diff --git a/ts/components/conversation/SessionRightPanel.tsx b/ts/components/conversation/SessionRightPanel.tsx
index 8076f5c4d..2869a6200 100644
--- a/ts/components/conversation/SessionRightPanel.tsx
+++ b/ts/components/conversation/SessionRightPanel.tsx
@@ -7,6 +7,8 @@ import useInterval from 'react-use/lib/useInterval';
 import styled from 'styled-components';
 import { Data } from '../../data/data';
 import {
+  ConversationInteractionStatus,
+  ConversationInteractionType,
   setDisappearingMessagesByConvoId,
   showAddModeratorsByConvoId,
   showInviteContactByConvoId,
@@ -27,6 +29,7 @@ import {
   useSelectedIsKickedFromGroup,
   useSelectedIsLeft,
   useSelectedIsPublic,
+  useSelectedLastMessage,
   useSelectedSubscriberCount,
   useSelectedWeAreAdmin,
 } from '../../state/selectors/selectedConversation';
@@ -220,6 +223,7 @@ export const SessionRightPanelWithDetails = () => {
   const isGroup = useSelectedIsGroup();
   const isPublic = useSelectedIsPublic();
   const weAreAdmin = useSelectedWeAreAdmin();
+  const lastMessage = useSelectedLastMessage();
 
   useEffect(() => {
     let isRunning = true;
@@ -263,6 +267,9 @@ export const SessionRightPanelWithDetails = () => {
   const hasDisappearingMessages = !isPublic && !commonNoShow;
   const leaveGroupString = isPublic
     ? window.i18n('leaveCommunity')
+    : lastMessage?.interactionType === ConversationInteractionType.Leave &&
+      lastMessage?.interactionStatus === ConversationInteractionStatus.Error
+    ? window.i18n('deleteConversation')
     : isKickedFromGroup
     ? window.i18n('youGotKickedFromGroup')
     : left
diff --git a/ts/components/menu/Menu.tsx b/ts/components/menu/Menu.tsx
index 3c0fae9bd..f4448d4ee 100644
--- a/ts/components/menu/Menu.tsx
+++ b/ts/components/menu/Menu.tsx
@@ -15,9 +15,12 @@ import {
   useIsPrivate,
   useIsPrivateAndFriend,
   useIsPublic,
+  useLastMessage,
   useWeAreAdmin,
 } from '../../hooks/useParamSelector';
 import {
+  ConversationInteractionStatus,
+  ConversationInteractionType,
   approveConvoAndSendResponse,
   blockConvoById,
   clearNickNameByConvoId,
@@ -134,6 +137,7 @@ export const LeaveGroupOrCommunityMenuItem = () => {
   const isKickedFromGroup = useIsKickedFromGroup(convoId);
   const isPrivate = useIsPrivate(convoId);
   const isPublic = useIsPublic(convoId);
+  const lastMessage = useLastMessage(convoId);
 
   if (!isKickedFromGroup && !isLeft && !isPrivate) {
     return (
@@ -142,7 +146,12 @@ export const LeaveGroupOrCommunityMenuItem = () => {
           showLeaveGroupByConvoId(convoId, username);
         }}
       >
-        {isPublic ? window.i18n('leaveCommunity') : window.i18n('leaveGroup')}
+        {isPublic
+          ? window.i18n('leaveCommunity')
+          : lastMessage?.interactionType === ConversationInteractionType.Leave &&
+            lastMessage?.interactionStatus === ConversationInteractionStatus.Error
+          ? window.i18n('deleteConversation')
+          : window.i18n('leaveGroup')}
       </Item>
     );
   }
diff --git a/ts/interactions/conversationInteractions.ts b/ts/interactions/conversationInteractions.ts
index e4e65e224..7823ec815 100644
--- a/ts/interactions/conversationInteractions.ts
+++ b/ts/interactions/conversationInteractions.ts
@@ -292,7 +292,45 @@ export function showLeavePrivateConversationbyConvoId(
   );
 }
 
-export function showLeaveGroupByConvoId(conversationId: string, name: string | undefined) {
+async function leaveGroupOrCommunityByConvoId(
+  conversationId: string,
+  isPublic: boolean,
+  forceDeleteLocal: boolean,
+  onClickClose?: () => void
+) {
+  try {
+    await updateConversationInteractionState({
+      conversationId,
+      type: ConversationInteractionType.Leave,
+      status: ConversationInteractionStatus.Start,
+    });
+
+    if (onClickClose) {
+      onClickClose();
+    }
+
+    if (isPublic) {
+      await getConversationController().deleteCommunity(conversationId, {
+        fromSyncMessage: false,
+      });
+    } else {
+      await getConversationController().deleteClosedGroup(conversationId, {
+        fromSyncMessage: false,
+        sendLeaveMessage: true,
+        forceDeleteLocal,
+      });
+    }
+    await clearConversationInteractionState({ conversationId });
+  } catch (err) {
+    window.log.warn(`showLeaveGroupByConvoId error: ${err}`);
+    await saveConversationInteractionErrorAsMessage({
+      conversationId,
+      interactionType: ConversationInteractionType.Leave,
+    });
+  }
+}
+
+export async function showLeaveGroupByConvoId(conversationId: string, name: string | undefined) {
   const conversation = getConversationController().get(conversationId);
 
   if (!conversation.isGroup()) {
@@ -304,6 +342,17 @@ export function showLeaveGroupByConvoId(conversationId: string, name: string | u
   const admins = conversation.get('groupAdmins') || [];
   const isAdmin = admins.includes(UserUtils.getOurPubKeyStrFromCache());
   const showOnlyGroupAdminWarning = isClosedGroup && isAdmin && admins.length === 1;
+  const lastMessageInteractionType = conversation.get('lastMessageInteractionType');
+  const lastMessageInteractionStatus = conversation.get('lastMessageInteractionStatus');
+
+  if (
+    !isPublic &&
+    lastMessageInteractionType === ConversationInteractionType.Leave &&
+    lastMessageInteractionStatus === ConversationInteractionStatus.Error
+  ) {
+    await leaveGroupOrCommunityByConvoId(conversationId, isPublic, true);
+    return;
+  }
 
   // if this is a community, or we legacy group are not admin, we can just show a confirmation dialog
 
@@ -312,31 +361,7 @@ export function showLeaveGroupByConvoId(conversationId: string, name: string | u
   };
 
   const onClickOk = async () => {
-    try {
-      await updateConversationInteractionState({
-        conversationId,
-        type: ConversationInteractionType.Leave,
-        status: ConversationInteractionStatus.Start,
-      });
-      onClickClose();
-      if (isPublic) {
-        await getConversationController().deleteCommunity(conversation.id, {
-          fromSyncMessage: false,
-        });
-      } else {
-        await getConversationController().deleteClosedGroup(conversation.id, {
-          fromSyncMessage: false,
-          sendLeaveMessage: true,
-        });
-      }
-      await clearConversationInteractionState({ conversationId });
-    } catch (err) {
-      window.log.warn(`showLeaveGroupByConvoId error: ${err}`);
-      await saveConversationInteractionErrorAsMessage({
-        conversationId,
-        interactionType: ConversationInteractionType.Leave,
-      });
-    }
+    await leaveGroupOrCommunityByConvoId(conversationId, isPublic, false, onClickClose);
   };
 
   if (showOnlyGroupAdminWarning) {
diff --git a/ts/session/conversations/ConversationController.ts b/ts/session/conversations/ConversationController.ts
index 93e944b99..1d7a12289 100644
--- a/ts/session/conversations/ConversationController.ts
+++ b/ts/session/conversations/ConversationController.ts
@@ -229,17 +229,22 @@ export class ConversationController {
 
   public async deleteClosedGroup(
     groupId: string,
-    options: DeleteOptions & { sendLeaveMessage: boolean }
+    options: DeleteOptions & { sendLeaveMessage: boolean; forceDeleteLocal?: boolean }
   ) {
     const conversation = await this.deleteConvoInitialChecks(groupId, 'LegacyGroup');
     if (!conversation || !conversation.isClosedGroup()) {
       return;
     }
-    window.log.info(`deleteClosedGroup: ${groupId}, sendLeaveMessage?:${options.sendLeaveMessage}`);
+
     getSwarmPollingInstance().removePubkey(groupId); // we don't need to keep polling anymore.
 
-    if (options.sendLeaveMessage) {
-      await leaveClosedGroup(groupId, options.fromSyncMessage);
+    if (!options.forceDeleteLocal) {
+      window.log.info(
+        `deleteClosedGroup: ${groupId}, sendLeaveMessage?:${options.sendLeaveMessage}`
+      );
+      if (options.sendLeaveMessage) {
+        await leaveClosedGroup(groupId, options.fromSyncMessage);
+      }
     }
 
     // if we were kicked or sent our left message, we have nothing to do more with that group.
diff --git a/ts/state/selectors/selectedConversation.ts b/ts/state/selectors/selectedConversation.ts
index 759ab8cbf..f30791be4 100644
--- a/ts/state/selectors/selectedConversation.ts
+++ b/ts/state/selectors/selectedConversation.ts
@@ -257,3 +257,7 @@ export function useSelectedNicknameOrProfileNameOrShortenedPubkey() {
 export function useSelectedWeAreAdmin() {
   return useSelector((state: StateType) => getSelectedConversation(state)?.weAreAdmin || false);
 }
+
+export function useSelectedLastMessage() {
+  return useSelector((state: StateType) => getSelectedConversation(state)?.lastMessage);
+}