diff --git a/src/praisonai-desktop/engine/server.py b/src/praisonai-desktop/engine/server.py
index b410c5f5e..598ec02ef 100644
--- a/src/praisonai-desktop/engine/server.py
+++ b/src/praisonai-desktop/engine/server.py
@@ -1674,11 +1674,16 @@ def do_POST(self):
             except (ValueError, TypeError):
                 self.send_error(400)
                 return
-            saved = save_settings(patch)
             if "launch_at_login" in patch:
-                saved = dict(saved)
-                saved["launch_at_login_result"] = set_launch_at_login(
-                    bool(patch["launch_at_login"]))
+                # Persist what actually happened, not what was asked. Writing
+                # the request first made the toggle report a login item that
+                # was never registered -- and survive restarts saying so.
+                result = set_launch_at_login(bool(patch["launch_at_login"]))
+                patch = {**patch, "launch_at_login": bool(result.get("enabled"))}
+                saved = dict(save_settings(patch))
+                saved["launch_at_login_result"] = result
+            else:
+                saved = save_settings(patch)
             self._json(saved)
             return
 
diff --git a/src/praisonai-desktop/engine/test_portability.py b/src/praisonai-desktop/engine/test_portability.py
index 211b4a0b9..219364784 100644
--- a/src/praisonai-desktop/engine/test_portability.py
+++ b/src/praisonai-desktop/engine/test_portability.py
@@ -689,5 +689,87 @@ def test_the_vocabulary_is_the_eleven_events_expected(self):
         self.assertEqual(self._emitted_events(), self.EXPECTED)
 
 
+class LaunchAtLogin(unittest.TestCase):
+    """The toggle must persist what actually happened, not what was asked.
+
+    Registering a login item only works in the installed macOS .app bundle:
+    `set_launch_at_login` returns {"enabled": False} everywhere else -- every
+    Windows and Linux user, and any macOS user running from a checkout. The
+    handler used to save the *request* and merely attach the honest result to
+    the response, which nothing read. So the toggle rendered on, persisted, and
+    survived restarts while no login item existed anywhere.
+    """
+
+    def setUp(self):
+        import io
+
+        self.home = pathlib.Path(tempfile.mkdtemp(prefix="praison-launch-"))
+        self._data_dir = server.DATA_DIR
+        self._settings_path = server.SETTINGS_PATH
+        self._set = server.set_launch_at_login
+        server.DATA_DIR = self.home
+        server.SETTINGS_PATH = self.home / "settings.json"
+        self._io = io
+
+    def tearDown(self):
+        server.DATA_DIR = self._data_dir
+        server.SETTINGS_PATH = self._settings_path
+        server.set_launch_at_login = self._set
+        shutil.rmtree(self.home, ignore_errors=True)
+
+    def _post_settings(self, patch):
+        """Drive the real /settings POST handler and return its JSON reply."""
+        body = json.dumps(patch).encode()
+
+        class FakeHandler(server.Handler):
+            def __init__(self):
+                self.path = "/settings"
+                self.headers = {"Content-Length": str(len(body))}
+                self.rfile = self._io_module.BytesIO(body)
+                self.wfile = self._io_module.BytesIO()
+
+            def send_response(self, *_a, **_k):
+                pass
+
+            def send_header(self, *_a, **_k):
+                pass
+
+            def end_headers(self):
+                pass
+
+        FakeHandler._io_module = self._io
+        handler = FakeHandler()
+        handler.do_POST()
+        raw = handler.wfile.getvalue()
+        return json.loads(raw) if raw else {}
+
+    def test_a_request_that_could_not_register_is_not_persisted_as_on(self):
+        # Stub the platform action to the answer every non-bundle host gives.
+        server.set_launch_at_login = lambda on: {
+            "ok": False, "enabled": False,
+            "message": "Only available in the installed app."}
+
+        reply = self._post_settings({"launch_at_login": True})
+
+        self.assertFalse(reply.get("launch_at_login"),
+                         "the toggle reported on though nothing was registered")
+        self.assertEqual(
+            reply.get("launch_at_login_result", {}).get("message"),
+            "Only available in the installed app.",
+            "the response dropped the explanation for why it did not stick")
+        self.assertFalse(
+            server.load_settings().get("launch_at_login"),
+            "the un-registered login item survived to the next launch")
+
+    def test_a_request_that_registered_is_persisted_as_on(self):
+        server.set_launch_at_login = lambda on: {"ok": True, "enabled": bool(on)}
+
+        reply = self._post_settings({"launch_at_login": True})
+
+        self.assertTrue(reply.get("launch_at_login"))
+        self.assertTrue(server.load_settings().get("launch_at_login"),
+                        "a real registration did not persist")
+
+
 if __name__ == "__main__":
     unittest.main(verbosity=2)
diff --git a/src/praisonai-desktop/ui/index.html b/src/praisonai-desktop/ui/index.html
index 9e67f1c62..fb73636f7 100644
--- a/src/praisonai-desktop/ui/index.html
+++ b/src/praisonai-desktop/ui/index.html
@@ -1832,8 +1832,19 @@ <h2>Fine-tune a model</h2>
 async function saveCfg(patch){
   CFG={...CFG,...patch}; applyPrefs(CFG);
   cfg = {...cfg, ...patch};
-  await fetch('http://127.0.0.1:'+PORT+'/settings',{method:'POST',
-    headers:{'content-type':'application/json'},body:JSON.stringify(patch)});
+  let saved=null;
+  try{
+    saved=await (await fetch('http://127.0.0.1:'+PORT+'/settings',{method:'POST',
+      headers:{'content-type':'application/json'},body:JSON.stringify(patch)})).json();
+  }catch{}
+  // The server persists what actually happened, not what we asked. Reconcile
+  // any key it wrote back so the current session never shows a value that was
+  // never saved -- e.g. "Open at login" the OS refused to register.
+  if(saved && typeof saved==='object'){
+    for(const k of Object.keys(patch)) if(k in saved){ CFG[k]=saved[k]; cfg[k]=saved[k]; }
+    applyPrefs(CFG);
+  }
+  return saved;
 }
 
 function control(def, onChange){
@@ -1985,10 +1996,18 @@ <h2>Fine-tune a model</h2>
     err.style.display='none';
     if(def.confirm && def.confirm.when(cfgGet(def.key),nv)
        && !await askConfirm(def.confirm.message,{ok:'Continue'})) { renderSettings(); return; }
-    await saveCfg({[def.key]:nv});
+    const saved=await saveCfg({[def.key]:nv});
     if(def.key==='theme') applyTheme(nv);
     if(def.key==='model') modelName.textContent=nv;
     renderSettings();
+    // If the OS declined to register the login item, the toggle has already
+    // snapped back to the persisted value above; tell the user why.
+    if(def.key==='launch_at_login' && saved && saved.launch_at_login_result
+       && nv && !saved.launch_at_login_result.enabled){
+      const r=document.getElementById('setting-launch_at_login');
+      const w=r&&r.querySelector('.warn');
+      if(w){ w.textContent=saved.launch_at_login_result.message||'Not available.'; w.style.display=''; }
+    }
   };
 
   const multiline = def.control.kind==='text' && def.control.multiline;