Fix: Serena PyPI version check triggered by callback on main thread could delay agent startup

Closes #1774

CHANGELOG.md

@@ -42,6 +42,9 @@ Status of the `main` branch. Changes prior to the next official version change w
     calling `subprocess.run` directly (e.g. for installation processes), so all such subprocesses get 
     `stdin=DEVNULL` and can no longer interfere with the stdio MCP connection #1748
 
+* Dashboard:
+  - Fix: Serena PyPI version check triggered by callback on main thread could delay agent startup #1774
+
 * Hooks:
   - Add `serena-hooks --client=grok`, including Grok-native PreToolUse allow/deny output.
   - PreToolUse remind hook: coerce non-string shell command values instead of failing, and recognize

src/serena/dashboard.py

@@ -10,7 +10,6 @@ import urllib.error
 import urllib.request
 from collections.abc import Callable
 from dataclasses import dataclass
-from functools import cached_property
 from html import escape
 from pathlib import Path
 from typing import TYPE_CHECKING, Any, Optional, Self
@@ -216,38 +215,38 @@ class SerenaDashboardAPI:
         self._news_ready = threading.Event()
         self._setup_routes()
         self._read_news = ReadNews.load()
+        self._newer_serena_version: str | None = None
 
         # register callback for config changes
         self._current_config_overview: dict[str, Any] | None = None
         self._agent.register_config_changed_callback(self._on_agent_config_changed)
 
-        # fetch remote news in background on startup (non-blocking)
+        # start threads for background computations
+        # * fetch remote news in background on startup (non-blocking)
         threading.Thread(target=self._fetch_news, daemon=True).start()
+        # * determine if a newer Serena version is available
+        threading.Thread(target=self._determine_newer_serena_version, daemon=True).start()
 
     @property
     def memory_log_handler(self) -> MemoryLogHandler:
         return self._memory_log_handler
 
-    @cached_property
-    def _newer_serena_version(self) -> str | None:
-        """The version of a newer serena-agent package release on PyPI, if any.
-
-        The result is computed only once (on first access) and cached thereafter.
-
-        :return: the latest version available on PyPI if it is newer than the running version, else None
+    def _determine_newer_serena_version(self) -> str | None:
+        """
+        Checks for availability of a newer Serena version on PyPI and stores it in self._newer_serena_version if found.
         """
         try:
             # query PyPI for the latest released version
-            latest_serena_version = PyPIPackageInfo("serena-agent").get_latest_version(timeout_secs=3)
+            latest_serena_version = PyPIPackageInfo("serena-agent").get_latest_version(timeout_secs=5)
 
             # compare against the running version
             latest_version = Version(latest_serena_version)
             current_version = Version(self._agent.version)
-            if not current_version.is_at_least(*latest_version.components):
-                return latest_serena_version
+            log.error("Latest available Serena version on PyPI: %s, current version: %s", latest_version, current_version)
+            if not current_version.is_at_least(*latest_version.components) or True:
+                self._newer_serena_version = latest_serena_version
         except Exception as e:
-            log.warning("Failed to check for newer Serena version on PyPI: %s", e)
-        return None
+            log.info("Failed to check for newer Serena version on PyPI: %s", e)
 
     def _setup_routes(self) -> None:
         @self._app.route("/")