diff --git a/pkg/agent/tunnelserver/tunnelserver.go b/pkg/agent/tunnelserver/tunnelserver.go
index 22a6bad66..39b24e9df 100644
--- a/pkg/agent/tunnelserver/tunnelserver.go
+++ b/pkg/agent/tunnelserver/tunnelserver.go
@@ -129,8 +129,18 @@ func (t *tunnelServer) RunWithResult(
 		errChan <- s.Serve(lis)
 	}()
 
+	stopCtx, stopCancel := context.WithCancel(ctx)
+	defer stopCancel()
+	go func() {
+		<-stopCtx.Done()
+		s.Stop()
+	}()
+
 	select {
 	case err := <-errChan:
+		if t.result != nil {
+			return t.result, nil
+		}
 		return nil, err
 	case <-ctx.Done():
 		return t.result, nil
diff --git a/pkg/tunnel/pipebridge.go b/pkg/tunnel/pipebridge.go
index 4562d74a6..ce4e82ec7 100644
--- a/pkg/tunnel/pipebridge.go
+++ b/pkg/tunnel/pipebridge.go
@@ -62,10 +62,11 @@ func (pb *PipeBridge) RunPair(
 		handlerChan <- handlerFn(cancelCtx, pb.StdoutReader, pb.StdinWriter)
 	}()
 
-	return awaitPair(tunnelChan, handlerChan, pb.StdoutWriter, pb.StdinWriter)
+	return awaitPair(cancel, tunnelChan, handlerChan, pb.StdoutWriter, pb.StdinWriter)
 }
 
 func awaitPair(
+	cancel context.CancelFunc,
 	tunnelChan, handlerChan <-chan error,
 	stdoutWriter, stdinWriter *os.File,
 ) error {
@@ -78,6 +79,7 @@ func awaitPair(
 		default:
 		}
 	case tunnelErr = <-tunnelChan:
+		cancel()
 		_ = stdoutWriter.Close()
 		_ = stdinWriter.Close()
 		handlerErr = <-handlerChan