diff --git a/lisp/dired.el b/lisp/dired.el
index e70467ca53b..a295ece128d 100644
--- a/lisp/dired.el
+++ b/lisp/dired.el
@@ -2504,17 +2504,33 @@ dired-mode-operate-menu
     ["Delete Image Tag..." image-dired-delete-tag
      :help "Delete image tag from current or marked files"]))
 
+(declare-function mailcap-file-default-commands "mailcap" (files))
+
 (defun dired-context-menu (menu click)
   "Populate MENU with Dired mode commands at CLICK."
   (when (mouse-posn-property (event-start click) 'dired-filename)
     (define-key menu [dired-separator] menu-bar-separator)
-    (let ((easy-menu (make-sparse-keymap "Immediate")))
+    (require 'mailcap nil t)
+    (let* ((filename (save-excursion
+                       (mouse-set-point click)
+                       (dired-get-filename nil t)))
+           (commands (mailcap-file-default-commands (list filename)))
+           (easy-menu (make-sparse-keymap "Immediate")))
       (easy-menu-define nil easy-menu nil
-        '("Immediate"
+        `("Immediate"
           ["Find This File" dired-mouse-find-file
            :help "Edit file at mouse click"]
           ["Find in Other Window" dired-mouse-find-file-other-window
-           :help "Edit file at mouse click in other window"]))
+           :help "Edit file at mouse click in other window"]
+          ,@(when commands
+              (list (cons "Open With"
+                          (mapcar (lambda (command)
+                                    `[,command
+                                      (lambda ()
+                                        (interactive)
+                                        (dired-do-async-shell-command
+                                         ,command nil (list ,filename)))])
+                                  commands))))))
       (dolist (item (reverse (lookup-key easy-menu [menu-bar immediate])))
         (when (consp item)
           (define-key menu (vector (car item)) (cdr item))))))