Q: I have an iPhone 5 and am using the latest iTunes for Mac. I have it synced to iCloud using iTunes Match. I wish to put some music on my iPhone but it says I have to download it from iTunes. However I have some files in iTunes that will not upload to iCloud. How do I get them onto my iPhone?
A: iTunes Match takes the place of a standard iTunes sync for putting music on your iOS device; once it’s enabled you can no longer put music onto your iPhone directly from iTunes—it must all be synced to iCloud so that it is accessible from there.
Other than disabling iTunes Match entirely, your only option is to get these files in your iTunes library to upload to your iTunes Match account. For a track to be eligible for uploading to iTunes Match it must be in MP3 or AAC format, encoded at a bit-rate higher than 96kbps and less than 200MB in size. ALAC, WAV, and AIFF files can also be uploaded to iTunes Match, but will be converted to 256kbps AAC and only uploaded if the resulting AAC file is less than 200MB in size. Apple also notes that “Songs encoded as MP3 or AAC that do not meet certain quality criteria will not be matched or uploaded to iCloud”, although it is unclear what this means specifically.
If you have tracks that appear to meet the above requirements but are still showing as ineligible, it may be as a result of some odd encoding or tagging within the files. Often in this case you can get these to either match or upload by converting them to 256kbps AAC using iTunes. This creates a copy of the track in the converted format that iTunes Match will then pick up and try to match against an existing iTunes Store track and upload if it cannot be matched.
To use iTunes to convert a track in your library to another format, first make sure the correct default audio format—AAC in this case—is selected under your Import Settings, which can be found in the General section of your iTunes Preferences.
Once you’ve confirmed this, simply select one or more tracks that you would like to convert, right-click and choose Create AAC Version. This option can also be found on the File menu in iTunes, under Create New Version.
iTunes should normally pick up this new track automatically within a minute or two and begin processing it for iTunes Match. If this doesn’t happen, you can right-click on the track and choose Add to iCloud to add those specific tracks or select Update iTunes Match from the Store menu in iTunes to go through your entire library and attempt to match or upload any additional new tracks.