diff --git a/public/scripts/group-chats.js b/public/scripts/group-chats.js
index cf371fa1b..8a1a6db46 100644
--- a/public/scripts/group-chats.js
+++ b/public/scripts/group-chats.js
@@ -1005,7 +1005,7 @@ function select_group_chats(groupId, skipAnimation) {
         }
 
         $("#dialogue_popup").data("group_id", groupId);
-        callPopup("<h3>Delete the group?</h3>", "del_group");
+        callPopup('<h3>Delete the group?</h3><p>This will also delete all your chats with that group. If you want to delete a single conversation, select a "View past chats" option in the lower left menu.</p>', "del_group");
     });
 
     updateFavButtonState(group?.fav ?? false);
diff --git a/server.js b/server.js
index ce7484a6d..1998123ea 100644
--- a/server.js
+++ b/server.js
@@ -2181,16 +2181,29 @@ app.post('/deletegroup', jsonParser, async (request, response) => {
 
     const id = request.body.id;
     const pathToGroup = path.join(directories.groups, sanitize(`${id}.json`));
-    const pathToChat = path.join(directories.groupChats, sanitize(`${id}.jsonl`));
+
+    try {
+        // Delete group chats
+        const group = json5.parse(fs.readFileSync(pathToGroup));
+
+        if (group && Array.isArray(group.chats)) {
+            for (const chat of group.chats) {
+                console.log('Deleting group chat', chat);
+                const pathToFile = path.join(directories.groupChats, `${id}.jsonl`);
+
+                if (fs.existsSync(pathToFile)) {
+                    fs.rmSync(pathToFile);
+                }
+            }
+        }
+    } catch (error) {
+        console.error('Could not delete group chats. Clean them up manually.', error);
+    }
 
     if (fs.existsSync(pathToGroup)) {
         fs.rmSync(pathToGroup);
     }
 
-    if (fs.existsSync(pathToChat)) {
-        fs.rmSync(pathToChat);
-    }
-
     return response.send({ ok: true });
 });