Hold Down The Shift Key and Choose File > Convert > Convert to [Import Preference]

Ignore the Convert ID3 Tags, there are times when that will be greyed out, but since it's not what you'ere trying to do, why worry about it?

I've carried out a bit more experimentation and discovered the following:

• if iTunes is busy converting a file when you click on Shift+File/Convert/Create MP3 Version, the "create mp3 version" command will be greyed out. So that suggests that you have managed to start the conversion of whichever song is currently selected and because iTunes is busy with that, the create command is greyed out. At that time, you might notice activity in the Now Playing window at the top of iTunes that tells you what it is converting, but it's quick, so you might miss it
• in the first screenshot I showed you, did you notice the song highlighted in blue, under the menu?

• The blue line is a song that's highlighted (selected). I've discovered that in Windows 10, if you have five or more songs highlighted when you use the Shift+File/Convert option, iTunes will ignore the shift option and instead will convert the songs that are highlighted. Extraordinary, I know. Oddly, Windows 7 will still carry out the folder option with at least six songs highlighted, but eventually, that too fails in the same way.

So - it appears to be very easy to cause iTunes to fail open the "convert a folder" option. All I can say therefore, is follow the instructions very carefully and if they don't work, try again, ensuring that you really are doing it in the precise manner outlined.

It does work, but it's all too easy for the user to make it fail.

File is on the top bar menu:

• As you can see, Convert is on the File menu. When you place your mouse over the Convert option, the next menu appears. In my case, I have iTunes set to create mp3 version
• if you fail to hold the shift key down when you click on Create MP3 Version, iTunes will simply convert the song (in iTunes) that is selected at the time
• so - ensure that the shift key is held down when clicking on Create MP3 Version and the following dialogue opens up:

• Use the list on the left of the window to navigate to the folder of your choice. You have presumably put the music into a sub-folder within the Music folder. So start by clicking on Music, as indicated in the screenshot

I checked today and the only way I could replicate the greyed out create mp3 version is if I let go of the Shift key before clicking on File and any song was only "part-selected", that is, it's selected but the highlight is in grey, not blue:

You must have the Shift key on your keyboard depressed when you click on File.

The only other way I've managed to break this is if I switched to something such as the Genres view and then tried Shift/File/Convert>Create mp3 Version which caused the message shown below to appear:

Try it again, but be very precise about how you select and click on the commands.

Okay, this appears to be more complicated than it needs to be, so much so that it raises the question about whether it's worth all this trouble to you?

In that respect, why do you need to convert these files in the first place. Which format are they in now?

iTunes will convert tracks that you select to be converted to the format currently defined by your import settings. You can convert tracks that have already been added to the library by selecting them in the library. It matters not where these files are stored on your drives, the converted tracks will be placed where iTunes wants to put them, typically <Media Folder>\Music\<Artist>\<Album>. When you use File > Add Folder to Library and iTunes finds media files that it cannot play natively, but can convert, such as those in WMA format, it will ask for permission to convert those files as part of the import. There is no option to choose where the converted tracks are stored, although I suppose you can adjust the path to the media folder ahead of time should you choose.

tt2