diff --git a/reposerver/gpgwatcher.go b/reposerver/gpgwatcher.go
index 9c2c9be790813..5b43d6a24ac76 100644
--- a/reposerver/gpgwatcher.go
+++ b/reposerver/gpgwatcher.go
@@ -19,7 +19,7 @@ func StartGPGWatcher(sourcePath string) error {
 	forceSync := false
 	watcher, err := fsnotify.NewWatcher()
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to create fsnotify Watcher: %w", err)
 	}
 	defer func(watcher *fsnotify.Watcher) {
 		if err = watcher.Close(); err != nil {
@@ -83,7 +83,7 @@ func StartGPGWatcher(sourcePath string) error {
 
 	err = watcher.Add(sourcePath)
 	if err != nil {
-		return err
+		return fmt.Errorf("failed to add a new source to the watcher: %w", err)
 	}
 	<-done
 	return fmt.Errorf("Abnormal termination of GPG watcher, refusing to continue.")
diff --git a/reposerver/server.go b/reposerver/server.go
index 007b7136e41ed..e1d611801c3ec 100644
--- a/reposerver/server.go
+++ b/reposerver/server.go
@@ -102,7 +102,7 @@ func NewServer(metricsServer *metrics.MetricsServer, cache *reposervercache.Cach
 	}
 	repoService := repository.NewService(metricsServer, cache, initConstants, argo.NewResourceTracking(), gitCredsStore, filepath.Join(os.TempDir(), "_argocd-repo"))
 	if err := repoService.Init(); err != nil {
-		return nil, err
+		return nil, fmt.Errorf("failed to initialize the repo service: %w", err)
 	}
 
 	return &ArgoCDRepoServer{