diff --git a/frontend/cli/cmd_dev.go b/frontend/cli/cmd_dev.go
index 455ac99169..829e4b8957 100644
--- a/frontend/cli/cmd_dev.go
+++ b/frontend/cli/cmd_dev.go
@@ -50,6 +50,9 @@ func (d *devCmd) Run(
 	verbClient ftlv1connect.VerbServiceClient,
 ) error {
 	startTime := time.Now()
+	logger := log.FromContext(ctx)
+	ctx, cancel := context.WithCancel(ctx)
+	defer cancel()
 	if len(d.Build.Dirs) == 0 {
 		d.Build.Dirs = projConfig.AbsModuleDirs()
 	}
@@ -78,6 +81,7 @@ func (d *devCmd) Run(
 		return nil
 	}
 	statusManager := terminal.FromContext(ctx)
+	defer statusManager.Close()
 	starting := statusManager.NewStatus("\u001B[92mStarting FTL Server 🚀\u001B[39m")
 
 	bindAllocator, err := bind.NewBindAllocator(d.ServeCmd.Bind, 1)
@@ -102,7 +106,9 @@ func (d *devCmd) Run(
 		}
 
 		g.Go(func() error {
-			return d.ServeCmd.run(ctx, projConfig, cm, sm, optional.Some(controllerReady), true, bindAllocator, controllerClient, provisionerClient, schemaEventSourceFactory, verbClient, true, devModeEndpointUpdates)
+			err := d.ServeCmd.run(ctx, projConfig, cm, sm, optional.Some(controllerReady), true, bindAllocator, controllerClient, provisionerClient, schemaEventSourceFactory, verbClient, true, devModeEndpointUpdates)
+			cancel()
+			return err
 		})
 	}
 
@@ -133,5 +139,10 @@ func (d *devCmd) Run(
 		return engine.Dev(ctx, d.Watch)
 	})
 
-	return g.Wait()
+	err = g.Wait()
+	if err != nil {
+		logger.Errorf(err, "error during dev")
+		return fmt.Errorf("error during dev: %w", err)
+	}
+	return nil
 }
diff --git a/frontend/cli/cmd_serve.go b/frontend/cli/cmd_serve.go
index b63cd6af2c..c2c6d7b8a8 100644
--- a/frontend/cli/cmd_serve.go
+++ b/frontend/cli/cmd_serve.go
@@ -116,7 +116,11 @@ func (s *serveCommonConfig) run(
 			// allow usage of --background and --stop together to "restart" the background process
 			_ = KillBackgroundServe(logger) //nolint:errcheck // ignore error here if the process is not running
 		}
-
+		_, err := controllerClient.Ping(ctx, connect.NewRequest(&ftlv1.PingRequest{}))
+		if err == nil {
+			// The controller is already running, bail out.
+			return fmt.Errorf("controller is already running")
+		}
 		if err := runInBackground(logger); err != nil {
 			return err
 		}
@@ -136,7 +140,11 @@ func (s *serveCommonConfig) run(
 	if s.Stop {
 		return KillBackgroundServe(logger)
 	}
-
+	_, err := controllerClient.Ping(ctx, connect.NewRequest(&ftlv1.PingRequest{}))
+	if err == nil {
+		// The controller is already running, bail out.
+		return fmt.Errorf("controller is already running")
+	}
 	if s.Provisioners > 0 {
 		logger.Debugf("Starting FTL with %d controller(s) and %d provisioner(s)", s.Controllers, s.Provisioners)
 	} else {
@@ -154,7 +162,7 @@ func (s *serveCommonConfig) run(
 			s.ObservabilityConfig.ExportOTEL = true
 		}
 	}
-	err := observability.Init(ctx, false, "", "ftl-serve", ftl.Version, s.ObservabilityConfig)
+	err = observability.Init(ctx, false, "", "ftl-serve", ftl.Version, s.ObservabilityConfig)
 	if err != nil {
 		return fmt.Errorf("observability init failed: %w", err)
 	}