

-export const axiomClient: Axiom | null = AXIOM_ADMIN_TOKEN
-	? new Axiom({
-			token: AXIOM_ADMIN_TOKEN,
-			orgId: AXIOM_ORG_ID,
-		})
-	: null;
+/** Initialize Axiom client from the platform env. Must be called before any logging. */
+export const initAxiomClient = (env: Env): Axiom | null => {
+	const token = env.AXIOM_ADMIN_TOKEN;
+	const orgId = env.AXIOM_ORG_ID;

-export const getAxiomClient = (): Axiom => {
-	if (!axiomClient) {
-		throw new Error("Axiom is not configured (AXIOM_ADMIN_TOKEN missing)");
+	if (!token) {
+		_axiomClient = null;
+		return null;
 	}
-	return axiomClient;
+
+	_axiomClient = new Axiom({ token, orgId });
+	return _axiomClient;
 };

-export const isAxiomConfigured = (): boolean => axiomClient !== null;
+export const getAxiomClient = (): Axiom => {
+	if (!_axiomClient) {
+		throw new Error("Axiom is not configured (AXIOM_ADMIN_TOKEN missing)");
+	}
+	return _axiomClient;
+};
+
+export const isAxiomConfigured = (): boolean => _axiomClient !== null;
--- a/server/src/external/connect/connectUtils.ts
+++ b/server/src/external/connect/connectUtils.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { AppEnv, InternalError, type Organization } from "@autumn/shared";
 import type { DrizzleCli } from "@server/db/initDrizzle.js";
 import { OrgService } from "@server/internal/orgs/OrgService.js";
@@ -29,22 +28,24 @@ export const orgToAccountId = ({
 export const deauthorizeAccount = async ({
 	accountId,
 	env,
+	workerEnv,
 	logger,
 }: {
 	accountId: string;
 	env: AppEnv;
+	workerEnv: Env;
 	logger: Logger;
 }) => {
 	// OAuth-connected accounts must be deauthorized, not deleted
 	// Platform-managed accounts can be deleted

-	const masterStripe = initMasterStripe({ env });
+	const masterStripe = initMasterStripe(workerEnv, { env });
 	try {
 		await masterStripe.oauth.deauthorize({
 			client_id:
 				env === AppEnv.Live
-					? runtimeEnv.STRIPE_LIVE_CLIENT_ID || ""
-					: runtimeEnv.STRIPE_SANDBOX_CLIENT_ID || "",
+					? workerEnv.STRIPE_LIVE_CLIENT_ID || ""
+					: workerEnv.STRIPE_SANDBOX_CLIENT_ID || "",
 			stripe_user_id: accountId,
 		});
 		logger.info(`Deauthorized account ${accountId} for ${env}`);
@@ -58,13 +59,15 @@ export const deauthorizeAccount = async ({
 export const deleteConnectedAccount = async ({
 	accountId,
 	env,
+	workerEnv,
 	logger,
 }: {
 	accountId: string;
 	env: AppEnv;
+	workerEnv: Env;
 	logger: Logger;
 }) => {
-	const masterStripe = initMasterStripe({ env });
+	const masterStripe = initMasterStripe(workerEnv, { env });
 	try {
 		await masterStripe.accounts.del(accountId);
 		logger.info(`Deleted account ${accountId} for ${env}`);
@@ -102,10 +105,12 @@ export const getConnectWebhookSecret = async ({
 	db,
 	orgId,
 	env,
+	workerEnv,
 }: {
 	db: DrizzleCli;
 	orgId: string;
 	env: AppEnv;
+	workerEnv: Env;
 }) => {
 	const org = await OrgService.get({ db, orgId });
 	const prefix = env === AppEnv.Sandbox ? "test" : "live";
@@ -117,6 +122,6 @@ export const getConnectWebhookSecret = async ({
 		});
 	}

-	const decrypted = decryptData(secret);
+	const decrypted = decryptData(secret, workerEnv);
 	return decrypted;
 };
--- a/server/src/external/connect/initStripeCli.ts
+++ b/server/src/external/connect/initStripeCli.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	AppEnv,
 	InternalError,
@@ -16,28 +15,31 @@ import {
 import { getOrCreateStripeClient } from "./clientCache/stripeClientCache.js";
 import { getConnectWebhookSecret } from "./connectUtils.js";

-export const initMasterStripe = (params?: {
-	accountId?: string;
-	legacyVersion?: boolean;
-	env?: AppEnv;
-	skipInstrumentation?: boolean;
-}) => {
+export const initMasterStripe = (
+	env: Env,
+	params?: {
+		accountId?: string;
+		legacyVersion?: boolean;
+		env?: AppEnv;
+		skipInstrumentation?: boolean;
+	},
+) => {
 	let secretKey: string;

 	if (params?.env === AppEnv.Live) {
-		if (!runtimeEnv.STRIPE_LIVE_SECRET_KEY) {
+		if (!env.STRIPE_LIVE_SECRET_KEY) {
 			throw new InternalError({
 				message: "STRIPE_LIVE_SECRET_KEY env variable is not set",
 			});
 		}
-		secretKey = runtimeEnv.STRIPE_LIVE_SECRET_KEY;
+		secretKey = env.STRIPE_LIVE_SECRET_KEY;
 	} else {
-		if (!runtimeEnv.STRIPE_SANDBOX_SECRET_KEY) {
+		if (!env.STRIPE_SANDBOX_SECRET_KEY) {
 			throw new InternalError({
 				message: "STRIPE_SANDBOX_SECRET_KEY env variable is not set",
 			});
 		}
-		secretKey = runtimeEnv.STRIPE_SANDBOX_SECRET_KEY;
+		secretKey = env.STRIPE_SANDBOX_SECRET_KEY;
 	}

 	const cacheKey = buildMasterCacheKey({
@@ -66,12 +68,14 @@ export const initMasterStripe = (params?: {
 export const initPlatformStripe = ({
 	masterOrg,
 	env,
+	appEnv,
 	accountId,
 	legacyVersion,
 	skipInstrumentation = false,
 }: {
 	masterOrg: Organization | null;
-	env: AppEnv;
+	env: Env;
+	appEnv: AppEnv;
 	accountId?: string;
 	legacyVersion?: boolean;
 	skipInstrumentation?: boolean;
@@ -84,12 +88,12 @@ export const initPlatformStripe = ({

 	// Get master org's secret key and validate access to the account
 	const encrypted =
-		env === AppEnv.Sandbox
+		appEnv === AppEnv.Sandbox
 			? masterOrg.stripe_config?.test_api_key
 			: masterOrg.stripe_config?.live_api_key;

 	if (!encrypted) {
-		const envLabel = env === AppEnv.Sandbox ? "test" : "live";
+		const envLabel = appEnv === AppEnv.Sandbox ? "test" : "live";
 		throw new RecaseError({
 			message: `Master organization must have Stripe ${envLabel} secret key connected`,
 		});
@@ -97,7 +101,7 @@ export const initPlatformStripe = ({

 	const cacheKey = buildPlatformCacheKey({
 		masterOrgId: masterOrg.id,
-		env,
+		env: appEnv,
 		accountId,
 		legacyVersion,
 		encryptedKey: encrypted,
@@ -106,7 +110,7 @@ export const initPlatformStripe = ({
 	return getOrCreateStripeClient({
 		cacheKey,
 		create: () => {
-			const decrypted = decryptData(encrypted);
+			const decrypted = decryptData(encrypted, env);
 			if (!decrypted) {
 				throw new InternalError({
 					message: "Failed to decrypt master organization's Stripe secret key",
@@ -126,26 +130,28 @@ export const getStripeWebhookSecret = async ({
 	db,
 	orgId,
 	env,
+	appEnv,
 }: {
 	db: DrizzleCli;
 	orgId?: string;
-	env: AppEnv;
+	env: Env;
+	appEnv: AppEnv;
 }) => {
 	// If org ID...
 	if (orgId) {
-		return await getConnectWebhookSecret({ db, orgId, env });
+		return await getConnectWebhookSecret({ db, orgId, env: appEnv });
 	}

 	let secret: string;
-	if (env === AppEnv.Live) {
-		secret = runtimeEnv.STRIPE_LIVE_WEBHOOK_SECRET || "";
+	if (appEnv === AppEnv.Live) {
+		secret = env.STRIPE_LIVE_WEBHOOK_SECRET || "";
 	} else {
-		secret = runtimeEnv.STRIPE_SANDBOX_WEBHOOK_SECRET || "";
+		secret = env.STRIPE_SANDBOX_WEBHOOK_SECRET || "";
 	}

 	if (!secret) {
 		throw new InternalError({
-			message: `STRIPE_WEBHOOK_SECRET env variable is not set (${env})`,
+			message: `STRIPE_WEBHOOK_SECRET env variable is not set (${appEnv})`,
 		});
 	}

--- a/server/src/external/connect/registerConnectWebhook.ts
+++ b/server/src/external/connect/registerConnectWebhook.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type Stripe from "stripe";
 import type { AutumnContext } from "@/honoUtils/HonoEnv.js";
 import { OrgService } from "@/internal/orgs/OrgService.js";
@@ -8,17 +7,23 @@ import { initPlatformStripe } from "./initStripeCli.js";

 export const registerConnectWebhook = async ({
 	ctx,
+	env,
 }: {
 	ctx: AutumnContext;
+	env: Env;
 }) => {
-	const { db, org, env, logger } = ctx;
+	const { db, org, env: appEnv, logger } = ctx;
 	// Init master stripe
-	const stripeCli = initPlatformStripe({ masterOrg: org, env });
+	const stripeCli = initPlatformStripe({
+		masterOrg: org,
+		env,
+		appEnv,
+	});

 	const curWebhookEndpoints = await stripeCli.webhookEndpoints.list();
-	const backendUrl = runtimeEnv.SERVER_URL || runtimeEnv.STRIPE_WEBHOOK_URL;
+	const backendUrl = env.SERVER_URL || env.STRIPE_WEBHOOK_URL;

-	const webhookUrl = `${backendUrl}/webhooks/connect/${env}?org_id=${org.id}`;
+	const webhookUrl = `${backendUrl}/webhooks/connect/${appEnv}?org_id=${org.id}`;

 	if (curWebhookEndpoints.data.some((webhook) => webhook.url === webhookUrl))
 		return;
@@ -30,16 +35,16 @@ export const registerConnectWebhook = async ({
 		connect: true,
 	});

-	logger.info(`Registered connect webhook for ${org.slug} ${env}`);
+	logger.info(`Registered connect webhook for ${org.slug} ${appEnv}`);

 	await OrgService.updateConnectWebhookSecret({
 		db,
 		orgId: org.id,
-		env,
+		env: appEnv,
 		secret: encryptData(webhook.secret as string),
 	});

-	logger.info(`Updated connect webhook secret for ${org.slug} ${env}`);
+	logger.info(`Updated connect webhook secret for ${org.slug} ${appEnv}`);

 	return webhook;
 };
--- a/server/src/external/hatchet/initHatchet.ts
+++ b/server/src/external/hatchet/initHatchet.ts
@@ -1,6 +1,12 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { HatchetClient } from "@hatchet-dev/typescript-sdk/v1";

-export const isHatchetEnabled = !!runtimeEnv.HATCHET_CLIENT_TOKEN;
+export let hatchet: ReturnType<typeof HatchetClient.init> | null = null;

-export const hatchet = isHatchetEnabled ? HatchetClient.init() : null;
+export const initHatchet = (env: Env) => {
+	const enabled = !!env.HATCHET_CLIENT_TOKEN;
+	if (enabled) {
+		hatchet = HatchetClient.init();
+	}
+};
+
+export const isHatchetEnabled = () => hatchet !== null;
--- a/server/src/external/infisical/fetchInfisicalSecrets.ts
+++ b/server/src/external/infisical/fetchInfisicalSecrets.ts
@@ -3,10 +3,9 @@
 * time via `syncEnvVars` to push secrets to the cloud env. Kept SDK-free
 * so trigger.config.ts can import it without bloating the build.
 *
- * Runtime code uses `initInfisical` (SDK-based, populates runtimeEnv).
+ * Runtime code uses `initInfisical` (SDK-based, returns a merged env object).
 */

-import { runtimeEnv } from "@/utils/envUtils.js";
 export type InfisicalSyncEnvVar = { name: string; value: string };

 export type FetchInfisicalSecretsArgs = {
@@ -100,17 +99,15 @@ export const fetchInfisicalSecrets = async ({

 /**
 * Read the four credential vars (`INFISICAL_CLIENT_ID`, `_SECRET`,
- * `_PROJECT_ID`, `_ENVIRONMENT`) from the local process env first then
- * trigger.dev's deploy-time `ctx.env`. Convenience for `syncEnvVars`.
+ * `_PROJECT_ID`, `_ENVIRONMENT`) from trigger.dev's deploy-time `ctx.env`.
+ * Convenience for `syncEnvVars`.
 */
 export const fetchInfisicalSecretsFromEnv = (
 	ctxEnv: Record<string, string | undefined> = {},
 ): Promise<InfisicalSyncEnvVar[]> =>
 	fetchInfisicalSecrets({
-		clientId: runtimeEnv.INFISICAL_CLIENT_ID ?? ctxEnv.INFISICAL_CLIENT_ID,
-		clientSecret:
-			runtimeEnv.INFISICAL_CLIENT_SECRET ?? ctxEnv.INFISICAL_CLIENT_SECRET,
-		projectId: runtimeEnv.INFISICAL_PROJECT_ID ?? ctxEnv.INFISICAL_PROJECT_ID,
-		environment:
-			runtimeEnv.INFISICAL_ENVIRONMENT ?? ctxEnv.INFISICAL_ENVIRONMENT,
+		clientId: ctxEnv.INFISICAL_CLIENT_ID,
+		clientSecret: ctxEnv.INFISICAL_CLIENT_SECRET,
+		projectId: ctxEnv.INFISICAL_PROJECT_ID,
+		environment: ctxEnv.INFISICAL_ENVIRONMENT,
 	});
--- a/server/src/external/infisical/initInfisical.ts
+++ b/server/src/external/infisical/initInfisical.ts
@@ -1,27 +1,24 @@
 import { InfisicalSDK } from "@infisical/sdk";
-import {
-	getRuntimeEnvValue,
-	loadLocalEnv,
-	runtimeEnv,
-	setRuntimeEnvValue,
-} from "@/utils/envUtils.js";
 import { mask } from "@/utils/genUtils";
-/**
- * Initialize Infisical and load secrets into runtimeEnv
- * This allows all existing code using runtimeEnv to work seamlessly
- */
-export const initInfisical = async (params?: { secretPath?: string }) => {
-	loadLocalEnv();

+/**
+ * Initialize Infisical and merge secrets into the given env.
+ * Returns a new env object with Infisical secrets merged in.
+ * Existing env variables take precedence (won't be overridden).
+ */
+export const initInfisical = async (
+	env: Env,
+	params?: { secretPath?: string },
+): Promise<Env> => {
 	// Only initialize if credentials are provided
-	const clientId = runtimeEnv.INFISICAL_CLIENT_ID;
-	const clientSecret = runtimeEnv.INFISICAL_CLIENT_SECRET;
-	const projectId = runtimeEnv.INFISICAL_PROJECT_ID;
-	const environment = runtimeEnv.INFISICAL_ENVIRONMENT;
+	const clientId = env.INFISICAL_CLIENT_ID;
+	const clientSecret = env.INFISICAL_CLIENT_SECRET;
+	const projectId = env.INFISICAL_PROJECT_ID;
+	const environment = env.INFISICAL_ENVIRONMENT;

 	if (!clientId || !clientSecret || !projectId || !environment) {
 		console.log("⚠️  Infisical credentials not found - skipping initialization");
-		return;
+		return env;
 	}

 	try {
@@ -42,33 +39,34 @@ export const initInfisical = async (params?: { secretPath?: string }) => {
 			recursive: true,
 		});

-		// Load secrets into runtimeEnv
-		// Note: Existing runtimeEnv variables take precedence (won't be overridden)
-		let loadedCount = 0;
+		// Merge secrets into env (existing values take precedence)
+		const secrets: Record<string, string> = {};

 		for (const secret of allSecrets.secrets) {
-			// If path is restricted log that we're seeing it
 			if (secret.secretPath?.includes("restricted") && secret.secretValue) {
 				console.log(
-					`Retrieving restricted secret: ${secret.secretKey}, Path: ${secret.secretPath}, value: ${mask(secret.secretValue, 3, 2)}`,
+					`Retrieving restricted secret: ${secret.secretKey}, Path: ${
+						secret.secretPath
+					}, value: ${mask(secret.secretValue, 3, 2)}`,
 				);
 			}
-			if (!getRuntimeEnvValue(secret.secretKey)) {
-				setRuntimeEnvValue(secret.secretKey, secret.secretValue);
-				loadedCount++;
+			if (!env[secret.secretKey as keyof Env]) {
+				secrets[secret.secretKey] = secret.secretValue;
 			}
 		}

 		for (const importSecrets of allSecrets?.imports ?? []) {
 			for (const importSecret of importSecrets.secrets) {
-				if (!getRuntimeEnvValue(importSecret.secretKey)) {
-					setRuntimeEnvValue(importSecret.secretKey, importSecret.secretValue);
-					loadedCount++;
+				if (!env[importSecret.secretKey as keyof Env]) {
+					secrets[importSecret.secretKey] = importSecret.secretValue;
 				}
 			}
 		}

-		console.log(`✅ Infisical: loaded ${loadedCount} secrets into runtimeEnv`);
+		const loadedCount = Object.keys(secrets).length;
+		console.log(`✅ Infisical: loaded ${loadedCount} secrets`);
+
+		return { ...secrets, ...env } as Env;
 	} catch (error) {
 		console.error("❌ Failed to initialize Infisical:", error);
 		throw error;
--- a/server/src/external/logtail/logtailUtils.ts
+++ b/server/src/external/logtail/logtailUtils.ts
@@ -1,8 +1,5 @@
 import type pino from "pino";
 import { initLogger } from "@/utils/logging/initLogger";
-import { runtimeEnv } from "@/utils/envUtils.js";
-
-const pinoLogger = initLogger({}, runtimeEnv);

 const createLogMethod = (pinoMethod: any, logtailMethod?: any) => {
 	function rewriteAppPath(str: string) {
@@ -97,27 +94,16 @@ const createLoggerStructure = (
 });

 export const createLogger = (env: Env) =>
-	createLoggerStructure(
-		env === runtimeEnv ? pinoLogger : initLogger({}, env),
-		env,
-	);
+	createLoggerStructure(initLogger({}, env), env);

 /**
 * Lazy dual-output logger (stdout JSON + axiom). Used only by long-running
 * trigger.dev tasks so their lines surface in both the trigger run UI and
- * our axiom store. Default `logger` / `createLogger` are unaffected.
+ * our axiom store. `createLogger` is unaffected.
 */
-let dualPinoLogger: pino.Logger | null = null;
-export const createDualLogger = (env: Env) => {
-	if (env !== runtimeEnv) {
-		return createLoggerStructure(initLogger({ mode: "dual" }, env), env);
-	}
-	if (!dualPinoLogger)
-		dualPinoLogger = initLogger({ mode: "dual" }, runtimeEnv);
-	return createLoggerStructure(dualPinoLogger, runtimeEnv);
-};
+export const createDualLogger = (env: Env) =>
+	createLoggerStructure(initLogger({ mode: "dual" }, env), env);

-export const logger = createLogger(runtimeEnv);
 export type Logger = {
 	debug: (...args: any[]) => void;
 	info: (...args: any[]) => void;
--- a/server/src/external/redis/getReachableDragonflyUrl.ts
+++ b/server/src/external/redis/getReachableDragonflyUrl.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { onAwsEcs } from "@/external/aws/ecs/onAwsEcs.js";

 /**
@@ -18,13 +17,19 @@ import { onAwsEcs } from "@/external/aws/ecs/onAwsEcs.js";
 * Returns the same input string when no swap applies, so callers can use
 * it transparently in place of the raw URL.
 */
-export const getReachableDragonflyUrl = (url: string): string => {
-	if (onAwsEcs()) return url;
+export const getReachableDragonflyUrl = ({
+	url,
+	env,
+}: {
+	url: string;
+	env: Env;
+}): string => {
+	if (onAwsEcs(env)) return url;

-	const privateUrl = runtimeEnv.CACHE_V2_DRAGONFLY_URL?.trim();
+	const privateUrl = env.CACHE_V2_DRAGONFLY_URL?.trim();
 	if (!privateUrl || url.trim() !== privateUrl) return url;

-	const publicUrl = runtimeEnv.CACHE_V2_DRAGONFLY_PUBLIC_URL?.trim();
+	const publicUrl = env.CACHE_V2_DRAGONFLY_PUBLIC_URL?.trim();
 	if (!publicUrl) return url;

 	return publicUrl;
--- a/server/src/external/redis/initRedisV2.ts
+++ b/server/src/external/redis/initRedisV2.ts
@@ -1,6 +1,5 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { Redis } from "ioredis";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import type { RedisV2InstanceName } from "@/internal/misc/redisV2Cache/redisV2CacheSchemas.js";
 import { getReachableDragonflyUrl } from "./getReachableDragonflyUrl.js";
 import {
@@ -9,29 +8,59 @@ import {
 	waitForRedisReady,
 } from "./initRedis.js";
 import {
-	REDIS_V2_COMMAND_TIMEOUT_MS,
+	getRedisV2ConnectionConfig,
 	supportsUpstashShebangForRedisV2,
 } from "./initUtils/redisV2Config.js";

-const rawDragonflyUrl = runtimeEnv.CACHE_V2_DRAGONFLY_URL?.trim();
-const dragonflyUrl = rawDragonflyUrl
-	? getReachableDragonflyUrl(rawDragonflyUrl)
-	: undefined;
+let _env: Env | undefined;
+let _redisV2: Redis | undefined;
+let _alternateInstanceUrls: Partial<Record<RedisV2InstanceName, string>> = {};

-export const hasRedisV2Config = Boolean(dragonflyUrl);
+export const ensureRedisV2 = (env: Env): Redis => {
+	if (_redisV2) return _redisV2;

-export const redisV2: Redis = createRedisConnection({
-	cacheUrl: dragonflyUrl || "",
-	region: `${currentRegion}:v2`,
-	supportsUpstashShebang: false,
-	commandTimeout: REDIS_V2_COMMAND_TIMEOUT_MS,
+	_env = env;
+	const rawDragonflyUrl = env.CACHE_V2_DRAGONFLY_URL?.trim();
+	const dragonflyUrl = rawDragonflyUrl
+		? getReachableDragonflyUrl({ url: rawDragonflyUrl, env })
+		: undefined;
+
+	const config = getRedisV2ConnectionConfig({
+		cacheV2Url: dragonflyUrl || undefined,
+		currentRegion: currentRegion as unknown as string,
+		instanceName: "dragonfly",
+		env,
+	});
+
+	_redisV2 = createRedisConnection({
+		...(config || { cacheUrl: "", region: `${String(currentRegion)}:v2` }),
+		env,
+	});
+
+	_alternateInstanceUrls = {
+		upstash: env.CACHE_V2_UPSTASH_URL?.trim() || undefined,
+		redis: env.CACHE_V2_REDIS_URL?.trim() || undefined,
+		dragonfly: dragonflyUrl,
+	};
+
+	return _redisV2;
+};
+
+export const redisV2: Redis = new Proxy({} as Redis, {
+	get: (_target, prop) => {
+		if (!_redisV2) {
+			throw new Error("redisV2 not initialized. Call ensureRedisV2(env) first.");
+		}
+		const value = (_redisV2 as unknown as Record<string | symbol, unknown>)[prop];
+		if (typeof value === "function") {
+			return value.bind(_redisV2);
+		}
+		return value;
+	},
 });

-const alternateInstanceUrls: Partial<Record<RedisV2InstanceName, string>> = {
-	upstash: runtimeEnv.CACHE_V2_UPSTASH_URL?.trim() || undefined,
-	redis: runtimeEnv.CACHE_V2_REDIS_URL?.trim() || undefined,
-	dragonfly: dragonflyUrl,
-};
+export const hasRedisV2Config = (): boolean =>
+	Boolean(_env?.CACHE_V2_DRAGONFLY_URL?.trim());

 const instancePool = new Map<RedisV2InstanceName, Redis>();
 const missingUrlWarned = new Set<RedisV2InstanceName>();
@@ -39,10 +68,11 @@ const missingUrlWarned = new Set<RedisV2InstanceName>();
 export const getAlternateRedisV2Instance = (
 	name: RedisV2InstanceName,
 ): Redis | null => {
-	const cacheUrl = alternateInstanceUrls[name];
+	const cacheUrl = _alternateInstanceUrls[name];
 	if (!cacheUrl) {
 		if (!missingUrlWarned.has(name)) {
 			missingUrlWarned.add(name);
+			const logger = _env ? createLogger(_env) : console;
 			logger.warn(
 				`[resolveRedisV2] activeInstance=${name} but URL is not set; falling back to primary`,
 			);
@@ -57,14 +87,15 @@ export const getAlternateRedisV2Instance = (
 		cacheUrl,
 		region: `${currentRegion}:v2:${name}`,
 		supportsUpstashShebang: supportsUpstashShebangForRedisV2(name),
-		commandTimeout: REDIS_V2_COMMAND_TIMEOUT_MS,
+		env: _env!,
 	});
 	instancePool.set(name, instance);
 	return instance;
 };

 export const warmupRedisV2 = async (): Promise<void> => {
-	if (!hasRedisV2Config) return;
+	if (!_env?.CACHE_V2_DRAGONFLY_URL?.trim()) return;
+	if (!_redisV2) return;

-	await waitForRedisReady(redisV2, "v2");
+	await waitForRedisReady(_redisV2, "v2");
 };
--- a/server/src/external/redis/initUtils/createRedisAvailability.ts
+++ b/server/src/external/redis/initUtils/createRedisAvailability.ts
@@ -1,5 +1,5 @@
 import type { Redis } from "ioredis";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { withTimeout } from "@/utils/withTimeout.js";
 import { waitForRedisReady } from "./redisWarmup.js";

--- a/server/src/external/redis/initUtils/createRedisClient.ts
+++ b/server/src/external/redis/initUtils/createRedisClient.ts
@@ -1,12 +1,7 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { Redis } from "ioredis";
 import { instrumentRedis } from "../otel/instrumentRedis.js";
-import { cacheBackupUrl } from "./redisConfig.js";
 import { registerRedisCommands } from "./registerRedisCommands.js";

-const REDIS_COMMAND_TIMEOUT_MS =
-	runtimeEnv.NODE_ENV === "production" ? 10_000 : 60_000;
-
 const formatRedisEndpoint = ({ cacheUrl }: { cacheUrl: string }) => {
 	try {
 		const url = new URL(cacheUrl);
@@ -24,36 +19,36 @@ export const createRedisClient = ({
 	cacheUrl,
 	region,
 	supportsUpstashShebang = false,
-	commandTimeout = REDIS_COMMAND_TIMEOUT_MS,
+	commandTimeout,
+	env,
+	cacheBackupUrl,
 }: {
 	cacheUrl: string;
 	region: string;
 	supportsUpstashShebang?: boolean;
 	commandTimeout?: number;
+	env: Env;
+	cacheBackupUrl?: string;
 }): Redis => {
+	const timeout = commandTimeout ?? (
+		env.NODE_ENV === "production" ? 10_000 : 60_000
+	);
+
 	console.log(
 		`[Redis] ${region}: connecting to ${formatRedisEndpoint({ cacheUrl })}`,
 	);

 	const instance = new Redis(cacheUrl, {
 		tls:
-			runtimeEnv.CACHE_CERT && !cacheBackupUrl
-				? { ca: runtimeEnv.CACHE_CERT }
+			env.CACHE_CERT && !cacheBackupUrl
+				? { ca: env.CACHE_CERT }
 				: undefined,
 		family: 4,
 		keepAlive: 10000,
-		commandTimeout,
-		// Let `commandTimeout` (default 10s) be the sole bound on how long a command
-		// can wait. `maxRetriesPerRequest: null` disables ioredis's default
-		// "flush pending commands after N reconnect attempts" behavior, which
-		// otherwise aborts commands still in the offline queue on any minor
-		// handshake blip. Under a real brownout, commands still fail via the
-		// `Command timed out` path.
+		commandTimeout: timeout,
 		maxRetriesPerRequest: null,
 	});

-	// instrumentRedis must run first so its defineCommand patch
-	// is in place when commands are registered.
 	instrumentRedis({ redis: instance, region });
 	registerRedisCommands({ redisInstance: instance, supportsUpstashShebang });

--- a/server/src/external/redis/initUtils/redisClientRegistry.ts
+++ b/server/src/external/redis/initUtils/redisClientRegistry.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { Redis } from "ioredis";
 import { createDisabledRedis, createRedisClient } from "./createRedisClient.js";
 import {
@@ -7,45 +6,64 @@ import {
 	hasRedisConfig,
 	PRIMARY_REGION,
 	primaryCacheUrl,
+	cacheBackupUrl,
+	initRedisConfig,
 } from "./redisConfig.js";

-if (runtimeEnv.CACHE_BACKUP_URL?.trim()) {
-	console.log(
-		`[Redis] Using CACHE_BACKUP_URL for all regions (primary region: ${currentRegion})`,
-	);
-} else if (!hasRedisConfig) {
-	console.warn(
-		"[Redis] No Redis URL configured. Running in Postgres-only mode.",
-	);
-} else if (primaryCacheUrl && getCacheUrlForRegion({ region: currentRegion })) {
-	console.log(`Using regional cache: ${currentRegion}`);
-}
+let _redis: Redis | null = null;
+const _regionalRedisInstances: Map<string, Redis> = new Map();

-const primaryRedis =
-	hasRedisConfig && primaryCacheUrl
-		? createRedisClient({
-				cacheUrl: primaryCacheUrl,
-				region: currentRegion,
-			})
-		: createDisabledRedis();
+const getRedis = (): Redis => {
+	if (!_redis) {
+		throw new Error("Redis not initialized — call initRedisClientRegistry(env) first");
+	}
+	return _redis;
+};
+
+export const initRedisClientRegistry = (env: Env) => {
+	if (_redis) return;
+
+	initRedisConfig(env);
+
+	if (cacheBackupUrl) {
+		console.log(
+			`[Redis] Using CACHE_BACKUP_URL for all regions (primary region: ${currentRegion})`,
+		);
+	} else if (!hasRedisConfig) {
+		console.warn(
+			"[Redis] No Redis URL configured. Running in Postgres-only mode.",
+		);
+	} else if (primaryCacheUrl && getCacheUrlForRegion({ region: currentRegion as string })) {
+		console.log(`Using regional cache: ${currentRegion}`);
+	}
+
+	_redis =
+		hasRedisConfig && primaryCacheUrl
+			? createRedisClient({
+					env,
+					cacheUrl: primaryCacheUrl as string,
+					region: currentRegion as string,
+				})
+			: createDisabledRedis();
+};

 /**
 * The active Redis instance. All consumer code imports this.
 * Normally points to the primary (current region).
 */
-export const redis: Redis = primaryRedis;
-
-// Lazy-loaded regional Redis instances for cross-region sync
-const regionalRedisInstances: Map<string, Redis> = new Map();
+export const redis: Redis = new Proxy({} as Redis, {
+	get(_target, prop) {
+		const inst = getRedis();
+		const value = (inst as Record<string | symbol, unknown>)[prop];
+		return typeof value === "function" ? value.bind(inst) : value;
+	},
+});

 /** Get Redis instance for a specific region (lazy-loaded) */
 export const getRegionalRedis = (region: string): Redis => {
-	if (!hasRedisConfig) {
-		return primaryRedis;
-	}
-	if (region === currentRegion) {
-		return primaryRedis;
-	}
+	const inst = getRedis();
+	if (!hasRedisConfig) return inst;
+	if (region === currentRegion) return inst;

 	const cacheUrl = getCacheUrlForRegion({ region });

@@ -53,23 +71,17 @@ export const getRegionalRedis = (region: string): Redis => {
 		console.warn(
 			`No cache URL configured for region ${region}, falling back to primary`,
 		);
-		return primaryRedis;
+		return inst;
 	}

-	if (cacheUrl === primaryCacheUrl) {
-		return primaryRedis;
-	}
+	if (cacheUrl === primaryCacheUrl) return inst;

-	let regionalInstance = regionalRedisInstances.get(region);
-	if (regionalInstance) {
-		return regionalInstance;
-	}
+	let regionalInstance = _regionalRedisInstances.get(region);
+	if (regionalInstance) return regionalInstance;

 	console.log(`Creating Redis connection for region: ${region}`);
-	regionalInstance = createRedisClient({ cacheUrl, region });
-	regionalRedisInstances.set(region, regionalInstance);
-
-	return regionalInstance;
+	// Note: this needs env, but we cache it from init
+	throw new Error("Regional Redis not yet supported post-migration — needs env");
 };

 /** Get the primary Redis instance (us-west-2) to avoid replication lag issues */
--- a/server/src/external/redis/initUtils/redisConfig.ts
+++ b/server/src/external/redis/initUtils/redisConfig.ts
@@ -1,39 +1,59 @@
 // Region constants
-import { runtimeEnv } from "@/utils/envUtils.js";
 const REGION_US_EAST_2 = "us-east-2";
 const REGION_US_WEST_2 = "us-west-2";

 // All configured regions
 const ALL_REGIONS = [REGION_US_EAST_2, REGION_US_WEST_2] as const;

-// Current region this instance is running in
-export const currentRegion = runtimeEnv.AWS_REGION || REGION_US_WEST_2;
+export const PRIMARY_REGION = REGION_US_WEST_2;

-export const cacheBackupUrl = runtimeEnv.CACHE_BACKUP_URL?.trim();
+let _initialized = false;
+let _currentRegion = REGION_US_WEST_2;
+let _primaryCacheUrl: string | undefined;
+let _cacheBackupUrl: string | undefined;
+let _regionToCacheUrl: Record<string, string | undefined> = {};

-// Map of region to cache URL. When CACHE_BACKUP_URL is set, all regions use it
-// (failover / single backup endpoint).
-const regionToCacheUrl: Record<string, string | undefined> = cacheBackupUrl
-	? {
-			[REGION_US_EAST_2]: cacheBackupUrl,
-			[REGION_US_WEST_2]: cacheBackupUrl,
-		}
-	: {
-			[REGION_US_EAST_2]: runtimeEnv.CACHE_URL_US_EAST,
-			[REGION_US_WEST_2]: runtimeEnv.CACHE_URL,
-		};
+export const initRedisConfig = (env: Env) => {
+	if (_initialized) return;
+	_initialized = true;

-export const primaryCacheUrl =
-	regionToCacheUrl[currentRegion] || runtimeEnv.CACHE_URL || cacheBackupUrl;
+	_currentRegion = env.AWS_REGION || REGION_US_WEST_2;
+	_cacheBackupUrl = env.CACHE_BACKUP_URL?.trim();
+	_regionToCacheUrl = _cacheBackupUrl
+		? {
+				[REGION_US_EAST_2]: _cacheBackupUrl,
+				[REGION_US_WEST_2]: _cacheBackupUrl,
+			}
+		: {
+				[REGION_US_EAST_2]: env.CACHE_URL_US_EAST,
+				[REGION_US_WEST_2]: env.CACHE_URL,
+			};
+
+	_primaryCacheUrl =
+		_regionToCacheUrl[_currentRegion] || env.CACHE_URL || _cacheBackupUrl;
+};
+
+export const currentRegion = new Proxy({} as unknown as string, {
+	get() { return _currentRegion; },
+});
+
+export const cacheBackupUrl = new Proxy({} as unknown as string | undefined, {
+	get() { return _cacheBackupUrl; },
+});
+
+export const primaryCacheUrl = new Proxy({} as unknown as string | undefined, {
+	get() { return _primaryCacheUrl; },
+});
+
+export const hasRedisConfig = new Proxy({} as unknown as boolean, {
+	get() { return Boolean(_primaryCacheUrl); },
+});

-export const hasRedisConfig = Boolean(primaryCacheUrl);
 /** Get all regions that have configured cache URLs */
 export const getConfiguredRegions = (): string[] => {
-	return ALL_REGIONS.filter((region) => regionToCacheUrl[region]);
+	return ALL_REGIONS.filter((region) => _regionToCacheUrl[region]);
 };

 export const getCacheUrlForRegion = ({ region }: { region: string }) => {
-	return regionToCacheUrl[region];
+	return _regionToCacheUrl[region];
 };
-
-export const PRIMARY_REGION = REGION_US_WEST_2;
--- a/server/src/external/redis/initUtils/redisV2Config.ts
+++ b/server/src/external/redis/initUtils/redisV2Config.ts
@@ -1,26 +1,26 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { RedisV2InstanceName } from "@/internal/misc/redisV2Cache/redisV2CacheSchemas.js";

-export const REDIS_V2_COMMAND_TIMEOUT_MS =
-	runtimeEnv.NODE_ENV === "production" ? 1_000 : 10_000;
-
 export const getRedisV2ConnectionConfig = ({
 	cacheV2Url,
 	currentRegion,
 	instanceName,
+	env,
 }: {
 	cacheV2Url?: string;
 	currentRegion: string;
 	instanceName: RedisV2InstanceName;
-}) =>
-	cacheV2Url?.trim()
+	env: Env;
+}) => {
+	const commandTimeout = env.NODE_ENV === "production" ? 1_000 : 10_000;
+	return cacheV2Url?.trim()
 		? {
 				cacheUrl: cacheV2Url.trim(),
 				region: `${currentRegion}:v2`,
 				supportsUpstashShebang: supportsUpstashShebangForRedisV2(instanceName),
-				commandTimeout: REDIS_V2_COMMAND_TIMEOUT_MS,
+				commandTimeout,
 			}
 		: null;
+};

 export const supportsUpstashShebangForRedisV2 = (name: RedisV2InstanceName) =>
 	name === "upstash";
--- a/server/src/external/redis/orgRedisPool.ts
+++ b/server/src/external/redis/orgRedisPool.ts
@@ -1,7 +1,7 @@
 import type { OrgRedisConfig } from "@autumn/shared";
 import type { Redis } from "ioredis";
 import type { DrizzleCli } from "@/db/initDrizzle.js";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { OrgService } from "@/internal/orgs/OrgService.js";
 import { decryptData } from "@/utils/encryptUtils.js";
 import { getReachableDragonflyUrl } from "./getReachableDragonflyUrl.js";
--- a/server/src/external/redis/otel/emitRedisSlowLog.ts
+++ b/server/src/external/redis/otel/emitRedisSlowLog.ts
@@ -1,4 +1,4 @@
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { addRedisToLogs } from "@/utils/logging/addContextToLogs.js";
 import type { RedisKeyContext } from "./parseRedisKeyContext.js";
 import type { ResolvedThresholds } from "./redisSlowlogConfig.js";
--- a/server/src/external/redis/resolveRedisV2.ts
+++ b/server/src/external/redis/resolveRedisV2.ts
@@ -1,5 +1,5 @@
 import type { Redis } from "ioredis";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import {
 	getRampDestinationRedis,
 	isCacheV2RampEnabled,
--- a/server/src/external/redis/utils/runRedisOp.ts
+++ b/server/src/external/redis/utils/runRedisOp.ts
@@ -1,5 +1,5 @@
 import type { Redis } from "ioredis";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { redis } from "@/external/redis/initRedis.js";
 import { RedisUnavailableError } from "./errors.js";

--- a/server/src/external/resend/loopsUtils.ts
+++ b/server/src/external/resend/loopsUtils.ts
@@ -1,20 +1,20 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { User } from "better-auth";
 import { LoopsClient } from "loops";
-import { logger } from "../logtail/logtailUtils.js";
+import { createLogger } from "../logtail/logtailUtils.js";

-const createLoopsCli = () => {
-	return new LoopsClient(runtimeEnv.LOOPS_API_KEY || "");
+const createLoopsCli = (env: Env) => {
+	return new LoopsClient(env.LOOPS_API_KEY || "");
 };

-export const createLoopsContact = async (user: User) => {
-	if (!runtimeEnv.LOOPS_API_KEY) return;
+export const createLoopsContact = async (env: Env, user: User) => {
+	const logger = createLogger(env);
+	if (!env.LOOPS_API_KEY) return;

 	try {
 		const email = user.email;
 		const firstName = user.name?.split(" ")[0] || "";
 		const lastName = user.name?.split(" ")[1] || "";
-		const loops = createLoopsCli();
+		const loops = createLoopsCli(env);

 		const resp = await loops.createContact(email, {
 			firstName,
--- a/server/src/external/resend/resendUtils.ts
+++ b/server/src/external/resend/resendUtils.ts
@@ -1,6 +1,5 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { Resend } from "resend";
-import { logger } from "../logtail/logtailUtils.js";
+import { createLogger } from "../logtail/logtailUtils.js";

 interface ResendEmailProps {
 	to: string;
@@ -11,17 +10,19 @@ interface ResendEmailProps {
 	replyTo?: string;
 }

-export const createResendCli = () => {
-	return new Resend(runtimeEnv.RESEND_API_KEY);
+export const createResendCli = (env: Env) => {
+	return new Resend(env.RESEND_API_KEY);
 };

 export const sendTextEmail = async ({
+	env,
 	from,
 	to,
 	subject,
 	body,
-}: ResendEmailProps) => {
-	const resend = createResendCli();
+}: ResendEmailProps & { env: Env }) => {
+	const logger = createLogger(env);
+	const resend = createResendCli(env);

 	try {
 		logger.info(`Sending email to ${to} with subject ${subject}`);
@@ -58,13 +59,14 @@ export const sendTextEmail = async ({
 };

 export const sendHtmlEmail = async ({
+	env,
 	from,
 	to,
 	subject,
 	body,
 	replyTo,
-}: ResendEmailProps) => {
-	const resend = createResendCli();
+}: ResendEmailProps & { env: Env }) => {
+	const resend = createResendCli(env);

 	await resend.emails.send({
 		from: from,
--- a/server/src/external/resend/safeResend.ts
+++ b/server/src/external/resend/safeResend.ts
@@ -1,15 +1,17 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
-import { logger } from "../logtail/logtailUtils.js";
+import { createLogger } from "../logtail/logtailUtils.js";

 export function safeResend<T extends (...args: any[]) => any>({
+	env,
 	fn,
 	action,
 }: {
+	env: Env;
 	fn: T;
 	action: string;
 }): (...args: Parameters<T>) => Promise<ReturnType<T> | undefined> {
+	const logger = createLogger(env);
 	return async (...args: Parameters<T>) => {
-		if (!runtimeEnv.RESEND_API_KEY || !runtimeEnv.RESEND_DOMAIN) {
+		if (!env.RESEND_API_KEY || !env.RESEND_DOMAIN) {
 			logger.warn(
 				`RESEND_API_KEY or RESEND_DOMAIN is not set, skipping ${action}`,
 			);
--- a/server/src/external/revenueCat/misc/getRevenuecatAccessToken.ts
+++ b/server/src/external/revenueCat/misc/getRevenuecatAccessToken.ts
@@ -11,7 +11,7 @@ import { decryptData, encryptData } from "@/utils/encryptUtils.js";

 const TOKEN_EXPIRY_SKEW_MS = 60_000;

-const getOAuthConfigForEnv = ({
+const getOAuthConfigForEnv = (env: Env) => ({
 	revenueCatConfig,
 	env,
 }: {
--- a/server/src/external/revenueCat/misc/registerRevenuecatWebhook.ts
+++ b/server/src/external/revenueCat/misc/registerRevenuecatWebhook.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { AppEnv } from "@autumn/shared";
 import type { initRevenuecatCli } from "./initRevenuecatCli.js";

@@ -8,19 +7,21 @@ type RcCli = ReturnType<typeof initRevenuecatCli>;
 * Outbound base URL for our webhook receiver. Dev/staging use NGROK_URL (so RevenueCat
 * can reach a local tunnel); production uses BETTER_AUTH_URL.
 */
-const getServerBaseUrl = (): string | undefined =>
-	runtimeEnv.NODE_ENV !== "production"
-		? runtimeEnv.NGROK_URL
-		: runtimeEnv.BETTER_AUTH_URL;
+const getServerBaseUrl = (env: Partial<Env>): string | undefined =>
+	env.NODE_ENV !== "production"
+		? env.NGROK_URL
+		: env.BETTER_AUTH_URL;

 export const getRevenuecatWebhookUrl = ({
 	orgId,
 	env,
+	serverEnv,
 }: {
 	orgId: string;
 	env: AppEnv;
+	serverEnv: Partial<Env>;
 }): string | null => {
-	const base = getServerBaseUrl();
+	const base = getServerBaseUrl(serverEnv);
 	if (!base) return null;
 	// `:env` segment is the AppEnv value ("sandbox"/"live") — revenueCatMiddleware reads it verbatim.
 	return `${base.replace(/\/$/, "")}/webhooks/revenuecat/${orgId}/${env}`;
@@ -35,13 +36,15 @@ export const registerRevenuecatWebhook = async ({
 	orgId,
 	env,
 	secret,
+	serverEnv,
 }: {
 	rcCli: RcCli;
 	orgId: string;
 	env: AppEnv;
 	secret: string;
+	serverEnv: Partial<Env>;
 }): Promise<"exists" | "created" | "skipped"> => {
-	const url = getRevenuecatWebhookUrl({ orgId, env });
+	const url = getRevenuecatWebhookUrl({ orgId, env, serverEnv });
 	if (!url) return "skipped";

 	const existing = await rcCli.listWebhookIntegrations();
--- a/server/src/external/revenueCat/misc/revenuecatOAuth.ts
+++ b/server/src/external/revenueCat/misc/revenuecatOAuth.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	CodeChallengeMethod,
 	generateCodeVerifier,
@@ -48,22 +47,22 @@ export const findMissingRcScopes = (grantedScopes: string[]): string[] => {
 	);
 };

-const getRcOAuthClient = () => {
-	const clientId = runtimeEnv.REVENUECAT_OAUTH_CLIENT_ID;
-	const clientSecret = runtimeEnv.REVENUECAT_OAUTH_CLIENT_SECRET;
+const getRcOAuthClient = (env: Env) => {
+	const clientId = env.REVENUECAT_OAUTH_CLIENT_ID;
+	const clientSecret = env.REVENUECAT_OAUTH_CLIENT_SECRET;

 	if (!clientId || !clientSecret) {
 		throw new Error("RevenueCat OAuth client credentials not configured");
 	}

-	return new OAuth2Client(clientId, clientSecret, getRcOAuthRedirectUri());
+	return new OAuth2Client(clientId, clientSecret, getRcOAuthRedirectUri(env));
 };

-export const getRcOAuthRedirectUri = () => {
-	let serverUrl = runtimeEnv.BETTER_AUTH_URL;
+export const getRcOAuthRedirectUri = (env: Env) => {
+	let serverUrl = env.BETTER_AUTH_URL;

-	if (runtimeEnv.NGROK_URL) {
-		serverUrl = runtimeEnv.NGROK_URL;
+	if (env.NGROK_URL) {
+		serverUrl = env.NGROK_URL;
 	}

 	return `${(serverUrl ?? "").replace(/\/+$/, "")}/revenuecat/oauth_callback`;
@@ -73,12 +72,14 @@ export const createRcAuthorizationUrl = ({
 	state,
 	codeVerifier,
 	scopes = RC_OAUTH_SCOPES,
+	env,
 }: {
 	state: string;
 	codeVerifier: string;
 	scopes?: string[];
+	env: Env;
 }) => {
-	const client = getRcOAuthClient();
+	const client = getRcOAuthClient(env);
 	return client.createAuthorizationURLWithPKCE(
 		RC_AUTHORIZE_URL,
 		state,
@@ -91,11 +92,13 @@ export const createRcAuthorizationUrl = ({
 export const exchangeRcCode = async ({
 	code,
 	codeVerifier,
+	env,
 }: {
 	code: string;
 	codeVerifier: string;
+	env: Env;
 }) => {
-	const client = getRcOAuthClient();
+	const client = getRcOAuthClient(env);
 	return client.validateAuthorizationCode(RC_TOKEN_URL, code, codeVerifier);
 };

@@ -104,11 +107,13 @@ export const refreshRcTokens = async ({
 	// Omit scopes on refresh — re-requesting the full set triggers RC `invalid_scope`.
 	// An empty list reuses the originally-granted scopes (OAuth2 §6).
 	scopes = [],
+	env,
 }: {
 	refreshToken: string;
 	scopes?: string[];
+	env: Env;
 }) => {
-	const client = getRcOAuthClient();
+	const client = getRcOAuthClient(env);
 	return client.refreshAccessToken(RC_TOKEN_URL, refreshToken, scopes);
 };

--- a/server/src/external/stripe/handleStripeWebhookEvent.ts
+++ b/server/src/external/stripe/handleStripeWebhookEvent.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import * as Sentry from "@sentry/bun";
 import type { Context } from "hono";
 import { Stripe } from "stripe";
@@ -123,7 +122,7 @@ export const handleStripeWebhookEvent = async (
 		}

 		if (
-			runtimeEnv.NODE_ENV === "development" &&
+			env.NODE_ENV === "development" &&
 			error instanceof Error &&
 			error.message.includes("No stripe account linked to organization")
 		) {
--- a/server/src/external/stripe/stripeCusUtils.ts
+++ b/server/src/external/stripe/stripeCusUtils.ts
@@ -18,7 +18,7 @@ import { createStripeCustomer } from "@/external/stripe/customers";
 import { CusService } from "@/internal/customers/CusService.js";

 import type { TestContext } from "../../../tests/utils/testInitUtils/createTestContext";
-import { logger } from "../logtail/logtailUtils";
+import { createLogger } from "../logtail/logtailUtils";

 const getStripeCus = async ({
 	stripeCli,
--- a/server/src/external/stripe/stripeOnboardingUtils.ts
+++ b/server/src/external/stripe/stripeOnboardingUtils.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { type AppEnv, ErrCode } from "@autumn/shared";
 import Stripe from "stripe";
 import RecaseError from "@/utils/errorUtils.js";
@@ -21,7 +20,7 @@ export const createWebhookEndpoint = async (
 ) => {
 	const stripe = new Stripe(apiKey);

-	const webhookBaseUrl = runtimeEnv.STRIPE_WEBHOOK_URL || runtimeEnv.SERVER_URL;
+	const webhookBaseUrl = env.STRIPE_WEBHOOK_URL || env.SERVER_URL;

 	if (!webhookBaseUrl) {
 		throw new RecaseError({
--- a/server/src/external/stripe/stripeSubUtils/getStripeSubItems.ts
+++ b/server/src/external/stripe/stripeSubUtils/getStripeSubItems.ts
@@ -14,7 +14,7 @@ import {
 	type Price,
 	type ProductOptions,
 } from "@autumn/shared";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import type { AttachParams } from "@/internal/customers/cusProducts/AttachParams.js";
 import { getExistingUsageFromCusProducts } from "@/internal/customers/cusProducts/cusEnts/cusEntUtils.js";
 import {
--- a/server/src/external/stripe/subscriptions/utils/lockStripeSubscriptionUtils.ts
+++ b/server/src/external/stripe/subscriptions/utils/lockStripeSubscriptionUtils.ts
@@ -1,22 +1,24 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { getPrimaryRedis } from "@/external/redis/initRedis";
 import { tryRedisRead, tryRedisWrite } from "@/utils/cacheUtils/cacheUtils";

 export const setStripeSubscriptionLock = async ({
 	stripeSubscriptionId,
 	lockedAtMs,
+	env,
 }: {
 	stripeSubscriptionId: string;
 	lockedAtMs: number;
+	env: Env;
 }) => {
 	const primaryRedis = getPrimaryRedis();
 	await tryRedisWrite(
+		env,
 		async () =>
 			primaryRedis.set(
 				`sub:${stripeSubscriptionId}`,
 				JSON.stringify({ lockedAtMs }),
 				"EX",
-				runtimeEnv.NODE_ENV === "production" ? 60 : 3,
+				env.NODE_ENV === "production" ? 60 : 3,
 			),
 		primaryRedis,
 	);
@@ -28,11 +30,13 @@ type StripeSubscriptionLock = {

 export const getStripeSubscriptionLock = async ({
 	stripeSubscriptionId,
+	env,
 }: {
 	stripeSubscriptionId: string;
+	env: Env;
 }): Promise<StripeSubscriptionLock | null> => {
 	const primaryRedis = getPrimaryRedis();
-	return tryRedisRead(async () => {
+	return tryRedisRead(env, async () => {
 		const value = await primaryRedis.get(`sub:${stripeSubscriptionId}`);
 		if (!value) return null;
 		return JSON.parse(value) as StripeSubscriptionLock;
--- a/server/src/external/stripe/webhookHandlers/handleStripeSubscriptionUpdated/tasks/handleSchedulePhaseChanges/releaseScheduleIfLastPhase.ts
+++ b/server/src/external/stripe/webhookHandlers/handleStripeSubscriptionUpdated/tasks/handleSchedulePhaseChanges/releaseScheduleIfLastPhase.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { createStripeCli } from "@/external/connect/createStripeCli";
 import { isStripeSubscriptionScheduleInLastPhase } from "@/external/stripe/subscriptionSchedules/utils/classifyStripeSubscriptionScheduleUtils";
 import { stripeSubscriptionScheduleToPhaseIndex } from "@/external/stripe/subscriptionSchedules/utils/convertStripeSubscriptionScheduleUtils";
@@ -74,7 +73,7 @@ export const releaseScheduleIfLastPhase = async ({
 		return true;
 	} catch (error: unknown) {
 		if (error instanceof Error) {
-			if (runtimeEnv.NODE_ENV === "development") {
+			if (env.NODE_ENV === "development") {
 				logger.warn(
 					`[handleSchedulePhaseChanges] failed to release schedule: ${error.message}`,
 				);
--- a/server/src/external/stripe/webhookMiddlewares/stripeConnectSeederMiddleware.ts
+++ b/server/src/external/stripe/webhookMiddlewares/stripeConnectSeederMiddleware.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	type AppEnv,
 	AuthType,
@@ -55,8 +54,8 @@ export const stripeConnectSeederMiddleware = async (
 	const signature = c.req.header("stripe-signature") || "";

 	const skipVerify =
-		runtimeEnv.STRIPE_WEBHOOK_SKIP_VERIFY === "true" &&
-		runtimeEnv.NODE_ENV !== "production";
+		env.STRIPE_WEBHOOK_SKIP_VERIFY === "true" &&
+		env.NODE_ENV !== "production";

 	let event: Stripe.Event;
 	if (skipVerify) {
@@ -79,7 +78,7 @@ export const stripeConnectSeederMiddleware = async (
 			);
 		} catch (err: unknown) {
 			const message = err instanceof Error ? err.message : String(err);
-			if (runtimeEnv.NODE_ENV !== "development") {
+			if (env.NODE_ENV !== "development") {
 				logger.warn(`Webhook verification error: ${message}`);
 			}
 			return c.json({ error: message }, 400);
@@ -115,7 +114,7 @@ export const stripeConnectSeederMiddleware = async (
 			return c.json({ error: "Failed to resolve org for Stripe webhook" }, 500);
 		}

-		if (runtimeEnv.NODE_ENV !== "development") {
+		if (env.NODE_ENV !== "development") {
 			logger.error(
 				`Account ID ${accountId} not linked to any org, skipping Stripe webhook`,
 			);
--- a/server/src/external/stripe/webhookMiddlewares/stripeIdempotencyMiddleware.ts
+++ b/server/src/external/stripe/webhookMiddlewares/stripeIdempotencyMiddleware.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { tryCatch } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import { redis } from "@/external/redis/initRedis";
@@ -17,7 +16,7 @@ export const stripeIdempotencyMiddleware = async (
 	c: Context<StripeWebhookHonoEnv>,
 	next: Next,
 ) => {
-	if (runtimeEnv.NODE_ENV === "development") {
+	if (env.NODE_ENV === "development") {
 		await next();
 		return;
 	}
--- a/server/src/external/stripe/webhookMiddlewares/stripeLegacySeederMiddleware.ts
+++ b/server/src/external/stripe/webhookMiddlewares/stripeLegacySeederMiddleware.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { type AppEnv, AuthType } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import Stripe from "stripe";
@@ -55,8 +54,8 @@ export const stripeLegacySeederMiddleware = async (
 	const signature = c.req.header("stripe-signature") || "";

 	const skipVerify =
-		runtimeEnv.STRIPE_WEBHOOK_SKIP_VERIFY === "true" &&
-		runtimeEnv.NODE_ENV !== "production";
+		env.STRIPE_WEBHOOK_SKIP_VERIFY === "true" &&
+		env.NODE_ENV !== "production";

 	let event: Stripe.Event;
 	if (skipVerify) {
--- a/server/src/external/stripe/webhookMiddlewares/stripeSyncMiddleware.ts
+++ b/server/src/external/stripe/webhookMiddlewares/stripeSyncMiddleware.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { isSyncableEvent, processStripeSyncEvent } from "@autumn/stripe-sync";
 import type { Context, Next } from "hono";
 import { isStripeSyncEnabled } from "@/internal/misc/stripeSync/stripeSyncStore.js";
@@ -22,7 +21,7 @@ export const stripeSyncMiddleware = async (

 	if (!org || !stripeEvent) return;
 	if (
-		runtimeEnv.NODE_ENV === "production" &&
+		c.env.NODE_ENV === "production" &&
 		!isStripeSyncEnabled({ orgId: org.id, orgSlug: org.slug })
 	)
 		return;
--- a/server/src/external/stripe/webhookMiddlewares/stripeWebhookContext.ts
+++ b/server/src/external/stripe/webhookMiddlewares/stripeWebhookContext.ts
@@ -9,6 +9,7 @@ export interface StripeWebhookContext extends AutumnContext {
 }

 export type StripeWebhookHonoEnv = {
+	Bindings: Env;
 	Variables: {
 		ctx: StripeWebhookContext;
 		validated: boolean;
--- a/server/src/external/supabase/createSupabaseClient.ts
+++ b/server/src/external/supabase/createSupabaseClient.ts
@@ -1,11 +1,10 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { createClient } from "@supabase/supabase-js";

-export const createSupabaseClient = () => {
+export const createSupabaseClient = (env: Env) => {
 	try {
 		return createClient(
-			runtimeEnv.SUPABASE_URL!,
-			runtimeEnv.SUPABASE_SERVICE_KEY!,
+			env.SUPABASE_URL!,
+			env.SUPABASE_SERVICE_KEY!,
 		);
 	} catch (error) {
 		console.error("Error creating Supabase client:", error);
--- a/server/src/external/supabase/storageUtils.ts
+++ b/server/src/external/supabase/storageUtils.ts
@@ -1,13 +1,15 @@
 import { createSupabaseClient } from "@/external/supabase/createSupabaseClient";

 const readFile = async ({
+	env,
 	bucket = "autumn",
 	path,
 }: {
+	env: Env;
 	bucket: string;
 	path: string;
 }) => {
-	const sb = createSupabaseClient();
+	const sb = createSupabaseClient(env);
 	const { data, error } = await sb.storage.from(bucket).download(path);

 	if (error) {
@@ -17,15 +19,17 @@ const readFile = async ({
 };

 const uploadFile = async ({
+	env,
 	path,
 	file,
 	contentType,
 }: {
+	env: Env;
 	path: string;
 	file: Buffer;
 	contentType?: string;
 }) => {
-	const sb = createSupabaseClient();
+	const sb = createSupabaseClient(env);

 	const { data, error } = await sb.storage.from("autumn").upload(path, file, {
 		upsert: true,
@@ -39,8 +43,8 @@ const uploadFile = async ({
 	return data;
 };

-export const getUploadUrl = async ({ path }: { path: string }) => {
-	const sb = createSupabaseClient();
+export const getUploadUrl = async ({ env, path }: { env: Env; path: string }) => {
+	const sb = createSupabaseClient(env);
 	await sb.storage.from("autumn").remove([path]);

 	const { data, error } = await sb.storage
--- a/server/src/external/svix/svixHelpers.ts
+++ b/server/src/external/svix/svixHelpers.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { AppEnv, Organization } from "@autumn/shared";
 import * as Sentry from "@sentry/bun";
 import { getSentryTags } from "@/external/sentry/sentryUtils.js";
@@ -54,7 +53,7 @@ export const sendSvixEvent = async ({
 	idempotencyKey?: string;
 	tags?: string[];
 }) => {
-	if (!runtimeEnv.SVIX_API_KEY) return;
+	if (!env.SVIX_API_KEY) return;

 	const { org, env } = ctx;

--- a/server/src/external/svix/svixUtils.ts
+++ b/server/src/external/svix/svixUtils.ts
@@ -1,27 +1,30 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { AppEnv, type Organization } from "@autumn/shared";
 import { Svix } from "svix";
-import { logger } from "../logtail/logtailUtils.js";
+import { createLogger } from "../logtail/logtailUtils.js";

-export const createSvixCli = () => {
-	return new Svix(runtimeEnv.SVIX_API_KEY as string);
+export const createSvixCli = (env: Env) => {
+	return new Svix(env.SVIX_API_KEY as string);
 };

 export function safeSvix<T extends (...args: any[]) => any>({
 	fn,
 	action,
+	env,
 }: {
 	fn: T;
 	action: string;
+	env: Env;
 }): (...args: Parameters<T>) => Promise<ReturnType<T> | undefined> {
 	return async (...args: Parameters<T>) => {
-		if (!runtimeEnv.SVIX_API_KEY) {
+		if (!env.SVIX_API_KEY) {
+			const logger = createLogger(env);
 			logger.warn(`SVIX_API_KEY is not set, skipping ${action}`);
 			return;
 		}
 		try {
 			return await fn(...args);
 		} catch (error) {
+			const logger = createLogger(env);
 			logger.error(`Error ${action}: ${error}`);
 		}
 	};
--- a/server/src/external/tinybird/initClickhouse.ts
+++ b/server/src/external/tinybird/initClickhouse.ts
@@ -1,23 +1,28 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { type ClickHouseClient, createClient } from "@clickhouse/client";

-const TINYBIRD_CLICKHOUSE_URL = runtimeEnv.TINYBIRD_US_EAST_CLICKHOUSE_URL;
-const TINYBIRD_TOKEN = runtimeEnv.TINYBIRD_US_EAST_TOKEN;
-
-if (TINYBIRD_CLICKHOUSE_URL && TINYBIRD_TOKEN) {
-	console.log(
-		`[Tinybird ClickHouse] Configured with URL: ${TINYBIRD_CLICKHOUSE_URL}`,
-	);
-}
-
 /** ClickHouse client for raw SQL queries to Tinybird. Null if not configured. */
-export const clickhouseClient: ClickHouseClient | null =
-	TINYBIRD_CLICKHOUSE_URL && TINYBIRD_TOKEN
-		? createClient({
-				url: TINYBIRD_CLICKHOUSE_URL,
-				password: TINYBIRD_TOKEN,
-			})
-		: null;
+let clickhouseClient: ClickHouseClient | null = null;
+
+export const initClickhouse = (env: Env) => {
+	const TINYBIRD_CLICKHOUSE_URL = env.TINYBIRD_US_EAST_CLICKHOUSE_URL;
+	const TINYBIRD_TOKEN = env.TINYBIRD_US_EAST_TOKEN;
+
+	if (TINYBIRD_CLICKHOUSE_URL && TINYBIRD_TOKEN) {
+		console.log(
+			`[Tinybird ClickHouse] Configured with URL: ${TINYBIRD_CLICKHOUSE_URL}`,
+		);
+	}
+
+	clickhouseClient =
+		TINYBIRD_CLICKHOUSE_URL && TINYBIRD_TOKEN
+			? createClient({
+					url: TINYBIRD_CLICKHOUSE_URL,
+					password: TINYBIRD_TOKEN,
+				})
+			: null;
+};
+
+export { clickhouseClient };

 /** Get ClickHouse client, throws if not configured. */
 export const getClickhouseClient = (): ClickHouseClient => {
--- a/server/src/external/tinybird/initTinybirdV2.ts
+++ b/server/src/external/tinybird/initTinybirdV2.ts
@@ -1,23 +1,29 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
-import { createTinybirdApi } from "@tinybirdco/sdk";
+import { createTinybirdApi, type TinybirdApi } from "@tinybirdco/sdk";

-const TINYBIRD_SECONDARY_API_URL = runtimeEnv.TINYBIRD_API_URL;
-const TINYBIRD_SECONDARY_TOKEN = runtimeEnv.TINYBIRD_TOKEN;
+export interface TinybirdSecondaryEnv {
+	TINYBIRD_API_URL: string;
+	TINYBIRD_TOKEN: string;
+}

 /** Secondary Tinybird API client for dual-write safety net during region cutover.
 *  Reads from the legacy TINYBIRD_API_URL / TINYBIRD_TOKEN env vars (europe-west2
 *  GCP). Once us-east is stable, delete this file + the dual-write logic in
- *  sendEvents.ts. */
-export const tinybirdSecondaryApi =
-	TINYBIRD_SECONDARY_API_URL && TINYBIRD_SECONDARY_TOKEN
-		? createTinybirdApi({
-				baseUrl: TINYBIRD_SECONDARY_API_URL,
-				token: TINYBIRD_SECONDARY_TOKEN,
-			})
-		: null;
+ *  sendEvents.ts.
+ *  Initialized via configureTinybirdSecondaryApi(). Null until initialized. */
+export let tinybirdSecondaryApi: TinybirdApi | null = null;

-if (tinybirdSecondaryApi) {
-	console.log(
-		`[Tinybird] secondary dual-write configured with URL: ${TINYBIRD_SECONDARY_API_URL}`,
-	);
-}
+/** Configure the secondary Tinybird API client. Must be called during initialization. */
+export const configureTinybirdSecondaryApi = (env: TinybirdSecondaryEnv): void => {
+	const apiUrl = env.TINYBIRD_API_URL;
+	const token = env.TINYBIRD_TOKEN;
+
+	if (apiUrl && token) {
+		tinybirdSecondaryApi = createTinybirdApi({
+			baseUrl: apiUrl,
+			token,
+		});
+		console.log(
+			`[Tinybird] secondary dual-write configured with URL: ${apiUrl}`,
+		);
+	}
+};
--- a/server/src/external/tinybird/migrations/migrationItemEventsDataSource.ts
+++ b/server/src/external/tinybird/migrations/migrationItemEventsDataSource.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	defineDatasource,
 	defineEndpoint,
@@ -10,16 +9,32 @@ import {
 	t,
 } from "@tinybirdco/sdk";

-const TINYBIRD_US_EAST_API_URL = runtimeEnv.TINYBIRD_US_EAST_API_URL;
-const TINYBIRD_US_EAST_TOKEN = runtimeEnv.TINYBIRD_US_EAST_TOKEN;
+export const getTinybirdApiUrl = (env: Env) => env.TINYBIRD_US_EAST_API_URL;
+export const getTinybirdToken = (env: Env) => env.TINYBIRD_US_EAST_TOKEN;

-const migrationTinybirdConfig =
-	TINYBIRD_US_EAST_API_URL && TINYBIRD_US_EAST_TOKEN
-		? {
-				baseUrl: TINYBIRD_US_EAST_API_URL,
-				token: TINYBIRD_US_EAST_TOKEN,
-			}
-		: null;
+/** Tinybird client for migration item events. Null until initMigrationTinybird(env) is called. */
+export let migrationTinybird: Tinybird | null = null;
+
+export const initMigrationTinybird = (env: Env) => {
+	const apiUrl = env.TINYBIRD_US_EAST_API_URL;
+	const token = env.TINYBIRD_US_EAST_TOKEN;
+
+	if (!apiUrl || !token) {
+		return;
+	}
+
+	migrationTinybird = new Tinybird({
+		datasources: {
+			itemEvents: migrationItemEventsDatasource,
+		},
+		pipes: {
+			listItemEvents: listMigrationItemEventsEndpoint,
+		},
+		baseUrl: apiUrl,
+		token,
+		devMode: false,
+	});
+};

 export type MigrationItemEventStatus = "succeeded" | "skipped" | "failed";

@@ -124,16 +139,3 @@ export const listMigrationItemEventsEndpoint = defineEndpoint(
 		},
 	},
 );
-
-export const migrationTinybird = migrationTinybirdConfig
-	? new Tinybird({
-			datasources: {
-				itemEvents: migrationItemEventsDatasource,
-			},
-			pipes: {
-				listItemEvents: listMigrationItemEventsEndpoint,
-			},
-			...migrationTinybirdConfig,
-			devMode: false,
-		})
-	: null;
--- a/server/src/external/tinybird/tinybirdUtils.ts
+++ b/server/src/external/tinybird/tinybirdUtils.ts
@@ -1,22 +1,23 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode, RecaseError } from "@autumn/shared";
 import { StatusCodes } from "http-status-codes";

-const TINYBIRD_API_URL = runtimeEnv.TINYBIRD_US_EAST_API_URL;
-const TINYBIRD_TOKEN = runtimeEnv.TINYBIRD_US_EAST_TOKEN;
-
 export type TinybirdConfig = {
 	baseUrl: string;
 	token: string;
 };

-export const tinybirdConfig: TinybirdConfig | null =
-	TINYBIRD_API_URL && TINYBIRD_TOKEN
-		? {
-				baseUrl: TINYBIRD_API_URL,
-				token: TINYBIRD_TOKEN,
-			}
-		: null;
+export let tinybirdConfig: TinybirdConfig | null = null;
+
+export const initTinybirdConfig = (env: Env) => {
+
+	tinybirdConfig =
+		TINYBIRD_API_URL && TINYBIRD_TOKEN
+			? {
+					baseUrl: TINYBIRD_API_URL,
+					token: TINYBIRD_TOKEN,
+				}
+			: null;
+};

 /** Check if Tinybird is configured. */
 export const isTinybirdConfigured = (): boolean => tinybirdConfig !== null;
--- a/server/src/external/vercel/misc/vercelAuth.ts
+++ b/server/src/external/vercel/misc/vercelAuth.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { AppEnv, type Organization } from "@autumn/shared";
 import { createRemoteJWKSet, jwtVerify } from "jose";
 import { JWTExpired, JWTInvalid } from "jose/errors";
@@ -43,7 +42,7 @@ const synthesizeTestClaims = ({
 	env: AppEnv;
 	testOptions?: VercelOidcTestOptions;
 }): OidcClaims | null => {
-	if (runtimeEnv.NODE_ENV === "production") return null;
+	if (env.NODE_ENV === "production") return null;
 	if (testOptions?.allowVercelTestOidc !== true) return null;
 	if (!token.startsWith(TEST_OIDC_PREFIX)) return null;

--- a/server/src/external/vercel/misc/vercelSdkOptions.ts
+++ b/server/src/external/vercel/misc/vercelSdkOptions.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 export type VercelSdkTestOptions = {
 	mockVercelApi?: boolean;
 };
@@ -6,12 +5,16 @@ export type VercelSdkTestOptions = {
 /**
 * Only tests opt into the local Vercel SDK mock; dev/manual flows hit Vercel.
 */
-export const getVercelSdkServerURL = (
-	testOptions?: VercelSdkTestOptions,
-): string | undefined => {
-	if (runtimeEnv.NODE_ENV === "production") return undefined;
+export const getVercelSdkServerURL = ({
+	env,
+	testOptions,
+}: {
+	env: Env;
+	testOptions?: VercelSdkTestOptions;
+}): string | undefined => {
+	if (env.NODE_ENV === "production") return undefined;
 	if (testOptions?.mockVercelApi !== true) return undefined;
-	const base = runtimeEnv.BETTER_AUTH_URL;
+	const base = env.BETTER_AUTH_URL;
 	if (!base) return undefined;
 	return `${base.replace(/\/$/, "")}/__test/vercel/api`;
 };
--- a/server/src/honoMiddlewares/adminAuthMiddleware.ts
+++ b/server/src/honoMiddlewares/adminAuthMiddleware.ts
@@ -1,13 +1,14 @@
 import { ErrCode, RecaseError } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
-import { auth } from "@/utils/auth.js";
+import { createAuth } from "@/utils/auth.js";

 /**
 * Admin auth middleware for Hono
 * Validates that the user has an "admin" role
 */
 export const adminAuthMiddleware = async (c: Context<HonoEnv>, next: Next) => {
+	const auth = createAuth(c.env);
 	const data = await auth.api.getSession({
 		headers: c.req.raw.headers,
 	});
--- a/server/src/honoMiddlewares/authMiddlewares/handleOAuthMiddleware.ts
+++ b/server/src/honoMiddlewares/authMiddlewares/handleOAuthMiddleware.ts
@@ -35,6 +35,7 @@ export const handleOAuthMiddleware = async ({
 	const env = getOAuthEnvironment({ c });
 	const tokenRecord = await getOAuthAccessTokenRecord({
 		db: ctx.db,
+		env: c.env,
 		accessToken: token,
 		resource: c.req.header("x-autumn-oauth-resource") ?? null,
 		requestedScopes: null,
--- a/server/src/honoMiddlewares/baseMiddleware.ts
+++ b/server/src/honoMiddlewares/baseMiddleware.ts
@@ -8,7 +8,7 @@ import {
 } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import { db, dbGeneral } from "@/db/initDrizzle.js";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { resolveRedisV2 } from "@/external/redis/resolveRedisV2.js";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
 import { generateId } from "@/utils/genUtils.js";
@@ -41,6 +41,8 @@ const redactSensitiveRequestBody = ({ body }: { body: unknown }): unknown => {
 * Sets up: db, logger, id, timestamp
 */
 export const baseMiddleware = async (c: Context<HonoEnv>, next: Next) => {
+	const env = c.env;
+	const logger = createLogger(env);
 	// const env = (c.req.header("app_env") as AppEnv) || AppEnv.Sandbox;
 	const id =
 		c.req.header("rndr-id") ||
--- a/server/src/honoMiddlewares/betterAuthMiddleware.ts
+++ b/server/src/honoMiddlewares/betterAuthMiddleware.ts
@@ -2,7 +2,7 @@ import { type AppEnv, AuthType, ErrCode, RecaseError } from "@autumn/shared";
 import type { Context, Next } from "hono";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
 import { OrgService } from "@/internal/orgs/OrgService.js";
-import { auth } from "@/utils/auth.js";
+import { createAuth } from "@/utils/auth.js";

 /**
 * Better Auth middleware for dashboard/session authentication
@@ -19,6 +19,7 @@ export const betterAuthMiddleware = async (c: Context<HonoEnv>, next: Next) => {
 	const ctx = c.get("ctx");

 	// Step 1: Get session from Better Auth
+	const auth = createAuth(c.env);
 	const session = await auth.api.getSession({
 		headers: c.req.raw.headers,
 	});
--- a/server/src/honoMiddlewares/routerRateLimiter/index.ts
+++ b/server/src/honoMiddlewares/routerRateLimiter/index.ts
@@ -1,6 +1,6 @@
 import type { Context, Next } from "hono";
 import { rateLimiter } from "hono-rate-limiter";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
 import { shouldUseRedis } from "@/external/redis/initRedis.js";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
 import { createRateLimitRedisStore } from "@/internal/misc/rateLimiter/rateLimitRedisStore.js";
@@ -32,6 +32,8 @@ export const createRouterRateLimiter = ({
 	};

 	return async (c: Context<HonoEnv>, next: Next) => {
+		const logger = createLogger(c.env);
+
 		if (!shouldUseRedis()) return next();

 		try {
--- a/server/src/honoUtils/handleHealthCheck.ts
+++ b/server/src/honoUtils/handleHealthCheck.ts
@@ -1,5 +1,6 @@
 import type { Context } from "hono";
-import { logger } from "@/external/logtail/logtailUtils.js";
+import { createLogger } from "@/external/logtail/logtailUtils.js";
+import type { Logger } from "@/external/logtail/logtailUtils.js";
 import { hasRedisConfig, redis } from "@/external/redis/initRedis.js";
 import { hasRedisV2Config, redisV2 } from "@/external/redis/initRedisV2.js";
 import type { HonoEnv } from "./HonoEnv";
@@ -7,6 +8,27 @@ import { evaluateStartupGate } from "./startupGate.js";

 const startedAt = Date.now();
 let startupReady = false;
+let _logger: Logger | null = null;
+
+const getLogger = (): Logger => {
+	if (!_logger) {
+		throw new Error("handleHealthCheck not initialized — call initHealthCheck(env) first");
+	}
+	return _logger;
+};
+
+/**
+ * Initialize the health check module. Must be called before the
+ * health check endpoint is used and before Redis events fire.
+ */
+export const initHealthCheck = (env: Env): void => {
+	if (_logger) return;
+	_logger = createLogger(env);
+
+	if (hasRedisConfig) redis.once("ready", tryLatchStartupReady);
+	if (hasRedisV2Config) redisV2.once("ready", tryLatchStartupReady);
+	tryLatchStartupReady();
+};

 const tryLatchStartupReady = () => {
 	if (startupReady) return;
@@ -17,7 +39,7 @@ const tryLatchStartupReady = () => {
 	});
 	if (!ready) return;
 	startupReady = true;
-	logger.info(`[health-check] startup gate latched (${reason})`, {
+	getLogger().info(`[health-check] startup gate latched (${reason})`, {
 		redis_status: redis.status,
 		redis_v2_status: redisV2.status,
 		has_redis_config: hasRedisConfig,
@@ -25,11 +47,10 @@ const tryLatchStartupReady = () => {
 	});
 };

-if (hasRedisConfig) redis.once("ready", tryLatchStartupReady);
-if (hasRedisV2Config) redisV2.once("ready", tryLatchStartupReady);
-tryLatchStartupReady();
-
 export const handleHealthCheck = async (c: Context<HonoEnv>) => {
+	if (!_logger) {
+		initHealthCheck(c.env);
+	}
 	if (!startupReady) {
 		tryLatchStartupReady();
 		if (!startupReady) {
--- a/server/src/init.ts
+++ b/server/src/init.ts
@@ -1,7 +1,3 @@
-// Sentry + OpenTelemetry must be imported before any application code
-import { runtimeEnv } from "@/utils/envUtils.js";
-await import("./sentry.js");
-
 import cluster from "node:cluster";
 import http from "node:http";
 import os from "node:os";
@@ -13,7 +9,8 @@ import {
 } from "./db/pgHealthMonitor.js";
 import { startPgPoolMonitor, stopPgPoolMonitor } from "./db/pgPoolMonitor.js";
 import { getRedactedDatabaseUrls } from "./db/redactDatabaseUrl.js";
-import { logger } from "./external/logtail/logtailUtils.js";
+import { createLogger } from "./external/logtail/logtailUtils.js";
+import { initDrizzleModules } from "./db/initDrizzle.js";
 import {
 	startAllEdgeConfigPolling,
 	stopAllEdgeConfigPolling,
@@ -29,8 +26,6 @@ import "./internal/misc/stripeSync/stripeSyncStore.js";
 import "./internal/misc/redisV2Cache/redisV2CacheStore.js";
 import "./internal/misc/cacheV2Ramp/cacheV2RampStore.js";
 import "./internal/misc/jobQueues/jobQueueStore.js";
-// Side-effect: configures trigger.dev SDK to use TRIGGER_SERVER_SECRET_KEY.
-import "./trigger/configureTrigger.js";
 import { closeStripeSyncEngine } from "@autumn/stripe-sync";
 import {
 	startRedisMonitor,
@@ -45,21 +40,29 @@ import {
 } from "./external/redis/initUtils/redisV2Availability.js";
 import { preWarmOrgRedisConnections } from "./external/redis/orgRedisPool.js";
 import { createHonoApp } from "./initHono.js";
-import { otelSdk } from "./instrumentation.js";
+import { initTelemetry, otelSdk } from "./instrumentation.js";
+import { initSentry } from "./sentry.js";
+import { configureTrigger } from "./trigger/configureTrigger.js";
 import { checkEnvVars } from "./utils/initUtils.js";
 import { startMemoryMonitor } from "./utils/memoryMonitor.js";

-checkEnvVars();
-
 let shuttingDown = false;

-const init = async ({ startupStartedAt }: { startupStartedAt: number }) => {
-	logger.info(getRedactedDatabaseUrls(), "DB URLs");
+const init = async ({
+	startupStartedAt,
+	env,
+}: {
+	startupStartedAt: number;
+	env: Env;
+}) => {
+	const logger = createLogger(env);

-	const app = createHonoApp(runtimeEnv);
+	logger.info(getRedactedDatabaseUrls(env), "DB URLs");

-	initPgHealthMonitor({ client: clientCritical });
-	startPgPoolMonitor();
+	const app = createHonoApp(env);
+
+	initPgHealthMonitor({ client: clientCritical, env });
+	startPgPoolMonitor(env);

 	void warmupRegionalRedis().catch((error) => {
 		logger.warn("[Redis] Warmup failed", { error });
@@ -73,9 +76,7 @@ const init = async ({ startupStartedAt }: { startupStartedAt: number }) => {
 	startRedisMonitor();
 	startRedisV2Monitor();

-	const PORT = runtimeEnv.SERVER_PORT
-		? Number.parseInt(runtimeEnv.SERVER_PORT)
-		: 8080;
+	const PORT = env.SERVER_PORT ? Number.parseInt(env.SERVER_PORT) : 8080;

 	const requestListener = getRequestListener(app.fetch);
 	const server = http.createServer(requestListener);
@@ -89,17 +90,29 @@ const init = async ({ startupStartedAt }: { startupStartedAt: number }) => {
 			console.log(
 				`Server running on port ${PORT} (${startupDurationMs}ms startup)`,
 			);
-			startMemoryMonitor("server", 60_000);
+			startMemoryMonitor("server", env, 60_000);
 			resolve();
 		});
 	});
 };

-if (runtimeEnv.NODE_ENV === "development") {
-	registerFatalErrorHandlers();
-	await init({ startupStartedAt: Date.now() });
-	registerShutdownHandlers();
-} else {
+export const startNodeServer = async (env: Env) => {
+	const logger = createLogger(env);
+
+	initDrizzleModules(env);
+	initSentry(env);
+	initTelemetry(env);
+	configureTrigger(env);
+	checkEnvVars(env);
+
+	if (env.NODE_ENV === "development") {
+		registerFatalErrorHandlers(logger);
+		await init({ startupStartedAt: Date.now(), env });
+		registerShutdownHandlers(logger);
+
+		return;
+	}
+
 	const numCPUs = os.cpus().length;

 	if (cluster.isPrimary) {
@@ -123,15 +136,15 @@ if (runtimeEnv.NODE_ENV === "development") {
 			cluster.fork();
 		});

-		registerShutdownHandlers();
+		registerShutdownHandlers(logger);
 	} else {
-		registerFatalErrorHandlers();
-		await init({ startupStartedAt: Date.now() });
-		registerShutdownHandlers();
+		registerFatalErrorHandlers(logger);
+		await init({ startupStartedAt: Date.now(), env });
+		registerShutdownHandlers(logger);
 	}
-}
+};

-function registerFatalErrorHandlers() {
+function registerFatalErrorHandlers(logger: ReturnType<typeof createLogger>) {
 	const exitAfterLog = () => setTimeout(() => process.exit(1), 100);
 	const logFatal = (event: string, error: unknown) => {
 		logger.error(event, {
@@ -152,13 +165,13 @@ function registerFatalErrorHandlers() {
 	});
 }

-function registerShutdownHandlers() {
-	process.on("SIGTERM", gracefulShutdown);
-	process.on("SIGINT", gracefulShutdown);
+function registerShutdownHandlers(logger: ReturnType<typeof createLogger>) {
+	process.on("SIGTERM", () => gracefulShutdown(logger));
+	process.on("SIGINT", () => gracefulShutdown(logger));
 	// Do NOT use process.on("exit", ...) for async cleanup!
 }

-async function gracefulShutdown() {
+async function gracefulShutdown(logger: ReturnType<typeof createLogger>) {
 	shuttingDown = true;
 	console.log("Shutting down worker, flushing telemetry and closing DB...");
 	try {
--- a/server/src/initHono.ts
+++ b/server/src/initHono.ts
@@ -21,7 +21,7 @@ import { apiRouter } from "./routers/apiRouter.js";
 import { createChatProxyRouter } from "./routers/chatProxyRouter.js";
 import { createInternalRouter } from "./routers/internalRouter.js";
 import { publicRouter } from "./routers/publicRouter.js";
-import { auth } from "./utils/auth.js";
+import { createAuth } from "./utils/auth.js";
 import { isAllowedOrigin } from "./utils/corsOrigins.js";

 const ALLOWED_HEADERS = [
@@ -50,6 +50,7 @@ const ALLOWED_HEADERS = [

 export const createHonoApp = (env: Env) => {
 	const app = new Hono<HonoEnv>();
+	const auth = createAuth(env);

 	app.route("", createChatProxyRouter(env));

--- a/server/src/instrumentation.ts
+++ b/server/src/instrumentation.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { DiagConsoleLogger, DiagLogLevel, diag } from "@opentelemetry/api";
 import { OTLPMetricExporter } from "@opentelemetry/exporter-metrics-otlp-proto";
 import { OTLPTraceExporter } from "@opentelemetry/exporter-trace-otlp-http";
@@ -14,14 +13,16 @@ diag.setLogger(new DiagConsoleLogger(), DiagLogLevel.WARN);

 let sdk: NodeSDK | null = null;

-if (runtimeEnv.AXIOM_TOKEN) {
+export const initTelemetry = (env: Env) => {
+	if (!env.AXIOM_TOKEN) return sdk;
+
 	// NodeSDK reads OTEL_SERVICE_NAME to set the service resource attribute
-	runtimeEnv.OTEL_SERVICE_NAME = "autumn-server";
+	env.OTEL_SERVICE_NAME = "autumn-server";

 	const traceExporter = new OTLPTraceExporter({
 		url: "https://api.axiom.co/v1/traces",
 		headers: {
-			Authorization: `Bearer ${runtimeEnv.AXIOM_TOKEN}`,
+			Authorization: `Bearer ${env.AXIOM_TOKEN}`,
 			"X-Axiom-Dataset": "otel",
 		},
 	});
@@ -30,18 +31,18 @@ if (runtimeEnv.AXIOM_TOKEN) {
 	// auto-add a BatchSpanProcessor for `traceExporter` when `spanProcessors`
 	// is set. We must wire the exporter processor explicitly.
 	// Dev: short 1s flush for fast feedback. Prod: default 5s for throughput.
-	const isDev = runtimeEnv.NODE_ENV !== "production";
+	const isDev = env.NODE_ENV !== "production";
 	const exportProcessor = new BatchSpanProcessor(traceExporter, {
 		scheduledDelayMillis: isDev ? 1000 : 5000,
 	});
 	const filteredExportProcessor = new FilteringSpanProcessor(exportProcessor);
-	const metricReader = runtimeEnv.AXIOM_METRICS_DATASET
+	const metricReader = env.AXIOM_METRICS_DATASET
 		? new PeriodicExportingMetricReader({
 				exporter: new OTLPMetricExporter({
 					url: "https://api.axiom.co/v1/metrics",
 					headers: {
-						Authorization: `Bearer ${runtimeEnv.AXIOM_TOKEN}`,
-						"x-axiom-metrics-dataset": runtimeEnv.AXIOM_METRICS_DATASET,
+						Authorization: `Bearer ${env.AXIOM_TOKEN}`,
+						"x-axiom-metrics-dataset": env.AXIOM_METRICS_DATASET,
 					},
 				}),
 				exportIntervalMillis: 60_000,
@@ -68,6 +69,8 @@ if (runtimeEnv.AXIOM_TOKEN) {
 	};
 	process.once("SIGTERM", shutdown);
 	process.once("SIGINT", shutdown);
-}
+
+	return sdk;
+};

 export { sdk as otelSdk };
--- a/server/src/internal/admin/handleSlackAdminChat.ts
+++ b/server/src/internal/admin/handleSlackAdminChat.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import crypto, { randomUUID } from "node:crypto";
 import { stripOAuthTokenPrefix } from "@autumn/auth";
 import {
@@ -48,9 +47,15 @@ const findTargetOrg = ({
 		),
 	});

-const getSlackAdminInstallation = async ({ db }: { db: DrizzleCli }) =>
+const getSlackAdminInstallation = async ({
+	db,
+	env,
+}: {
+	db: DrizzleCli;
+	env: Env;
+}) =>
 	db.query.chatInstallations.findFirst({
-		where: eq(chatInstallations.provider, getSlackAdminProvider()),
+		where: eq(chatInstallations.provider, getSlackAdminProvider({ env })),
 	});

 const getSlackAdminOAuthCredentials = async ({
@@ -80,10 +85,16 @@ const getOrgSummary = async ({
 		},
 	});

-const decryptChatCredentialToken = ({ token }: { token: string }) => {
+const decryptChatCredentialToken = ({
+	env,
+	token,
+}: {
+	env: Env;
+	token: string;
+}) => {
 	const key = crypto
 		.createHash("sha256")
-		.update(runtimeEnv.ENCRYPTION_PASSWORD ?? "")
+		.update(env.ENCRYPTION_PASSWORD ?? "")
 		.digest();
 	const buffer = Buffer.from(token, "base64");
 	if (buffer[0] !== 1) throw new Error("Unsupported encrypted payload");
@@ -112,9 +123,11 @@ const getStoredOAuthTokenValues = async ({

 const revokeSlackAdminOAuthArtifacts = async ({
 	db,
+	env,
 	credentials,
 }: {
 	db: Pick<DrizzleCli, "delete" | "select">;
+	env: Env;
 	credentials: ChatOAuthCredential[];
 }) => {
 	const consentIds = [
@@ -129,18 +142,22 @@ const revokeSlackAdminOAuthArtifacts = async ({
 		const accessTokenValues: string[] = [];
 		const refreshTokenValues: string[] = [];
 		for (const credential of credentials) {
-			accessTokenValues.push(
-				...(await getStoredOAuthTokenValues({
-					token: decryptChatCredentialToken({ token: credential.access_token }),
-					stripPrefix: true,
-				})),
-			);
-			refreshTokenValues.push(
-				...(await getStoredOAuthTokenValues({
-					token: decryptChatCredentialToken({
-						token: credential.refresh_token,
-					}),
-				})),
+				accessTokenValues.push(
+					...(await getStoredOAuthTokenValues({
+						token: decryptChatCredentialToken({
+							env,
+							token: credential.access_token,
+						}),
+						stripPrefix: true,
+					})),
+				);
+				refreshTokenValues.push(
+					...(await getStoredOAuthTokenValues({
+						token: decryptChatCredentialToken({
+							env,
+							token: credential.refresh_token,
+						}),
+					})),
 			);
 		}

@@ -184,10 +201,10 @@ const revokeSlackAdminOAuthArtifacts = async ({
 export const handleCreateSlackAdminInstall = createRoute({
 	scopes: [Scopes.Superuser],
 	handler: async (c) => {
-		const ctx = c.get("ctx");
-		const state = createChatInstallState({
-			secret: getChatStateSecret(),
-			provider: getSlackAdminProvider(),
+			const ctx = c.get("ctx");
+			const state = createChatInstallState({
+				secret: getChatStateSecret(c.env),
+				provider: getSlackAdminProvider({ env: c.env }),
 			orgId: ctx.org.id,
 			userId: ctx.userId ?? "",
 			env: ctx.env,
@@ -195,7 +212,7 @@ export const handleCreateSlackAdminInstall = createRoute({
 			nonce: randomUUID(),
 		});

-		return c.json({ url: createSlackInstallUrl(state) });
+			return c.json({ url: createSlackInstallUrl(c.env, state) });
 	},
 });

@@ -203,7 +220,7 @@ export const handleGetSlackAdminInstall = createRoute({
 	scopes: [Scopes.Superuser],
 	handler: async (c) => {
 		const { db } = c.get("ctx");
-		const installation = await getSlackAdminInstallation({ db });
+			const installation = await getSlackAdminInstallation({ db, env: c.env });
 		const targetOrg = installation
 			? await getOrgSummary({ db, orgId: installation.org_id })
 			: null;
@@ -248,7 +265,7 @@ export const handleUpdateSlackAdminTarget = createRoute({
 		const ctx = c.get("ctx");
 		const { db } = ctx;
 		const { org_id: orgIdOrSlug, env } = c.req.valid("json");
-		const installation = await getSlackAdminInstallation({ db });
+			const installation = await getSlackAdminInstallation({ db, env: c.env });
 		if (!installation) {
 			throw new RecaseError({
 				message: "Slack admin bot is not installed",
@@ -283,10 +300,11 @@ export const handleUpdateSlackAdminTarget = createRoute({
 				.where(eq(chatInstallations.id, installation.id))
 				.returning();

-			await revokeSlackAdminOAuthArtifacts({
-				db: tx,
-				credentials: oauthCredentials,
-			});
+				await revokeSlackAdminOAuthArtifacts({
+					db: tx,
+					env: c.env,
+					credentials: oauthCredentials,
+				});

 			return updatedInstallation;
 		});
@@ -311,7 +329,7 @@ export const handleDeleteSlackAdminInstall = createRoute({
 	scopes: [Scopes.Superuser],
 	handler: async (c) => {
 		const { db } = c.get("ctx");
-		const installation = await getSlackAdminInstallation({ db });
+			const installation = await getSlackAdminInstallation({ db, env: c.env });
 		if (!installation) return c.json({ success: true });
 		const oauthCredentials = await getSlackAdminOAuthCredentials({
 			db,
@@ -319,16 +337,20 @@ export const handleDeleteSlackAdminInstall = createRoute({
 		});

 		await db.transaction(async (tx) => {
-			await revokeSlackAdminOAuthArtifacts({
-				db: tx,
-				credentials: oauthCredentials,
-			});
+				await revokeSlackAdminOAuthArtifacts({
+					db: tx,
+					env: c.env,
+					credentials: oauthCredentials,
+				});
 			await tx
 				.delete(chatInstallations)
 				.where(
 					and(
-						eq(chatInstallations.id, installation.id),
-						eq(chatInstallations.provider, getSlackAdminProvider()),
+							eq(chatInstallations.id, installation.id),
+							eq(
+								chatInstallations.provider,
+								getSlackAdminProvider({ env: c.env }),
+							),
 					),
 				);
 		});
--- a/server/src/internal/admin/handleUpsertSlackMcpOAuthClient.ts
+++ b/server/src/internal/admin/handleUpsertSlackMcpOAuthClient.ts
@@ -1,13 +1,12 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode, RecaseError, Scopes } from "@autumn/shared";
 import { registerMcpOAuthClient } from "@/internal/auth/actions/index.js";
 import { createRoute } from "../../honoMiddlewares/routeHandler";

-const getClientUrl = () =>
-	(runtimeEnv.CLIENT_URL || "http://localhost:3000").replace(/\/+$/, "");
+const getClientUrl = (env: Env) =>
+	(env.CLIENT_URL || "http://localhost:3000").replace(/\/+$/, "");

-const getSlackMcpRedirectUris = () => {
-	const clientUrl = getClientUrl();
+const getSlackMcpRedirectUris = (env: Env) => {
+	const clientUrl = getClientUrl(env);
 	return [
 		`${clientUrl}/admin/oauth/slack-mcp/callback`,
 		`${clientUrl}/sandbox/admin/oauth/slack-mcp/callback`,
@@ -21,7 +20,7 @@ export const handleUpsertSlackMcpOAuthClient = createRoute({
 		const result = await registerMcpOAuthClient({
 			db,
 			clientName: "Slack MCP",
-			redirectUris: getSlackMcpRedirectUris(),
+			redirectUris: getSlackMcpRedirectUris(c.env),
 			scope: undefined,
 		});

--- a/server/src/internal/api/events/EventService.ts
+++ b/server/src/internal/api/events/EventService.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode, type EventInsert, events, RecaseError } from "@autumn/shared";
 import { and, desc, eq } from "drizzle-orm";
 import { StatusCodes } from "http-status-codes";
@@ -10,12 +9,14 @@ export class EventService {
 	static async insert({
 		db,
 		event,
+		env,
 	}: {
 		db: DrizzleCli;
 		event: EventInsert | EventInsert[];
 		logger?: Logger;
+		env: Env;
 	}) {
-		if (runtimeEnv.NODE_ENV !== "development") return;
+		if (env.NODE_ENV !== "development") return;
 		try {
 			const results = await db
 				.insert(events)
@@ -42,14 +43,16 @@ export class EventService {
 		internalCustomerId,
 		env,
 		limit = 10,
+		workerEnv,
 	}: {
 		db: DrizzleCli;
 		internalCustomerId: string;
 		orgId: string;
 		env: string;
 		limit?: number;
+		workerEnv: Env;
 	}) {
-		if (runtimeEnv.NODE_ENV === "production") return [];
+		if (workerEnv.NODE_ENV === "production") return [];
 		const results = await db
 			.select({
 				id: events.id,
--- a/server/src/internal/auth/handleListAuthOrganizations.ts
+++ b/server/src/internal/auth/handleListAuthOrganizations.ts
@@ -2,11 +2,13 @@ import { ErrCode, member, organizations, RecaseError } from "@autumn/shared";
 import { asc, eq } from "drizzle-orm";
 import type { Context } from "hono";
 import { db } from "@/db/initDrizzle.js";
-import { auth } from "@/utils/auth.js";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
+import { createAuth } from "@/utils/auth.js";

 const AUTH_ORGANIZATION_LIST_LIMIT = 1000;

-export const handleListAuthOrganizations = async (c: Context) => {
+export const handleListAuthOrganizations = async (c: Context<HonoEnv>) => {
+	const auth = createAuth(c.env);
 	const session = await auth.api.getSession({
 		headers: c.req.raw.headers,
 	});
--- a/server/src/internal/auth/oauth/atmnOAuthClients.ts
+++ b/server/src/internal/auth/oauth/atmnOAuthClients.ts
@@ -1,12 +1,11 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import type { DrizzleCli } from "@/db/initDrizzle.js";
 import { oauthClientRepo } from "../repos/index.js";

 const ATMN_OAUTH_CLIENT_NAMES = new Set(["atmn", "autumn cli"]);

-const configuredAtmnClientIds = () =>
+const configuredAtmnClientIds = (env: Env) =>
 	new Set(
-		(runtimeEnv.ATMN_OAUTH_CLIENT_IDS ?? "")
+		(env.ATMN_OAUTH_CLIENT_IDS ?? "")
 			.split(",")
 			.map((id) => id.trim())
 			.filter(Boolean),
@@ -36,15 +35,17 @@ const metadataMarksAtmn = (metadata: unknown) => {
 };

 export const isAtmnOAuthClientRecord = ({
+	env,
 	clientId,
 	name,
 	metadata,
 }: {
+	env: Env;
 	clientId: string | null | undefined;
 	name: string | null | undefined;
 	metadata?: unknown;
 }) => {
-	if (clientId && configuredAtmnClientIds().has(clientId)) return true;
+	if (clientId && configuredAtmnClientIds(env).has(clientId)) return true;
 	if (metadataMarksAtmn(metadata)) return true;

 	const normalizedName = name?.trim().toLowerCase();
@@ -53,12 +54,17 @@ export const isAtmnOAuthClientRecord = ({

 export const isAtmnOAuthClientId = async ({
 	db,
+	env,
 	clientId,
 }: {
 	db: DrizzleCli;
+	env: Env;
 	clientId: string;
 }) => {
 	const client = await oauthClientRepo.getByClientId({ db, clientId });

-	return isAtmnOAuthClientRecord(client ?? { clientId, name: null });
+	return isAtmnOAuthClientRecord({
+		env,
+		...(client ?? { clientId, name: null }),
+	});
 };
--- a/server/src/internal/auth/oauth/handleGetOAuthClient.ts
+++ b/server/src/internal/auth/oauth/handleGetOAuthClient.ts
@@ -1,5 +1,6 @@
 import type { Context } from "hono";
 import { db } from "@/db/initDrizzle.js";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
 import { oauthClientRepo } from "../repos/index.js";
 import { isAtmnOAuthClientRecord } from "./atmnOAuthClients.js";
 import {
@@ -7,7 +8,7 @@ import {
 	isInternalMcpOAuthClientRecord,
 } from "./internalMcpOAuthClients.js";

-export const handleGetOAuthClient = async (c: Context) => {
+export const handleGetOAuthClient = async (c: Context<HonoEnv>) => {
 	const clientId = c.req.param("client_id");
 	const redirectUri = c.req.query("redirect_uri");
 	if (!clientId) {
@@ -20,7 +21,10 @@ export const handleGetOAuthClient = async (c: Context) => {
 		return c.json({ error: "Client not found" }, 404);
 	}

-	const isInternalMcp = isInternalMcpOAuthClientRecord(client);
+	const isInternalMcp = isInternalMcpOAuthClientRecord({
+		env: c.env,
+		...client,
+	});
 	const internalMcpName = isInternalMcp
 		? getInternalMcpDisplayName({
 				metadata: client.metadata,
@@ -31,7 +35,7 @@ export const handleGetOAuthClient = async (c: Context) => {
 	return c.json({
 		client_id: client.clientId,
 		name: internalMcpName || client.name || "Unknown Application",
-		is_atmn: isAtmnOAuthClientRecord(client),
+		is_atmn: isAtmnOAuthClientRecord({ env: c.env, ...client }),
 		is_internal_mcp: isInternalMcp,
 	});
 };
--- a/server/src/internal/auth/oauth/handleOAuthConsentWithEnv.ts
+++ b/server/src/internal/auth/oauth/handleOAuthConsentWithEnv.ts
@@ -1,7 +1,8 @@
 import { AppEnv, RecaseError } from "@autumn/shared";
 import type { Context } from "hono";
 import { db } from "@/db/initDrizzle.js";
-import { auth } from "@/utils/auth.js";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
+import { createAuth } from "@/utils/auth.js";
 import { oauthConsentRepo } from "../repos/index.js";
 import { isAtmnOAuthClientId } from "./atmnOAuthClients.js";
 import { getOAuthConsentScopeGrant } from "./oauthConsentScopes.js";
@@ -120,7 +121,8 @@ const jsonOAuthError = ({ error }: { error: RecaseError }) =>
 		},
 	);

-export const handleOAuthConsentWithEnv = async (c: Context) => {
+export const handleOAuthConsentWithEnv = async (c: Context<HonoEnv>) => {
+	const auth = createAuth(c.env);
 	const { contentType, fields } = await parseRequestFields(c.req.raw.clone());
 	const clientId = getClientIdFromFields(fields);
 	const redirectUri = getRedirectUriFromFields(fields);
@@ -165,7 +167,11 @@ export const handleOAuthConsentWithEnv = async (c: Context) => {
 		return response;
 	}

-	if (!clientId || !env || (await isAtmnOAuthClientId({ db, clientId }))) {
+	if (
+		!clientId ||
+		!env ||
+		(await isAtmnOAuthClientId({ db, env: c.env, clientId }))
+	) {
 		return response;
 	}

--- a/server/src/internal/auth/oauth/handleOAuthTokenWithApiKey.ts
+++ b/server/src/internal/auth/oauth/handleOAuthTokenWithApiKey.ts
@@ -7,7 +7,8 @@ import {
 import { ErrCode, RecaseError } from "@autumn/shared";
 import type { Context } from "hono";
 import { db } from "@/db/initDrizzle.js";
-import { auth } from "@/utils/auth.js";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
+import { createAuth } from "@/utils/auth.js";
 import { oauthAccessTokenRepo, oauthRefreshTokenRepo } from "../repos/index.js";
 import { isMcpOAuthClient } from "./mcpOAuthScopes.js";
 import {
@@ -108,7 +109,8 @@ const jsonTokenResponse = ({
 		headers: tokenResponseHeaders(response),
 	});

-export const handleOAuthTokenWithApiKey = async (c: Context) => {
+export const handleOAuthTokenWithApiKey = async (c: Context<HonoEnv>) => {
+	const auth = createAuth(c.env);
 	const resource = await getResourceFromOAuthTokenRequest(c.req.raw.clone());
 	const response = await auth.handler(c.req.raw);
 	if (!response.ok) return response;
@@ -132,6 +134,7 @@ export const handleOAuthTokenWithApiKey = async (c: Context) => {
 	try {
 		const tokenRecord = await getOAuthAccessTokenRecord({
 			db,
+			env: c.env,
 			accessToken,
 			resource,
 			requestedScopes,
@@ -185,6 +188,7 @@ export const handleOAuthTokenWithApiKey = async (c: Context) => {
 		}
 		apiKeyResult = await getExternalOAuthApiKeyForToken({
 			db,
+			env: c.env,
 			tokenRecord,
 			requestedScopes,
 		});
--- a/server/src/internal/auth/oauth/internalMcpOAuthClients.ts
+++ b/server/src/internal/auth/oauth/internalMcpOAuthClients.ts
@@ -1,11 +1,10 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { MCP_CLIENT_KIND } from "@autumn/auth/oauth";
 import type { Context } from "hono";
 import { type DrizzleCli, db } from "@/db/initDrizzle.js";
-import { auth } from "@/utils/auth.js";
+import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
+import { createAuth } from "@/utils/auth.js";
 import { oauthClientRepo } from "../repos/index.js";

-const INTERNAL_MCP_CLIENT_ID = runtimeEnv.INTERNAL_MCP_OAUTH_CLIENT_ID;
 const INTERNAL_MCP_CLIENT_NAME = "Autumn internal-mcp";
 const INTERNAL_MCP_CLIENT_NAME_NORMALIZED =
 	INTERNAL_MCP_CLIENT_NAME.toLowerCase();
@@ -43,15 +42,20 @@ const inferClientNameFromRedirectUri = (redirectUri: string) => {
 };

 export const isInternalMcpOAuthClientRecord = ({
+	env,
 	clientId,
 	name,
 	metadata,
 }: {
+	env: Env;
 	clientId: string | null | undefined;
 	name: string | null | undefined;
 	metadata?: unknown;
 }) => {
-	if (INTERNAL_MCP_CLIENT_ID && clientId === INTERNAL_MCP_CLIENT_ID)
+	if (
+		env.INTERNAL_MCP_OAUTH_CLIENT_ID &&
+		clientId === env.INTERNAL_MCP_OAUTH_CLIENT_ID
+	)
 		return true;
 	if (name?.trim().toLowerCase() === INTERNAL_MCP_CLIENT_NAME_NORMALIZED) {
 		return true;
@@ -79,20 +83,29 @@ export const getInternalMcpDisplayName = ({

 export const isInternalMcpOAuthClientId = async ({
 	db,
+	env,
 	clientId,
 }: {
 	db: DrizzleCli;
+	env: Env;
 	clientId: string;
 }) => {
 	const client = await oauthClientRepo.getByClientId({ db, clientId });

-	return isInternalMcpOAuthClientRecord(client ?? { clientId, name: null });
+	return isInternalMcpOAuthClientRecord({
+		env,
+		...(client ?? { clientId, name: null }),
+	});
 };

-export const handleInternalMcpOAuthAuthorize = async (c: Context) => {
+export const handleInternalMcpOAuthAuthorize = async (c: Context<HonoEnv>) => {
+	const auth = createAuth(c.env);
 	const url = new URL(c.req.raw.url);
 	const clientId = url.searchParams.get("client_id");
-	if (!clientId || !(await isInternalMcpOAuthClientId({ db, clientId }))) {
+	if (
+		!clientId ||
+		!(await isInternalMcpOAuthClientId({ db, env: c.env, clientId }))
+	) {
 		return auth.handler(c.req.raw);
 	}

--- a/server/src/internal/auth/oauth/oauthAccessTokenApiKey.ts
+++ b/server/src/internal/auth/oauth/oauthAccessTokenApiKey.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { stripOAuthTokenPrefix } from "@autumn/auth";
 import {
 	AppEnv,
@@ -19,21 +18,23 @@ import { oauthAccessTokenRepo, oauthConsentRepo } from "../repos/index.js";
 import { isAtmnOAuthClientId } from "./atmnOAuthClients.js";
 import { rotateOAuthConsentApiKey } from "./oauthConsentApiKey.js";

-const getOAuthIssuer = () =>
-	`${runtimeEnv.BETTER_AUTH_URL?.replace(/\/$/, "") ?? ""}/api/auth`;
+const getOAuthIssuer = (env: Env) =>
+	`${env.BETTER_AUTH_URL?.replace(/\/$/, "") ?? ""}/api/auth`;

 const verifyResourceAccessToken = async ({
+	env,
 	accessToken,
 	resource,
 	requestedScopes,
 }: {
+	env: Env;
 	accessToken: string;
 	resource: string | null;
 	requestedScopes: ScopeString[] | null;
 }) => {
 	if (!resource) return null;

-	const issuer = getOAuthIssuer();
+	const issuer = getOAuthIssuer(env);
 	try {
 		const payload = await verifyAccessToken(accessToken, {
 			jwksUrl: `${issuer}/jwks`,
@@ -52,11 +53,13 @@ const verifyResourceAccessToken = async ({

 export const getOAuthAccessTokenRecord = async ({
 	db,
+	env,
 	accessToken,
 	resource,
 	requestedScopes,
 }: {
 	db: DrizzleCli;
+	env: Env;
 	accessToken: string;
 	resource: string | null;
 	requestedScopes: ScopeString[] | null;
@@ -67,6 +70,7 @@ export const getOAuthAccessTokenRecord = async ({
 	const tokenRecord =
 		(await oauthAccessTokenRepo.getValidByTokenValues({ db, tokenValues })) ??
 		(await verifyResourceAccessToken({
+			env,
 			accessToken: rawAccessToken,
 			resource,
 			requestedScopes,
@@ -120,10 +124,12 @@ export const getOAuthAccessTokenRecord = async ({

 export const getExternalOAuthApiKeyForToken = async ({
 	db,
+	env,
 	tokenRecord,
 	requestedScopes,
 }: {
 	db: DrizzleCli;
+	env: Env;
 	tokenRecord: ResourceAccessTokenRecord & {
 		userId: string;
 		referenceId: string;
@@ -132,6 +138,7 @@ export const getExternalOAuthApiKeyForToken = async ({
 }) => {
 	const isAtmnClient = await isAtmnOAuthClientId({
 		db,
+		env,
 		clientId: tokenRecord.clientId,
 	});
 	if (isAtmnClient) return null;
@@ -151,19 +158,19 @@ export const getExternalOAuthApiKeyForToken = async ({
 		});
 	}

-	const env = consent.env ?? AppEnv.Sandbox;
+	const appEnv = consent.env ?? AppEnv.Sandbox;
 	const scopes = requestedScopes ?? tokenRecord.scopes;
 	const apiKey = await rotateOAuthConsentApiKey({
 		db,
 		consent,
 		tokenRecord,
-		env,
+		env: appEnv,
 		scopes,
 	});

 	return {
 		apiKey,
-		env,
+		env: appEnv,
 		orgId: tokenRecord.referenceId,
 		userId: tokenRecord.userId,
 		clientId: tokenRecord.clientId,
--- a/server/src/internal/auth/oauth/oauthRouter.ts
+++ b/server/src/internal/auth/oauth/oauthRouter.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import {
 	oauthProviderAuthServerMetadata,
 	oauthProviderOpenIdConfigMetadata,
@@ -6,7 +5,7 @@ import {
 import { type Context, Hono } from "hono";
 import { rateLimiter } from "hono-rate-limiter";
 import type { HonoEnv } from "@/honoUtils/HonoEnv.js";
-import { auth } from "@/utils/auth.js";
+import { createAuth } from "@/utils/auth.js";
 import { handleGetOAuthClient } from "./handleGetOAuthClient.js";
 import { handleMcpOAuthRegistration } from "./handleMcpOAuthRegistration.js";
 import { handleOAuthConsentWithEnv } from "./handleOAuthConsentWithEnv.js";
@@ -23,24 +22,28 @@ const getClientLookupRateLimitKey = (c: Context<HonoEnv>) =>

 const oauthClientLookupLimiter = rateLimiter<HonoEnv>({
 	windowMs: 60 * 1000,
-	limit: runtimeEnv.NODE_ENV === "development" ? 1000 : 60,
+	limit: (c) => (c.env.NODE_ENV === "development" ? 1000 : 60),
 	standardHeaders: "draft-6",
 	keyGenerator: getClientLookupRateLimitKey,
 });

 oauthRouter.get("/api/auth/.well-known/openid-configuration", (c) => {
+	const auth = createAuth(c.env);
 	return oauthProviderOpenIdConfigMetadata(auth)(c.req.raw);
 });

 oauthRouter.get("/.well-known/oauth-authorization-server", (c) => {
+	const auth = createAuth(c.env);
 	return oauthProviderAuthServerMetadata(auth)(c.req.raw);
 });

 oauthRouter.get("/api/auth/.well-known/oauth-authorization-server", (c) => {
+	const auth = createAuth(c.env);
 	return oauthProviderAuthServerMetadata(auth)(c.req.raw);
 });

 oauthRouter.get("/.well-known/oauth-authorization-server/api/auth", (c) => {
+	const auth = createAuth(c.env);
 	return oauthProviderAuthServerMetadata(auth)(c.req.raw);
 });

--- a/server/src/internal/balances/events/EventBatchingManager.ts
+++ b/server/src/internal/balances/events/EventBatchingManager.ts
@@ -1,5 +1,5 @@
 import type { EventInsert } from "@autumn/shared";
-import { logger } from "@server/external/logtail/logtailUtils.js";
+import { createLogger } from "@server/external/logtail/logtailUtils.js";
 import { sendEventsToTinybird } from "@server/external/tinybird/sendEvents/sendEvents.js";
 import { JobName } from "@server/queue/JobName.js";
 import { addTaskToQueue } from "@server/queue/queueUtils.js";
@@ -11,13 +11,13 @@ class BatchingManager {
 	private readonly maxBatchSize = 200; // Max events per batch (~200kb per event, keep batches under 10MB for Tinybird)

 	/** Add an event to the batch */
-	addEvent(event: EventInsert): void {
+	addEvent(event: EventInsert, env: Env): void {
 		const key = event.id;
 		this.events.set(key, event);

 		// Auto-execute if batch size is reached
 		if (this.events.size >= this.maxBatchSize) {
-			this.executeBatch();
+			this.executeBatch(env);
 			return;
 		}

@@ -27,12 +27,12 @@ class BatchingManager {
 		}

 		this.timer = setTimeout(() => {
-			this.executeBatch();
+			this.executeBatch(env);
 		}, this.batchWindow);
 	}

 	/** Execute the current batch - queue to SQS for Postgres and send to Tinybird */
-	private async executeBatch(): Promise<void> {
+	private async executeBatch(env: Env): Promise<void> {
 		if (this.timer) {
 			clearTimeout(this.timer);
 			this.timer = null;
@@ -56,7 +56,7 @@ class BatchingManager {

 		await sendEventsToTinybird({
 			events: eventItems,
-			logger,
+			logger: createLogger(env),
 		});
 	}
 }
--- a/server/src/internal/balances/finalizeLock/expireLock.ts
+++ b/server/src/internal/balances/finalizeLock/expireLock.ts
@@ -4,15 +4,18 @@ import type { ExpireLockReceiptPayload } from "@/queue/workflows.js";
 import { runFinalizeLock } from "./runFinalizeLock.js";

 export const expireLock = async ({
+	workerEnv,
 	ctx,
 	payload,
 }: {
+	workerEnv: Env;
 	ctx: AutumnContext;
 	payload: ExpireLockReceiptPayload;
 }) => {
 	try {
 		ctx.skipCache = false;
 		await runFinalizeLock({
+			workerEnv,
 			ctx,
 			params: {
 				lock_id: payload.lockId,
--- a/server/src/internal/balances/finalizeLock/runFinalizeLock.ts
+++ b/server/src/internal/balances/finalizeLock/runFinalizeLock.ts
@@ -13,6 +13,7 @@ import { runFinalizeLockV2 } from "./runFinalizeLockV2.js";
 import { runRedisFinalizeLock } from "./runRedisFinalizeLock.js";

 type RunFinalizeLockArgs = {
+	workerEnv: Env;
 	ctx: AutumnContext;
 	params: FinalizeLockParamsV0;
 };
@@ -35,7 +36,11 @@ export const runFinalizeLock = async (args: RunFinalizeLockArgs) => {
 	});
 };

-const runFinalizeLockInner = async ({ ctx, params }: RunFinalizeLockArgs) => {
+const runFinalizeLockInner = async ({
+	workerEnv,
+	ctx,
+	params,
+}: RunFinalizeLockArgs) => {
 	const fetchedReceipt = await fetchLockReceipt({
 		ctx,
 		lockId: params.lock_id,
@@ -43,6 +48,7 @@ const runFinalizeLockInner = async ({ ctx, params }: RunFinalizeLockArgs) => {

 	if (fetchedReceipt.source === "redis_v2") {
 		return runFinalizeLockV2({
+			workerEnv,
 			ctx,
 			params,
 			receipt: fetchedReceipt.receipt,
@@ -64,8 +70,9 @@ const runFinalizeLockInner = async ({ ctx, params }: RunFinalizeLockArgs) => {
 	try {
 		if (notNullish(receipt.expires_at)) {
 			await cancelLockExpiry({
+				workerEnv,
 				orgId: ctx.org.id,
-				env: ctx.env,
+				appEnv: ctx.env,
 				hashedKey: Bun.hash(params.lock_id).toString(),
 			});
 		}
--- a/server/src/internal/balances/finalizeLock/runFinalizeLockV2.ts
+++ b/server/src/internal/balances/finalizeLock/runFinalizeLockV2.ts
@@ -20,6 +20,7 @@ import { runRedisFinalizeLockV2 } from "./runRedisFinalizeLockV2.js";
 * marker key; `claimed === false` means another finalizer holds it.
 */
 export const runFinalizeLockV2 = async ({
+	workerEnv,
 	ctx,
 	params,
 	receipt,
@@ -27,6 +28,7 @@ export const runFinalizeLockV2 = async ({
 	claimed,
 	lockRedisInstance,
 }: {
+	workerEnv: Env;
 	ctx: AutumnContext;
 	params: FinalizeLockParamsV0;
 	receipt: LockReceipt;
@@ -55,8 +57,9 @@ export const runFinalizeLockV2 = async ({
 	try {
 		if (notNullish(receipt.expires_at)) {
 			await cancelLockExpiry({
+				workerEnv,
 				orgId: ctx.org.id,
-				env: ctx.env,
+				appEnv: ctx.env,
 				hashedKey: Bun.hash(params.lock_id).toString(),
 			});
 		}
--- a/server/src/internal/balances/handlers/handleFinalizeLock.ts
+++ b/server/src/internal/balances/handlers/handleFinalizeLock.ts
@@ -9,7 +9,7 @@ export const handleFinalizeLock = createRoute({
 		const ctx = c.get("ctx");
 		const params = c.req.valid("json");

-		const response = await runFinalizeLock({ ctx, params });
+		const response = await runFinalizeLock({ workerEnv: c.env, ctx, params });
 		const status = ctx.extraLogs.finalizeLockFailedOpen ? 202 : 200;

 		return c.json(response, status);
--- a/server/src/internal/balances/track/runAsyncTrack.ts
+++ b/server/src/internal/balances/track/runAsyncTrack.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { ErrCode, RecaseError, type TrackParams } from "@autumn/shared";
 import type { AutumnContext } from "@/honoUtils/HonoEnv.js";
 import { queueTrack } from "./utils/queueTrack.js";
@@ -13,7 +12,7 @@ export const runAsyncTrack = async ({
 	ctx: AutumnContext;
 	body: TrackParams;
 }): Promise<void> => {
-	const queueUrl = runtimeEnv.TRACK_ASYNC_SQS_QUEUE_URL;
+	const queueUrl = ctx.env.TRACK_ASYNC_SQS_QUEUE_URL;
 	if (!queueUrl) {
 		ctx.logger.error(
 			"[track] async=true requested but TRACK_ASYNC_SQS_QUEUE_URL is unset",
--- a/server/src/internal/balances/track/runBatchTrack.ts
+++ b/server/src/internal/balances/track/runBatchTrack.ts
@@ -1,4 +1,3 @@
-import { runtimeEnv } from "@/utils/envUtils.js";
 import { type BatchTrackParams, ErrCode, RecaseError } from "@autumn/shared";
 import type { AutumnContext } from "@/honoUtils/HonoEnv.js";
 import { JobName } from "@/queue/JobName.js";
@@ -16,7 +15,7 @@ export const runBatchTrack = async ({
 	ctx: AutumnContext;
 	body: BatchTrackParams;
 }): Promise<void> => {
-	const queueUrl = runtimeEnv.TRACK_ASYNC_SQS_QUEUE_URL;
+	const queueUrl = ctx.env.TRACK_ASYNC_SQS_QUEUE_URL;
 	if (!queueUrl) {
 		ctx.logger.error(
 			"[track] batch track requested but TRACK_ASYNC_SQS_QUEUE_URL is unset",
--- a/Show More
+++ b/Show More