diff --git a/internal/proxy/director/layer/authn/oidc/client.go b/internal/proxy/director/layer/authn/oidc/client.go
index e65203a..5f2b1c5 100644
--- a/internal/proxy/director/layer/authn/oidc/client.go
+++ b/internal/proxy/director/layer/authn/oidc/client.go
@@ -69,7 +69,7 @@ func (c *Client) login(w http.ResponseWriter, r *http.Request, sess *sessions.Se
 	sess.Values[sessionKeyPostLoginRedirectURL] = postLoginRedirectURL
 
 	if err := sess.Save(r, w); err != nil {
-		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not save session"))
+		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not save session"))
 
 		return
 	}
diff --git a/internal/proxy/director/layer/queue/queue.go b/internal/proxy/director/layer/queue/queue.go
index e07638e..4e2e7dc 100644
--- a/internal/proxy/director/layer/queue/queue.go
+++ b/internal/proxy/director/layer/queue/queue.go
@@ -54,7 +54,7 @@ func (q *Queue) Middleware(layer *store.Layer) proxy.Middleware {
 
 			options, err := fromStoreOptions(layer.Options, q.defaultKeepAlive)
 			if err != nil {
-				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not parse layer options"))
+				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not parse layer options"))
 				return
 			}
 
@@ -89,7 +89,7 @@ func (q *Queue) Middleware(layer *store.Layer) proxy.Middleware {
 
 			rank, err := q.adapter.Touch(ctx, queueName, sessionID)
 			if err != nil {
-				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not retrieve session rank"))
+				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not update queue session rank"))
 				return
 			}
 
@@ -142,7 +142,7 @@ func (q *Queue) renderQueuePage(w http.ResponseWriter, r *http.Request, queueNam
 
 	status, err := q.adapter.Status(ctx, queueName)
 	if err != nil {
-		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not retrieve queue status"))
+		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not retrieve queue status"))
 		return
 	}
 
@@ -191,7 +191,7 @@ func (q *Queue) renderQueuePage(w http.ResponseWriter, r *http.Request, queueNam
 	var buf bytes.Buffer
 
 	if err := q.tmpl.ExecuteTemplate(&buf, "queue", templateData); err != nil {
-		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not render queue page"))
+		director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not render queue page"))
 		return
 	}
 
diff --git a/internal/proxy/director/layer/rewriter/layer.go b/internal/proxy/director/layer/rewriter/layer.go
index db85eff..3dd1e2e 100644
--- a/internal/proxy/director/layer/rewriter/layer.go
+++ b/internal/proxy/director/layer/rewriter/layer.go
@@ -31,7 +31,7 @@ func (l *Layer) Middleware(layer *store.Layer) proxy.Middleware {
 
 			options, err := fromStoreOptions(layer.Options)
 			if err != nil {
-				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.New("could not parse layer options"))
+				director.HandleError(ctx, w, r, http.StatusInternalServerError, errors.Wrap(err, "could not parse layer options"))
 				return
 			}