diff --git a/packages/desktop-client/src/components/manager/ConfigServer.tsx b/packages/desktop-client/src/components/manager/ConfigServer.tsx
index 7f2b0c152a..2e72d1335c 100644
--- a/packages/desktop-client/src/components/manager/ConfigServer.tsx
+++ b/packages/desktop-client/src/components/manager/ConfigServer.tsx
@@ -56,6 +56,10 @@ export function ElectronServerConfig({
   const [startingSyncServer, setStartingSyncServer] = useState(false);
 
   const onConfigureSyncServer = async () => {
+    if (startingSyncServer) {
+      return; // Prevent multiple clicks
+    }
+
     if (
       isNaN(electronServerPort) ||
       electronServerPort <= 0 ||
@@ -221,23 +225,23 @@ export function ElectronServerConfig({
           >
             <Label title={t('')} style={{ textAlign: 'left', width: '7ch' }} />
             {!electronSyncServerRunning ? (
-              <Button
+              <ButtonWithLoading
                 variant="primary"
                 style={{ padding: 10, width: '8ch' }}
                 onPress={onConfigureSyncServer}
-                isPending={startingSyncServer}
+                isLoading={startingSyncServer}
               >
                 <Trans>Start</Trans>
-              </Button>
+              </ButtonWithLoading>
             ) : (
-              <Button
+              <ButtonWithLoading
                 variant="primary"
                 style={{ padding: 10, width: '8ch' }}
                 onPress={onConfigureSyncServer}
-                isPending={startingSyncServer}
+                isLoading={startingSyncServer}
               >
                 <Trans>Save</Trans>
-              </Button>
+              </ButtonWithLoading>
             )}
           </View>
         </View>
diff --git a/packages/sync-server/src/app.ts b/packages/sync-server/src/app.ts
index 427680116f..62db2b8597 100644
--- a/packages/sync-server/src/app.ts
+++ b/packages/sync-server/src/app.ts
@@ -156,6 +156,15 @@ function parseHTTPSConfig(value: string) {
   return fs.readFileSync(value);
 }
 
+function sendServerStartedMessage() {
+  // Signify to any parent process that the server has started. Used in electron desktop app
+  // @ts-ignore-error electron types
+  process.parentPort?.postMessage({ type: 'server-started' });
+  console.log(
+    'Listening on ' + config.get('hostname') + ':' + config.get('port') + '...',
+  );
+}
+
 export async function run() {
   const portVal = config.get('port');
   const port = typeof portVal === 'string' ? parseInt(portVal) : portVal;
@@ -186,16 +195,12 @@ export async function run() {
       key: parseHTTPSConfig(config.get('https.key')),
       cert: parseHTTPSConfig(config.get('https.cert')),
     };
-    https.createServer(httpsOptions, app).listen(port, hostname);
+    https.createServer(httpsOptions, app).listen(port, hostname, () => {
+      sendServerStartedMessage();
+    });
   } else {
-    app.listen(port, hostname);
+    app.listen(port, hostname, () => {
+      sendServerStartedMessage();
+    });
   }
-
-  // Signify to any parent process that the server has started. Used in electron desktop app
-  // @ts-ignore-error electron types
-  process.parentPort?.postMessage({ type: 'server-started' });
-
-  console.log(
-    'Listening on ' + config.get('hostname') + ':' + config.get('port') + '...',
-  );
 }
diff --git a/upcoming-release-notes/5303.md b/upcoming-release-notes/5303.md
new file mode 100644
index 0000000000..77d6771c7b
--- /dev/null
+++ b/upcoming-release-notes/5303.md
@@ -0,0 +1,6 @@
+---
+category: Bugfix
+authors: [MikesGlitch]
+---
+
+Fix server-started message invoking too early, causing desktop app server configuration flakiness.