diff --git a/ts/components/conversation/right-panel/overlay/message-info/OverlayMessageInfo.tsx b/ts/components/conversation/right-panel/overlay/message-info/OverlayMessageInfo.tsx
index c1e3c7bb3..4d90cf20f 100644
--- a/ts/components/conversation/right-panel/overlay/message-info/OverlayMessageInfo.tsx
+++ b/ts/components/conversation/right-panel/overlay/message-info/OverlayMessageInfo.tsx
@@ -103,7 +103,7 @@ const StyledMessageInfoContainer = styled.div`
 `;
 
 type MessageInfoProps = {
-  errors: Array<Error>;
+  errors?: string;
   attachments: Array<PropsForAttachment>;
 };
 
@@ -151,10 +151,7 @@ async function getPropsForMessageInfo(
       }
     }
 
-    // This will make the error message for outgoing key errors a bit nicer
-    const errors = (found.get('errors') || []).map((error: any) => {
-      return error;
-    });
+    const errors = found.get('errors');
 
     const toRet: MessageInfoProps = {
       errors,
diff --git a/ts/components/conversation/right-panel/overlay/message-info/components/MessageInfo.tsx b/ts/components/conversation/right-panel/overlay/message-info/components/MessageInfo.tsx
index 4097f142e..2c60a0732 100644
--- a/ts/components/conversation/right-panel/overlay/message-info/components/MessageInfo.tsx
+++ b/ts/components/conversation/right-panel/overlay/message-info/components/MessageInfo.tsx
@@ -1,5 +1,3 @@
-import { isEmpty } from 'lodash';
-
 import styled from 'styled-components';
 import { MessageFrom } from '.';
 import {
@@ -117,7 +115,7 @@ const DebugMessageInfo = ({ messageId }: { messageId: string }) => {
   );
 };
 
-export const MessageInfo = ({ messageId, errors }: { messageId: string; errors: Array<Error> }) => {
+export const MessageInfo = ({ messageId, errors }: { messageId: string; errors?: string }) => {
   const sender = useMessageSender(messageId);
   const direction = useMessageDirection(messageId);
   const sentAt = useMessageTimestamp(messageId);
@@ -138,15 +136,6 @@ export const MessageInfo = ({ messageId, errors }: { messageId: string; errors:
     formatStr: formatTimestampStr,
   });
 
-  const hasError = !isEmpty(errors);
-  const errorString = hasError
-    ? errors?.reduce((previous, current, currentIndex) => {
-        return `${previous}${current.message}${
-          errors.length > 1 && currentIndex < errors.length - 1 ? ', ' : ''
-        }`;
-      }, '')
-    : null;
-
   return (
     <Flex container={true} flexDirection="column">
       <LabelWithInfo label={window.i18n('sent')} info={sentAtStr} />
@@ -157,13 +146,13 @@ export const MessageInfo = ({ messageId, errors }: { messageId: string; errors:
       ) : null}
       <SpacerSM />
       <MessageFrom sender={sender} isSenderAdmin={isSenderAdmin} />
-      {hasError && (
+      {!!errors && (
         <>
           <SpacerSM />
           <LabelWithInfo
             title={window.i18n('helpReportABugExportLogsSaveToDesktopDescription')}
             label={`${window.i18n('theError')}:`}
-            info={errorString || window.i18n('errorUnknown')}
+            info={errors || window.i18n('errorUnknown')}
             dataColor={'var(--danger-color)'}
             onClick={() => {
               void saveLogToDesktop();
diff --git a/ts/data/data.ts b/ts/data/data.ts
index 99ce43b28..99346d488 100644
--- a/ts/data/data.ts
+++ b/ts/data/data.ts
@@ -616,6 +616,16 @@ async function findAllMessageHashesInConversationMatchingAuthor(
   return msgAttrs.map((msg: any) => new MessageModel(msg));
 }
 
+async function fetchAllGroupUpdateFailedMessage(groupPk: GroupPubkeyType) {
+  const msgAttrs = await channels.fetchAllGroupUpdateFailedMessage(groupPk);
+
+  if (!msgAttrs || isEmpty(msgAttrs) || !isArray(msgAttrs)) {
+    return [];
+  }
+
+  return msgAttrs.map((msg: any) => new MessageModel(msg));
+}
+
 async function getMessagesBySentAt(sentAt: number): Promise<MessageCollection> {
   const messages = await channels.getMessagesBySentAt(sentAt);
   return new MessageCollection(messages);
@@ -902,6 +912,7 @@ export const Data = {
   findAllMessageFromSendersInConversation,
   findAllMessageHashesInConversation,
   findAllMessageHashesInConversationMatchingAuthor,
+  fetchAllGroupUpdateFailedMessage,
   getMessagesBySentAt,
   getExpiredMessages,
   getOutgoingWithoutExpiresAt,
diff --git a/ts/data/dataInit.ts b/ts/data/dataInit.ts
index 2696fe343..e4e63d97b 100644
--- a/ts/data/dataInit.ts
+++ b/ts/data/dataInit.ts
@@ -56,6 +56,7 @@ const channelsToMake = new Set([
   'findAllMessageFromSendersInConversation',
   'findAllMessageHashesInConversation',
   'findAllMessageHashesInConversationMatchingAuthor',
+  'fetchAllGroupUpdateFailedMessage',
   'getMessageCount',
   'filterAlreadyFetchedOpengroupMessage',
   'getMessagesBySenderAndSentAt',
diff --git a/ts/models/conversation.ts b/ts/models/conversation.ts
index 5f71d712d..8c1fa5840 100644
--- a/ts/models/conversation.ts
+++ b/ts/models/conversation.ts
@@ -841,7 +841,7 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
       const error = new Error('Network is not available');
       error.name = 'SendMessageNetworkError';
       (error as any).number = this.id;
-      await messageModel.saveErrors([error]);
+      await messageModel.saveErrors(error);
       await this.commit();
 
       return;
@@ -2204,8 +2204,10 @@ export class ConversationModel extends Backbone.Model<ConversationAttributes> {
       }
 
       throw new TypeError(`Invalid conversation type: '${this.get('type')}'`);
-    } catch (e) {
-      await message.saveErrors(e);
+    } catch (e: unknown) {
+      if (e instanceof Error) {
+        await message.saveErrors(e);
+      }
     }
   }
 
diff --git a/ts/models/message.ts b/ts/models/message.ts
index 2d90d2266..2aaaec6c1 100644
--- a/ts/models/message.ts
+++ b/ts/models/message.ts
@@ -3,7 +3,7 @@ import Backbone from 'backbone';
 import autoBind from 'auto-bind';
 import filesize from 'filesize';
 import { GroupPubkeyType, PubkeyType } from 'libsession_util_nodejs';
-import { cloneDeep, debounce, isEmpty, size as lodashSize, partition, pick, uniq } from 'lodash';
+import { cloneDeep, debounce, isEmpty, size as lodashSize, uniq } from 'lodash';
 import { SignalService } from '../protobuf';
 import { ConvoHub } from '../session/conversations';
 import { ContentMessage } from '../session/messages/outgoing';
@@ -886,7 +886,7 @@ export class MessageModel extends Backbone.Model<MessageAttributes> {
       return null;
     }
 
-    this.set({ errors: null, sent: false, sent_to: [] });
+    this.set({ errors: undefined, sent: false, sent_to: [] });
     await this.commit();
     try {
       const conversation: ConversationModel | undefined = this.getConversation();
@@ -987,21 +987,14 @@ export class MessageModel extends Backbone.Model<MessageAttributes> {
         message: closedGroupVisibleMessage,
         namespace: SnodeNamespaces.LegacyClosedGroup,
       });
-    } catch (e) {
-      await this.saveErrors(e);
+    } catch (e: unknown) {
+      if (e instanceof Error) {
+        await this.saveErrors(e);
+      }
       return null;
     }
   }
 
-  public removeOutgoingErrors(number: string) {
-    const errors = partition(
-      this.get('errors'),
-      e => e.number === number && e.name === 'SendMessageNetworkError'
-    );
-    this.set({ errors: errors[1] });
-    return errors[0][0];
-  }
-
   public getConversation(): ConversationModel | undefined {
     // This needs to be an unsafe call, because this method is called during
     //   initial module setup. We may be in the middle of the initial fetch to
@@ -1114,32 +1107,14 @@ export class MessageModel extends Backbone.Model<MessageAttributes> {
     await this.commit();
   }
 
-  public async saveErrors(providedErrors: any) {
-    let errors = providedErrors;
-
-    if (!(errors instanceof Array)) {
-      errors = [errors];
+  public async saveErrors(providedError: Error) {
+    if (!(providedError instanceof Error)) {
+      throw new Error('saveErrors expects a single error to be provided');
     }
-    errors.forEach((e: any) => {
-      window?.log?.error(
-        'Message.saveErrors:',
-        e && e.reason ? e.reason : null,
-        e && e.stack ? e.stack : e
-      );
-    });
-    errors = errors.map((e: any) => {
-      if (
-        e.constructor === Error ||
-        e.constructor === TypeError ||
-        e.constructor === ReferenceError
-      ) {
-        return pick(e, 'name', 'message', 'code', 'number', 'reason');
-      }
-      return e;
-    });
-    errors = errors.concat(this.get('errors') || []);
 
-    this.set({ errors });
+    const errorStr = `${providedError.name} - "${providedError.message || 'unknown error message'}"`;
+
+    this.set({ errors: errorStr });
     await this.commit();
   }
 
diff --git a/ts/models/messageType.ts b/ts/models/messageType.ts
index f7ab0ba43..6904dff43 100644
--- a/ts/models/messageType.ts
+++ b/ts/models/messageType.ts
@@ -44,7 +44,7 @@ export interface MessageAttributes {
   groupInvitation?: { url: string | undefined; name: string } | undefined;
   attachments?: any;
   conversationId: string;
-  errors?: any;
+  errors?: string;
   flags?: number;
   hasAttachments: 1 | 0;
   hasFileAttachments: 1 | 0;
diff --git a/ts/node/migration/sessionMigrations.ts b/ts/node/migration/sessionMigrations.ts
index 54dc29800..76ad85aaf 100644
--- a/ts/node/migration/sessionMigrations.ts
+++ b/ts/node/migration/sessionMigrations.ts
@@ -108,6 +108,7 @@ const LOKI_SCHEMA_VERSIONS = [
   updateToSessionSchemaVersion37,
   updateToSessionSchemaVersion38,
   updateToSessionSchemaVersion39,
+  updateToSessionSchemaVersion40,
 ];
 
 function updateToSessionSchemaVersion1(currentVersion: number, db: BetterSqlite3.Database) {
@@ -2025,6 +2026,27 @@ function updateToSessionSchemaVersion39(currentVersion: number, db: BetterSqlite
   console.log(`updateToSessionSchemaVersion${targetVersion}: success!`);
 }
 
+function updateToSessionSchemaVersion40(currentVersion: number, db: BetterSqlite3.Database) {
+  const targetVersion = 40;
+  if (currentVersion >= targetVersion) {
+    return;
+  }
+
+  console.log(`updateToSessionSchemaVersion${targetVersion}: starting...`);
+
+  db.transaction(() => {
+    // the 'errors' field used to do different things. We need to extract it to be a single string.
+    db.exec(`ALTER TABLE ${MESSAGES_TABLE} ADD COLUMN errors TEXT;`);
+    db.exec(`UPDATE ${MESSAGES_TABLE}
+      SET json = json_remove(json, '$.errors');
+    `);
+
+    writeSessionSchemaVersion(targetVersion, db);
+  })();
+
+  console.log(`updateToSessionSchemaVersion${targetVersion}: success!`);
+}
+
 export function printTableColumns(table: string, db: BetterSqlite3.Database) {
   console.info(db.pragma(`table_info('${table}');`));
 }
diff --git a/ts/node/sql.ts b/ts/node/sql.ts
index 92a7dfa65..eb99b61c8 100644
--- a/ts/node/sql.ts
+++ b/ts/node/sql.ts
@@ -851,6 +851,7 @@ function saveMessage(data: MessageAttributes) {
     expirationStartTimestamp,
     flags,
     messageHash,
+    errors,
   } = data;
 
   if (!id) {
@@ -884,6 +885,7 @@ function saveMessage(data: MessageAttributes) {
     unread,
     flags: flags ?? 0,
     messageHash,
+    errors,
   };
 
   assertGlobalInstance()
@@ -909,7 +911,8 @@ function saveMessage(data: MessageAttributes) {
     type,
     unread,
     flags,
-    messageHash
+    messageHash,
+    errors
   ) values (
     $id,
     $json,
@@ -931,7 +934,8 @@ function saveMessage(data: MessageAttributes) {
     $type,
     $unread,
     $flags,
-    $messageHash
+    $messageHash,
+    $errors
   );`
     )
     .run(payload);
@@ -1191,6 +1195,29 @@ function findAllMessageHashesInConversationMatchingAuthor(
   return map(rows, row => jsonToObject(row.json));
 }
 
+function fetchAllGroupUpdateFailedMessage(
+  groupPk: GroupPubkeyType,
+  instance?: BetterSqlite3.Database
+) {
+  if (!groupPk) {
+    return [];
+  }
+  const rows = assertGlobalInstanceOrInstance(instance)
+    .prepare(
+      `SELECT json FROM ${MESSAGES_TABLE} WHERE conversationId = ? AND JSON_EXTRACT(json, '$.group_update') IS NOT NULL AND errors IS NOT NULL;`
+    )
+    .all(groupPk);
+
+  if (!rows || isEmpty(rows)) {
+    return [];
+  }
+  const objs = map(rows, row => jsonToObject(row.json)).filter(m => {
+    return !isEmpty(m);
+  });
+
+  return objs;
+}
+
 function cleanUpExpirationTimerUpdateHistory(
   conversationId: string,
   isPrivate: boolean,
@@ -2730,6 +2757,7 @@ export const sqlNode = {
   findAllMessageFromSendersInConversation,
   findAllMessageHashesInConversation,
   findAllMessageHashesInConversationMatchingAuthor,
+  fetchAllGroupUpdateFailedMessage,
   getUnreadByConversation,
   getUnreadDisappearingByConversation,
   markAllAsReadByConversationNoExpiration,
diff --git a/ts/receiver/queuedJob.ts b/ts/receiver/queuedJob.ts
index 63f42b356..fe8ef0613 100644
--- a/ts/receiver/queuedJob.ts
+++ b/ts/receiver/queuedJob.ts
@@ -312,7 +312,7 @@ async function handleRegularMessage(
     body: rawDataMessage.body,
     conversationId: conversation.id,
     messageHash,
-    errors: [],
+    errors: undefined,
   });
 
   const serverTimestamp = message.get('serverTimestamp');
diff --git a/ts/session/apis/snode_api/SnodeRequestTypes.ts b/ts/session/apis/snode_api/SnodeRequestTypes.ts
index 7a32423c8..3afeb73d9 100644
--- a/ts/session/apis/snode_api/SnodeRequestTypes.ts
+++ b/ts/session/apis/snode_api/SnodeRequestTypes.ts
@@ -1384,3 +1384,18 @@ export type BatchStoreWithExtraParams =
   | DeleteHashesFromUserNodeSubRequest
   | SubaccountRevokeSubRequest
   | SubaccountUnrevokeSubRequest;
+
+export type StoreUserInitiatedMessage =
+  | StoreGroupMessageSubRequest
+  | StoreLegacyGroupMessageSubRequest
+  | StoreUserMessageSubRequest;
+
+export function isStoreUserInitiatedMessage(
+  request: SnodeAPISubRequest<string>
+): request is StoreUserInitiatedMessage {
+  return (
+    request instanceof StoreGroupMessageSubRequest ||
+    request instanceof StoreLegacyGroupMessageSubRequest ||
+    request instanceof StoreUserMessageSubRequest
+  );
+}
diff --git a/ts/session/sending/MessageSender.ts b/ts/session/sending/MessageSender.ts
index 4e65a6bc4..a2c544db6 100644
--- a/ts/session/sending/MessageSender.ts
+++ b/ts/session/sending/MessageSender.ts
@@ -16,6 +16,7 @@ import {
   DeleteAllFromGroupMsgNodeSubRequest,
   DeleteHashesFromGroupNodeSubRequest,
   DeleteHashesFromUserNodeSubRequest,
+  isStoreUserInitiatedMessage,
   MethodBatchType,
   RawSnodeSubRequests,
   StoreGroupInfoSubRequest,
@@ -559,6 +560,18 @@ async function sendEncryptedDataToSnode<T extends GroupPubkeyType | PubkeyType>(
     return batchResults;
   } catch (e) {
     window.log.warn(`sendEncryptedDataToSnode failed with ${e.message}`);
+    const sortedSubRequestsWithMsg = sortedSubRequests.filter(r => isStoreUserInitiatedMessage(r));
+    for (let index = 0; index < sortedSubRequestsWithMsg.length; index++) {
+      const request = sortedSubRequestsWithMsg[index];
+      if (request.dbMessageIdentifier) {
+        // eslint-disable-next-line no-await-in-loop
+        await MessageSentHandler.handleSwarmMessageSentFailure(
+          { device: destination, identifier: request.dbMessageIdentifier },
+          e
+        );
+      }
+    }
+
     return null;
   }
 }
@@ -660,11 +673,7 @@ async function handleBatchResultWithSubRequests({
 
     // there are some things we need to do when storing messages
     // for groups/legacy groups or user (but not for config messages)
-    if (
-      subRequest instanceof StoreGroupMessageSubRequest ||
-      subRequest instanceof StoreLegacyGroupMessageSubRequest ||
-      subRequest instanceof StoreUserMessageSubRequest
-    ) {
+    if (isStoreUserInitiatedMessage(subRequest)) {
       const storedAt = batchResult?.[index]?.body?.t;
       const storedHash = batchResult?.[index]?.body?.hash;
       const subRequestStatusCode = batchResult?.[index]?.code;
diff --git a/ts/session/sending/MessageSentHandler.ts b/ts/session/sending/MessageSentHandler.ts
index c503f2f7a..268892876 100644
--- a/ts/session/sending/MessageSentHandler.ts
+++ b/ts/session/sending/MessageSentHandler.ts
@@ -143,6 +143,7 @@ async function handleSwarmMessageSentSuccess(
     sent_to: sentTo,
     sent: true,
     sent_at: effectiveTimestamp,
+    errors: undefined,
   });
 
   DisappearingMessages.checkForExpiringOutgoingMessage(fetchedMessage, 'handleMessageSentSuccess');
diff --git a/ts/session/utils/job_runners/jobs/GroupSyncJob.ts b/ts/session/utils/job_runners/jobs/GroupSyncJob.ts
index cdaa19452..4c094bed0 100644
--- a/ts/session/utils/job_runners/jobs/GroupSyncJob.ts
+++ b/ts/session/utils/job_runners/jobs/GroupSyncJob.ts
@@ -13,6 +13,7 @@ import {
 import {
   DeleteAllFromGroupMsgNodeSubRequest,
   DeleteHashesFromGroupNodeSubRequest,
+  MAX_SUBREQUESTS_COUNT,
   StoreGroupKeysSubRequest,
   StoreGroupMessageSubRequest,
   SubaccountRevokeSubRequest,
@@ -38,6 +39,13 @@ import {
 import { DURATION } from '../../../constants';
 import { WithAllow401s } from '../../../types/with';
 import type { WithTimeoutMs } from '../../../apis/snode_api/requestWith';
+import { Data } from '../../../../data/data';
+import { GroupUpdateInfoChangeMessage } from '../../../messages/outgoing/controlMessage/group_v2/to_group/GroupUpdateInfoChangeMessage';
+import { NetworkTime } from '../../../../util/NetworkTime';
+import { SignalService } from '../../../../protobuf';
+import { getSodiumRenderer } from '../../../crypto';
+import { DisappearingMessages } from '../../../disappearing_messages';
+import { GroupUpdateMemberChangeMessage } from '../../../messages/outgoing/controlMessage/group_v2/to_group/GroupUpdateMemberChangeMessage';
 
 const defaultMsBetweenRetries = 15000; // a long time between retries, to avoid running multiple jobs at the same time, when one was postponed at the same time as one already planned (5s)
 const defaultMaxAttempts = 2;
@@ -223,6 +231,111 @@ async function pushChangesToGroupSwarmIfNeeded({
   return RunJobResult.Success;
 }
 
+async function allFailedToSentGroupControlMessagesToRetry(groupPk: GroupPubkeyType) {
+  try {
+    const sodium = await getSodiumRenderer();
+    const msgsToResend = await Data.fetchAllGroupUpdateFailedMessage(groupPk);
+    const firstChunk = msgsToResend.slice(0, Math.floor(MAX_SUBREQUESTS_COUNT / 2));
+    const convo = ConvoHub.use().get(groupPk);
+    if (!convo) {
+      throw new Error('allFailedToSentGroupControlMessagesToRetry: convo not found');
+    }
+    const group = await UserGroupsWrapperActions.getGroup(groupPk);
+    if (!group || !group.secretKey || isEmpty(group.secretKey)) {
+      throw new Error('allFailedToSentGroupControlMessagesToRetry: group secret key is not found');
+    }
+    const secretKey = group.secretKey;
+    const extraStoreRequests = await StoreGroupRequestFactory.makeGroupMessageSubRequest(
+      firstChunk.map(m => {
+        const groupUpdate = m.get('group_update');
+        const createAtNetworkTimestamp = m.get('sent_at') || NetworkTime.now();
+        const identifier = m.get('id');
+        if (!group.secretKey) {
+          return null;
+        }
+        const shared = {
+          groupPk,
+          identifier,
+          createAtNetworkTimestamp,
+          secretKey,
+          sodium,
+          ...DisappearingMessages.getExpireDetailsForOutgoingMessage(
+            convo,
+            createAtNetworkTimestamp
+          ),
+        };
+        if (groupUpdate?.avatarChange) {
+          return new GroupUpdateInfoChangeMessage({
+            typeOfChange: SignalService.GroupUpdateInfoChangeMessage.Type.AVATAR,
+            ...shared,
+          });
+        }
+        if (groupUpdate?.name) {
+          return new GroupUpdateInfoChangeMessage({
+            typeOfChange: SignalService.GroupUpdateInfoChangeMessage.Type.NAME,
+            updatedName: groupUpdate.name || '',
+            ...shared,
+          });
+        }
+        if (groupUpdate?.joined?.length) {
+          return new GroupUpdateMemberChangeMessage({
+            typeOfChange: 'added',
+            added: groupUpdate.joined,
+            ...shared,
+          });
+        }
+        if (groupUpdate?.joinedWithHistory?.length) {
+          return new GroupUpdateMemberChangeMessage({
+            typeOfChange: 'addedWithHistory',
+            added: groupUpdate.joinedWithHistory,
+            ...shared,
+          });
+        }
+        if (groupUpdate?.kicked?.length) {
+          return new GroupUpdateMemberChangeMessage({
+            typeOfChange: 'removed',
+            removed: groupUpdate.kicked,
+            ...shared,
+          });
+        }
+        if (groupUpdate?.promoted?.length) {
+          return new GroupUpdateMemberChangeMessage({
+            typeOfChange: 'promoted',
+            promoted: groupUpdate.promoted,
+            ...shared,
+          });
+        }
+        const expirationTimerUpdate = m.get('expirationTimerUpdate');
+        if (expirationTimerUpdate) {
+          return new GroupUpdateInfoChangeMessage({
+            typeOfChange: SignalService.GroupUpdateInfoChangeMessage.Type.DISAPPEARING_MESSAGES,
+            ...shared,
+            updatedExpirationSeconds: expirationTimerUpdate.expireTimer,
+            expirationType: expirationTimerUpdate.expirationType || 'unknown',
+          });
+        }
+        window.log.warn(
+          `allFailedToSentGroupControlMessagesToRetry unhandled result for ms ${shared.identifier}`
+        );
+        return null;
+      }),
+      group
+    );
+
+    if (!extraStoreRequests.length) {
+      return;
+    }
+
+    await pushChangesToGroupSwarmIfNeeded({
+      groupPk,
+      extraStoreRequests,
+      allow401s: false,
+    });
+  } catch (e) {
+    window.log.warn('failed');
+  }
+}
+
 class GroupSyncJob extends PersistedJob<GroupSyncPersistedData> {
   constructor({
     identifier, // this has to be the group's pubkey
@@ -263,6 +376,8 @@ class GroupSyncJob extends PersistedJob<GroupSyncPersistedData> {
         return RunJobResult.PermanentFailure;
       }
 
+      await allFailedToSentGroupControlMessagesToRetry(thisJobDestination);
+
       // return await so we catch exceptions in here
       return await GroupSync.pushChangesToGroupSwarmIfNeeded({
         groupPk: thisJobDestination,