fix(feedback): handle paused delivery assignees

Co-Authored-By: Paperclip <noreply@paperclip.ing>

packages/shared/src/index.ts

@@ -1011,6 +1011,7 @@ export type {
   IssueExecutionDecision,
   IssueComment,
   IssueCommentFeedbackDelivery,
+  IssueFeedbackDeliveryRetryNoInvokableAssigneeReason,
   IssueFeedbackDeliveryRetryResponse,
   IssueCommentDerivedAuthorSource,
   IssueCommentMetadata,

packages/shared/src/types/index.ts

@@ -650,6 +650,7 @@ export type {
   IssueExecutionDecision,
   IssueComment,
   IssueCommentFeedbackDelivery,
+  IssueFeedbackDeliveryRetryNoInvokableAssigneeReason,
   IssueFeedbackDeliveryRetryResponse,
   IssueCommentDerivedAuthorSource,
   IssueCommentMetadata,

packages/shared/src/types/issue.ts

@@ -986,8 +986,22 @@ export interface IssueCommentFeedbackDelivery {
   batchedCommentCount: number;
 }
 
+export type IssueFeedbackDeliveryRetryNoInvokableAssigneeReason =
+  | "missing"
+  | "paused"
+  | "terminated"
+  | "pending_approval"
+  | "unknown_status"
+  | "manager_missing"
+  | "manager_company_mismatch"
+  | "manager_terminated"
+  | "reporting_cycle"
+  | "reporting_chain_too_deep";
+
 export interface IssueFeedbackDeliveryRetryResponse {
   outcome: "queued" | "already_queued" | "not_exhausted" | "no_invokable_assignee";
+  /** Present only when `outcome` is `no_invokable_assignee`. */
+  reason: IssueFeedbackDeliveryRetryNoInvokableAssigneeReason | null;
   message: string;
   feedbackDelivery: IssueCommentFeedbackDelivery | null;
 }

server/src/__tests__/issue-feedback-delivery-retry-routes.test.ts

@@ -0,0 +1,168 @@
+import { randomUUID } from "node:crypto";
+import express from "express";
+import request from "supertest";
+import { afterAll, afterEach, beforeAll, describe, expect, it } from "vitest";
+import {
+  activityLog,
+  agents,
+  agentWakeupRequests,
+  companies,
+  createDb,
+  issueRecoveryActions,
+  issues,
+} from "@paperclipai/db";
+import {
+  getEmbeddedPostgresTestSupport,
+  startEmbeddedPostgresTestDatabase,
+} from "./helpers/embedded-postgres.js";
+import { errorHandler } from "../middleware/index.js";
+import { issueRoutes } from "../routes/issues.js";
+import {
+  FEEDBACK_DELIVERY_RECOVERY_ACTION_KIND,
+  FEEDBACK_DELIVERY_RECOVERY_CAUSE,
+} from "../services/recovery/feedback-delivery.js";
+
+const embeddedPostgresSupport = await getEmbeddedPostgresTestSupport();
+const describeEmbeddedPostgres = embeddedPostgresSupport.supported ? describe : describe.skip;
+
+if (!embeddedPostgresSupport.supported) {
+  console.warn(
+    `Skipping embedded Postgres feedback-delivery retry route tests on this host: ${
+      embeddedPostgresSupport.reason ?? "unsupported environment"
+    }`,
+  );
+}
+
+describeEmbeddedPostgres("issue feedback-delivery retry routes", () => {
+  let db!: ReturnType<typeof createDb>;
+  let tempDb: Awaited<ReturnType<typeof startEmbeddedPostgresTestDatabase>> | null = null;
+
+  beforeAll(async () => {
+    tempDb = await startEmbeddedPostgresTestDatabase("paperclip-feedback-delivery-retry-routes-");
+    db = createDb(tempDb.connectionString);
+  }, 20_000);
+
+  afterEach(async () => {
+    await db.delete(issueRecoveryActions);
+    await db.delete(activityLog);
+    await db.delete(issues);
+    await db.delete(agentWakeupRequests);
+    await db.delete(agents);
+    await db.delete(companies);
+  });
+
+  afterAll(async () => {
+    await tempDb?.cleanup();
+  });
+
+  function createApp(companyId: string) {
+    const app = express();
+    app.use(express.json());
+    app.use((req, _res, next) => {
+      req.actor = {
+        type: "board",
+        userId: "board-user",
+        companyIds: [companyId],
+        memberships: [{ companyId, membershipRole: "admin", status: "active" }],
+        isInstanceAdmin: false,
+        source: "session",
+      };
+      next();
+    });
+    app.use("/api", issueRoutes(db, {} as any));
+    app.use(errorHandler);
+    return app;
+  }
+
+  async function seedExhaustedDelivery(input: { agentStatus?: string; withAgent?: boolean } = {}) {
+    const companyId = randomUUID();
+    const issueId = randomUUID();
+    const agentId = input.withAgent === false ? null : randomUUID();
+    const rootWakeupRequestId = randomUUID();
+    const sourceCommentId = randomUUID();
+    const issuePrefix = `F${companyId.replace(/-/g, "").slice(0, 6).toUpperCase()}`;
+
+    await db.insert(companies).values({
+      id: companyId,
+      name: "Paperclip",
+      issuePrefix,
+      requireBoardApprovalForNewAgents: false,
+    });
+    if (agentId) {
+      await db.insert(agents).values({
+        id: agentId,
+        companyId,
+        name: "CodexCoder",
+        role: "engineer",
+        status: input.agentStatus ?? "paused",
+        adapterType: "codex_local",
+        adapterConfig: {},
+        runtimeConfig: {},
+        permissions: {},
+      });
+    }
+    await db.insert(issues).values({
+      id: issueId,
+      companyId,
+      title: "Feedback delivery exhausted",
+      status: "in_review",
+      priority: "medium",
+      assigneeAgentId: agentId,
+      issueNumber: 1,
+      identifier: `${issuePrefix}-1`,
+    });
+    await db.insert(issueRecoveryActions).values({
+      companyId,
+      sourceIssueId: issueId,
+      kind: FEEDBACK_DELIVERY_RECOVERY_ACTION_KIND,
+      status: "active",
+      ownerType: agentId ? "agent" : "board",
+      ownerAgentId: agentId,
+      previousOwnerAgentId: agentId,
+      returnOwnerAgentId: agentId,
+      cause: FEEDBACK_DELIVERY_RECOVERY_CAUSE,
+      fingerprint: `feedback_delivery:${companyId}:${issueId}:${agentId ?? "missing"}:${rootWakeupRequestId}`,
+      evidence: {
+        rootWakeupRequestId,
+        outstandingCommentIds: [sourceCommentId],
+      },
+      nextAction: "Deliver the outstanding feedback",
+      attemptCount: 1,
+      maxAttempts: 1,
+    });
+
+    return { companyId, issueId };
+  }
+
+  it("returns a paused reason instead of leaking the wakeup 409", async () => {
+    const { companyId, issueId } = await seedExhaustedDelivery({ agentStatus: "paused" });
+
+    const res = await request(createApp(companyId))
+      .post(`/api/issues/${issueId}/feedback-delivery/retry`)
+      .send({});
+
+    expect(res.status, JSON.stringify(res.body)).toBe(200);
+    expect(res.body).toMatchObject({
+      outcome: "no_invokable_assignee",
+      reason: "paused",
+      message: "This delivery's agent is paused. Unpause the agent before retrying.",
+    });
+    expect(await db.select().from(agentWakeupRequests)).toHaveLength(0);
+    expect(await db.select().from(activityLog)).toHaveLength(0);
+  });
+
+  it("distinguishes a missing assignee from a paused one", async () => {
+    const { companyId, issueId } = await seedExhaustedDelivery({ withAgent: false });
+
+    const res = await request(createApp(companyId))
+      .post(`/api/issues/${issueId}/feedback-delivery/retry`)
+      .send({});
+
+    expect(res.status, JSON.stringify(res.body)).toBe(200);
+    expect(res.body).toMatchObject({
+      outcome: "no_invokable_assignee",
+      reason: "missing",
+      message: "This delivery has no agent to retry against. Reassign the task first.",
+    });
+  });
+});

server/src/routes/issues.ts

@@ -113,6 +113,7 @@ import {
   FEEDBACK_DELIVERY_RETRY_WAKE_REASON,
   FEEDBACK_DELIVERY_WAKE_COMMENT_IDS_KEY,
 } from "../services/recovery/feedback-delivery.js";
+import { evaluateAgentInvokabilityFromDb } from "../services/agent-invokability.js";
 import { getTelemetryClient } from "../telemetry.js";
 import { isUniqueViolation } from "../db-errors.js";
 import type { StorageService } from "../storage/types.js";
@@ -10826,6 +10827,7 @@ export function issueRoutes(
       const states = await readStates();
       res.json({
         outcome: "not_exhausted",
+        reason: null,
         message: "This task has no exhausted feedback delivery to retry.",
         feedbackDelivery: states.values().next().value ?? null,
       } satisfies IssueFeedbackDeliveryRetryResponse);
@@ -10849,12 +10851,40 @@ export function issueRoutes(
     if (!targetAgentId || !rootWakeupRequestId) {
       res.json({
         outcome: "no_invokable_assignee",
+        reason: "missing",
         message: "This delivery has no agent to retry against. Reassign the task first.",
         feedbackDelivery: (await readStates()).get(outstandingCommentIds[0] ?? "") ?? null,
       } satisfies IssueFeedbackDeliveryRetryResponse);
       return;
     }
 
+    const targetAgent = await db
+      .select({
+        id: agents.id,
+        companyId: agents.companyId,
+        name: agents.name,
+        reportsTo: agents.reportsTo,
+        status: agents.status,
+      })
+      .from(agents)
+      .where(and(eq(agents.id, targetAgentId), eq(agents.companyId, issue.companyId)))
+      .then((rows) => rows[0] ?? null);
+    const invokability = await evaluateAgentInvokabilityFromDb(db, targetAgent);
+    if (!invokability.invokable) {
+      const message = invokability.reason === "paused"
+        ? "This delivery's agent is paused. Unpause the agent before retrying."
+        : invokability.reason === "pending_approval"
+          ? "This delivery's agent is waiting for approval. Approve or reassign the agent before retrying."
+          : "This delivery has no invokable agent to retry against. Reassign the task first.";
+      res.json({
+        outcome: "no_invokable_assignee",
+        reason: invokability.reason,
+        message,
+        feedbackDelivery: (await readStates()).get(outstandingCommentIds[0] ?? "") ?? null,
+      } satisfies IssueFeedbackDeliveryRetryResponse);
+      return;
+    }
+
     const statesBefore = await readStates();
     const alreadyInFlight = outstandingCommentIds.some(
       (commentId) => statesBefore.get(commentId)?.retryInFlight === true,
@@ -10862,6 +10892,7 @@ export function issueRoutes(
     if (alreadyInFlight) {
       res.json({
         outcome: "already_queued",
+        reason: null,
         message: "A delivery retry is already queued.",
         feedbackDelivery: statesBefore.get(outstandingCommentIds[0] ?? "") ?? null,
       } satisfies IssueFeedbackDeliveryRetryResponse);
@@ -10919,6 +10950,7 @@ export function issueRoutes(
     const projected = latestCommentId ? statesAfter.get(latestCommentId) ?? null : null;
     res.json({
       outcome: "queued",
+      reason: null,
       message: "Retrying feedback delivery.",
       // Deferred behind a live run still reads as in-flight to the operator, so
       // fall back to a synthetic in-flight projection rather than reporting a

ui/src/components/FeedbackDeliveryState.test.tsx

@@ -13,6 +13,7 @@ import {
   FeedbackDeliveryFooterStatus,
   FeedbackDeliveryNotice,
   feedbackDeliveryAnchorId,
+  feedbackDeliveryRetryErrorMessage,
   isIssueCommentFeedbackDelivery,
   useFeedbackDeliveryTransientSuccess,
 } from "./FeedbackDeliveryState";
@@ -318,6 +319,30 @@ describe("FeedbackDeliveryNotice — exhausted", () => {
     ).toBe(false);
   });
 
+  it("shows an actionable paused-agent retry failure inline", () => {
+    const message = feedbackDeliveryRetryErrorMessage({
+      outcome: "no_invokable_assignee",
+      reason: "paused",
+      message: "server fallback",
+      feedbackDelivery: delivery(),
+    });
+    const node = render(
+      <FeedbackDeliveryNotice delivery={delivery()} onRetry={() => {}} retryError={message} />,
+    );
+    expect(node.querySelector("[data-testid='feedback-delivery-retry-error']")?.textContent).toBe(
+      "The assigned agent is paused. Unpause the agent before retrying.",
+    );
+  });
+
+  it("keeps missing-assignee retry guidance distinct from paused guidance", () => {
+    expect(feedbackDeliveryRetryErrorMessage({
+      outcome: "no_invokable_assignee",
+      reason: "missing",
+      message: "This delivery has no agent to retry against. Reassign the task first.",
+      feedbackDelivery: delivery(),
+    })).toBe("This delivery has no agent to retry against. Reassign the task first.");
+  });
+
   it("hides retry from a viewer without the authority to trigger it", () => {
     const node = render(<FeedbackDeliveryNotice delivery={delivery({ canRetry: false })} />);
     expect(node.querySelector("[data-testid='feedback-delivery-retry']")).toBeNull();

ui/src/components/FeedbackDeliveryState.tsx

@@ -1,7 +1,10 @@
 import { useEffect, useRef, useState } from "react";
 import { Link } from "react-router-dom";
 import { CircleCheck, RefreshCw } from "lucide-react";
-import type { IssueCommentFeedbackDelivery } from "@paperclipai/shared";
+import type {
+  IssueCommentFeedbackDelivery,
+  IssueFeedbackDeliveryRetryResponse,
+} from "@paperclipai/shared";
 
 import { InlineBanner } from "@/components/InlineBanner";
 import { SystemNotice } from "@/components/SystemNotice";
@@ -19,6 +22,19 @@ export const FEEDBACK_DELIVERY_RETRYING_REVEAL_MS = 400;
 /** How long the ephemeral "Delivered after retry" confirmation stays visible. */
 export const FEEDBACK_DELIVERY_TRANSIENT_SUCCESS_MS = 5000;
 
+export function feedbackDeliveryRetryErrorMessage(
+  response: IssueFeedbackDeliveryRetryResponse,
+) {
+  if (response.outcome !== "no_invokable_assignee") return response.message;
+  if (response.reason === "paused") {
+    return "The assigned agent is paused. Unpause the agent before retrying.";
+  }
+  if (response.reason === "pending_approval") {
+    return "The assigned agent is waiting for approval. Approve or reassign it before retrying.";
+  }
+  return response.message;
+}
+
 const FEEDBACK_DELIVERY_STATES = [
   "retrying",
   "exhausted_needs_attention",
@@ -232,13 +248,13 @@ export function FeedbackDeliveryNotice({
   delivery,
   onRetry,
   retryPending = false,
-  retryError = false,
+  retryError = null,
   className,
 }: {
   delivery: IssueCommentFeedbackDelivery;
   onRetry?: (commentId: string) => void;
   retryPending?: boolean;
-  retryError?: boolean;
+  retryError?: string | boolean | null;
   className?: string;
 }) {
   const anchorId = feedbackDeliveryAnchorId(delivery.sourceCommentId);
@@ -349,7 +365,9 @@ export function FeedbackDeliveryNotice({
           </p>
           {retryError ? (
             <p data-testid="feedback-delivery-retry-error" className="font-medium">
-              Couldn&apos;t start another retry. Try again.
+              {typeof retryError === "string"
+                ? retryError
+                : "Couldn't start another retry. Try again."}
             </p>
           ) : null}
         </div>

ui/src/components/IssueChatThread.tsx

@@ -222,6 +222,7 @@ interface IssueChatMessageContext {
   retryingFeedbackDeliveryCommentId?: string | null;
   /** Comment id whose last retry request failed, so the banner can say so inline. */
   failedFeedbackDeliveryRetryCommentId?: string | null;
+  feedbackDeliveryRetryErrorMessage?: string | null;
   onImageClick?: (src: string) => void;
   onAcceptInteraction?: (
     interaction:
@@ -547,6 +548,7 @@ interface IssueChatThreadProps {
   onRetryFeedbackDelivery?: (commentId: string) => Promise<void> | void;
   retryingFeedbackDeliveryCommentId?: string | null;
   failedFeedbackDeliveryRetryCommentId?: string | null;
+  feedbackDeliveryRetryErrorMessage?: string | null;
   onDeleteComment?: (commentId: string) => Promise<void> | void;
   interruptingQueuedRunId?: string | null;
   stoppingRunId?: string | null;
@@ -1479,6 +1481,7 @@ function IssueChatUserMessage({
     onRetryFeedbackDelivery,
     retryingFeedbackDeliveryCommentId,
     failedFeedbackDeliveryRetryCommentId,
+    feedbackDeliveryRetryErrorMessage,
     currentUserId,
     userProfileMap,
   } = useContext(IssueChatCtx);
@@ -1687,7 +1690,11 @@ function IssueChatUserMessage({
             delivery={feedbackDelivery}
             onRetry={onRetryFeedbackDelivery}
             retryPending={retryingFeedbackDeliveryCommentId === feedbackDelivery.sourceCommentId}
-            retryError={failedFeedbackDeliveryRetryCommentId === feedbackDelivery.sourceCommentId}
+            retryError={
+              failedFeedbackDeliveryRetryCommentId === feedbackDelivery.sourceCommentId
+                ? feedbackDeliveryRetryErrorMessage ?? true
+                : false
+            }
           />
         ) : null}
       </div>
@@ -4440,6 +4447,7 @@ export function IssueChatThread({
   onRetryFeedbackDelivery,
   retryingFeedbackDeliveryCommentId = null,
   failedFeedbackDeliveryRetryCommentId = null,
+  feedbackDeliveryRetryErrorMessage = null,
   interruptingQueuedRunId = null,
   stoppingRunId = null,
   onImageClick,
@@ -5021,6 +5029,7 @@ export function IssueChatThread({
       onRetryFeedbackDelivery: stableOnRetryFeedbackDelivery,
       retryingFeedbackDeliveryCommentId,
       failedFeedbackDeliveryRetryCommentId,
+      feedbackDeliveryRetryErrorMessage,
       onImageClick: stableOnImageClick,
       onAcceptInteraction: stableOnAcceptInteraction,
       onRejectInteraction: stableOnRejectInteraction,
@@ -5053,6 +5062,7 @@ export function IssueChatThread({
       stableOnRetryFeedbackDelivery,
       retryingFeedbackDeliveryCommentId,
       failedFeedbackDeliveryRetryCommentId,
+      feedbackDeliveryRetryErrorMessage,
       stableOnImageClick,
       stableOnAcceptInteraction,
       stableOnRejectInteraction,

ui/src/components/TaskChatThread.tsx

@@ -139,6 +139,7 @@ export function TaskChatThread(props: TaskChatThreadProps) {
     onRetryFeedbackDelivery,
     retryingFeedbackDeliveryCommentId,
     failedFeedbackDeliveryRetryCommentId,
+    feedbackDeliveryRetryErrorMessage,
   } = props;
 
   const liveWorkLinks = useMemo(
@@ -687,6 +688,7 @@ export function TaskChatThread(props: TaskChatThreadProps) {
             onRetryFeedbackDelivery={onRetryFeedbackDelivery}
             retryingFeedbackDeliveryCommentId={retryingFeedbackDeliveryCommentId}
             failedFeedbackDeliveryRetryCommentId={failedFeedbackDeliveryRetryCommentId}
+            feedbackDeliveryRetryErrorMessage={feedbackDeliveryRetryErrorMessage}
             tail={tailRunId || bottomBlockerLinks ? (
               <>
                 {tailRunId ? (

ui/src/components/task-chat/TaskChatBubble.tsx

@@ -44,6 +44,7 @@ interface TaskChatBubbleProps {
   onRetryFeedbackDelivery?: (commentId: string) => Promise<void> | void;
   retryingFeedbackDeliveryCommentId?: string | null;
   failedFeedbackDeliveryRetryCommentId?: string | null;
+  feedbackDeliveryRetryErrorMessage?: string | null;
 }
 
 function initialsForName(name: string) {
@@ -79,6 +80,7 @@ export function TaskChatBubble({
   onRetryFeedbackDelivery,
   retryingFeedbackDeliveryCommentId,
   failedFeedbackDeliveryRetryCommentId,
+  feedbackDeliveryRetryErrorMessage,
 }: TaskChatBubbleProps) {
   // Clicking an embedded image opens the full-screen lightbox (with download);
   // arrow keys walk across the other images in the same bubble.
@@ -235,6 +237,8 @@ export function TaskChatBubble({
           }
           retryError={
             failedFeedbackDeliveryRetryCommentId === item.feedbackDelivery.sourceCommentId
+              ? feedbackDeliveryRetryErrorMessage ?? true
+              : false
           }
         />
       ) : null}

ui/src/components/task-chat/TaskChatThreadView.tsx

@@ -46,6 +46,7 @@ interface TaskChatThreadViewProps {
   onRetryFeedbackDelivery?: (commentId: string) => Promise<void> | void;
   retryingFeedbackDeliveryCommentId?: string | null;
   failedFeedbackDeliveryRetryCommentId?: string | null;
+  feedbackDeliveryRetryErrorMessage?: string | null;
   /** Content appended inside the transcript scroller after the settled thread. */
   tail?: ReactNode;
   /** Optional streaming-aware key when `tail` changes without changing `items`. */
@@ -65,6 +66,7 @@ function renderItem(
   onRetryFeedbackDelivery?: (commentId: string) => Promise<void> | void,
   retryingFeedbackDeliveryCommentId?: string | null,
   failedFeedbackDeliveryRetryCommentId?: string | null,
+  feedbackDeliveryRetryErrorMessage?: string | null,
 ) {
   switch (item.kind) {
     case "message": {
@@ -82,6 +84,7 @@ function renderItem(
           onRetryFeedbackDelivery={onRetryFeedbackDelivery}
           retryingFeedbackDeliveryCommentId={retryingFeedbackDeliveryCommentId}
           failedFeedbackDeliveryRetryCommentId={failedFeedbackDeliveryRetryCommentId}
+          feedbackDeliveryRetryErrorMessage={feedbackDeliveryRetryErrorMessage}
           attachedTurn={
             item.attachedTurn ? (
               <TaskChatTurn
@@ -152,6 +155,7 @@ export function TaskChatThreadView({
   onRetryFeedbackDelivery,
   retryingFeedbackDeliveryCommentId,
   failedFeedbackDeliveryRetryCommentId,
+  feedbackDeliveryRetryErrorMessage,
   tail,
   contentKey,
   className,
@@ -176,6 +180,7 @@ export function TaskChatThreadView({
             onRetryFeedbackDelivery,
             retryingFeedbackDeliveryCommentId,
             failedFeedbackDeliveryRetryCommentId,
+            feedbackDeliveryRetryErrorMessage,
           )}
         </div>
       ))}

ui/src/pages/IssueDetail.tsx

@@ -100,6 +100,7 @@ import {
   type IssueChatRunFinalizationAction,
 } from "../components/IssueChatThread";
 import { TaskChatThread } from "../components/TaskChatThread";
+import { feedbackDeliveryRetryErrorMessage } from "../components/FeedbackDeliveryState";
 import type { TaskChatIssueBrief } from "../components/task-chat/TaskChatDescriptionBubble";
 import { useClassicTaskInterfaceEnabled } from "../hooks/useClassicTaskInterfaceEnabled";
 import { workModeMetaFor } from "../lib/work-mode-meta";
@@ -962,6 +963,7 @@ type IssueDetailChatTabProps = {
   onRetryFeedbackDelivery?: (commentId: string) => void;
   retryingFeedbackDeliveryCommentId?: string | null;
   failedFeedbackDeliveryRetryCommentId?: string | null;
+  feedbackDeliveryRetryErrorMessage?: string | null;
   onResolveRecoveryAction?: (outcome: import("../components/IssueRecoveryActionCard").RecoveryResolveOutcome) => void;
   onReissueIsolatedRecoveryAction?: (request: import("../components/IssueRecoveryActionCard").RecoveryReissueRequest) => void;
   reissueIsolatedRecoveryActionPending?: boolean;
@@ -1070,6 +1072,7 @@ const IssueDetailChatTab = memo(function IssueDetailChatTab({
   onRetryFeedbackDelivery,
   retryingFeedbackDeliveryCommentId,
   failedFeedbackDeliveryRetryCommentId,
+  feedbackDeliveryRetryErrorMessage,
   recoveryAction,
   onResolveRecoveryAction,
   onReissueIsolatedRecoveryAction,
@@ -1349,6 +1352,7 @@ const IssueDetailChatTab = memo(function IssueDetailChatTab({
         onRetryFeedbackDelivery={onRetryFeedbackDelivery}
         retryingFeedbackDeliveryCommentId={retryingFeedbackDeliveryCommentId ?? null}
         failedFeedbackDeliveryRetryCommentId={failedFeedbackDeliveryRetryCommentId ?? null}
+        feedbackDeliveryRetryErrorMessage={feedbackDeliveryRetryErrorMessage ?? null}
         onResolveRecoveryAction={onResolveRecoveryAction}
         onReissueIsolatedRecoveryAction={onReissueIsolatedRecoveryAction}
         reissueIsolatedRecoveryActionPending={reissueIsolatedRecoveryActionPending}
@@ -4196,6 +4200,8 @@ export function IssueDetail() {
     useState<string | null>(null);
   const [retryingFeedbackDeliveryCommentId, setRetryingFeedbackDeliveryCommentId] =
     useState<string | null>(null);
+  const [feedbackDeliveryRetryFailureMessage, setFeedbackDeliveryRetryFailureMessage] =
+    useState<string | null>(null);
   const retryFeedbackDelivery = useMutation({
     // The commentId is carried so the banner that was pressed owns the pending
     // and error state; the request itself is scoped to the issue's one open
@@ -4204,6 +4210,7 @@ export function IssueDetail() {
     onMutate: (input) => {
       setRetryingFeedbackDeliveryCommentId(input.commentId);
       setFailedFeedbackDeliveryRetryCommentId(null);
+      setFeedbackDeliveryRetryFailureMessage(null);
     },
     onSuccess: (result, variables) => {
       // The delivery state lives on the comment, so the thread is the cache that
@@ -4212,10 +4219,14 @@ export function IssueDetail() {
       invalidateIssueDetail();
       if (result.outcome === "queued" || result.outcome === "already_queued") return;
       setFailedFeedbackDeliveryRetryCommentId(variables.commentId);
+      setFeedbackDeliveryRetryFailureMessage(feedbackDeliveryRetryErrorMessage(result));
       pushToast({ title: "Couldn't retry delivery", body: result.message, tone: "error" });
     },
     onError: (err, variables) => {
       setFailedFeedbackDeliveryRetryCommentId(variables.commentId);
+      setFeedbackDeliveryRetryFailureMessage(
+        err instanceof Error ? err.message : "Unable to retry feedback delivery.",
+      );
       pushToast({
         title: "Couldn't retry delivery",
         body: err instanceof Error ? err.message : "Unable to retry feedback delivery.",
@@ -5263,6 +5274,7 @@ export function IssueDetail() {
               onRetryFeedbackDelivery={handleRetryFeedbackDelivery}
               retryingFeedbackDeliveryCommentId={retryingFeedbackDeliveryCommentId}
               failedFeedbackDeliveryRetryCommentId={failedFeedbackDeliveryRetryCommentId}
+              feedbackDeliveryRetryErrorMessage={feedbackDeliveryRetryFailureMessage}
               onResolveRecoveryAction={handleResolveRecoveryAction}
               onReissueIsolatedRecoveryAction={handleReissueIsolatedRecoveryAction}
               reissueIsolatedRecoveryActionPending={reissueIsolatedRecoveryAction.isPending}