diff --git a/ts/components/conversation/header/ConversationHeaderSelectionOverlay.tsx b/ts/components/conversation/header/ConversationHeaderSelectionOverlay.tsx
index deb3fcf9d..66032e816 100644
--- a/ts/components/conversation/header/ConversationHeaderSelectionOverlay.tsx
+++ b/ts/components/conversation/header/ConversationHeaderSelectionOverlay.tsx
@@ -3,11 +3,7 @@ import React from 'react';
 import { useDispatch, useSelector } from 'react-redux';
 import useKey from 'react-use/lib/useKey';
 
-import {
-  deleteMessagesById,
-  deleteMessagesByIdForEveryone,
-  deleteMessagesForX,
-} from '../../../interactions/conversations/unsendingInteractions';
+import { deleteMessagesForX } from '../../../interactions/conversations/unsendingInteractions';
 import { resetSelectedMessageIds } from '../../../state/ducks/conversations';
 import { getSelectedMessageIds } from '../../../state/selectors/conversations';
 import {
@@ -22,15 +18,6 @@ import {
 } from '../../basic/SessionButton';
 import { SessionIconButton } from '../../icon';
 
-function onDeleteSelectedMessagesForEveryone(
-  selectedConversationKey: string,
-  selectedMessageIds: Array<string>
-) {
-  if (selectedConversationKey) {
-    void deleteMessagesByIdForEveryone(selectedMessageIds, selectedConversationKey);
-  }
-}
-
 export const SelectionOverlay = () => {
   const selectedMessageIds = useSelector(getSelectedMessageIds);
   const selectedConversationKey = useSelectedConversationKey();
@@ -73,7 +60,11 @@ export const SelectionOverlay = () => {
     }
   );
 
-  const isOnlyServerDeletable = isPublic;
+  // `enforceDeleteServerSide` should check for message statuses too, but when we have multiple selected,
+  // some might be sent and some in an error state. We default to trying to delete all of them server side first,
+  // which might fail. If that fails, the user will need to do a delete for all the ones sent already, and a manual delete
+  // for each ones which is in an error state.
+  const enforceDeleteServerSide = isPublic;
 
   const classNameAndId = 'message-selection-overlay';
 
@@ -90,16 +81,13 @@ export const SelectionOverlay = () => {
             buttonShape={SessionButtonShape.Square}
             buttonType={SessionButtonType.Solid}
             text={window.i18n('delete')}
-            onClick={() => {
+            onClick={async () => {
               if (selectedConversationKey) {
-                if (isOnlyServerDeletable) {
-                  void onDeleteSelectedMessagesForEveryone(
-                    selectedConversationKey,
-                    selectedMessageIds
-                  );
-                } else {
-                  void deleteMessagesById(selectedMessageIds, selectedConversationKey);
-                }
+                await deleteMessagesForX(
+                  selectedMessageIds,
+                  selectedConversationKey,
+                  enforceDeleteServerSide
+                );
               }
             }}
           />
diff --git a/ts/components/conversation/message/message-content/MessageContextMenu.tsx b/ts/components/conversation/message/message-content/MessageContextMenu.tsx
index 78f46450b..d8112c676 100644
--- a/ts/components/conversation/message/message-content/MessageContextMenu.tsx
+++ b/ts/components/conversation/message/message-content/MessageContextMenu.tsx
@@ -91,12 +91,15 @@ const DeleteItem = ({ messageId }: { messageId: string }) => {
 
   const isDeletable = useMessageIsDeletable(messageId);
   const isDeletableForEveryone = useMessageIsDeletableForEveryone(messageId);
+  const messageStatus = useMessageStatus(messageId);
+
+  const enforceDeleteServerSide = isPublic && messageStatus !== 'error';
 
   const onDelete = useCallback(() => {
     if (convoId) {
-      void deleteMessagesForX([messageId], convoId, isPublic);
+      void deleteMessagesForX([messageId], convoId, enforceDeleteServerSide);
     }
-  }, [convoId, isPublic, messageId]);
+  }, [convoId, enforceDeleteServerSide, messageId]);
 
   if (!convoId || (isPublic && !isDeletableForEveryone) || (!isPublic && !isDeletable)) {
     return null;
diff --git a/ts/interactions/conversations/unsendingInteractions.ts b/ts/interactions/conversations/unsendingInteractions.ts
index 16e33e1a7..828c05903 100644
--- a/ts/interactions/conversations/unsendingInteractions.ts
+++ b/ts/interactions/conversations/unsendingInteractions.ts
@@ -303,7 +303,7 @@ const doDeleteSelectedMessages = async ({
   }
 
   const isAllOurs = selectedMessages.every(message => ourDevicePubkey === message.getSource());
-  if (conversation.isPublic()) {
+  if (conversation.isPublic() && deleteForEveryone) {
     await doDeleteSelectedMessagesInSOGS(selectedMessages, conversation, isAllOurs);
     return;
   }
@@ -341,14 +341,14 @@ const doDeleteSelectedMessages = async ({
 export async function deleteMessagesForX(
   messageIds: Array<string>,
   conversationId: string,
-  isPublic: boolean
+  /** should only be enforced for messages successfully sent on communities */
+  enforceDeleteServerSide: boolean
 ) {
   if (conversationId) {
-    if (!isPublic) {
-      void deleteMessagesById(messageIds, conversationId);
-    }
-    if (isPublic) {
-      void deleteMessagesByIdForEveryone(messageIds, conversationId);
+    if (enforceDeleteServerSide) {
+      await deleteMessagesByIdForEveryone(messageIds, conversationId);
+    } else {
+      await deleteMessagesById(messageIds, conversationId);
     }
   }
 }