diff --git a/ts/challenge.ts b/ts/challenge.ts
index 0f4d5daea7..9d8e45b59c 100644
--- a/ts/challenge.ts
+++ b/ts/challenge.ts
@@ -22,6 +22,7 @@ import * as Errors from './types/errors';
 import { HTTPError } from './textsecure/Errors';
 import type { SendMessageChallengeData } from './textsecure/Errors';
 import * as log from './logging/log';
+import { drop } from './util/drop';
 
 export type ChallengeResponse = Readonly<{
   captcha: string;
@@ -75,6 +76,7 @@ export type RegisteredChallengeType = Readonly<{
   reason: string;
   retryAt?: number;
   token?: string;
+  silent: boolean;
 }>;
 
 type SolveOptionsType = Readonly<{
@@ -210,7 +212,7 @@ export class ChallengeHandler {
     }
 
     if (challenge.token) {
-      void this.solve({ reason, token: challenge.token });
+      drop(this.solve({ reason, token: challenge.token }));
     }
   }
 
@@ -247,7 +249,7 @@ export class ChallengeHandler {
         setTimeout(() => {
           this.startTimers.delete(conversationId);
 
-          void this.startQueue(conversationId);
+          drop(this.startQueue(conversationId));
         }, waitTime)
       );
       log.info(
@@ -269,7 +271,9 @@ export class ChallengeHandler {
       return;
     }
 
-    void this.solve({ token: challenge.token, reason });
+    if (!challenge.silent) {
+      drop(this.solve({ token: challenge.token, reason }));
+    }
   }
 
   public onResponse(response: IPCResponse): void {
@@ -282,8 +286,13 @@ export class ChallengeHandler {
     handler.resolve(response.data);
   }
 
-  public async unregister(conversationId: string): Promise<void> {
-    log.info(`challenge: unregistered conversation ${conversationId}`);
+  public async unregister(
+    conversationId: string,
+    source: string
+  ): Promise<void> {
+    log.info(
+      `challenge: unregistered conversation ${conversationId} via ${source}`
+    );
     this.registeredConversations.delete(conversationId);
     this.pendingStarts.delete(conversationId);
 
@@ -343,7 +352,7 @@ export class ChallengeHandler {
       return;
     }
 
-    await this.unregister(conversationId);
+    await this.unregister(conversationId, 'startQueue');
 
     if (this.registeredConversations.size === 0) {
       this.options.setChallengeStatus('idle');
diff --git a/ts/jobs/JobQueue.ts b/ts/jobs/JobQueue.ts
index 8cd58fdd9b..09d1454564 100644
--- a/ts/jobs/JobQueue.ts
+++ b/ts/jobs/JobQueue.ts
@@ -13,6 +13,7 @@ import * as log from '../logging/log';
 import { JobLogger } from './JobLogger';
 import * as Errors from '../types/errors';
 import type { LoggerType } from '../types/Logging';
+import { drop } from '../util/drop';
 
 const noopOnCompleteCallbacks = {
   resolve: noop,
@@ -43,6 +44,12 @@ type JobQueueOptions = {
   logger?: LoggerType;
 };
 
+export enum JOB_STATUS {
+  SUCCESS = 'SUCCESS',
+  NEEDS_RETRY = 'NEEDS_RETRY',
+  ERROR = 'ERROR',
+}
+
 export abstract class JobQueue<T> {
   private readonly maxAttempts: number;
 
@@ -119,7 +126,7 @@ export abstract class JobQueue<T> {
   protected abstract run(
     job: Readonly<ParsedJob<T>>,
     extra?: Readonly<{ attempt?: number; log?: LoggerType }>
-  ): Promise<void>;
+  ): Promise<JOB_STATUS.NEEDS_RETRY | undefined>;
 
   protected getQueues(): ReadonlySet<PQueue> {
     return new Set([this.defaultInMemoryQueue]);
@@ -144,7 +151,7 @@ export abstract class JobQueue<T> {
         log.info(`${this.logPrefix} is shutting down. Can't accept more work.`);
         break;
       }
-      void this.enqueueStoredJob(storedJob);
+      drop(this.enqueueStoredJob(storedJob));
     }
   }
 
@@ -201,7 +208,9 @@ export abstract class JobQueue<T> {
     return this.defaultInMemoryQueue;
   }
 
-  private async enqueueStoredJob(storedJob: Readonly<StoredJob>) {
+  protected async enqueueStoredJob(
+    storedJob: Readonly<StoredJob>
+  ): Promise<void> {
     assertDev(
       storedJob.queueType === this.queueType,
       'Received a mis-matched queue type'
@@ -242,50 +251,78 @@ export abstract class JobQueue<T> {
 
     const result:
       | undefined
-      | { success: true }
-      | { success: false; err: unknown } = await queue.add(async () => {
-      for (let attempt = 1; attempt <= this.maxAttempts; attempt += 1) {
-        const isFinalAttempt = attempt === this.maxAttempts;
+      | { status: JOB_STATUS.SUCCESS }
+      | { status: JOB_STATUS.NEEDS_RETRY }
+      | { status: JOB_STATUS.ERROR; err: unknown } = await queue.add(
+      async () => {
+        for (let attempt = 1; attempt <= this.maxAttempts; attempt += 1) {
+          const isFinalAttempt = attempt === this.maxAttempts;
 
-        logger.attempt = attempt;
+          logger.attempt = attempt;
 
-        log.info(
-          `${this.logPrefix} running job ${storedJob.id}, attempt ${attempt} of ${this.maxAttempts}`
-        );
-
-        if (this.isShuttingDown) {
-          log.warn(
-            `${this.logPrefix} returning early for job ${storedJob.id}; shutting down`
-          );
-          return { success: false, err: new Error('Shutting down') };
-        }
-
-        try {
-          // We want an `await` in the loop, as we don't want a single job running more
-          //   than once at a time. Ideally, the job will succeed on the first attempt.
-          // eslint-disable-next-line no-await-in-loop
-          await this.run(parsedJob, { attempt, log: logger });
           log.info(
-            `${this.logPrefix} job ${storedJob.id} succeeded on attempt ${attempt}`
+            `${this.logPrefix} running job ${storedJob.id}, attempt ${attempt} of ${this.maxAttempts}`
           );
-          return { success: true };
-        } catch (err: unknown) {
-          log.error(
-            `${this.logPrefix} job ${
-              storedJob.id
-            } failed on attempt ${attempt}. ${Errors.toLogFormat(err)}`
-          );
-          if (isFinalAttempt) {
-            return { success: false, err };
+
+          if (this.isShuttingDown) {
+            log.warn(
+              `${this.logPrefix} returning early for job ${storedJob.id}; shutting down`
+            );
+            return {
+              status: JOB_STATUS.ERROR,
+              err: new Error('Shutting down'),
+            };
+          }
+
+          try {
+            // We want an `await` in the loop, as we don't want a single job running more
+            //   than once at a time. Ideally, the job will succeed on the first attempt.
+            // eslint-disable-next-line no-await-in-loop
+            const jobStatus = await this.run(parsedJob, {
+              attempt,
+              log: logger,
+            });
+            if (!jobStatus) {
+              log.info(
+                `${this.logPrefix} job ${storedJob.id} succeeded on attempt ${attempt}`
+              );
+              return { status: JOB_STATUS.SUCCESS };
+            }
+            log.info(
+              `${this.logPrefix} job ${storedJob.id} returned status ${jobStatus} on attempt ${attempt}`
+            );
+            return { status: jobStatus };
+          } catch (err: unknown) {
+            log.error(
+              `${this.logPrefix} job ${
+                storedJob.id
+              } failed on attempt ${attempt}. ${Errors.toLogFormat(err)}`
+            );
+            if (isFinalAttempt) {
+              return { status: JOB_STATUS.ERROR, err };
+            }
           }
         }
+
+        // This should never happen. See the assertion below.
+        return undefined;
       }
+    );
 
-      // This should never happen. See the assertion below.
-      return undefined;
-    });
-
-    if (result?.success || !this.isShuttingDown) {
+    if (result?.status === JOB_STATUS.NEEDS_RETRY) {
+      const addJobSuccess = await this.retryJobOnQueueIdle({
+        storedJob,
+        job: parsedJob,
+        logger,
+      });
+      if (!addJobSuccess) {
+        await this.store.delete(storedJob.id);
+      }
+    }
+    if (
+      result?.status === JOB_STATUS.SUCCESS ||
+      (result?.status === JOB_STATUS.ERROR && !this.isShuttingDown)
+    ) {
       await this.store.delete(storedJob.id);
     }
 
@@ -293,13 +330,26 @@ export abstract class JobQueue<T> {
       result,
       'The job never ran. This indicates a developer error in the job queue'
     );
-    if (result.success) {
-      resolve();
-    } else {
+    if (result.status === JOB_STATUS.ERROR) {
       reject(result.err);
+    } else {
+      resolve();
     }
   }
 
+  async retryJobOnQueueIdle({
+    logger,
+  }: {
+    job: Readonly<ParsedJob<T>>;
+    storedJob: Readonly<StoredJob>;
+    logger: LoggerType;
+  }): Promise<boolean> {
+    logger.error(
+      `retryJobOnQueueIdle: not implemented for queue ${this.queueType}; dropping job`
+    );
+    return false;
+  }
+
   async shutdown(): Promise<void> {
     const queues = this.getQueues();
     log.info(
diff --git a/ts/jobs/conversationJobQueue.ts b/ts/jobs/conversationJobQueue.ts
index 314f16ffa4..1c95cabd68 100644
--- a/ts/jobs/conversationJobQueue.ts
+++ b/ts/jobs/conversationJobQueue.ts
@@ -9,7 +9,7 @@ import * as durations from '../util/durations';
 import { exponentialBackoffMaxAttempts } from '../util/exponentialBackoff';
 import { InMemoryQueues } from './helpers/InMemoryQueues';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
-import { JobQueue } from './JobQueue';
+import { JOB_STATUS, JobQueue } from './JobQueue';
 
 import { sendNormalMessage } from './helpers/sendNormalMessage';
 import { sendDirectExpirationTimerUpdate } from './helpers/sendDirectExpirationTimerUpdate';
@@ -33,7 +33,7 @@ import { strictAssert } from '../util/assert';
 import { missingCaseError } from '../util/missingCaseError';
 import { explodePromise } from '../util/explodePromise';
 import type { Job } from './Job';
-import type { ParsedJob } from './types';
+import type { ParsedJob, StoredJob } from './types';
 import type SendMessage from '../textsecure/SendMessage';
 import type { ServiceIdString } from '../types/ServiceId';
 import { commonShouldJobContinue } from './helpers/commonShouldJobContinue';
@@ -44,6 +44,9 @@ import { sendResendRequest } from './helpers/sendResendRequest';
 import { sendNullMessage } from './helpers/sendNullMessage';
 import { sendSenderKeyDistribution } from './helpers/sendSenderKeyDistribution';
 import { sendSavedProto } from './helpers/sendSavedProto';
+import { drop } from '../util/drop';
+import { isInPast } from '../util/timestamp';
+import { clearTimeoutIfNecessary } from '../util/clearTimeoutIfNecessary';
 
 // Note: generally, we only want to add to this list. If you do need to change one of
 //   these values, you'll likely need to write a database migration.
@@ -62,6 +65,7 @@ export const conversationQueueJobEnum = z.enum([
   'Story',
   'Receipts',
 ]);
+type ConversationQueueJobEnum = z.infer<typeof conversationQueueJobEnum>;
 
 const deleteForEveryoneJobDataSchema = z.object({
   type: z.literal(conversationQueueJobEnum.enum.DeleteForEveryone),
@@ -234,7 +238,92 @@ export type ConversationQueueJobBundle = {
 const MAX_RETRY_TIME = durations.DAY;
 const MAX_ATTEMPTS = exponentialBackoffMaxAttempts(MAX_RETRY_TIME);
 
+function shouldSendShowCaptcha(type: ConversationQueueJobEnum): boolean {
+  if (type === 'DeleteForEveryone') {
+    return true;
+  }
+  if (type === 'DeleteStoryForEveryone') {
+    return true;
+  }
+  if (type === 'DirectExpirationTimerUpdate') {
+    return true;
+  }
+  if (type === 'GroupUpdate') {
+    return false;
+  }
+  if (type === 'NormalMessage') {
+    return true;
+  }
+  if (type === 'NullMessage') {
+    return false;
+  }
+  if (type === 'ProfileKey') {
+    return false;
+  }
+  if (type === 'Reaction') {
+    return false;
+  }
+  if (type === 'ResendRequest') {
+    return false;
+  }
+  if (type === 'SavedProto') {
+    return false;
+  }
+  if (type === 'SenderKeyDistribution') {
+    return false;
+  }
+  if (type === 'Story') {
+    return true;
+  }
+  if (type === 'Receipts') {
+    return false;
+  }
+
+  throw missingCaseError(type);
+}
+
+enum RETRY_STATUS {
+  BLOCKED = 'BLOCKED',
+  BLOCKED_WITH_JOBS = 'BLOCKED_WITH_JOBS',
+  UNBLOCKED = 'UNBLOCKED',
+}
+
+type ConversationData = Readonly<
+  | {
+      // When we get a retryAt from a 428 error, we immediately record it, but we don't
+      //   yet have a job to retry. We should, very soon, when the job returns
+      //   JOB_STATUS.NEEDS_RETRY. This should be a very short-lived state.
+      status: RETRY_STATUS.BLOCKED;
+      callback: undefined;
+      jobsNeedingRetry: undefined;
+      retryAt: number;
+    }
+  | {
+      // This is the next stage, when we've added at least one job needing retry, and we
+      //   have a callback registered to run on queue idle (or be called directly).
+      status: RETRY_STATUS.BLOCKED_WITH_JOBS;
+      callback: () => void;
+      jobsNeedingRetry: Array<Readonly<StoredJob>>;
+      retryAt: number;
+      retryAtTimeout?: NodeJS.Timeout;
+    }
+  | {
+      // When we discover that we can now run these deferred jobs, we flip into this
+      //   state, which should be short-lived. We very quickly re-enqueue all
+      //   jobsNeedingRetry, and erase perConversationData for this conversation.
+      status: RETRY_STATUS.UNBLOCKED;
+      callback: () => void;
+      jobsNeedingRetry: Array<Readonly<StoredJob>>;
+      retryAt: undefined;
+      retryAtTimeout?: NodeJS.Timeout;
+    }
+>;
+
 export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
+  private readonly perConversationData = new Map<
+    string,
+    ConversationData | undefined
+  >();
   private readonly inMemoryQueues = new InMemoryQueues();
   private readonly verificationWaitMap = new Map<
     string,
@@ -244,6 +333,7 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
       promise: Promise<unknown>;
     }
   >();
+  private callbackCount = 0;
 
   override getQueues(): ReadonlySet<PQueue> {
     return this.inMemoryQueues.allQueues;
@@ -254,14 +344,17 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
     insert?: (job: ParsedJob<ConversationQueueJobData>) => Promise<void>
   ): Promise<Job<ConversationQueueJobData>> {
     const { conversationId, type } = data;
-    strictAssert(
-      window.Signal.challengeHandler,
-      'conversationJobQueue.add: Missing challengeHandler!'
-    );
-    window.Signal.challengeHandler.maybeSolve({
-      conversationId,
-      reason: `conversationJobQueue.add(${conversationId}, ${type})`,
-    });
+
+    if (shouldSendShowCaptcha(data.type)) {
+      strictAssert(
+        window.Signal.challengeHandler,
+        'conversationJobQueue.add: Missing challengeHandler!'
+      );
+      window.Signal.challengeHandler.maybeSolve({
+        conversationId,
+        reason: `conversationJobQueue.add(${conversationId}, ${type})`,
+      });
+    }
 
     return super.add(data, insert);
   }
@@ -310,18 +403,239 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
       globalLogger.warn(
         `resolveVerificationWaiter: Missing waiter for conversation ${conversationId}.`
       );
+      this.unblockConversationRetries(conversationId);
     }
   }
 
+  private unblockConversationRetries(conversationId: string) {
+    const logId = `unblockConversationRetries/${conversationId}`;
+
+    const perConversationData = this.perConversationData.get(conversationId);
+    if (!perConversationData) {
+      return;
+    }
+
+    const { status, callback } = perConversationData;
+    if (status === RETRY_STATUS.BLOCKED) {
+      globalLogger.info(
+        `${logId}: Deleting previous BLOCKED state; had no jobs`
+      );
+      this.perConversationData.delete(conversationId);
+    } else if (status === RETRY_STATUS.BLOCKED_WITH_JOBS) {
+      globalLogger.info(
+        `${logId}: Moving previous WAITING state to UNBLOCKED, calling callback directly`
+      );
+      this.perConversationData.set(conversationId, {
+        ...perConversationData,
+        status: RETRY_STATUS.UNBLOCKED,
+        retryAt: undefined,
+      });
+      callback();
+    } else if (status === RETRY_STATUS.UNBLOCKED) {
+      globalLogger.warn(
+        `${logId}: We're still in UNBLOCKED state; calling callback directly`
+      );
+      callback();
+    } else {
+      throw missingCaseError(status);
+    }
+  }
+
+  private captureRetryAt(conversationId: string, retryAt: number | undefined) {
+    const logId = `captureRetryAt/${conversationId}`;
+
+    const newRetryAt = retryAt || Date.now() + MINUTE;
+    const perConversationData = this.perConversationData.get(conversationId);
+    if (!perConversationData) {
+      if (!retryAt) {
+        globalLogger.warn(
+          `${logId}: No existing data, using retryAt of ${newRetryAt}`
+        );
+      }
+      this.perConversationData.set(conversationId, {
+        status: RETRY_STATUS.BLOCKED,
+        retryAt: newRetryAt,
+        callback: undefined,
+        jobsNeedingRetry: undefined,
+      });
+
+      return;
+    }
+
+    const { status, retryAt: existingRetryAt } = perConversationData;
+    if (existingRetryAt && existingRetryAt >= newRetryAt) {
+      globalLogger.warn(
+        `${logId}: New newRetryAt ${newRetryAt} isn't after existing retryAt ${existingRetryAt}, dropping`
+      );
+      return;
+    }
+
+    if (
+      status === RETRY_STATUS.BLOCKED ||
+      status === RETRY_STATUS.BLOCKED_WITH_JOBS
+    ) {
+      globalLogger.info(
+        `${logId}: Updating to newRetryAt ${newRetryAt} from existing retryAt ${existingRetryAt}, status ${status}`
+      );
+      this.perConversationData.set(conversationId, {
+        ...perConversationData,
+        retryAt: newRetryAt,
+      });
+    } else if (status === RETRY_STATUS.UNBLOCKED) {
+      globalLogger.info(
+        `${logId}: Updating to newRetryAt ${newRetryAt} from previous UNBLOCKED status`
+      );
+      this.perConversationData.set(conversationId, {
+        ...perConversationData,
+        status: RETRY_STATUS.BLOCKED_WITH_JOBS,
+        retryAt: newRetryAt,
+      });
+    } else {
+      throw missingCaseError(status);
+    }
+  }
+
+  override async retryJobOnQueueIdle({
+    job,
+    storedJob,
+    logger,
+  }: {
+    job: Readonly<ParsedJob<ConversationQueueJobData>>;
+    storedJob: Readonly<StoredJob>;
+    logger: LoggerType;
+  }): Promise<boolean> {
+    const { conversationId } = job.data;
+    const logId = `retryJobOnQueueIdle/${conversationId}/${job.id}`;
+    const perConversationData = this.perConversationData.get(conversationId);
+
+    if (!perConversationData) {
+      logger.warn(`${logId}: no data for conversation; using default retryAt`);
+    } else {
+      logger.warn(
+        `${logId}: adding to existing data with status ${perConversationData.status}`
+      );
+    }
+
+    const { status, retryAt, jobsNeedingRetry, callback } =
+      perConversationData || {
+        status: RETRY_STATUS.BLOCKED,
+        retryAt: Date.now() + MINUTE,
+      };
+
+    const newJobsNeedingRetry = (jobsNeedingRetry || []).concat([storedJob]);
+    logger.info(
+      `${logId}: job added to retry queue with status ${status}; ${newJobsNeedingRetry.length} items now in queue`
+    );
+
+    const newCallback =
+      callback || this.createRetryCallback(conversationId, job.id);
+
+    if (
+      status === RETRY_STATUS.BLOCKED ||
+      status === RETRY_STATUS.BLOCKED_WITH_JOBS
+    ) {
+      this.perConversationData.set(conversationId, {
+        status: RETRY_STATUS.BLOCKED_WITH_JOBS,
+        retryAt,
+        jobsNeedingRetry: newJobsNeedingRetry,
+        callback: newCallback,
+      });
+    } else {
+      this.perConversationData.set(conversationId, {
+        status: RETRY_STATUS.UNBLOCKED,
+        retryAt,
+        jobsNeedingRetry: newJobsNeedingRetry,
+        callback: newCallback,
+      });
+    }
+
+    if (newCallback !== callback) {
+      const queue = this.getInMemoryQueue(job);
+      drop(
+        // eslint-disable-next-line more/no-then
+        queue.onIdle().then(() => {
+          globalLogger.info(`${logId}: Running callback due to queue.onIdle`);
+          newCallback();
+        })
+      );
+    }
+
+    return true;
+  }
+
+  private createRetryCallback(conversationId: string, jobId: string) {
+    this.callbackCount += 1;
+    const id = this.callbackCount;
+
+    globalLogger.info(
+      `createRetryCallback/${conversationId}/${id}: callback created for job ${jobId}`
+    );
+
+    return () => {
+      const logId = `retryCallback/${conversationId}/${id}`;
+
+      const perConversationData = this.perConversationData.get(conversationId);
+      if (!perConversationData) {
+        globalLogger.warn(`${logId}: no perConversationData, returning early.`);
+        return;
+      }
+
+      const { status, retryAt } = perConversationData;
+      if (status === RETRY_STATUS.BLOCKED) {
+        globalLogger.warn(
+          `${logId}: Still in blocked state, no jobs to retry. Clearing perConversationData.`
+        );
+        this.perConversationData.delete(conversationId);
+        return;
+      }
+
+      const { callback, jobsNeedingRetry, retryAtTimeout } =
+        perConversationData;
+
+      if (retryAtTimeout) {
+        clearTimeoutIfNecessary(retryAtTimeout);
+      }
+
+      if (!retryAt || isInPast(retryAt)) {
+        globalLogger.info(
+          `${logId}: retryAt is ${retryAt}; queueing ${jobsNeedingRetry?.length} jobs needing retry`
+        );
+
+        // We're starting to retry jobs; remove the challenge handler
+        drop(window.Signal.challengeHandler?.unregister(conversationId, logId));
+
+        jobsNeedingRetry?.forEach(job => {
+          drop(this.enqueueStoredJob(job));
+        });
+        this.perConversationData.delete(conversationId);
+        return;
+      }
+
+      const timeLeft = retryAt - Date.now();
+      globalLogger.info(
+        `${logId}: retryAt ${retryAt} is in the future, scheduling timeout for ${timeLeft}ms`
+      );
+
+      this.perConversationData.set(conversationId, {
+        ...perConversationData,
+        retryAtTimeout: setTimeout(() => {
+          globalLogger.info(`${logId}: Running callback due to timeout`);
+          callback();
+        }, timeLeft),
+      });
+    };
+  }
+
   protected async run(
     {
       data,
       timestamp,
     }: Readonly<{ data: ConversationQueueJobData; timestamp: number }>,
     { attempt, log }: Readonly<{ attempt: number; log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     const { type, conversationId } = data;
     const isFinalAttempt = attempt >= MAX_ATTEMPTS;
+    const perConversationData = this.perConversationData.get(conversationId);
 
     await window.ConversationController.load();
 
@@ -330,6 +644,11 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
       throw new Error(`Failed to find conversation ${conversationId}`);
     }
 
+    if (perConversationData?.retryAt && !shouldSendShowCaptcha(type)) {
+      // If we return this value, JobQueue will call retryJobOnQueueIdle for this job
+      return JOB_STATUS.NEEDS_RETRY;
+    }
+
     let timeRemaining: number;
     let shouldContinue: boolean;
     let count = 0;
@@ -350,10 +669,24 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
         break;
       }
 
-      if (window.Signal.challengeHandler?.isRegistered(conversationId)) {
+      const isChallengeRegistered =
+        window.Signal.challengeHandler?.isRegistered(conversationId);
+      if (!isChallengeRegistered) {
+        this.unblockConversationRetries(conversationId);
+      }
+
+      if (isChallengeRegistered && shouldSendShowCaptcha(type)) {
         if (this.isShuttingDown) {
           throw new Error("Shutting down, can't wait for captcha challenge.");
         }
+
+        window.Signal.challengeHandler?.maybeSolve({
+          conversationId,
+          reason:
+            'conversationJobQueue.run/addWaiter(' +
+            `${conversation.idForLogging()}, ${type}, ${timestamp})`,
+        });
+
         log.info(
           'captcha challenge is pending for this conversation; waiting at most 5m...'
         );
@@ -386,7 +719,7 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
           log.warn(
             "Cancelling profile share, we don't want to wait for pending verification."
           );
-          return;
+          return undefined;
         }
 
         if (this.isShuttingDown) {
@@ -498,10 +831,14 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
           );
         }
       }
+
+      return undefined;
     } catch (error: unknown) {
       const untrustedServiceIds: Array<ServiceIdString> = [];
 
-      const processError = (toProcess: unknown) => {
+      const processError = (
+        toProcess: unknown
+      ): undefined | typeof JOB_STATUS.NEEDS_RETRY => {
         if (toProcess instanceof OutgoingIdentityKeyError) {
           const failedConversation = window.ConversationController.getOrCreate(
             toProcess.identifier,
@@ -513,28 +850,47 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
             log.error(
               `failedConversation: Conversation ${failedConversation.idForLogging()} missing serviceId!`
             );
-            return;
+            return undefined;
           }
           untrustedServiceIds.push(serviceId);
         } else if (toProcess instanceof SendMessageChallengeError) {
-          void window.Signal.challengeHandler?.register(
-            {
-              conversationId,
-              createdAt: Date.now(),
-              retryAt: toProcess.retryAt,
-              token: toProcess.data?.token,
-              reason:
-                'conversationJobQueue.run(' +
-                `${conversation.idForLogging()}, ${type}, ${timestamp})`,
-            },
-            toProcess.data
+          const silent = !shouldSendShowCaptcha(type);
+
+          drop(
+            window.Signal.challengeHandler?.register(
+              {
+                conversationId,
+                createdAt: Date.now(),
+                retryAt: toProcess.retryAt,
+                token: toProcess.data?.token,
+                reason:
+                  'conversationJobQueue.run(' +
+                  `${conversation.idForLogging()}, ${type}, ${timestamp})`,
+                silent,
+              },
+              toProcess.data
+            )
           );
+
+          if (silent) {
+            this.captureRetryAt(conversationId, toProcess.retryAt);
+            return JOB_STATUS.NEEDS_RETRY;
+          }
         }
+        return undefined;
       };
 
-      processError(error);
+      const value = processError(error);
+      if (value) {
+        return value;
+      }
+
       if (error instanceof SendMessageProtoError) {
-        (error.errors || []).forEach(processError);
+        const values = (error.errors || []).map(processError);
+        const innerValue = values.find(item => Boolean(item));
+        if (innerValue) {
+          return innerValue;
+        }
       }
 
       if (untrustedServiceIds.length) {
@@ -542,14 +898,14 @@ export class ConversationJobQueue extends JobQueue<ConversationQueueJobData> {
           log.warn(
             `Cancelling profile share, since there were ${untrustedServiceIds.length} untrusted send targets.`
           );
-          return;
+          return undefined;
         }
 
         if (type === jobSet.Receipts) {
           log.warn(
             `Cancelling receipt send, since there were ${untrustedServiceIds.length} untrusted send targets.`
           );
-          return;
+          return undefined;
         }
 
         log.error(
diff --git a/ts/jobs/helpers/sendStory.ts b/ts/jobs/helpers/sendStory.ts
index 1db8c69d95..1d134582b1 100644
--- a/ts/jobs/helpers/sendStory.ts
+++ b/ts/jobs/helpers/sendStory.ts
@@ -444,6 +444,7 @@ export async function sendStory(
                 reason:
                   'conversationJobQueue.run(' +
                   `${conversation.idForLogging()}, story, ${timestamp}/${distributionId})`,
+                silent: false,
               },
               error.data
             );
diff --git a/ts/jobs/readSyncJobQueue.ts b/ts/jobs/readSyncJobQueue.ts
index 58bc34be13..ef6f347036 100644
--- a/ts/jobs/readSyncJobQueue.ts
+++ b/ts/jobs/readSyncJobQueue.ts
@@ -13,6 +13,7 @@ import {
 import { strictAssert } from '../util/assert';
 import { isRecord } from '../util/isRecord';
 
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 
@@ -31,7 +32,7 @@ export class ReadSyncJobQueue extends JobQueue<ReadSyncJobData> {
   protected async run(
     { data, timestamp }: Readonly<{ data: ReadSyncJobData; timestamp: number }>,
     { attempt, log }: Readonly<{ attempt: number; log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     await runSyncJob({
       attempt,
       log,
@@ -40,6 +41,8 @@ export class ReadSyncJobQueue extends JobQueue<ReadSyncJobData> {
       timestamp,
       type: SyncTypeList.Read,
     });
+
+    return undefined;
   }
 }
 
diff --git a/ts/jobs/removeStorageKeyJobQueue.ts b/ts/jobs/removeStorageKeyJobQueue.ts
index 8b3e86fc32..c911ef6a34 100644
--- a/ts/jobs/removeStorageKeyJobQueue.ts
+++ b/ts/jobs/removeStorageKeyJobQueue.ts
@@ -3,7 +3,9 @@
 
 import { z } from 'zod';
 
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
+
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 
 const removeStorageKeyJobDataSchema = z.object({
@@ -24,12 +26,16 @@ export class RemoveStorageKeyJobQueue extends JobQueue<RemoveStorageKeyJobData>
 
   protected async run({
     data,
-  }: Readonly<{ data: RemoveStorageKeyJobData }>): Promise<void> {
+  }: Readonly<{ data: RemoveStorageKeyJobData }>): Promise<
+    typeof JOB_STATUS.NEEDS_RETRY | undefined
+  > {
     await new Promise<void>(resolve => {
       window.storage.onready(resolve);
     });
 
     await window.storage.remove(data.key);
+
+    return undefined;
   }
 }
 
diff --git a/ts/jobs/reportSpamJobQueue.ts b/ts/jobs/reportSpamJobQueue.ts
index 24ba8811e3..6ab92b41a1 100644
--- a/ts/jobs/reportSpamJobQueue.ts
+++ b/ts/jobs/reportSpamJobQueue.ts
@@ -10,6 +10,7 @@ import type { LoggerType } from '../types/Logging';
 import { aciSchema } from '../types/ServiceId';
 import { map } from '../util/iterables';
 
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 import { parseIntWithFallback } from '../util/parseIntWithFallback';
@@ -49,7 +50,7 @@ export class ReportSpamJobQueue extends JobQueue<ReportSpamJobData> {
   protected async run(
     { data }: Readonly<{ data: ReportSpamJobData }>,
     { log }: Readonly<{ log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     const { aci: senderAci, token, serverGuids } = data;
 
     await new Promise<void>(resolve => {
@@ -58,7 +59,7 @@ export class ReportSpamJobQueue extends JobQueue<ReportSpamJobData> {
 
     if (!isDeviceLinked()) {
       log.info("reportSpamJobQueue: skipping this job because we're unlinked");
-      return;
+      return undefined;
     }
 
     await waitForOnline(window.navigator, window);
@@ -72,6 +73,8 @@ export class ReportSpamJobQueue extends JobQueue<ReportSpamJobData> {
           server.reportMessage({ senderAci, serverGuid, token })
         )
       );
+
+      return undefined;
     } catch (err: unknown) {
       if (!(err instanceof HTTPError)) {
         throw err;
@@ -88,7 +91,7 @@ export class ReportSpamJobQueue extends JobQueue<ReportSpamJobData> {
         log.info(
           'reportSpamJobQueue: server responded with 508. Giving up on this job'
         );
-        return;
+        return undefined;
       }
 
       if (isRetriable4xxStatus(code) || is5xxStatus(code)) {
@@ -106,7 +109,7 @@ export class ReportSpamJobQueue extends JobQueue<ReportSpamJobData> {
         log.error(
           `reportSpamJobQueue: server responded with ${code} status code. Giving up on this job`
         );
-        return;
+        return undefined;
       }
 
       throw err;
diff --git a/ts/jobs/singleProtoJobQueue.ts b/ts/jobs/singleProtoJobQueue.ts
index 6b5c540bfb..4208650e18 100644
--- a/ts/jobs/singleProtoJobQueue.ts
+++ b/ts/jobs/singleProtoJobQueue.ts
@@ -8,6 +8,7 @@ import * as Bytes from '../Bytes';
 import type { LoggerType } from '../types/Logging';
 import { exponentialBackoffMaxAttempts } from '../util/exponentialBackoff';
 import type { ParsedJob } from './types';
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 import { DAY } from '../util/durations';
@@ -51,7 +52,7 @@ export class SingleProtoJobQueue extends JobQueue<SingleProtoJobData> {
       timestamp,
     }: Readonly<{ data: SingleProtoJobData; timestamp: number }>,
     { attempt, log }: Readonly<{ attempt: number; log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     const timeRemaining = timestamp + MAX_RETRY_TIME - Date.now();
     const isFinalAttempt = attempt >= MAX_ATTEMPTS;
 
@@ -62,7 +63,7 @@ export class SingleProtoJobQueue extends JobQueue<SingleProtoJobData> {
       skipWait: false,
     });
     if (!shouldContinue) {
-      return;
+      return undefined;
     }
 
     const {
@@ -87,19 +88,19 @@ export class SingleProtoJobQueue extends JobQueue<SingleProtoJobData> {
       log.info(
         `conversation ${conversation.idForLogging()} is not accepted; refusing to send`
       );
-      return;
+      return undefined;
     }
     if (isConversationUnregistered(conversation.attributes)) {
       log.info(
         `conversation ${conversation.idForLogging()} is unregistered; refusing to send`
       );
-      return;
+      return undefined;
     }
     if (conversation.isBlocked()) {
       log.info(
         `conversation ${conversation.idForLogging()} is blocked; refusing to send`
       );
-      return;
+      return undefined;
     }
 
     const proto = Proto.Content.decode(Bytes.fromBase64(protoBase64));
@@ -133,6 +134,8 @@ export class SingleProtoJobQueue extends JobQueue<SingleProtoJobData> {
         toThrow: error,
       });
     }
+
+    return undefined;
   }
 }
 
diff --git a/ts/jobs/viewOnceOpenJobQueue.ts b/ts/jobs/viewOnceOpenJobQueue.ts
index d90a5862c2..7eb1653acc 100644
--- a/ts/jobs/viewOnceOpenJobQueue.ts
+++ b/ts/jobs/viewOnceOpenJobQueue.ts
@@ -13,6 +13,7 @@ import {
 import { strictAssert } from '../util/assert';
 import { isRecord } from '../util/isRecord';
 
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 
@@ -34,7 +35,7 @@ export class ViewOnceOpenJobQueue extends JobQueue<ViewOnceOpenJobData> {
       timestamp,
     }: Readonly<{ data: ViewOnceOpenJobData; timestamp: number }>,
     { attempt, log }: Readonly<{ attempt: number; log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     await runSyncJob({
       attempt,
       log,
@@ -43,6 +44,8 @@ export class ViewOnceOpenJobQueue extends JobQueue<ViewOnceOpenJobData> {
       timestamp,
       type: SyncTypeList.ViewOnceOpen,
     });
+
+    return undefined;
   }
 }
 
diff --git a/ts/jobs/viewSyncJobQueue.ts b/ts/jobs/viewSyncJobQueue.ts
index 26ec9cdcf0..840607d5f8 100644
--- a/ts/jobs/viewSyncJobQueue.ts
+++ b/ts/jobs/viewSyncJobQueue.ts
@@ -13,6 +13,7 @@ import {
 import { strictAssert } from '../util/assert';
 import { isRecord } from '../util/isRecord';
 
+import type { JOB_STATUS } from './JobQueue';
 import { JobQueue } from './JobQueue';
 import { jobQueueDatabaseStore } from './JobQueueDatabaseStore';
 
@@ -31,7 +32,7 @@ export class ViewSyncJobQueue extends JobQueue<ViewSyncJobData> {
   protected async run(
     { data, timestamp }: Readonly<{ data: ViewSyncJobData; timestamp: number }>,
     { attempt, log }: Readonly<{ attempt: number; log: LoggerType }>
-  ): Promise<void> {
+  ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
     await runSyncJob({
       attempt,
       log,
@@ -40,6 +41,8 @@ export class ViewSyncJobQueue extends JobQueue<ViewSyncJobData> {
       timestamp,
       type: SyncTypeList.View,
     });
+
+    return undefined;
   }
 }
 
diff --git a/ts/test-both/challenge_test.ts b/ts/test-both/challenge_test.ts
index 93464bcad2..f7502c76ce 100644
--- a/ts/test-both/challenge_test.ts
+++ b/ts/test-both/challenge_test.ts
@@ -57,6 +57,7 @@ describe('ChallengeHandler', () => {
       retryAt: NOW + DEFAULT_RETRY_AFTER,
       createdAt: NOW - SECOND,
       reason: 'test',
+      silent: false,
       ...options,
     };
   };
@@ -185,7 +186,7 @@ describe('ChallengeHandler', () => {
     await createHandler();
 
     for (const challenge of challenges) {
-      await handler.unregister(challenge.conversationId);
+      await handler.unregister(challenge.conversationId, 'test');
     }
 
     for (const challenge of challenges) {
@@ -223,7 +224,7 @@ describe('ChallengeHandler', () => {
       autoSolve: true,
       expireAfter: -1,
     });
-    await handler.unregister(one.conversationId);
+    await handler.unregister(one.conversationId, 'test');
 
     challengeStatus = 'idle';
     await newHandler.load();
diff --git a/ts/test-mock/messaging/edit_test.ts b/ts/test-mock/messaging/edit_test.ts
index 5acd9511e2..485f60ed51 100644
--- a/ts/test-mock/messaging/edit_test.ts
+++ b/ts/test-mock/messaging/edit_test.ts
@@ -147,7 +147,7 @@ describe('editing', function (this: Mocha.Suite) {
         .locator(`.module-message__text >> "${initialMessageBody}"`)
         .waitFor();
 
-      debug('waiting for receipts for original message');
+      debug('waiting for outgoing receipts for original message');
       const receipts = await app.waitForReceipts();
       assert.strictEqual(receipts.type, ReceiptType.Read);
       assert.strictEqual(receipts.timestamps.length, 1);
diff --git a/ts/test-mock/rate-limit/viewed_test.ts b/ts/test-mock/rate-limit/viewed_test.ts
index 4db8b0d562..6e5af5e0d0 100644
--- a/ts/test-mock/rate-limit/viewed_test.ts
+++ b/ts/test-mock/rate-limit/viewed_test.ts
@@ -20,6 +20,7 @@ describe('challenge/receipts', function (this: Mocha.Suite) {
   let bootstrap: Bootstrap;
   let app: App;
   let contact: PrimaryDevice;
+  let contactB: PrimaryDevice;
 
   beforeEach(async () => {
     bootstrap = new Bootstrap({
@@ -34,6 +35,9 @@ describe('challenge/receipts', function (this: Mocha.Suite) {
     contact = await server.createPrimaryDevice({
       profileName: 'Jamie',
     });
+    contactB = await server.createPrimaryDevice({
+      profileName: 'Kim',
+    });
 
     let state = StorageState.getEmpty();
 
@@ -55,13 +59,28 @@ describe('challenge/receipts', function (this: Mocha.Suite) {
       },
       ServiceIdKind.PNI
     );
+    state = state.addContact(
+      contactB,
+      {
+        whitelisted: true,
+        serviceE164: contactB.device.number,
+        identityKey: contactB.getPublicKey(ServiceIdKind.PNI).serialize(),
+        pni: toUntaggedPni(contactB.device.pni),
+        givenName: 'Kim',
+      },
+      ServiceIdKind.PNI
+    );
 
     // Just to make PNI Contact visible in the left pane
     state = state.pin(contact, ServiceIdKind.PNI);
+    state = state.pin(contactB, ServiceIdKind.PNI);
 
     const ourKey = await desktop.popSingleUseKey();
     await contact.addSingleUseKey(desktop, ourKey);
 
+    const ourKeyB = await desktop.popSingleUseKey();
+    await contactB.addSingleUseKey(desktop, ourKeyB);
+
     await phone.setStorageState(state);
   });
 
@@ -95,11 +114,18 @@ describe('challenge/receipts', function (this: Mocha.Suite) {
       .locator(`[data-testid="${contact.toContact().aci}"]`)
       .click();
 
-    debug('Accept conversation from contact');
+    debug('Accept conversation from contact - does not trigger captcha!');
     await conversationStack
       .locator('.module-message-request-actions button >> "Accept"')
       .click();
 
+    debug('Sending a message back to user - will trigger captcha!');
+    {
+      const input = await app.waitForEnabledComposer();
+      await input.type('Hi, good to hear from you!');
+      await input.press('Enter');
+    }
+
     debug('Waiting for challenge');
     const request = await app.waitForChallenge();
 
@@ -114,14 +140,122 @@ describe('challenge/receipts', function (this: Mocha.Suite) {
       target: contact.device.aci,
     });
 
-    debug(`rate limited requests: ${requests}`);
-    assert.strictEqual(requests, 1);
+    debug(`Rate-limited requests: ${requests}`);
+    assert.strictEqual(requests, 1, 'rate limit requests');
 
-    debug('Waiting for receipts');
+    debug('Waiting for outgoing read receipt');
     const receipts = await app.waitForReceipts();
 
     assert.strictEqual(receipts.type, ReceiptType.Read);
-    assert.strictEqual(receipts.timestamps.length, 1);
+    assert.strictEqual(receipts.timestamps.length, 1, 'receipts');
     assert.strictEqual(receipts.timestamps[0], timestamp);
   });
+
+  it('should send non-bubble in ConvoA when ConvoB completes challenge', async () => {
+    const { server, desktop } = bootstrap;
+
+    debug(
+      `Rate limiting (desktop: ${desktop.aci}) -> (ContactA: ${contact.device.aci})`
+    );
+    server.rateLimit({ source: desktop.aci, target: contact.device.aci });
+    debug(
+      `Rate limiting (desktop: ${desktop.aci}) -> (ContactB: ${contactB.device.aci})`
+    );
+    server.rateLimit({ source: desktop.aci, target: contactB.device.aci });
+
+    const window = await app.getWindow();
+    const leftPane = window.locator('#LeftPane');
+    const conversationStack = window.locator('.Inbox__conversation-stack');
+
+    debug('Sending a message from ContactA');
+    const timestampA = bootstrap.getTimestamp();
+    await contact.sendText(desktop, 'Hello there!', {
+      timestamp: timestampA,
+    });
+
+    debug(`Opening conversation with ContactA (${contact.toContact().aci})`);
+    await leftPane
+      .locator(`[data-testid="${contact.toContact().aci}"]`)
+      .click();
+
+    debug('Accept conversation from ContactA - does not trigger captcha!');
+    await conversationStack
+      .locator('.module-message-request-actions button >> "Accept"')
+      .click();
+
+    debug('Sending a message from ContactB');
+    const timestampB = bootstrap.getTimestamp();
+    await contactB.sendText(desktop, 'Hey there!', {
+      timestamp: timestampB,
+    });
+
+    debug(`Opening conversation with ContactB (${contact.toContact().aci})`);
+    await leftPane
+      .locator(`[data-testid="${contactB.toContact().aci}"]`)
+      .click();
+
+    debug('Accept conversation from ContactB - does not trigger captcha!');
+    await conversationStack
+      .locator('.module-message-request-actions button >> "Accept"')
+      .click();
+
+    debug('Sending a message back to ContactB - will trigger captcha!');
+    {
+      const input = await app.waitForEnabledComposer();
+      await input.type('Hi, good to hear from you!');
+      await input.press('Enter');
+    }
+
+    debug('Waiting for challenge');
+    const request = await app.waitForChallenge();
+
+    debug('Solving challenge');
+    await app.solveChallenge({
+      seq: request.seq,
+      data: { captcha: 'anything' },
+    });
+
+    const requestsA = server.stopRateLimiting({
+      source: desktop.aci,
+      target: contact.device.aci,
+    });
+    const requestsB = server.stopRateLimiting({
+      source: desktop.aci,
+      target: contactB.device.aci,
+    });
+
+    debug(`Rate-limited requests to A: ${requestsA}`);
+    assert.strictEqual(requestsA, 1, 'rate limit requests');
+
+    debug(`Rate-limited requests to B: ${requestsA}`);
+    assert.strictEqual(requestsB, 1, 'rate limit requests');
+
+    debug('Waiting for outgoing read receipt #1');
+    const receipts1 = await app.waitForReceipts();
+
+    assert.strictEqual(receipts1.type, ReceiptType.Read);
+    assert.strictEqual(receipts1.timestamps.length, 1, 'receipts');
+    if (
+      !receipts1.timestamps.includes(timestampA) &&
+      !receipts1.timestamps.includes(timestampB)
+    ) {
+      throw new Error(
+        'receipts1: Failed to find both timestampA and timestampB'
+      );
+    }
+
+    debug('Waiting for outgoing read receipt #2');
+    const receipts2 = await app.waitForReceipts();
+
+    assert.strictEqual(receipts2.type, ReceiptType.Read);
+    assert.strictEqual(receipts2.timestamps.length, 1, 'receipts');
+    if (
+      !receipts2.timestamps.includes(timestampA) &&
+      !receipts2.timestamps.includes(timestampB)
+    ) {
+      throw new Error(
+        'receipts2: Failed to find both timestampA and timestampB'
+      );
+    }
+  });
 });
diff --git a/ts/test-node/jobs/JobQueue_test.ts b/ts/test-node/jobs/JobQueue_test.ts
index b35113a01e..18461c9144 100644
--- a/ts/test-node/jobs/JobQueue_test.ts
+++ b/ts/test-node/jobs/JobQueue_test.ts
@@ -16,6 +16,7 @@ import { missingCaseError } from '../../util/missingCaseError';
 import { drop } from '../../util/drop';
 import type { LoggerType } from '../../types/Logging';
 
+import type { JOB_STATUS } from '../../jobs/JobQueue';
 import { JobQueue } from '../../jobs/JobQueue';
 import type { ParsedJob, StoredJob, JobQueueStore } from '../../jobs/types';
 import { sleep } from '../../util/sleep';
@@ -38,8 +39,13 @@ describe('JobQueue', () => {
           return testJobSchema.parse(data);
         }
 
-        async run({ data }: ParsedJob<TestJobData>): Promise<void> {
+        async run({
+          data,
+        }: ParsedJob<TestJobData>): Promise<
+          typeof JOB_STATUS.NEEDS_RETRY | undefined
+        > {
           results.add(data.a + data.b);
+          return undefined;
         }
       }
 
@@ -83,13 +89,15 @@ describe('JobQueue', () => {
           return z.number().parse(data);
         }
 
-        async run(): Promise<void> {
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           try {
             updateActiveJobCount(1);
             await sleep(1);
           } finally {
             updateActiveJobCount(-1);
           }
+
+          return undefined;
         }
       }
 
@@ -142,8 +150,8 @@ describe('JobQueue', () => {
           return testQueue;
         }
 
-        run(): Promise<void> {
-          return Promise.resolve();
+        run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -175,8 +183,8 @@ describe('JobQueue', () => {
           return z.string().parse(data);
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -243,8 +251,8 @@ describe('JobQueue', () => {
           return z.string().parse(data);
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -291,7 +299,11 @@ describe('JobQueue', () => {
           return data;
         }
 
-        async run({ data }: ParsedJob<TestJobData>): Promise<void> {
+        async run({
+          data,
+        }: ParsedJob<TestJobData>): Promise<
+          typeof JOB_STATUS.NEEDS_RETRY | undefined
+        > {
           switch (data) {
             case 'foo':
               fooAttempts += 1;
@@ -308,6 +320,7 @@ describe('JobQueue', () => {
             default:
               throw missingCaseError(data);
           }
+          return undefined;
         }
       }
 
@@ -360,7 +373,7 @@ describe('JobQueue', () => {
         async run(
           _: unknown,
           { attempt }: Readonly<{ attempt: number }>
-        ): Promise<void> {
+        ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           attempts.push(attempt);
           throw new Error('this job always fails');
         }
@@ -405,10 +418,12 @@ describe('JobQueue', () => {
         async run(
           _: unknown,
           { log }: Readonly<{ log: LoggerType }>
-        ): Promise<void> {
+        ): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           log.info(uniqueString);
           log.warn(uniqueString);
           log.error(uniqueString);
+
+          return undefined;
         }
       }
 
@@ -450,8 +465,8 @@ describe('JobQueue', () => {
           throw new Error('uh oh');
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -494,7 +509,9 @@ describe('JobQueue', () => {
           throw new Error('invalid data!');
         }
 
-        run(job: { data: string }): Promise<void> {
+        run(job: {
+          data: string;
+        }): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           return run(job);
         }
       }
@@ -528,8 +545,8 @@ describe('JobQueue', () => {
           throw new Error('invalid data!');
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -562,8 +579,8 @@ describe('JobQueue', () => {
           return undefined;
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -596,8 +613,9 @@ describe('JobQueue', () => {
           return data;
         }
 
-        async run(): Promise<void> {
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           events.push('running');
+          return undefined;
         }
       }
 
@@ -629,8 +647,8 @@ describe('JobQueue', () => {
           return undefined;
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -670,7 +688,7 @@ describe('JobQueue', () => {
           return undefined;
         }
 
-        async run(): Promise<void> {
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
           events.push('running');
           throw new Error('uh oh');
         }
@@ -751,8 +769,13 @@ describe('JobQueue', () => {
           return z.number().parse(data);
         }
 
-        async run({ data }: Readonly<{ data: number }>): Promise<void> {
+        async run({
+          data,
+        }: Readonly<{ data: number }>): Promise<
+          typeof JOB_STATUS.NEEDS_RETRY | undefined
+        > {
           eventEmitter.emit('run', data);
+          return undefined;
         }
       }
 
@@ -794,8 +817,8 @@ describe('JobQueue', () => {
           return data;
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }
 
@@ -827,8 +850,8 @@ describe('JobQueue', () => {
           return undefined;
         }
 
-        async run(): Promise<void> {
-          return Promise.resolve();
+        async run(): Promise<typeof JOB_STATUS.NEEDS_RETRY | undefined> {
+          return Promise.resolve(undefined);
         }
       }