diff --git a/apps/server/src/engine/service.ts b/apps/server/src/engine/service.ts
index 8b49d254f..fece1f507 100644
--- a/apps/server/src/engine/service.ts
+++ b/apps/server/src/engine/service.ts
@@ -754,6 +754,8 @@ export class AgentService {
         if (error instanceof LostLeaseError || context.signal.aborted) throw error;
         await context.guard();
         const failures = Number(task.state.failures ?? 0) + 1;
+        // Each streak of failures (after a success or a resume) gets its own alerts.
+        const failureStreak = Number(task.state.failureStreak ?? 0) + (failures === 1 ? 1 : 0);
         const detail = error instanceof Error ? error.message : "Page check failed";
         const nextCheckAt = new Date(
           Date.now() + Math.min(60, 2 ** failures) * 60000,
@@ -778,10 +780,11 @@ export class AgentService {
             ...task.state,
             failures,
             resumingMonitor: false,
+            failureStreak,
             notice: {
               title: "Watch needs attention",
               body: detail,
-              key: `watch-error:${task.id}:${failures >= 5 ? "paused" : "retry"}`,
+              key: `watch-error:${task.id}:${failureStreak}:${failures >= 5 ? "paused" : "retry"}`,
             },
           },
         };
diff --git a/tests/monitor-recovery.test.ts b/tests/monitor-recovery.test.ts
index 023cc6ffe..8d40eb234 100644
--- a/tests/monitor-recovery.test.ts
+++ b/tests/monitor-recovery.test.ts
@@ -191,7 +191,7 @@ test("the paused alert is delivered when the final failure outcome is lost", asy
   assert.equal(task?.status, "paused");
   assert.equal((await db.get<Monitor>(owner, "monitors", monitor.id))?.status, "paused");
   const pausedId = createHash("sha256")
-    .update(`watch-error:${monitor.taskId}:paused`)
+    .update(`watch-error:${monitor.taskId}:1:paused`)
     .digest("hex");
   const paused = (await read<AgentNotification[]>("/notifications")).filter(
     (item) => item.id === pausedId,
diff --git a/tests/workflows.test.ts b/tests/workflows.test.ts
index 404b11abb..9a3d254fa 100644
--- a/tests/workflows.test.ts
+++ b/tests/workflows.test.ts
@@ -158,6 +158,40 @@ test("failed page checks back off, expose the error, and pause after repeated fa
   assert.equal((await db.get<Monitor>(owner, "monitors", monitor.id))?.status, "paused");
 });
 
+test("each failure streak of a watch raises its own alerts after it is resumed", async () => {
+  const monitor = await server.agent.createMonitor(owner, {
+    title: "Resumed availability",
+    url: "https://example.com",
+  });
+  const failUntilPaused = async () => {
+    for (let i = 1; i <= 5; i++) {
+      await server.agent.worker.tick();
+      const task = await server.agent.getTask(owner, monitor.taskId);
+      if (i < 5)
+        await db.compareAndSwap(
+          owner,
+          "tasks",
+          task.id,
+          { status: "scheduled" },
+          { nextRunAt: "2020-01-01T00:00:00Z" },
+        );
+    }
+    assert.equal((await server.agent.getTask(owner, monitor.taskId)).status, "paused");
+  };
+  const alerts = async () =>
+    (await db.list<AgentNotification>(owner, "notifications")).filter(
+      (n) => n.taskId === monitor.taskId && n.title === "Watch needs attention",
+    );
+  await failUntilPaused();
+  assert.equal((await alerts()).length, 2, "one retry alert and one paused alert");
+  await server.agent.controlMonitor(owner, monitor.id, "resume");
+  await failUntilPaused();
+  assert.equal((await alerts()).length, 4, "the second streak alerts again");
+  // Replaying the same outcome must not duplicate the alert.
+  await server.agent.worker.tick();
+  assert.equal((await alerts()).length, 4);
+});
+
 test("dismissal racing acceptance never creates work for a dismissed idea", async () => {
   for (let i = 0; i < 4; i++) {
     const idea: Idea = {