diff --git a/.changeset/fix-waitforevent-stale-waiter.md b/.changeset/fix-waitforevent-stale-waiter.md
new file mode 100644
index 0000000000..46ed57e9db
--- /dev/null
+++ b/.changeset/fix-waitforevent-stale-waiter.md
@@ -0,0 +1,7 @@
+---
+"@cloudflare/workflows-shared": patch
+---
+
+Fix `waitForEvent` delivering events to stale waiters after timeout.
+
+When a `step.waitForEvent()` call timed out, its resolver was not removed from the workflow's internal waiters map. This meant the next `step.waitForEvent()` for the same event type would have its incoming event consumed by the dead resolver instead of the live one, causing the workflow to hang indefinitely.
diff --git a/packages/workflows-shared/src/context.ts b/packages/workflows-shared/src/context.ts
index f76f82eeaf..a4248e9df9 100644
--- a/packages/workflows-shared/src/context.ts
+++ b/packages/workflows-shared/src/context.ts
@@ -861,7 +861,7 @@ export class Context extends RpcTarget {
 				}
 			}
 			const callbacks = this.#engine.waiters.get(options.type) ?? [];
-			callbacks.push(resolve);
+			callbacks.push([cacheKey, resolve]);
 
 			this.#engine.waiters.set(options.type, callbacks);
 		});
@@ -886,6 +886,14 @@ export class Context extends RpcTarget {
 				: timeoutPromise(ms(options.timeout), true),
 			pausePromise,
 		]).catch(async (error) => {
+			const callbacks = this.#engine.waiters.get(options.type);
+			if (callbacks) {
+				const idx = callbacks.findIndex(([key]) => key === cacheKey);
+				if (idx !== -1) {
+					callbacks.splice(idx, 1);
+				}
+			}
+
 			this.#engine.writeLog(
 				InstanceEvent.WAIT_TIMED_OUT,
 				cacheKey,
diff --git a/packages/workflows-shared/src/engine.ts b/packages/workflows-shared/src/engine.ts
index 40eaa86efc..cb35c0d7b8 100644
--- a/packages/workflows-shared/src/engine.ts
+++ b/packages/workflows-shared/src/engine.ts
@@ -101,8 +101,12 @@ export class Engine extends DurableObject<Env> {
 	engineAbortController: AbortController = new AbortController();
 	pauseController: AbortController = new AbortController();
 
-	waiters: Map<string, Array<(event: Event | PromiseLike<Event>) => void>> =
-		new Map();
+	waiters: Map<
+		string,
+		Array<
+			[cacheKey: string, resolve: (event: Event | PromiseLike<Event>) => void]
+		>
+	> = new Map();
 	eventMap: Map<string, Array<Event>> = new Map();
 
 	constructor(state: DurableObjectState, env: Env) {
@@ -506,9 +510,10 @@ export class Engine extends DurableObject<Env> {
 			// Attempt to get the callback and run it
 			const callbacks = this.waiters.get(event.type);
 			if (callbacks) {
-				const callback = callbacks[0];
-				if (callback) {
-					callback(event);
+				const entry = callbacks[0];
+				if (entry) {
+					const [, resolve] = entry;
+					resolve(event);
 					// Remove it from the list of callbacks
 					callbacks.shift();
 					this.waiters.set(event.type, callbacks);
diff --git a/packages/workflows-shared/tests/engine.test.ts b/packages/workflows-shared/tests/engine.test.ts
index caec69ecc8..5505dbf80f 100644
--- a/packages/workflows-shared/tests/engine.test.ts
+++ b/packages/workflows-shared/tests/engine.test.ts
@@ -182,6 +182,109 @@ describe("Engine", () => {
 		}, 500);
 	});
 
+	it("waitForEvent should not deliver events to timed-out events with the same type", async ({
+		expect,
+	}) => {
+		const instanceId = "WAIT-FOR-EVENT-STALE-WAITER";
+		const engineStub = await runWorkflow(instanceId, async (_, step) => {
+			const results: Array<{
+				iteration: number;
+				received: boolean;
+			}> = [];
+
+			for (let i = 1; i <= 3; i++) {
+				try {
+					await step.waitForEvent(`my-event-waiter-${i}`, {
+						type: "my-event",
+						timeout: 500,
+					});
+					results.push({ iteration: i, received: true });
+				} catch {
+					results.push({ iteration: i, received: false });
+				}
+			}
+
+			return { results };
+		});
+
+		// 1st waitForEvent iteration - should receive event
+		await vi.waitUntil(
+			async () => {
+				const logs = (await engineStub.readLogs()) as EngineLogs;
+				return (
+					logs.logs.filter((val) => val.event === InstanceEvent.WAIT_START)
+						.length >= 1
+				);
+			},
+			{ timeout: 500 }
+		);
+
+		await engineStub.receiveEvent({
+			type: "my-event",
+			timestamp: new Date(),
+			payload: { iteration: 1 },
+		});
+
+		await vi.waitUntil(
+			async () => {
+				const logs = (await engineStub.readLogs()) as EngineLogs;
+				return (
+					logs.logs.filter((val) => val.event === InstanceEvent.WAIT_START)
+						.length >= 2
+				);
+			},
+			{ timeout: 500 }
+		);
+
+		// 2nd waitForEvent iteration - should timeout (500ms)
+		await vi.waitUntil(
+			async () => {
+				const logs = (await engineStub.readLogs()) as EngineLogs;
+				return logs.logs.some(
+					(val) => val.event === InstanceEvent.WAIT_TIMED_OUT
+				);
+			},
+			{ timeout: 1000 }
+		);
+
+		// 3rd waitForEvent iteration - should receive event
+		await vi.waitUntil(
+			async () => {
+				const logs = (await engineStub.readLogs()) as EngineLogs;
+				return (
+					logs.logs.filter((val) => val.event === InstanceEvent.WAIT_START)
+						.length >= 3
+				);
+			},
+			{ timeout: 500 }
+		);
+
+		await engineStub.receiveEvent({
+			type: "my-event",
+			timestamp: new Date(),
+			payload: { iteration: 3 },
+		});
+
+		await vi.waitUntil(
+			async () => {
+				const logs = (await engineStub.readLogs()) as EngineLogs;
+				return logs.logs.some(
+					(val) => val.event === InstanceEvent.WORKFLOW_SUCCESS
+				);
+			},
+			{ timeout: 1000 }
+		);
+
+		const logs = (await engineStub.readLogs()) as EngineLogs;
+		// Iterations 1 and 3 received events; iteration 2 timed out
+		expect(
+			logs.logs.filter((val) => val.event === InstanceEvent.WAIT_COMPLETE)
+		).toHaveLength(2);
+		expect(
+			logs.logs.filter((val) => val.event === InstanceEvent.WAIT_TIMED_OUT)
+		).toHaveLength(1);
+	});
+
 	it("should restore state from storage when accountId is undefined", async ({
 		expect,
 	}) => {