diff --git a/scripts/setup/link-test-stripe-account.ts b/scripts/setup/link-test-stripe-account.ts
new file mode 100644
index 000000000..4d8a9ee8f
--- /dev/null
+++ b/scripts/setup/link-test-stripe-account.ts
@@ -0,0 +1,169 @@
+#!/usr/bin/env bun
+import { AppEnv, organizations } from "@autumn/shared";
+import { eq } from "drizzle-orm";
+import { initDrizzle } from "@server/db/initDrizzle.js";
+import { createStripeCli } from "@server/external/connect/createStripeCli.js";
+import { initMasterStripe } from "@server/external/connect/initStripeCli.js";
+import { OrgService } from "@server/internal/orgs/OrgService.js";
+import { clearOrgCache } from "@server/internal/orgs/orgUtils/clearOrgCache.js";
+import { loadLocalEnv } from "@server/utils/envUtils.js";
+
+loadLocalEnv();
+
+const args = process.argv.slice(2);
+
+const readFlag = (name: string) => {
+	const inline = args.find((arg) => arg.startsWith(`${name}=`));
+	if (inline) return inline.slice(name.length + 1);
+
+	const idx = args.indexOf(name);
+	return idx === -1 ? undefined : args[idx + 1];
+};
+
+const hasFlag = (name: string) => args.includes(name);
+
+const usage = () => {
+	console.log(`Usage:
+  bun stripe:link-test -- --account-id=acct_...
+  bun stripe:link-test -- --latest --email=unit-test-org@test.com
+  bun stripe:link-test -- --list --email=unit-test-org@test.com
+
+Options:
+  --org=<slug-or-id>       Autumn org to update. Defaults to TESTS_ORG.
+  --env=<sandbox|live>     Stripe environment. Defaults to sandbox.
+  --account-id=<acct_...>  Connected Stripe account ID to link.
+  --email=<email>          Filter Stripe connected accounts by email.
+  --latest                 Link the newest connected account matching --email.
+  --clear-secret-key       Clear the org's direct Stripe key for this env so Connect is used.
+  --list                   Print matching connected accounts without updating.
+`);
+};
+
+if (hasFlag("--help") || hasFlag("-h")) {
+	usage();
+	process.exit(0);
+}
+
+const env =
+	(readFlag("--env") || "sandbox").toLowerCase() === "live"
+		? AppEnv.Live
+		: AppEnv.Sandbox;
+const orgRef = readFlag("--org") || process.env.TESTS_ORG;
+const email = readFlag("--email");
+const accountIdArg = readFlag("--account-id");
+
+if (!orgRef) {
+	throw new Error("Missing org. Pass --org=<slug-or-id> or set TESTS_ORG.");
+}
+
+const { db, client } = initDrizzle();
+
+const getOrg = async () => {
+	const bySlug = await OrgService.getBySlug({ db, slug: orgRef });
+	if (bySlug) return bySlug;
+
+	return await OrgService.get({ db, orgId: orgRef });
+};
+
+const listAccounts = async () => {
+	const stripe = initMasterStripe({ env, skipInstrumentation: true });
+	const accounts = await stripe.accounts.list({ limit: 100 });
+
+	return accounts.data
+		.filter((account) => !email || account.email === email)
+		.sort((a, b) => b.created - a.created);
+};
+
+try {
+	const org = await getOrg();
+	const accounts = await listAccounts();
+
+	if (hasFlag("--list")) {
+		console.log(
+			JSON.stringify(
+				accounts.map((account) => ({
+					id: account.id,
+					email: account.email,
+					created: new Date(account.created * 1000).toISOString(),
+					charges_enabled: account.charges_enabled,
+					details_submitted: account.details_submitted,
+				})),
+				null,
+				2,
+			),
+		);
+		process.exit(0);
+	}
+
+	const accountId =
+		accountIdArg || (hasFlag("--latest") ? accounts[0]?.id : undefined);
+
+	if (!accountId) {
+		throw new Error(
+			"Missing account. Pass --account-id=acct_... or use --latest with --email=...",
+		);
+	}
+
+	const directKeyField =
+		env === AppEnv.Sandbox ? "test_api_key" : "live_api_key";
+	const directWebhookSecretField =
+		env === AppEnv.Sandbox ? "test_webhook_secret" : "live_webhook_secret";
+	const hasDirectKey = Boolean(org.stripe_config?.[directKeyField]);
+
+	if (hasDirectKey && !hasFlag("--clear-secret-key")) {
+		throw new Error(
+			`${org.slug} has stripe_config.${directKeyField}; createStripeCli will prefer that over Connect. Re-run with --clear-secret-key to use the OAuth account.`,
+		);
+	}
+
+	const stripe = initMasterStripe({ env, accountId, skipInstrumentation: true });
+	await stripe.accounts.retrieve();
+
+	await OrgService.updateStripeConnect({
+		db,
+		orgId: org.id,
+		accountId,
+		env,
+	});
+
+	if (hasDirectKey) {
+		await db
+			.update(organizations)
+			.set({
+				stripe_config: {
+					...(org.stripe_config || {}),
+					[directKeyField]: null,
+					[directWebhookSecretField]: null,
+				},
+			})
+			.where(eq(organizations.id, org.id));
+		await clearOrgCache({ db, orgId: org.id });
+	}
+
+	const updatedOrg = await OrgService.get({ db, orgId: org.id });
+	const resolvedStripe = createStripeCli({
+		org: updatedOrg,
+		env,
+		skipInstrumentation: true,
+	});
+	const resolvedAccount = await resolvedStripe.accounts.retrieve();
+
+	console.log(
+		JSON.stringify(
+			{
+				org: { id: updatedOrg.id, slug: updatedOrg.slug },
+				env,
+				linked_account_id: accountId,
+				resolved_account_id: resolvedAccount.id,
+				test_stripe_connect: updatedOrg.test_stripe_connect,
+				live_stripe_connect: updatedOrg.live_stripe_connect,
+			},
+			null,
+			2,
+		),
+	);
+} finally {
+	await client.end();
+}
+
+process.exit(0);
diff --git a/server/src/external/stripe/webhookMiddlewares/stripeWebhookEarlyAckMiddleware.ts b/server/src/external/stripe/webhookMiddlewares/stripeWebhookEarlyAckMiddleware.ts
new file mode 100644
index 000000000..f791d8ea2
--- /dev/null
+++ b/server/src/external/stripe/webhookMiddlewares/stripeWebhookEarlyAckMiddleware.ts
@@ -0,0 +1,25 @@
+import type { Context, Next } from "hono";
+import type { StripeWebhookHonoEnv } from "./stripeWebhookContext";
+
+export const stripeWebhookEarlyAckMiddleware = async (
+	c: Context<StripeWebhookHonoEnv>,
+	next: Next,
+) => {
+	const ctx = c.get("ctx");
+	const runWebhook = () =>
+		Promise.resolve()
+			.then(next)
+			.catch((error) => {
+				ctx.logger.error(`Stripe webhook background processing failed: ${error}`, {
+					error,
+				});
+			});
+
+	try {
+		c.executionCtx.waitUntil(runWebhook());
+	} catch {
+		setImmediate(() => void runWebhook());
+	}
+
+	return c.json({ received: true }, 200);
+};
diff --git a/server/tests/unit/webhooks/stripe-webhook-early-ack.test.ts b/server/tests/unit/webhooks/stripe-webhook-early-ack.test.ts
new file mode 100644
index 000000000..929d56f59
--- /dev/null
+++ b/server/tests/unit/webhooks/stripe-webhook-early-ack.test.ts
@@ -0,0 +1,97 @@
+import { describe, expect, test } from "bun:test";
+import { Hono } from "hono";
+import { stripeWebhookEarlyAckMiddleware } from "@/external/stripe/webhookMiddlewares/stripeWebhookEarlyAckMiddleware";
+
+const wait = (ms = 0) => new Promise((resolve) => setTimeout(resolve, ms));
+
+const createApp = () => {
+	const app = new Hono();
+
+	app.use("*", async (c, next) => {
+		(c as any).set("ctx", {
+			logger: {
+				error: () => {},
+			},
+		});
+		await next();
+	});
+
+	return app;
+};
+
+describe("stripeWebhookEarlyAckMiddleware", () => {
+	test("uses executionCtx.waitUntil when the runtime provides it", async () => {
+		const waits: Promise<unknown>[] = [];
+		let processed = false;
+		const response = await stripeWebhookEarlyAckMiddleware(
+			{
+				get: () => ({
+					logger: { error: () => {} },
+				}),
+				json: (body: unknown, status: number) =>
+					new Response(JSON.stringify(body), { status }),
+				executionCtx: {
+					waitUntil: (promise: Promise<unknown>) => waits.push(promise),
+				},
+			} as never,
+			async () => {
+				processed = true;
+			},
+		);
+
+		expect(response.status).toBe(200);
+		expect(await response.json()).toEqual({ received: true });
+		expect(waits).toHaveLength(1);
+
+		await waits[0];
+		expect(processed).toBe(true);
+	});
+
+	test("returns 200 before downstream webhook processing completes", async () => {
+		const app = createApp();
+		let resolveProcessing!: () => void;
+		let processed = false;
+		const processing = new Promise<void>((resolve) => {
+			resolveProcessing = resolve;
+		});
+
+		app.post(
+			"/webhook",
+			stripeWebhookEarlyAckMiddleware as never,
+			async (c) => {
+				await processing;
+				processed = true;
+				return c.json({ processed: true }, 200);
+			},
+		);
+
+		const response = await app.request("/webhook", { method: "POST" });
+
+		expect(response.status).toBe(200);
+		expect(await response.json()).toEqual({ received: true });
+		expect(processed).toBe(false);
+
+		resolveProcessing();
+		await wait(5);
+		expect(processed).toBe(true);
+	});
+
+	test("does not run downstream webhook processing before returning", async () => {
+		const app = createApp();
+		let started = false;
+
+		app.post("/webhook", stripeWebhookEarlyAckMiddleware as never, (c) => {
+			started = true;
+			return c.json({ processed: true }, 200);
+		});
+
+		const response = await app.request("/webhook", { method: "POST" });
+
+		expect(response.status).toBe(200);
+		expect(await response.json()).toEqual({ received: true });
+		expect(started).toBe(false);
+
+		await wait(5);
+		expect(started).toBe(true);
+	});
+});