diff --git a/thunar/thunar-io-jobs.c b/thunar/thunar-io-jobs.c
index f118f55f..23941d21 100644
--- a/thunar/thunar-io-jobs.c
+++ b/thunar/thunar-io-jobs.c
@@ -805,6 +805,7 @@ _thunar_io_jobs_trash (ThunarJob  *job,
 {
   ThunarThumbnailCache *thumbnail_cache;
   ThunarApplication    *application;
+  ThunarJobResponse     response;
   GError               *err = NULL;
   GList                *file_list;
   GList                *lp;
@@ -831,6 +832,19 @@ _thunar_io_jobs_trash (ThunarJob  *job,
       /* trash the file or folder */
       g_file_trash (lp->data, exo_job_get_cancellable (EXO_JOB (job)), &err);
 
+      if (err != NULL)
+        {
+          response = thunar_job_ask_delete (job, "%s", err->message);
+
+          g_clear_error (&err);
+
+          if (response == THUNAR_JOB_RESPONSE_CANCEL)
+            break;
+
+          if (response == THUNAR_JOB_RESPONSE_YES)
+            g_file_delete (lp->data, exo_job_get_cancellable (EXO_JOB (job)), &err);
+        }
+
       /* update the thumbnail cache */
       thunar_thumbnail_cache_cleanup_file (thumbnail_cache, lp->data);
     }
diff --git a/thunar/thunar-job.c b/thunar/thunar-job.c
index e6cbe018..119e4d15 100644
--- a/thunar/thunar-job.c
+++ b/thunar/thunar-job.c
@@ -64,6 +64,7 @@ struct _ThunarJobPrivate
 {
   ThunarJobResponse earlier_ask_create_response;
   ThunarJobResponse earlier_ask_overwrite_response;
+  ThunarJobResponse earlier_ask_delete_response;
   ThunarJobResponse earlier_ask_skip_response;
   GList            *total_files;
   guint             n_total_files;
@@ -206,6 +207,7 @@ thunar_job_init (ThunarJob *job)
   job->priv = thunar_job_get_instance_private (job);
   job->priv->earlier_ask_create_response = 0;
   job->priv->earlier_ask_overwrite_response = 0;
+  job->priv->earlier_ask_delete_response = 0;
   job->priv->earlier_ask_skip_response = 0;
   job->priv->n_total_files = 0;
 }
@@ -357,6 +359,63 @@ thunar_job_ask_overwrite (ThunarJob   *job,
 
 
 
+ThunarJobResponse
+thunar_job_ask_delete (ThunarJob   *job,
+                       const gchar *format,
+                       ...)
+{
+  ThunarJobResponse response;
+  va_list           var_args;
+
+  _thunar_return_val_if_fail (THUNAR_IS_JOB (job), THUNAR_JOB_RESPONSE_CANCEL);
+  _thunar_return_val_if_fail (format != NULL, THUNAR_JOB_RESPONSE_CANCEL);
+
+  /* check if the user already cancelled the job */
+  if (G_UNLIKELY (exo_job_is_cancelled (EXO_JOB (job))))
+    return THUNAR_JOB_RESPONSE_CANCEL;
+
+  /* check if the user said "Delete All" earlier */
+  if (G_UNLIKELY (job->priv->earlier_ask_delete_response == THUNAR_JOB_RESPONSE_YES_ALL))
+    return THUNAR_JOB_RESPONSE_YES;
+
+  /* check if the user said "Delete None" earlier */
+  if (G_UNLIKELY (job->priv->earlier_ask_delete_response == THUNAR_JOB_RESPONSE_NO_ALL))
+    return THUNAR_JOB_RESPONSE_NO;
+
+  /* ask the user what he wants to do */
+  va_start (var_args, format);
+  response = _thunar_job_ask_valist (job, format, var_args,
+                                     _("Do you want to delete it?"),
+                                     THUNAR_JOB_RESPONSE_YES
+                                     | THUNAR_JOB_RESPONSE_YES_ALL
+                                     | THUNAR_JOB_RESPONSE_NO
+                                     | THUNAR_JOB_RESPONSE_NO_ALL
+                                     | THUNAR_JOB_RESPONSE_CANCEL);
+  va_end (var_args);
+
+  /* remember response for later */
+  job->priv->earlier_ask_delete_response = response;
+
+  /* translate response */
+  switch (response)
+    {
+    case THUNAR_JOB_RESPONSE_YES_ALL:
+      response = THUNAR_JOB_RESPONSE_YES;
+      break;
+
+    case THUNAR_JOB_RESPONSE_NO_ALL:
+      response = THUNAR_JOB_RESPONSE_NO;
+      break;
+
+    default:
+      break;
+    }
+
+  return response;
+}
+
+
+
 ThunarJobResponse
 thunar_job_ask_create (ThunarJob   *job,
                        const gchar *format,
diff --git a/thunar/thunar-job.h b/thunar/thunar-job.h
index c28e33d3..9c0a7b41 100644
--- a/thunar/thunar-job.h
+++ b/thunar/thunar-job.h
@@ -78,6 +78,9 @@ ThunarJobResponse thunar_job_ask_create             (ThunarJob       *job,
 ThunarJobResponse thunar_job_ask_overwrite          (ThunarJob       *job,
                                                      const gchar     *format,
                                                      ...);
+ThunarJobResponse thunar_job_ask_delete             (ThunarJob       *job,
+                                                     const gchar     *format,
+                                                     ...);
 ThunarJobResponse thunar_job_ask_replace            (ThunarJob       *job,
                                                      GFile           *source_path,
                                                      GFile           *target_path,