diff --git a/_locales/en/messages.json b/_locales/en/messages.json
index 35e26b3f4..2ec7a8a49 100644
--- a/_locales/en/messages.json
+++ b/_locales/en/messages.json
@@ -100,7 +100,11 @@
   "deleteMessagesQuestion": "Delete $count$ messages?",
   "deleteMessageQuestion": "Delete this message?",
   "deleteMessages": "Delete Messages",
+  "deleteMessagesConfirmation": "Permanently delete the messages in this conversation?",
   "deleteConversation": "Delete Conversation",
+  "deleteConversationConfirmation": "Are you sure you want to delete your conversation with $name$?",
+  "deleteConversationFailed": "Failed to leave the Conversation!",
+  "leaving": "Leaving...",
   "deleted": "$count$ deleted",
   "messageDeletedPlaceholder": "This message has been deleted",
   "from": "From:",
@@ -111,7 +115,6 @@
   "groupMembers": "Members",
   "moreInformation": "More information",
   "resend": "Resend",
-  "deleteConversationConfirmation": "Permanently delete the messages in this conversation?",
   "clear": "Clear",
   "clearAllData": "Clear All Data",
   "deleteAccountWarning": "This will permanently delete your messages and contacts.",
@@ -256,8 +259,11 @@
   "userBanFailed": "Ban failed!",
   "leaveGroup": "Leave Group",
   "leaveAndRemoveForEveryone": "Leave Group and Remove for Everyone",
-  "leaveGroupConfirmation": "Are you sure you want to leave this group?",
+  "leaveGroupConfirmation": "Are you sure you want to leave $name$?",
   "leaveGroupConfirmationAdmin": "As you are the admin of this group, if you leave it it will be removed for every current members. Are you sure you want to leave this group?",
+  "leaveGroupFailed": "Failed to leave Group!",
+  "leaveCommunity": "Leave Community",
+  "leaveCommunityFailed": "Failed to leave Community!",
   "cannotRemoveCreatorFromGroup": "Cannot remove this user",
   "cannotRemoveCreatorFromGroupDesc": "You cannot remove this user as they are the creator of the group.",
   "noContactsForGroup": "You don't have any contacts yet",
diff --git a/ts/components/conversation/SessionRightPanel.tsx b/ts/components/conversation/SessionRightPanel.tsx
index 6f15fe3f7..a6b3d8ff2 100644
--- a/ts/components/conversation/SessionRightPanel.tsx
+++ b/ts/components/conversation/SessionRightPanel.tsx
@@ -40,6 +40,7 @@ import { SessionDropdown } from '../basic/SessionDropdown';
 import { SpacerLG } from '../basic/Text';
 import { MediaItemType } from '../lightbox/LightboxGallery';
 import { MediaGallery } from './media-gallery/MediaGallery';
+import { useConversationUsername } from '../../hooks/useParamSelector';
 
 async function getMediaGalleryProps(
   conversationId: string
@@ -208,6 +209,8 @@ export const SessionRightPanelWithDetails = () => {
   const [media, setMedia] = useState<Array<MediaItemType>>([]);
 
   const selectedConvoKey = useSelectedConversationKey();
+  // TODO we need to test what happens to the localisad string without a group name
+  const selectedUsername = useConversationUsername(selectedConvoKey) || selectedConvoKey;
   const isShowing = useSelector(isRightPanelShowing);
   const subscriberCount = useSelectedSubscriberCount();
 
diff --git a/ts/components/dialog/SessionConfirm.tsx b/ts/components/dialog/SessionConfirm.tsx
index 0169d3f2a..dcb6c333a 100644
--- a/ts/components/dialog/SessionConfirm.tsx
+++ b/ts/components/dialog/SessionConfirm.tsx
@@ -1,4 +1,4 @@
-import React, { useState } from 'react';
+import React, { useEffect, useState } from 'react';
 import { SessionHtmlRenderer } from '../basic/SessionHTMLRenderer';
 import { updateConfirmModal } from '../../state/ducks/modalDialog';
 import { SpacerLG } from '../basic/Text';
@@ -10,6 +10,10 @@ import { Dispatch } from '@reduxjs/toolkit';
 import { shell } from 'electron';
 import { MessageInteraction } from '../../interactions';
 
+export type ConfirmationStatus = 'loading' | 'success' | 'error';
+// TODO expand support for other confirmation actions
+export type ConfirmationType = 'delete-conversation';
+
 export interface SessionConfirmDialogProps {
   message?: string;
   messageSub?: string;
@@ -29,6 +33,7 @@ export interface SessionConfirmDialogProps {
    * function to run on close click. Closes modal after execution by default
    */
   onClickCancel?: () => any;
+
   okText?: string;
   cancelText?: string;
   hideCancel?: boolean;
@@ -38,6 +43,9 @@ export interface SessionConfirmDialogProps {
   iconSize?: SessionIconSize;
   shouldShowConfirm?: boolean | undefined;
   showExitIcon?: boolean | undefined;
+  status?: ConfirmationStatus;
+  confirmationType?: ConfirmationType;
+  conversationId?: string;
 }
 
 export const SessionConfirm = (props: SessionConfirmDialogProps) => {
@@ -73,8 +81,10 @@ export const SessionConfirm = (props: SessionConfirmDialogProps) => {
         await onClickOk();
       } catch (e) {
         window.log.warn(e);
+        window.inboxStore?.dispatch(updateConfirmModal({ ...props, status: 'error' }));
       } finally {
         setIsLoading(false);
+        window.inboxStore?.dispatch(updateConfirmModal({ ...props, status: 'success' }));
       }
     }
 
@@ -102,6 +112,12 @@ export const SessionConfirm = (props: SessionConfirmDialogProps) => {
     window.inboxStore?.dispatch(updateConfirmModal(null));
   };
 
+  useEffect(() => {
+    if (isLoading) {
+      window.inboxStore?.dispatch(updateConfirmModal({ ...props, status: 'loading' }));
+    }
+  }, [isLoading]);
+
   return (
     <SessionWrapperModal
       title={title}
diff --git a/ts/components/leftpane/conversation-list-item/MessageItem.tsx b/ts/components/leftpane/conversation-list-item/MessageItem.tsx
index dbffb1b45..6c55d0c6d 100644
--- a/ts/components/leftpane/conversation-list-item/MessageItem.tsx
+++ b/ts/components/leftpane/conversation-list-item/MessageItem.tsx
@@ -3,9 +3,11 @@ import { isEmpty } from 'lodash';
 import React from 'react';
 import { useSelector } from 'react-redux';
 import {
+  useConfirmModalStatusAndType,
   useConversationPropsById,
   useHasUnread,
   useIsPrivate,
+  useIsPublic,
   useIsTyping,
 } from '../../../hooks/useParamSelector';
 import { isSearching } from '../../../state/selectors/search';
@@ -14,6 +16,7 @@ import { TypingAnimation } from '../../conversation/TypingAnimation';
 import { MessageBody } from '../../conversation/message/message-content/MessageBody';
 import { OutgoingMessageStatus } from '../../conversation/message/message-content/OutgoingMessageStatus';
 import { useConvoIdFromContext } from './ConvoIdContext';
+import { assertUnreachable } from '../../../types/sqlSharedTypes';
 
 function useLastMessageFromConvo(convoId: string) {
   const convoProps = useConversationPropsById(convoId);
@@ -27,6 +30,7 @@ export const MessageItem = () => {
   const conversationId = useConvoIdFromContext();
   const lastMessage = useLastMessageFromConvo(conversationId);
   const isGroup = !useIsPrivate(conversationId);
+  const isCommunity = useIsPublic(conversationId);
 
   const hasUnread = useHasUnread(conversationId);
   const isConvoTyping = useIsTyping(conversationId);
@@ -34,10 +38,37 @@ export const MessageItem = () => {
 
   const isSearchingMode = useSelector(isSearching);
 
+  const confirmModal = useConfirmModalStatusAndType();
+
   if (!lastMessage && !isConvoTyping) {
     return null;
   }
-  const text = lastMessage?.text || '';
+
+  let text = lastMessage?.text || '';
+  if (confirmModal?.conversationId === conversationId && confirmModal?.type) {
+    window.log.debug(`WIP: updating status for ${confirmModal?.type} ${confirmModal.status}`);
+    switch (confirmModal?.type) {
+      case 'delete-conversation':
+        const failText = isCommunity
+          ? ''
+          : isGroup
+          ? window.i18n('leaveGroupFailed')
+          : window.i18n('deleteConversationFailed');
+
+        text =
+          confirmModal.status === 'error'
+            ? failText
+            : confirmModal.status === 'loading'
+            ? window.i18n('leaving')
+            : '';
+        break;
+      default:
+        assertUnreachable(
+          confirmModal?.type,
+          `MessageItem: Missing case error "${confirmModal?.type}"`
+        );
+    }
+  }
 
   if (isEmpty(text)) {
     return null;
diff --git a/ts/components/menu/Menu.tsx b/ts/components/menu/Menu.tsx
index f9e277815..e4acdfe40 100644
--- a/ts/components/menu/Menu.tsx
+++ b/ts/components/menu/Menu.tsx
@@ -29,6 +29,7 @@ import {
   showBanUserByConvoId,
   showInviteContactByConvoId,
   showLeaveGroupByConvoId,
+  showLeavePrivateConversationbyConvoId,
   showRemoveModeratorsByConvoId,
   showUnbanUserByConvoId,
   showUpdateGroupNameByConvoId,
@@ -174,6 +175,7 @@ export const DeleteGroupOrCommunityMenuItem = () => {
 
 export const LeaveGroupMenuItem = () => {
   const convoId = useConvoIdFromContext();
+  const username = useConversationUsername(convoId) || convoId;
   const isPublic = useIsPublic(convoId);
   const isLeft = useIsLeft(convoId);
   const isKickedFromGroup = useIsKickedFromGroup(convoId);
@@ -183,7 +185,7 @@ export const LeaveGroupMenuItem = () => {
     return (
       <Item
         onClick={() => {
-          showLeaveGroupByConvoId(convoId);
+          showLeaveGroupByConvoId(convoId, username);
         }}
       >
         {window.i18n('leaveGroup')}
@@ -447,6 +449,7 @@ export const DeleteMessagesMenuItem = () => {
  */
 export const DeletePrivateConversationMenuItem = () => {
   const convoId = useConvoIdFromContext();
+  const username = useConversationUsername(convoId) || convoId;
   const isRequest = useIsIncomingRequest(convoId);
   const isPrivate = useIsPrivate(convoId);
 
@@ -456,11 +459,8 @@ export const DeletePrivateConversationMenuItem = () => {
 
   return (
     <Item
-      onClick={async () => {
-        await getConversationController().delete1o1(convoId, {
-          fromSyncMessage: false,
-          justHidePrivate: true,
-        });
+      onClick={() => {
+        showLeavePrivateConversationbyConvoId(convoId, username);
       }}
     >
       {window.i18n('deleteConversation')}
diff --git a/ts/hooks/useParamSelector.ts b/ts/hooks/useParamSelector.ts
index df837c162..783163399 100644
--- a/ts/hooks/useParamSelector.ts
+++ b/ts/hooks/useParamSelector.ts
@@ -267,3 +267,14 @@ export function useMentionedUs(conversationId?: string): boolean {
 export function useIsTyping(conversationId?: string): boolean {
   return useConversationPropsById(conversationId)?.isTyping || false;
 }
+
+export function useConfirmModalStatusAndType() {
+  return useSelector((state: StateType) => {
+    if (!state.modals.confirmModal) {
+      return null;
+    }
+
+    const { status, confirmationType: type, conversationId } = state.modals.confirmModal;
+    return { status, type, conversationId };
+  });
+}
diff --git a/ts/interactions/conversationInteractions.ts b/ts/interactions/conversationInteractions.ts
index 6b6c7ca27..88e34af45 100644
--- a/ts/interactions/conversationInteractions.ts
+++ b/ts/interactions/conversationInteractions.ts
@@ -225,48 +225,90 @@ export async function showUpdateGroupMembersByConvoId(conversationId: string) {
   window.inboxStore?.dispatch(updateGroupMembersModal({ conversationId }));
 }
 
-export function showLeaveGroupByConvoId(conversationId: string) {
+export function showLeavePrivateConversationbyConvoId(conversationId: string, name: string) {
+  const conversation = getConversationController().get(conversationId);
+
+  if (!conversation.isPrivate()) {
+    throw new Error('showLeavePrivateConversationDialog() called with a non private convo.');
+  }
+
+  const onClickClose = () => {
+    window?.inboxStore?.dispatch(updateConfirmModal(null));
+  };
+
+  const onClickOk = async () => {
+    await getConversationController().delete1o1(conversationId, {
+      fromSyncMessage: false,
+      justHidePrivate: true,
+    });
+    onClickClose();
+  };
+
+  window?.inboxStore?.dispatch(
+    updateConfirmModal({
+      title: window.i18n('deleteConversation'),
+      message: window.i18n('deleteConversationConfirmation', [name]),
+      onClickOk,
+      okText: window.i18n('delete'),
+      okTheme: SessionButtonColor.Danger,
+      onClickClose,
+      confirmationType: 'delete-conversation',
+      conversationId,
+    })
+  );
+}
+
+export function showLeaveGroupByConvoId(conversationId: string, name?: string) {
   const conversation = getConversationController().get(conversationId);
 
   if (!conversation.isGroup()) {
     throw new Error('showLeaveGroupDialog() called with a non group convo.');
   }
 
-  const title = window.i18n('leaveGroup');
-  const message = window.i18n('leaveGroupConfirmation');
+  const isClosedGroup = conversation.isClosedGroup() || false;
+  const isPublic = conversation.isPublic() || false;
   const isAdmin = (conversation.get('groupAdmins') || []).includes(
     UserUtils.getOurPubKeyStrFromCache()
   );
-  const isClosedGroup = conversation.isClosedGroup() || false;
-  const isPublic = conversation.isPublic() || false;
 
   // if this is a community, or we legacy group are not admin, we can just show a confirmation dialog
+
+  const onClickClose = () => {
+    window?.inboxStore?.dispatch(updateConfirmModal(null));
+  };
+
+  const onClickOk = async () => {
+    if (isPublic) {
+      await getConversationController().deleteCommunity(conversation.id, {
+        fromSyncMessage: false,
+      });
+    } else {
+      await getConversationController().deleteClosedGroup(conversation.id, {
+        fromSyncMessage: false,
+        sendLeaveMessage: true,
+      });
+    }
+    onClickClose();
+  };
+
+  // TODO Communities don't need confirmation modal and have different logic
   if (isPublic || (isClosedGroup && !isAdmin)) {
-    const onClickClose = () => {
-      window.inboxStore?.dispatch(updateConfirmModal(null));
-    };
     window.inboxStore?.dispatch(
       updateConfirmModal({
-        title,
-        message,
-        onClickOk: async () => {
-          if (isPublic) {
-            await getConversationController().deleteCommunity(conversation.id, {
-              fromSyncMessage: false,
-            });
-          } else {
-            await getConversationController().deleteClosedGroup(conversation.id, {
-              fromSyncMessage: false,
-              sendLeaveMessage: true,
-            });
-          }
-          onClickClose();
-        },
+        title: isPublic ? window.i18n('leaveCommunity') : window.i18n('leaveGroup'),
+        message: window.i18n('leaveGroupConfirmation', name ? [name] : undefined),
+        onClickOk,
+        okText: window.i18n('delete'),
+        okTheme: SessionButtonColor.Danger,
         onClickClose,
+        confirmationType: 'delete-conversation',
+        conversationId,
       })
     );
     return;
   }
+
+  // TODO use different admin modal from figma with add another admin option
   window.inboxStore?.dispatch(
     adminLeaveClosedGroup({
       conversationId,
@@ -354,7 +396,7 @@ export function deleteAllMessagesByConvoIdWithConfirmation(conversationId: strin
   window?.inboxStore?.dispatch(
     updateConfirmModal({
       title: window.i18n('deleteMessages'),
-      message: window.i18n('deleteConversationConfirmation'),
+      message: window.i18n('deleteMessagesConfirmation'),
       onClickOk,
       okTheme: SessionButtonColor.Danger,
       onClickClose,
diff --git a/ts/session/conversations/ConversationController.ts b/ts/session/conversations/ConversationController.ts
index 0dddc0e1a..9a7d93a5f 100644
--- a/ts/session/conversations/ConversationController.ts
+++ b/ts/session/conversations/ConversationController.ts
@@ -266,6 +266,7 @@ export class ConversationController {
       conversation.set({
         priority: CONVERSATION_PRIORITIES.hidden,
       });
+      // TODO based on some sort of arg we should remove the contacts messages
       // We don't remove entries from the contacts wrapper, so better keep corresponding convo volatile info for now (it will be pruned if needed)
       await conversation.commit(); // this updates the wrappers content to reflect the hidden state
     } else {
diff --git a/ts/types/LocalizerKeys.ts b/ts/types/LocalizerKeys.ts
index 1c7f7a0e0..243495b5a 100644
--- a/ts/types/LocalizerKeys.ts
+++ b/ts/types/LocalizerKeys.ts
@@ -100,7 +100,11 @@ export type LocalizerKeys =
   | 'deleteMessagesQuestion'
   | 'deleteMessageQuestion'
   | 'deleteMessages'
+  | 'deleteMessagesConfirmation'
   | 'deleteConversation'
+  | 'deleteConversationConfirmation'
+  | 'deleteConversationFailed'
+  | 'leaving'
   | 'deleted'
   | 'messageDeletedPlaceholder'
   | 'from'
@@ -111,7 +115,6 @@ export type LocalizerKeys =
   | 'groupMembers'
   | 'moreInformation'
   | 'resend'
-  | 'deleteConversationConfirmation'
   | 'clear'
   | 'clearAllData'
   | 'deleteAccountWarning'
@@ -258,6 +261,9 @@ export type LocalizerKeys =
   | 'leaveAndRemoveForEveryone'
   | 'leaveGroupConfirmation'
   | 'leaveGroupConfirmationAdmin'
+  | 'leaveGroupFailed'
+  | 'leaveCommunity'
+  | 'leaveCommunityFailed'
   | 'cannotRemoveCreatorFromGroup'
   | 'cannotRemoveCreatorFromGroupDesc'
   | 'noContactsForGroup'