diff --git a/packages/bot-runner/lib/command-runner.ts b/packages/bot-runner/lib/command-runner.ts
index c43ec5a01a0..b52b2ef5e13 100644
--- a/packages/bot-runner/lib/command-runner.ts
+++ b/packages/bot-runner/lib/command-runner.ts
@@ -51,6 +51,9 @@ export function makeEnqueueRunCommand(
         runAs,
         command,
         commandInput,
+        // Interactive command: a command error is a normal result to hand back
+        // to the user, not a job failure.
+        alertOnError: false,
       },
       queuePublisher,
       dbAdapter,
diff --git a/packages/bot-runner/tests/bot-runner-test.ts b/packages/bot-runner/tests/bot-runner-test.ts
index 164c327a5c0..5f2a1f2b0ec 100644
--- a/packages/bot-runner/tests/bot-runner-test.ts
+++ b/packages/bot-runner/tests/bot-runner-test.ts
@@ -229,6 +229,7 @@ module('timeline handler', () => {
           runAs: '@alice:localhost',
           command: '@cardstack/boxel-host/commands/show-card/default',
           commandInput: {},
+          alertOnError: false,
         },
       },
       'enqueues expected command payload',
diff --git a/packages/bot-runner/tests/command-runner-test.ts b/packages/bot-runner/tests/command-runner-test.ts
index cd7f55a310c..96304201fc7 100644
--- a/packages/bot-runner/tests/command-runner-test.ts
+++ b/packages/bot-runner/tests/command-runner-test.ts
@@ -133,6 +133,7 @@ module('command runner', () => {
           runAs: '@alice:localhost',
           command: '@cardstack/boxel-host/commands/show-card/default',
           commandInput: { cardId: 'http://localhost:4201/test/Person/1' },
+          alertOnError: false,
         },
       },
       'publishes expected run-command payload',
@@ -337,6 +338,7 @@ module('command runner', () => {
             },
           ],
         },
+        alertOnError: false,
       },
       'enqueues PR card creation in submissions realm',
     );
@@ -359,6 +361,7 @@ module('command runner', () => {
             },
           },
         },
+        alertOnError: false,
       },
       'persists prCard link on the workflow card immediately after create-pr-card succeeds (so retry on later failure can reuse the existing PrCard)',
     );
@@ -385,6 +388,7 @@ module('command runner', () => {
             },
           },
         },
+        alertOnError: false,
       },
       'clears prior error attributes on the workflow card after the GitHub PR succeeds, re-asserting the prCard link to survive any stale-fetch race',
     );
diff --git a/packages/realm-server/handlers/handle-run-command.ts b/packages/realm-server/handlers/handle-run-command.ts
index 6b9d594a94b..7badcc042b6 100644
--- a/packages/realm-server/handlers/handle-run-command.ts
+++ b/packages/realm-server/handlers/handle-run-command.ts
@@ -82,6 +82,9 @@ export default function handleRunCommand({
           runAs: userId,
           command,
           commandInput: commandInput ?? null,
+          // Interactive endpoint: a command error is returned to the caller,
+          // not treated as a job failure.
+          alertOnError: false,
         },
         queue,
         dbAdapter,
diff --git a/packages/realm-server/handlers/handle-webhook-receiver.ts b/packages/realm-server/handlers/handle-webhook-receiver.ts
index 7699836e7ff..8a7063d5189 100644
--- a/packages/realm-server/handlers/handle-webhook-receiver.ts
+++ b/packages/realm-server/handlers/handle-webhook-receiver.ts
@@ -157,6 +157,9 @@ export default function handleWebhookReceiverRequest({
             runAs,
             command: commandURL,
             commandInput,
+            // Webhook-triggered command: an error is handled per-command by the
+            // caller, not surfaced as a job failure.
+            alertOnError: false,
           },
           queue,
           dbAdapter,
diff --git a/packages/realm-server/scripts/sync-openrouter-models.ts b/packages/realm-server/scripts/sync-openrouter-models.ts
index c29b510b51e..dde72367f96 100644
--- a/packages/realm-server/scripts/sync-openrouter-models.ts
+++ b/packages/realm-server/scripts/sync-openrouter-models.ts
@@ -55,6 +55,10 @@ export async function enqueueSyncOpenRouterModels({
     runAs: REALM_USERNAME,
     command: COMMAND_SPECIFIER,
     commandInput: { realmIdentifier: realmURL },
+    // System-initiated cron job: a command error must reject the job (Sentry +
+    // rejected status) rather than resolve silently, so a broken sync surfaces
+    // instead of quietly leaving the model realm stale.
+    alertOnError: true,
   };
 
   try {
diff --git a/packages/realm-server/tests/run-command-task-test.ts b/packages/realm-server/tests/run-command-task-test.ts
index 16c1117eb66..816273db587 100644
--- a/packages/realm-server/tests/run-command-task-test.ts
+++ b/packages/realm-server/tests/run-command-task-test.ts
@@ -21,5 +21,13 @@ module(basename(import.meta.filename), function () {
     test('passes scoped command through unchanged', async function (assert) {
       await runSharedTest(runCommandTaskTests, assert, {});
     });
+
+    test('throws when alertOnError is set and the command returns an error', async function (assert) {
+      await runSharedTest(runCommandTaskTests, assert, {});
+    });
+
+    test('throws when alertOnError is set and runAs lacks permissions', async function (assert) {
+      await runSharedTest(runCommandTaskTests, assert, {});
+    });
   });
 });
diff --git a/packages/runtime-common/tasks/run-command.ts b/packages/runtime-common/tasks/run-command.ts
index d664480c933..8d37243f7f6 100644
--- a/packages/runtime-common/tasks/run-command.ts
+++ b/packages/runtime-common/tasks/run-command.ts
@@ -17,6 +17,15 @@ export interface RunCommandArgs extends JSONTypes.Object {
   runAs: string;
   command: string;
   commandInput: JSONTypes.Object | null;
+  // When true, a command that finishes with an error status makes the job
+  // throw rather than resolving with the error in-band. The queue then marks
+  // the job rejected and reports it to Sentry. Interactive callers (bot-runner,
+  // the run-command HTTP endpoint, webhooks) pass false so a command error
+  // stays a normal result to hand back to the user. System-initiated jobs
+  // (cron syncs) pass true so a persistently failing job is never silent.
+  // Required (not optional) so the args object satisfies JSONTypes.Object's
+  // JSON-shape index signature, which excludes `undefined`.
+  alertOnError: boolean;
 }
 
 // No coalesce handler: each run-command enqueue is a distinct invocation
@@ -35,8 +44,27 @@ const runCommand: Task<RunCommandArgs, RunCommandResponse> = ({
   matrixURL,
 }) =>
   async function (args) {
-    let { jobInfo, realmURL, realmUsername, runAs, command, commandInput } =
-      args;
+    let {
+      jobInfo,
+      realmURL,
+      realmUsername,
+      runAs,
+      command,
+      commandInput,
+      alertOnError,
+    } = args;
+    // Turn an error outcome into either a thrown failure (so the queue rejects
+    // the job and reports it to Sentry) or an in-band error result, depending
+    // on whether the caller asked to be alerted.
+    let fail = (message: string): RunCommandResponse => {
+      if (alertOnError) {
+        throw new Error(message);
+      }
+      return {
+        status: 'error',
+        error: message,
+      };
+    };
     log.debug(
       `${jobIdentity(jobInfo)} starting run-command for job: ${JSON.stringify({
         realmURL,
@@ -58,10 +86,7 @@ const runCommand: Task<RunCommandArgs, RunCommandResponse> = ({
       let message = `${jobIdentity(jobInfo)} ${runAs} does not have permissions in ${normalizedRealmURL}`;
       log.error(message);
       reportStatus(jobInfo, 'finish');
-      return {
-        status: 'error',
-        error: message,
-      };
+      return fail(message);
     }
 
     // Include JWTs for all realms the user has access to
@@ -82,10 +107,7 @@ const runCommand: Task<RunCommandArgs, RunCommandResponse> = ({
       let message = `${jobIdentity(jobInfo)} invalid command specifier`;
       log.error(message, { command, realmURL: normalizedRealmURL });
       reportStatus(jobInfo, 'finish');
-      return {
-        status: 'error',
-        error: message,
-      };
+      return fail(message);
     }
 
     let augmentedCommandInput = commandInput
@@ -101,6 +123,13 @@ const runCommand: Task<RunCommandArgs, RunCommandResponse> = ({
     });
 
     reportStatus(jobInfo, 'finish');
+
+    if (alertOnError && result.status === 'error') {
+      let message = `${jobIdentity(jobInfo)} command ${command} failed in ${normalizedRealmURL}: ${result.error ?? 'unknown error'}`;
+      log.error(message);
+      throw new Error(message);
+    }
+
     return result;
   };
 
diff --git a/packages/runtime-common/tests/run-command-task-shared-tests.ts b/packages/runtime-common/tests/run-command-task-shared-tests.ts
index 455535921e5..7f2f7ed0099 100644
--- a/packages/runtime-common/tests/run-command-task-shared-tests.ts
+++ b/packages/runtime-common/tests/run-command-task-shared-tests.ts
@@ -109,6 +109,7 @@ const tests = Object.freeze({
       runAs: '@alice:localhost',
       command: '@cardstack/boxel-host/commands/show-card/default',
       commandInput: {},
+      alertOnError: false,
       jobInfo: { id: 1 } as any,
     });
 
@@ -150,6 +151,7 @@ const tests = Object.freeze({
       runAs: '@alice:localhost',
       command: '   ',
       commandInput: {},
+      alertOnError: false,
       jobInfo: { id: 2 } as any,
     });
 
@@ -201,6 +203,7 @@ const tests = Object.freeze({
       runAs: '@alice',
       command: 'http://localhost:4200/commands/create-submission',
       commandInput: null,
+      alertOnError: false,
       jobInfo: { id: 3 } as any,
     });
 
@@ -255,6 +258,7 @@ const tests = Object.freeze({
       runAs: '@alice:localhost',
       command: '@cardstack/catalog/commands/create-submission/default',
       commandInput: { listingId: 'http://localhost:4201/catalog/AppListing/1' },
+      alertOnError: false,
       jobInfo: { id: 4 } as any,
     });
 
@@ -267,6 +271,64 @@ const tests = Object.freeze({
       accessibleRealms: ['http://localhost:4201/experiments/'],
     });
   },
+
+  'throws when alertOnError is set and the command returns an error': async (
+    assert,
+  ) => {
+    assert.expect(2);
+    let task = runCommand(
+      makeTaskArgs({
+        dbRows: [
+          {
+            username: '@alice:localhost',
+            realm_url: 'http://localhost:4201/experiments/',
+            read: true,
+            write: true,
+            realm_owner: false,
+          },
+        ],
+        prerenderResult: { status: 'error', error: 'boom' },
+      }),
+    );
+
+    // A thrown task lets the queue mark the job rejected and report it to
+    // Sentry, instead of resolving with the error swallowed in-band.
+    await assert.rejects(
+      task({
+        realmURL: 'http://localhost:4201/experiments/',
+        realmUsername: '@alice:localhost',
+        runAs: '@alice:localhost',
+        command: '@cardstack/catalog/commands/sync-openrouter-models/default',
+        commandInput: {},
+        alertOnError: true,
+        jobInfo: { id: 5 } as any,
+      }),
+      /boom/,
+      'rejects with the command error when alertOnError is set',
+    );
+    assert.true(true, 'did not resolve in-band');
+  },
+
+  'throws when alertOnError is set and runAs lacks permissions': async (
+    assert,
+  ) => {
+    assert.expect(1);
+    let task = runCommand(makeTaskArgs({ dbRows: [] }));
+
+    await assert.rejects(
+      task({
+        realmURL: 'http://localhost:4201/experiments/',
+        realmUsername: '@alice:localhost',
+        runAs: '@alice:localhost',
+        command: '@cardstack/catalog/commands/sync-openrouter-models/default',
+        commandInput: {},
+        alertOnError: true,
+        jobInfo: { id: 6 } as any,
+      }),
+      /does not have permissions in/,
+      'a permission failure rejects the job when alertOnError is set',
+    );
+  },
 } as SharedTests<{}>);
 
 export default tests;