diff --git a/cockatrice/src/interface/window_main.cpp b/cockatrice/src/interface/window_main.cpp
index f0e616615..b49146101 100644
--- a/cockatrice/src/interface/window_main.cpp
+++ b/cockatrice/src/interface/window_main.cpp
@@ -708,6 +708,12 @@ void MainWindow::applyStartupDestination()
         return;
     }
 
+    // A cockatrice:// link owns the startup connection while its chain runs;
+    // connecting here would race (and tear down) the link's own connection.
+    if (skipStartupAutoConnect) {
+        return;
+    }
+
     const int destination = SettingsCache::instance().tabs().getStartupTabIndex();
     if (destination != StartupTab::StartupTabServer && destination != StartupTab::StartupTabServerRoom) {
         return;
@@ -936,6 +942,16 @@ void MainWindow::onUrlChainFinished(bool connected)
     if (connected || !skipStartupAutoConnect || getRemoteClient()->getStatus() != StatusDisconnected) {
         return;
     }
+
+    if (startupDestinationConnectsToServer()) {
+        // Users whose startup tab is a Server / Server Room connect through the
+        // startup destination, not through auto-connect; retry that instead.
+        qCInfo(WindowMainStartupAutoconnectLog) << "URL chain ended without a connection; retrying startup destination";
+        skipStartupAutoConnect = false;
+        applyStartupDestination();
+        return;
+    }
+
     qCInfo(WindowMainStartupAutoconnectLog) << "URL chain ended without a connection; retrying startup connect";
     skipStartupAutoConnect = false;
     attemptStartupAutoConnect();
diff --git a/cockatrice/src/main.cpp b/cockatrice/src/main.cpp
index 3eca19770..1a3d20d6b 100644
--- a/cockatrice/src/main.cpp
+++ b/cockatrice/src/main.cpp
@@ -331,9 +331,17 @@ int main(int argc, char *argv[])
     // URL connects to the server named in the URL, so the window's own startup
     // auto-connect must not race against it (two connectToServer calls tear
     // each other down via doDisconnectFromServer).
-    const bool hasUrlActivation = std::any_of(startupFiles.begin(), startupFiles.end(), [](const QString &file) {
+    bool hasUrlActivation = std::any_of(startupFiles.begin(), startupFiles.end(), [](const QString &file) {
         return file.startsWith(QStringLiteral("cockatrice://"));
     });
+#ifdef Q_OS_MAC
+    // On macOS the launch can arrive through the URL scheme instead of as a
+    // positional argument (captured in pendingMacUrls); count those too or the
+    // window would auto-connect into the link's own connection attempt.
+    hasUrlActivation = hasUrlActivation ||
+                       std::any_of(pendingMacUrls.cbegin(), pendingMacUrls.cend(),
+                                   [](const QString &url) { return url.startsWith(QStringLiteral("cockatrice://")); });
+#endif
     ui.setSkipStartupAutoConnect(hasUrlActivation);
 
     auto handleActivation = [&ui](const QString &file) {