diff --git a/ee/desktop/runner/runner.go b/ee/desktop/runner/runner.go
index f36a8ca6d..a07da2342 100644
--- a/ee/desktop/runner/runner.go
+++ b/ee/desktop/runner/runner.go
@@ -153,7 +153,7 @@ func New(k types.Knapsack, opts ...desktopUsersProcessesRunnerOption) (*DesktopU
 
 	rs, err := runnerserver.New(runner.logger, k)
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("creating desktop runner server: %w", err)
 	}
 
 	runner.runnerServer = rs
diff --git a/ee/desktop/runner/server/server.go b/ee/desktop/runner/server/server.go
index 4fa4a6e1d..52a267a17 100644
--- a/ee/desktop/runner/server/server.go
+++ b/ee/desktop/runner/server/server.go
@@ -39,7 +39,7 @@ type controlRequestIntervalOverrider interface {
 func New(logger log.Logger, controlRequestIntervalOverrider controlRequestIntervalOverrider) (*RunnerServer, error) {
 	listener, err := net.Listen("tcp", "localhost:0")
 	if err != nil {
-		return nil, err
+		return nil, fmt.Errorf("creating net listener: %w", err)
 	}
 
 	rs := &RunnerServer{