diff --git a/packages/code-link-cli/src/controller.ts b/packages/code-link-cli/src/controller.ts
index 842bfd738..60edcbd72 100644
--- a/packages/code-link-cli/src/controller.ts
+++ b/packages/code-link-cli/src/controller.ts
@@ -1095,8 +1095,6 @@ async function executeEffect(
  * Starts the sync controller with the given configuration
  */
 export async function start(config: Config): Promise<void> {
-    status("Waiting for Plugin connection...")
-
     const hashTracker = createHashTracker()
     const fileMetadataCache = new FileMetadataCache()
     const pendingRenameConfirmations = new Map<string, PendingRenameConfirmation>()
@@ -1163,6 +1161,8 @@ export async function start(config: Config): Promise<void> {
         throw new Error("TLS certificate generation failed")
     }
 
+    status("Waiting for Plugin connection...")
+
     // WebSocket Connection (always WSS)
     const connection = await initConnection(config.port, certs)
 
diff --git a/packages/code-link-cli/src/helpers/certs.ts b/packages/code-link-cli/src/helpers/certs.ts
index 18c1d5b04..b0ea4ebce 100644
--- a/packages/code-link-cli/src/helpers/certs.ts
+++ b/packages/code-link-cli/src/helpers/certs.ts
@@ -91,6 +91,7 @@ export async function getOrCreateCerts(): Promise<CertBundle | null> {
 
         status("Generating local certificates to connect securely. You may be asked for your password.")
         await generateCerts(mkcertPath)
+        status("Successfully generated certificates.")
 
         const key = await fs.readFile(SERVER_KEY_PATH, "utf-8")
         const cert = await fs.readFile(SERVER_CERT_PATH, "utf-8")