Winamp normally adds at least one option to the Windows Explorer context menu, so that when you right-click on audio files or folders you can have them “Play in Winamp“. This command works equally for the audio files themselves and for shortcuts to audio files, as well as for folders and for shortcuts to folders that contain audio files.

You may face a serious problem, when this context option exists, but it won’t work with shortcuts to folders. It works just fine when you right click on a folder that contains audio files, but not when you right click on a shortcut to that folder.

Re-installing Winamp won’t be of any help. Most probably some other program you installed recently, like Mp3Tag, has changed the default Windows folder settings. You can correct this, by downloading a registry file. For security reasons the file is zipped. Extract its contents to a folder of your choice and run the file named “win7-folder-default-config.reg” to reset folder settings to the default state. After that Winamp (or other players) should work fine.

Please note that after reverting to the default settings, some of your programs may lose their place in the folders’ context (right  click) menu, including Winamp itself. You can have them again appear in the context menu, by going to their preferences and selecting again the relevant options, or even by re-installing them. Of course, you must not do this for programs that damage the Winamp entries.

You can also avoid reverting to the default folder configuration and use other, worse in my opinion, methods, such as putting Winamp itself to the “Send To” context menu of Windows Explorer, or creating yourself a Play and an Enqueue command for shortcuts (read the next pages for these).

Putting Winamp to the “Send To” context menu

To do this, copy the Winamp executable (normally at c:\program files\winamp), and navigate to the “Send To” folder (normally at c:\Users\YOUR USER NAME\AppData\Roaming\Microsoft\Windows\SendTo). When you are in this folder, right click on an empty space of the folder and select the option “Paste Shortcut“.

Now you have created a shortcut to the Winamp executable right in the Send To folder of Windows. Next time you need to play in Winamp an audio folder by right clicking on a shortcut to that folder, do not choose the Winamp’s Play context menu, but go to “Send To” and use this menu to send your files to Winamp.

To do the same for Enqueuing your files to Winamp, placing them at the bottom of the playlist, just create in the Send To folder another shortcut to the Winamp executable, right click on it to open its properties and replace the target with:

"C:\Program Files\Winamp\winamp.exe" /ADD "%1"

You can change the path to Winamp according to your specific system configuration, but leave the quotes in their place, they are needed. Don’t forget to give a different name to this shortcut, to know when you are going to play or enqueue a folder.

Creating Play & Enqueue Context Menus

The side-effect of this solution is that you will have those commands appear whenever you right click shortcuts – even if these shortcuts do not lead to audio files or folders. The benefit of this solution is that you will have the commands available faster, without having to enter first the “Send To” submenu.

1) Download this small and efficient program called Default Programs Editor.

2) Run the program and select the “File Type Settings” option and then the “Context Menu” option.

3) Locate the lnk extension (this is the extension that shortcuts use), and press the “Next” button.

4) Add a new command, with the name Sh Play in Winamp. (The Sh stands for “shortcut”; we use it mainly in order to distinguish this command from the default non-functioning command of Winamp itself, which will keep appearing in the menu).

5) At the “Program path” box, write the path to Winamp, adding the special modifier “%1”

"C:\Program Files\Winamp\winamp.exe" "%1"

Press “Next” and save. Repeat the same steps to create an “Sh Enqueue in Winamp” command. At the program path use also the /ADD modifier:

"C:\Program Files\Winamp\winamp.exe" /ADD "%1"