With iTunes in the Cloud, the music you purchase in iTunes appears automatically on all your devices. You can also download your past iTunes purchases. If you want all the benefits of iTunes in the Cloud for music you haven’t purchased from iTunes, iTunes Match is the perfect solution. It lets you store your entire collection, including music you’ve ripped from CDs or purchased somewhere other than iTunes. However, you may have noticed those mysterious cloud status icons scattered through your tracks.

In my library, I saw a fairly substantial number of ‘ineligible’ icons, mostly on tracks that I had imported from my CD collection years and years ago. Checking the standards of the iTunes Match process, Apple’s tech note shows that only certain music files are fit for matching. If your music was encoded below a bitrate of 96 kbps, iTunes Match will simply skip over it.

So how to get these vintage tracks synchronized with iTunes Match? Or how to prepare an media library for iTunes Match? The best way to get video or audio files for iTunes Match is to download it through the Internet, or transfer it into the appropriate format from other files already on your computer. Just like downloaded or self-ripped music, these videos don’t always arrive properly labeled in iTunes Match, so you’ll have to do that yourself.

Part 1. What kinds of Content Can iTunes Match Upload or Match?

You can match or upload any music format that’s compatible with iTunes. That includes AAC, Protected (DRM) AAC (.m4p), MP3, WAV, AIFF, Apple Lossless, and more. You can also re-download music videos from the iTunes Store that you originally purchased, but the service will not match video content, nor any other iTunes file types (PDF booklets, Voice Memos).

According to a support document Apple released, you also won’t be able to match or upload certain types of Music files: files over 200MB, DRM-encumbered tracks that you aren’t authorized to play, DRM-encoded songs purchased from an iTunes Store other than the U.S. version, and any music encoded at less than 96kbps.

You can fool iTunes Match on that last one, however, if you create an AAC version of the song within iTunes (Advanced -> Create AAC Version), and then attempt to match that version.

Part 2. Preparing a Media library for iTunes Match

iTunes Match will try to match every track it can, regardless of whether it is DRM protected and which account it was purchased with. In order to handle DRM protected tracks, your computer must simply be authorized for the account that was used to purchase those tracks. There are three types of tracks that can exist in the world of iTunes Match:

Accessing Purchased Video Content Within iTunes

These are tracks that are made accessible directly from the purchase history of the iTunes Store account that you are using for iTunes Match. The initial iTunes Match setup process actually doesn’t try to do anything with these tracks—when you sign up to iTunes Match, it’s just all immediately made available in your account based on your purchase history, and it’s also worth noting that they do not count against the 25,000 track limit for iTunes Match. These will be unprotected 256kbps AAC versions regardless of what format they were originally purchased in.

Get Matched Media Content onto iTunes Match

These are tracks in your library from other sources that have been matched with corresponding tracks on the iTunes Store and made available through iTunes Match. These will also be made available as unprotected, 256kbps AAC versions regardless of the format and bit-rate of the original item in your iTunes library.

Trasfer Your Uploaded Media Files onto iTunes Match

These are tracks that could not be matched to anything on the iTunes Store, for whatever reason, and have therefore been directly uploaded to the iTunes Match servers. As these are just direct copies of what’s in your library to begin with,  the versions available from iTunes Match will be identical to the original format.

Other types of video content – certain other Internet video files, and DVDs you’re legally allowed to rip – must first be converted into an iTunes-recognized video format before they can be imported into your iTunes Match. Here i’ll show you how to convert all media files to iTunes Match compatible format with iFunia Media Converter for Mac:

iFunia Video Converter for Mac

1. Run iFunia Media Converter for Mac, Drag the video file from the Finder onto the main window.

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Alternatively, you can open the file by click the “Add Files”/”Add DVD” button.

2. Open the format list and select the iTunes Match supported Video/Audio output format listed above;

3. Once you’ve got all your videos queued up, Click “Start” and you’ll soon have an iTunes Match-ready video library at your disposal