diff --git a/gio/glocalfile.c b/gio/glocalfile.c
index bc33af644..7b70c614c 100644
--- a/gio/glocalfile.c
+++ b/gio/glocalfile.c
@@ -1997,6 +1997,8 @@ g_local_file_trash (GFile         *file,
   GVfsClass *class;
   GVfs *vfs;
   int errsv;
+  size_t basename_len;
+  GError *my_error = NULL;
 
   if (glib_should_use_portal ())
     return g_trash_portal_trash_file (file, error);
@@ -2224,40 +2226,91 @@ g_local_file_trash (GFile         *file,
   g_free (trashdir);
 
   basename = g_path_get_basename (local->filename);
+  basename_len = strlen (basename);
   i = 1;
   trashname = NULL;
   infofile = NULL;
-  do {
-    g_free (trashname);
-    g_free (infofile);
-    
-    trashname = get_unique_filename (basename, i++);
-    infoname = g_strconcat (trashname, ".trashinfo", NULL);
-    infofile = g_build_filename (infodir, infoname, NULL);
-    g_free (infoname);
+  while (TRUE)
+    {
+      g_free (trashname);
+      g_free (infofile);
 
-    fd = g_open (infofile, O_CREAT | O_EXCL | O_CLOEXEC, 0666);
-    errsv = errno;
-  } while (fd == -1 && errsv == EEXIST);
+      /* Make sure we can create a unique info file */
+      trashname = get_unique_filename (basename, i++);
+      infoname = g_strconcat (trashname, ".trashinfo", NULL);
+      infofile = g_build_filename (infodir, infoname, NULL);
+      g_free (infoname);
+
+      fd = g_open (infofile, O_CREAT | O_EXCL | O_CLOEXEC, 0666);
+      errsv = errno;
+
+      if (fd == -1)
+        {
+          if (errsv == EEXIST)
+            continue;
+          else if (errsv == ENAMETOOLONG)
+            {
+              if (basename_len <= strlen (".trashinfo"))
+                break; /* fail with ENAMETOOLONG */
+              basename_len -= strlen (".trashinfo");
+              basename[basename_len] = '\0';
+              i = 1;
+              continue;
+            }
+          else
+            break; /* fail with other error */
+        }
+
+      (void) g_close (fd, NULL);
+
+      /* Make sure we can write the info file */
+      if (!g_file_set_contents_full (infofile, NULL, 0,
+                                     G_FILE_SET_CONTENTS_CONSISTENT | G_FILE_SET_CONTENTS_ONLY_EXISTING,
+                                     0600, &my_error))
+        {
+          g_unlink (infofile);
+          if (g_error_matches (my_error,
+                               G_FILE_ERROR,
+                               G_FILE_ERROR_NAMETOOLONG))
+            {
+              if (basename_len <= strlen (".XXXXXX"))
+                break; /* fail with ENAMETOOLONG */
+              basename_len -= strlen (".XXXXXX");
+              basename[basename_len] = '\0';
+              i = 1;
+              g_clear_error (&my_error);
+              continue;
+            }
+          else
+            break; /* fail with other error */
+        }
+
+      /* file created */
+      break;
+    }
 
   g_free (basename);
   g_free (infodir);
 
-  if (fd == -1)
+  if (fd == -1 || my_error)
     {
       g_free (filesdir);
       g_free (topdir);
       g_free (trashname);
       g_free (infofile);
 
-      g_set_io_error (error,
-		      _("Unable to create trashing info file for %s: %s"),
-                      file, errsv);
+      if (my_error)
+        g_propagate_error (error, my_error);
+      else
+        {
+          g_set_io_error (error,
+                          _("Unable to create trashing info file for %s: %s"),
+                          file, errsv);
+        }
+
       return FALSE;
     }
 
-  (void) g_close (fd, NULL);
-
   /* Write the full content of the info file before trashing to make
    * sure someone doesn't read an empty file.  See #749314
    */
diff --git a/gio/tests/trash.c b/gio/tests/trash.c
index 63b4fee89..277f6ca70 100644
--- a/gio/tests/trash.c
+++ b/gio/tests/trash.c
@@ -26,6 +26,7 @@
 #include <glib/gstdio.h>
 #include <gio/gio.h>
 #include <gio/gunixmounts.h>
+#include <fcntl.h>
 
 /* Test that g_file_trash() returns G_IO_ERROR_NOT_SUPPORTED for files on system mounts. */
 static void
@@ -188,6 +189,79 @@ test_trash_symlinks (void)
   g_free (target);
 }
 
+/* Test that long filename are handled correctly */
+static void
+test_trash_long_filename (void)
+{
+  const gchar *long_filename = "test_trash_long_filename_aaaaaaaaaaaaaaaaaaaaaaaaa" \
+    "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" \
+    "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" \
+    "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" \
+    "aaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa" \
+    "aaaaa"; /* 255 bytes */
+  gchar *filepath;
+  int fd;
+  GFile *file;
+  GError *error = NULL;
+
+  /* The test assumes that test file is located on ext fs. */
+  filepath = g_build_filename (g_get_home_dir (), long_filename, NULL);
+  fd = g_open (filepath, O_CREAT | O_RDONLY, 0666);
+  if (fd == -1)
+    {
+      g_test_skip ("Failed to create test file");
+      g_free (filepath);
+      return;
+    }
+  (void) g_close (fd, NULL);
+  file = g_file_new_for_path (filepath);
+  g_file_trash (file, NULL, &error);
+  g_unlink (filepath);
+  g_assert_no_error (error);
+
+  /* Delete trashed version of test file */
+  {
+    GFileEnumerator *enumerator;
+    GFile *trash;
+
+    trash = g_file_new_for_uri ("trash:///");
+    enumerator = g_file_enumerate_children (trash,
+                                            G_FILE_ATTRIBUTE_STANDARD_NAME ","
+                                            G_FILE_ATTRIBUTE_TRASH_ORIG_PATH,
+                                            G_FILE_QUERY_INFO_NOFOLLOW_SYMLINKS,
+                                            NULL, NULL);
+
+    if (enumerator)
+      {
+        GFileInfo *info;
+
+        while ((info = g_file_enumerator_next_file (enumerator, NULL, NULL)) != NULL)
+          {
+            const char *origpath = g_file_info_get_attribute_byte_string (info, G_FILE_ATTRIBUTE_TRASH_ORIG_PATH);
+
+            if (strcmp (filepath, origpath) == 0)
+              {
+                GFile *item = g_file_get_child (trash, g_file_info_get_name (info));
+                g_file_delete (item, NULL, NULL);
+                g_object_unref (item);
+                g_object_unref (info);
+                break;
+              }
+
+            g_object_unref (info);
+          }
+
+        g_file_enumerator_close (enumerator, NULL, NULL);
+        g_object_unref (enumerator);
+      }
+    g_object_unref (trash);
+  }
+
+  g_free (filepath);
+  g_object_unref (file);
+  g_clear_error (&error);
+}
+
 int
 main (int argc, char *argv[])
 {
@@ -195,6 +269,7 @@ main (int argc, char *argv[])
 
   g_test_add_func ("/trash/not-supported", test_trash_not_supported);
   g_test_add_func ("/trash/symlinks", test_trash_symlinks);
+  g_test_add_func ("/trash/long-filename", test_trash_long_filename);
 
   return g_test_run ();
 }