diff --git a/windows/winui/MainWindow.xaml.cpp b/windows/winui/MainWindow.xaml.cpp
index e7370feb..1ec29d90 100644
--- a/windows/winui/MainWindow.xaml.cpp
+++ b/windows/winui/MainWindow.xaml.cpp
@@ -3307,6 +3307,10 @@ fire_and_forget MainWindow::ConfigureAICommitClick(IInspectable const&, RoutedEv
 }
 
 void MainWindow::CheckForUpdatesClick(IInspectable const&, RoutedEventArgs const&) {
+    checkForUpdates();
+}
+
+void MainWindow::checkForUpdates() {
 #if defined(_M_ARM64)
     session_->checkForUpdates("arm64");
 #elif defined(_M_X64)
@@ -4013,6 +4017,10 @@ void MainWindow::RootLoaded(IInspectable const&, RoutedEventArgs const&) {
     } else {
         showWorkbenchSurface();
     }
+    if (!startupUpdateCheckStarted_) {
+        startupUpdateCheckStarted_ = true;
+        checkForUpdates();
+    }
 }
 
 void MainWindow::showWelcomeSurface() {
diff --git a/windows/winui/MainWindow.xaml.h b/windows/winui/MainWindow.xaml.h
index f937868f..3a212e4a 100644
--- a/windows/winui/MainWindow.xaml.h
+++ b/windows/winui/MainWindow.xaml.h
@@ -227,6 +227,7 @@ struct MainWindow : MainWindowT<MainWindow> {
 private:
     void showWelcomeSurface();
     void showWorkbenchSurface();
+    void checkForUpdates();
     void renderWelcomeProjects(std::string query = {});
     struct NavigationTarget {
         std::string relativePath;
@@ -412,6 +413,7 @@ struct MainWindow : MainWindowT<MainWindow> {
     bool externalConflictVisible_ = false;
     bool terminalUiUpdating_ = false;
     bool showWelcomeOnLoad_ = false;
+    bool startupUpdateCheckStarted_ = false;
     std::uint64_t terminalRevision_ = 0;
     double bottomPanelHeight_ = 290.0;
 };