From 7db3a7f933e2636331a5c5bc0133323e7f5dfef2 Mon Sep 17 00:00:00 2001
From: YeonGyu-Kim <code.yeon.gyu@gmail.com>
Date: Tue, 19 May 2026 13:49:01 +0900
Subject: [PATCH] fix(team-mode): preserve live delivery holds after ambiguous
 prompt failure

---
 .../team-mode/tools/messaging.test.ts         | 39 +++++++++++++++++++
 src/features/team-mode/tools/messaging.ts     | 31 +++++++++++++++
 2 files changed, 70 insertions(+)

diff --git a/src/features/team-mode/tools/messaging.test.ts b/src/features/team-mode/tools/messaging.test.ts
index bb1474ad2..13dca9c6d 100644
--- a/src/features/team-mode/tools/messaging.test.ts
+++ b/src/features/team-mode/tools/messaging.test.ts
@@ -14,6 +14,7 @@ import {
   clearAllSessionPromptParams,
   getSessionPromptParams,
 } from "../../../shared/session-prompt-params-state"
+import { releaseAllPromptAsyncReservationsForTesting } from "../../../hooks/shared/prompt-async-gate"
 import { listUnreadMessages } from "../team-mailbox/inbox"
 import { BroadcastNotPermittedError } from "../team-mailbox/send"
 import { getInboxDir, resolveBaseDir } from "../team-registry/paths"
@@ -87,6 +88,7 @@ afterEach(() => {
   clearTeamSessionRegistry()
   SessionCategoryRegistry.clear()
   clearAllSessionPromptParams()
+  releaseAllPromptAsyncReservationsForTesting()
   _resetForTesting()
 })
 
@@ -630,6 +632,43 @@ describe("createTeamSendMessageTool", () => {
     expect(inboxEntries).toHaveLength(1)
   })
 
+  test("#given live delivery promptAsync fails after dispatch may have been accepted #when delivery falls back #then it keeps the delivered message reserved instead of surfacing a duplicate unread", async () => {
+    // given
+    const fixture = await createTeamFixture()
+    let promptCalls = 0
+    const failingClient = {
+      session: {
+        promptAsync: async () => {
+          promptCalls += 1
+          throw new Error("JSON Parse error: Unexpected EOF")
+        },
+      },
+    } satisfies LiveDeliveryClient
+    const liveTool = createTeamSendMessageTool(fixture.config, failingClient)
+
+    // when
+    await liveTool.execute({
+      teamRunId: fixture.teamRunId,
+      to: "m2",
+      body: "maybe already accepted",
+    }, fixture.toolContext(fixture.memberOneSessionId))
+
+    // then
+    expect(promptCalls).toBe(1)
+    const unread = await listUnreadMessages(fixture.teamRunId, "m2", fixture.config)
+    expect(unread).toHaveLength(0)
+
+    const inboxDir = getInboxDir(resolveBaseDir(fixture.config), fixture.teamRunId, "m2")
+    const inboxEntries = (await readdir(inboxDir)).filter((entry) => entry.endsWith(".json"))
+    expect(inboxEntries).toHaveLength(1)
+    expect(inboxEntries[0]?.startsWith(".delivering-")).toBe(true)
+
+    const { loadRuntimeState: loadState } = await import("../team-state-store/store")
+    const runtimeState = await loadState(fixture.teamRunId, fixture.config)
+    const recipient = runtimeState.members.find((member) => member.name === "m2")
+    expect(recipient?.pendingInjectedMessageIds).toHaveLength(1)
+  })
+
   test("reserves the message during live delivery so concurrent listings cannot surface it", async () => {
     // given
     const fixture = await createTeamFixture()
diff --git a/src/features/team-mode/tools/messaging.ts b/src/features/team-mode/tools/messaging.ts
index 3c95a8b5a..f1b03b4ad 100644
--- a/src/features/team-mode/tools/messaging.ts
+++ b/src/features/team-mode/tools/messaging.ts
@@ -68,6 +68,26 @@ const TeamSendMessageArgsSchema = z.object({
 
 type DeliveryReservation = Awaited<ReturnType<typeof reserveMessageForDelivery>>
 
+function extractPromptFailureMessage(error: unknown): string {
+  if (typeof error === "string") return error
+  if (error instanceof Error) return error.message
+  if (typeof error === "object" && error !== null) {
+    const record = error as Record<string, unknown>
+    if (typeof record.message === "string") return record.message
+    try {
+      return JSON.stringify(error)
+    } catch {
+      return ""
+    }
+  }
+  return String(error)
+}
+
+function shouldKeepReservationAfterFailedLivePrompt(error: unknown): boolean {
+  const message = extractPromptFailureMessage(error)
+  return message.includes("Unexpected EOF") || message.includes("timed out")
+}
+
 async function resolveTeamRuntimeDetails(
   teamRunId: string,
   sessionID: string,
@@ -210,6 +230,17 @@ async function deliverLive(
           query: { directory: recipientMember.worktreePath ?? directory },
         },
       })
+      if (promptResult.status === "failed" && shouldKeepReservationAfterFailedLivePrompt(promptResult.error)) {
+        await markLiveDeliveryPending(teamRunId, recipientName, message.messageId, config)
+        log("[team-mailbox] live delivery prompt failed after dispatch attempt, keeping reservation pending", {
+          teamRunId,
+          recipient: recipientName,
+          recipientSessionId,
+          messageId: message.messageId,
+          error: promptResult.error instanceof Error ? promptResult.error.message : String(promptResult.error),
+        })
+        continue
+      }
       if (promptResult.status !== "dispatched") {
         log("[team-mailbox] live delivery skipped by promptAsync gate, falling back to inbox injection", {
           status: promptResult.status,