fix(team-mode): preserve live delivery holds after ambiguous prompt failure

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,