fix(unstable-agent-babysitter): respect active sessions

Ultraworked with [Sisyphus](https://github.com/code-yeongyu/oh-my-openagent)

Co-authored-by: Sisyphus <clio-agent@sisyphuslabs.ai>

src/hooks/unstable-agent-babysitter/index.test.ts

@@ -2,6 +2,7 @@ import { afterEach, describe, expect, test } from "bun:test"
 import { _resetForTesting, setMainSession } from "../../features/claude-code-session-state"
 import type { BackgroundTask } from "../../features/background-agent"
 import { OMO_INTERNAL_INITIATOR_MARKER } from "../../shared/internal-initiator-marker"
+import { releaseAllPromptAsyncReservationsForTesting } from "../shared/prompt-async-gate"
 import { createUnstableAgentBabysitterHook } from "./index"
 
 const projectDir = process.cwd()
@@ -49,7 +50,7 @@ function createTask(overrides: Partial<BackgroundTask> = {}): BackgroundTask {
     status: "running",
     progress: {
       toolCalls: 1,
-      lastUpdate: new Date(),
+      lastUpdate: new Date(Date.now() - 121000),
       lastMessage: "still working",
       lastMessageAt: new Date(Date.now() - 121000),
     },
@@ -61,6 +62,7 @@ function createTask(overrides: Partial<BackgroundTask> = {}): BackgroundTask {
 describe("unstable-agent-babysitter hook", () => {
   afterEach(() => {
     _resetForTesting()
+    releaseAllPromptAsyncReservationsForTesting()
   })
 
   test("settles idle before injecting a reminder", async () => {
@@ -290,4 +292,281 @@ describe("unstable-agent-babysitter hook", () => {
     expect(payload.body?.model).toEqual({ providerID: "openai", modelID: "gpt-4" })
     expect(payload.body?.variant).toBe("max")
   })
+
+  test("#given the main session has a fresh user message #when it becomes idle #then babysitter does not inject a reminder", async () => {
+    // given
+    const originalNow = Date.now
+    Date.now = () => 10 * 60 * 1000
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: {
+        "main-1": [
+          { info: { role: "user", time: { created: Date.now() - 1_500 } } },
+        ],
+        "bg-1": [
+          { info: { role: "assistant" }, parts: [{ type: "thinking", thinking: "deep thought" }] },
+        ],
+      },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 1,
+        lastUpdate: new Date(0),
+        lastMessage: "still working",
+        lastMessageAt: new Date(0),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(0)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given the latest main-session message is assistant output after a fresh user message #when it becomes idle #then babysitter may inject a reminder", async () => {
+    // given
+    const originalNow = Date.now
+    Date.now = () => 10 * 60 * 1000
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: {
+        "main-1": [
+          { info: { role: "user", time: { created: Date.now() - 1_500 } } },
+          { info: { role: "assistant", time: { created: Date.now() - 500 }, agent: "sisyphus" } },
+        ],
+        "bg-1": [
+          { info: { role: "assistant" }, parts: [{ type: "thinking", thinking: "deep thought" }] },
+        ],
+      },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 1,
+        lastUpdate: new Date(0),
+        lastMessage: "still working",
+        lastMessageAt: new Date(0),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(1)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given an unstable task has a fresh progress update after its last message #when the main session idles #then babysitter does not treat it as hung", async () => {
+    // given
+    const originalNow = Date.now
+    Date.now = () => 10 * 60 * 1000
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 2,
+        lastUpdate: new Date(Date.now() - 1_000),
+        lastMessage: "still working",
+        lastMessageAt: new Date(Date.now() - 5 * 60 * 1000),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(0)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given an unstable task has stale progress and stale last message #when the main session idles #then babysitter still reminds", async () => {
+    // given
+    const originalNow = Date.now
+    Date.now = () => 10 * 60 * 1000
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 2,
+        lastUpdate: new Date(Date.now() - 5 * 60 * 1000),
+        lastMessage: "still working",
+        lastMessageAt: new Date(Date.now() - 5 * 60 * 1000),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(1)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given a reminder was already sent before an abort #when a user message resumes the session within cooldown #then no duplicate reminder is injected", async () => {
+    // given
+    const originalNow = Date.now
+    let currentNow = 10 * 60 * 1000
+    Date.now = () => currentNow
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 1,
+        lastUpdate: new Date(0),
+        lastMessage: "still working",
+        lastMessageAt: new Date(0),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+      await hook.event({ event: { type: "session.error", properties: { sessionID: "main-1", error: { name: "AbortError" } } } })
+      currentNow += 1_000
+      await hook.event({ event: { type: "message.updated", properties: { sessionID: "main-1", info: { role: "user" } } } })
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(1)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given a reminder was already sent before a stop event #when assistant activity resumes within cooldown #then no duplicate reminder is injected", async () => {
+    // given
+    const originalNow = Date.now
+    let currentNow = 10 * 60 * 1000
+    Date.now = () => currentNow
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({
+      progress: {
+        toolCalls: 1,
+        lastUpdate: new Date(0),
+        lastMessage: "still working",
+        lastMessageAt: new Date(0),
+      },
+    })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    try {
+      // when
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+      await hook.event({ event: { type: "session.stop", properties: { sessionID: "main-1" } } })
+      currentNow += 1_000
+      await hook.event({ event: { type: "message.updated", properties: { sessionID: "main-1", info: { role: "assistant" } } } })
+      await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+      // then
+      expect(promptCalls.length).toBe(1)
+    } finally {
+      Date.now = originalNow
+    }
+  })
+
+  test("#given unstable task agent is a config key #when babysitter builds a reminder #then the reminder uses the canonical display name", async () => {
+    // given
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({ agent: "sisyphus" })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    // when
+    await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+    // then
+    const payload = promptCalls[0]?.input as { body?: { parts?: Array<{ text?: string }> } } | undefined
+    const text = payload?.body?.parts?.[0]?.text ?? ""
+    expect(text).toContain("Agent: Sisyphus - Ultraworker")
+    expect(text).not.toContain("Agent: sisyphus")
+  })
+
+  test("#given unstable task agent is a legacy display name #when babysitter builds a reminder #then the reminder uses the current display name", async () => {
+    // given
+    setMainSession("main-1")
+    const promptCalls: Array<{ input: unknown }> = []
+    const ctx = createMockPluginInput({
+      messagesBySession: { "main-1": [], "bg-1": [] },
+      promptCalls,
+    })
+    const backgroundManager = createBackgroundManager([createTask({ agent: "Sisyphus (Ultraworker)" })])
+    const hook = createUnstableAgentBabysitterHook(ctx, {
+      backgroundManager,
+      config: { timeout_ms: 120000 },
+    })
+
+    // when
+    await hook.event({ event: { type: "session.idle", properties: { sessionID: "main-1" } } })
+
+    // then
+    const payload = promptCalls[0]?.input as { body?: { parts?: Array<{ text?: string }> } } | undefined
+    const text = payload?.body?.parts?.[0]?.text ?? ""
+    expect(text).toContain("Agent: Sisyphus - Ultraworker")
+    expect(text).not.toContain("Agent: Sisyphus (Ultraworker)")
+  })
 })

src/hooks/unstable-agent-babysitter/unstable-agent-babysitter-hook.ts

@@ -7,6 +7,7 @@ import { isAbortError } from "../../shared/is-abort-error"
 import {
   buildReminder,
   extractMessages,
+  getMessageCreatedAt,
   getMessageInfo,
   getMessageParts,
   isUnstableTask,
@@ -17,6 +18,7 @@ import { dispatchInternalPrompt } from "../shared/prompt-async-gate"
 const HOOK_NAME = "unstable-agent-babysitter"
 const DEFAULT_TIMEOUT_MS = 120000
 const COOLDOWN_MS = 5 * 60 * 1000
+const USER_MESSAGE_IN_PROGRESS_WINDOW_MS = 2000
 
 type BabysittingConfig = {
   timeout_ms?: number
@@ -122,6 +124,38 @@ async function getThinkingSummary(ctx: BabysitterContext, sessionID: string): Pr
   }
 }
 
+async function latestMainSessionUserMessageIsInProgress(ctx: BabysitterContext, sessionID: string, now: number): Promise<boolean> {
+  try {
+    const messagesResp = await ctx.client.session.messages({
+      path: { id: sessionID },
+    })
+    const messages = extractMessages(messagesResp)
+    for (let index = messages.length - 1; index >= 0; index--) {
+      const message = messages[index]
+      const role = getMessageInfo(message)?.role
+      if (role === "user") {
+        const createdAt = getMessageCreatedAt(message)
+        return createdAt !== undefined && now - createdAt <= USER_MESSAGE_IN_PROGRESS_WINDOW_MS
+      }
+      if (role === "assistant" || role === "tool") {
+        return false
+      }
+    }
+    return false
+  } catch (error) {
+    log(`[${HOOK_NAME}] Failed to inspect recent main session user activity`, { sessionID, error: String(error) })
+    return false
+  }
+}
+
+function getTaskLastActivityAt(task: { progress?: { lastUpdate?: Date; lastMessageAt?: Date } }): Date | undefined {
+  const lastMessageAt = task.progress?.lastMessageAt
+  const lastUpdate = task.progress?.lastUpdate
+  if (!lastMessageAt) return lastUpdate
+  if (!lastUpdate) return lastMessageAt
+  return lastUpdate.getTime() > lastMessageAt.getTime() ? lastUpdate : lastMessageAt
+}
+
 export function createUnstableAgentBabysitterHook(ctx: BabysitterContext, options: BabysitterOptions) {
   const reminderCooldowns = new Map<string, number>()
   const cancelledSessions = new Set<string>()
@@ -134,7 +168,6 @@ export function createUnstableAgentBabysitterHook(ctx: BabysitterContext, option
       if (!sessionID || !isAbortError(props?.error)) return
 
       cancelledSessions.add(sessionID)
-      reminderCooldowns.clear()
       log(`[${HOOK_NAME}] Marked session cancelled`, { sessionID })
       return
     }
@@ -144,7 +177,6 @@ export function createUnstableAgentBabysitterHook(ctx: BabysitterContext, option
       if (!sessionID) return
 
       cancelledSessions.add(sessionID)
-      reminderCooldowns.clear()
       log(`[${HOOK_NAME}] Marked session cancelled via session.stop`, { sessionID })
       return
     }
@@ -193,15 +225,19 @@ export function createUnstableAgentBabysitterHook(ctx: BabysitterContext, option
 
     const timeoutMs = options.config?.timeout_ms ?? DEFAULT_TIMEOUT_MS
     const now = Date.now()
+    if (await latestMainSessionUserMessageIsInProgress(ctx, mainSessionID, now)) {
+      log(`[${HOOK_NAME}] Skipped reminder: main session has recent user activity`, { sessionID: mainSessionID })
+      return
+    }
 
     for (const task of tasks) {
       if (task.status !== "running") continue
       if (!isUnstableTask(task)) continue
 
-      const lastMessageAt = task.progress?.lastMessageAt
+      const lastActivityAt = getTaskLastActivityAt(task)
-      if (!lastMessageAt) continue
+      if (!lastActivityAt) continue
 
-      const idleMs = now - lastMessageAt.getTime()
+      const idleMs = now - lastActivityAt.getTime()
       if (idleMs < timeoutMs) continue
 
       const lastReminderAt = reminderCooldowns.get(task.id)