One trick for getting iTunes Match to recognize older tracks

Welcome, iTunes Match users. After you've coughed over your 25 bucks and waited all night for your music library to reconcile with the great iCloud in the sky, you may have noticed those mysterious cloud status icons scattered through your tracks. Apple's tech note summarizes the icons; Macworld's thorough rundown gives more status detail and recommends that you add the iCloud Status column to your iTunes list view for diagnostic purposes.

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. Some of my most vintage files show a 'Date Modified' in 1999, and were encoded into MPEG-1 Layer 2 (yes, an MP2 file) with MPecker or SoundJam MP (get off my lawn). Most of these, however, were recognized just fine by iTunes Match; more recent files seemed to have trouble.

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.

When I took a closer look at my problem tracks, the issue was clear: in an attempt to save some disk space way back when, I had opted to go with variable-bitrate (VBR) MP3 files when ripping these CDs. This took somewhat longer, but kept quality reasonably high while creating smaller files.

Present-day me is now somewhat irked with past-me; how to get these vintage tracks synchronized with iTunes Match? I figured out a way, which was independently pointed out by Lex Friedman last week.

As Richard enthusiastically realized in June, one of the most helpful features of iTunes Match is how it 'normalizes' any tracks that exist in the iTunes store catalog up to 256 kbps AAC files, the same quality as iTunes Plus music that you buy from the store. While he was interested in lowering the storage requirements of his audiophile-friendly (and massive) ALAC files, this fix works in the other direction: getting low-bitrate or variable-bitrate files up to the standards of current-day digital music.

Step 1: Sort your library by the iCloud Status or cloud icon column. Just click on the column name to sort the track list, and then scroll to the end where all the ineligible songs are. You can take this an album at a time, to keep it simple. In the image above, you see an album's worth of ineligible songs. You can click a track and choose Get Info (⌘-I) from the File menu to verify that the problem is inadequate bitrate.

Step 2: Double-check your iTunes import/conversion settings. You'll find these under the iTunes preferences, in General, when you click the button marked "Import Settings." For our purposes, AAC 128 kpbs "High Quality" is fine, and chances are that's the default setting you already had. Click OK and close the Preferences dialog.

Step 3: Select all the tracks in the album you want to iCloud-ify. Right-click or control-click any of the selected tracks and choose "Create AAC Version" (also available under the Advanced menu in iTunes). Watch the tracks convert before your eyes.

Step 4: Once the conversion is done, you'll have two copies of those songs in your library: the older VBR tracks, and the just-converted AAC 128 tracks. iTunes Match automatically kicks in and begins scanning the 'new' tracks, and (since they now meet the minimum criteria for matching) they're matched!

If they exist in the iTunes store, the iCloud versions of them will be the store's iTunes Plus 256 kpbs version; if not, they'll be the 128 kbps AAC versions you just created. You can tell the difference by looking in the iCloud Status column, which will helpfully say 'Matched' or 'Uploaded.'

At this point, for your tracks with 'Uploaded' status, what you've got is what you've got: VBR originals and AAC re-conversions, which may be a bit lower quality than the source files. If you have the disk space to keep both, you can, or give the AACs a listen and see if they sound OK to you. The other alternative is going back to the CDs to capture those files at a higher bitrate.

For the tracks with 'Matched' status, however, you can revitalize them to current standards by actually -- gulp! -- deleting your local copies and downloading the matched versions to replace them. Macworld has a walkthrough of using Smart Playlists to do this for the entire library, or you can go an album at a time if it makes you nervous to delete huge tracts of tracks (or if your Internet connectivity is metered and you can't safely download gigabytes of music at one go). Simply delete both your originals and your local matches -- careful NOT to check the box to delete from iCloud -- and note that the matched tracks stay listed, with a little download icon next to them. Click it to grab the full-glory version of the song back from iCloud, or optionally just leave it in the cloud until you need it again to save yourself some disk space.

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