diff --git a/ts/test-electron/util/sendToGroup_test.ts b/ts/test-electron/util/sendToGroup_test.ts
index 42b7c80f1..68523430b 100644
--- a/ts/test-electron/util/sendToGroup_test.ts
+++ b/ts/test-electron/util/sendToGroup_test.ts
@@ -3,9 +3,24 @@
 
 import { assert } from 'chai';
 
-import { _analyzeSenderKeyDevices, _waitForAll } from '../../util/sendToGroup';
+import {
+  _analyzeSenderKeyDevices,
+  _waitForAll,
+  _shouldFailSend,
+} from '../../util/sendToGroup';
 
 import type { DeviceType } from '../../textsecure/Types.d';
+import {
+  ConnectTimeoutError,
+  HTTPError,
+  MessageError,
+  OutgoingIdentityKeyError,
+  OutgoingMessageError,
+  SendMessageChallengeError,
+  SendMessageNetworkError,
+  SendMessageProtoError,
+  UnregisteredUserError,
+} from '../../textsecure/Errors';
 
 describe('sendToGroup', () => {
   describe('#_analyzeSenderKeyDevices', () => {
@@ -135,7 +150,7 @@ describe('sendToGroup', () => {
   });
 
   describe('#_waitForAll', () => {
-    it('returns nothing if new and previous lists are the same', async () => {
+    it('returns result of provided tasks', async () => {
       const task1 = () => Promise.resolve(1);
       const task2 = () => Promise.resolve(2);
       const task3 = () => Promise.resolve(3);
@@ -148,4 +163,158 @@ describe('sendToGroup', () => {
       assert.deepEqual(result, [1, 2, 3]);
     });
   });
+
+  describe('#_shouldFailSend', () => {
+    it('returns false for a generic error', async () => {
+      const error = new Error('generic');
+      assert.isFalse(_shouldFailSend(error, 'testing generic'));
+    });
+
+    it("returns true for any error with 'untrusted' identity", async () => {
+      const error = new Error('This was an untrusted identity.');
+      assert.isTrue(_shouldFailSend(error, 'logId'));
+    });
+
+    it('returns true for certain types of error subclasses', async () => {
+      assert.isTrue(
+        _shouldFailSend(
+          new OutgoingIdentityKeyError(
+            'something',
+            new Uint8Array(),
+            200,
+            new Uint8Array()
+          ),
+          'testing OutgoingIdentityKeyError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new UnregisteredUserError(
+            'something',
+            new HTTPError('something', {
+              code: 400,
+              headers: {},
+            })
+          ),
+          'testing UnregisteredUserError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new ConnectTimeoutError('something'),
+          'testing ConnectTimeoutError'
+        )
+      );
+    });
+
+    it('returns false for unspecified error codes', () => {
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      const error: any = new Error('generic');
+
+      error.code = 422;
+      assert.isFalse(_shouldFailSend(error, 'testing generic 422'));
+
+      error.code = 204;
+      assert.isFalse(_shouldFailSend(error, 'testing generic 204'));
+    });
+
+    it('returns true for a specified error codes', () => {
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      const error: any = new Error('generic');
+      error.code = 401;
+
+      assert.isTrue(_shouldFailSend(error, 'testing generic'));
+      assert.isTrue(
+        _shouldFailSend(
+          new HTTPError('something', {
+            code: 404,
+            headers: {},
+          }),
+          'testing HTTPError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new OutgoingMessageError(
+            'something',
+            null,
+            null,
+            new HTTPError('something', {
+              code: 413,
+              headers: {},
+            })
+          ),
+          'testing OutgoingMessageError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new SendMessageNetworkError(
+            'something',
+            null,
+            new HTTPError('something', {
+              code: 428,
+              headers: {},
+            })
+          ),
+          'testing SendMessageNetworkError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new SendMessageChallengeError(
+            'something',
+            new HTTPError('something', {
+              code: 500,
+              headers: {},
+            })
+          ),
+          'testing SendMessageChallengeError'
+        )
+      );
+      assert.isTrue(
+        _shouldFailSend(
+          new MessageError(
+            'something',
+            new HTTPError('something', {
+              code: 508,
+              headers: {},
+            })
+          ),
+          'testing MessageError'
+        )
+      );
+    });
+    it('returns true for errors inside of SendMessageProtoError', () => {
+      assert.isTrue(
+        _shouldFailSend(
+          new SendMessageProtoError({}),
+          'testing missing errors list'
+        )
+      );
+
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      const error: any = new Error('generic');
+      error.code = 401;
+
+      assert.isTrue(
+        _shouldFailSend(
+          new SendMessageProtoError({ errors: [error] }),
+          'testing one error with code'
+        )
+      );
+
+      assert.isTrue(
+        _shouldFailSend(
+          new SendMessageProtoError({
+            errors: [
+              new Error('something'),
+              new ConnectTimeoutError('something'),
+            ],
+          }),
+          'testing ConnectTimeoutError'
+        )
+      );
+    });
+  });
 });
diff --git a/ts/util/sendToGroup.ts b/ts/util/sendToGroup.ts
index dec1224bd..ae2ef0cd7 100644
--- a/ts/util/sendToGroup.ts
+++ b/ts/util/sendToGroup.ts
@@ -23,12 +23,19 @@ import { Address } from '../types/Address';
 import { QualifiedAddress } from '../types/QualifiedAddress';
 import { UUID } from '../types/UUID';
 import { isEnabled } from '../RemoteConfig';
+import { isRecord } from './isRecord';
 
 import { isOlderThan } from './timestamp';
 import type {
   GroupSendOptionsType,
   SendOptionsType,
 } from '../textsecure/SendMessage';
+import {
+  ConnectTimeoutError,
+  OutgoingIdentityKeyError,
+  SendMessageProtoError,
+  UnregisteredUserError,
+} from '../textsecure/Errors';
 import type { HTTPError } from '../textsecure/Errors';
 import { IdentityKeys, SenderKeys, Sessions } from '../LibSignalStores';
 import type { ConversationModel } from '../models/conversations';
@@ -188,10 +195,7 @@ export async function sendContentMessageToGroup({
         throw error;
       }
 
-      if (error.name.includes('untrusted identity')) {
-        log.error(
-          `sendToGroup/${logId}: Failed with 'untrusted identity' error, re-throwing`
-        );
+      if (_shouldFailSend(error, logId)) {
         throw error;
       }
 
@@ -653,6 +657,86 @@ export async function sendToGroupViaSenderKey(options: {
 
 // Utility Methods
 
+export function _shouldFailSend(error: unknown, logId: string): boolean {
+  const logError = (message: string) => {
+    log.error(`_shouldFailSend/${logId}: ${message}`);
+  };
+
+  if (error instanceof Error && error.message.includes('untrusted identity')) {
+    logError("'untrusted identity' error, failing.");
+    return true;
+  }
+
+  if (error instanceof OutgoingIdentityKeyError) {
+    logError('OutgoingIdentityKeyError error, failing.');
+    return true;
+  }
+
+  if (error instanceof UnregisteredUserError) {
+    logError('UnregisteredUserError error, failing.');
+    return true;
+  }
+
+  if (error instanceof ConnectTimeoutError) {
+    logError('ConnectTimeoutError error, failing.');
+    return true;
+  }
+
+  // Known error types captured here:
+  //   HTTPError
+  //   OutgoingMessageError
+  //   SendMessageNetworkError
+  //   SendMessageChallengeError
+  //   MessageError
+  if (isRecord(error) && typeof error.code === 'number') {
+    if (error.code === 401) {
+      logError('Permissions error, failing.');
+      return true;
+    }
+
+    if (error.code === 404) {
+      logError('Missing user or endpoint error, failing.');
+      return true;
+    }
+
+    if (error.code === 413) {
+      logError('Rate limit error, failing.');
+      return true;
+    }
+
+    if (error.code === 428) {
+      logError('Challenge error, failing.');
+      return true;
+    }
+
+    if (error.code === 500) {
+      logError('Server error, failing.');
+      return true;
+    }
+
+    if (error.code === 508) {
+      logError('Fail job error, failing.');
+      return true;
+    }
+  }
+
+  if (error instanceof SendMessageProtoError) {
+    if (!error.errors || !error.errors.length) {
+      logError('SendMessageProtoError had no errors, failing.');
+      return true;
+    }
+
+    for (const innerError of error.errors) {
+      const shouldFail = _shouldFailSend(innerError, logId);
+      if (shouldFail) {
+        return true;
+      }
+    }
+  }
+
+  return false;
+}
+
 export async function _waitForAll<T>({
   tasks,
   maxConcurrency = MAX_CONCURRENCY,