Don't-Miss Stories

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What's to be done about iTunes? Tweak? Strip? Split?

Each iteration of iTunes invites the question: How else might this be done? Chris Breen ponders the possibilities.

Ask the iTunes Guy: When a large iOS update won't fit your iPhone

iTunes Guy Kirk McElhearn answers simple (but common) questions including fitting an iOS 8 update on a packed iPhone, turning an iPhone into an iPod, and cross-border gifting.

Ask the iTunes Guy: Re-download audiobooks, watch Netflix offline, and more

Kirk McElhearn returns to discuss matters of prohibited audiobook re-downloading, lossless audio file conversion, what's not in your playlists, and inability to download Netflix and Hulu content.

Ask the iTunes Guy: Inconsistent buttons and faulty gapless playback

iTunes Guy Kirk McElhearn returns to discuss three iTunes issues—inconsistent Next and Previous buttons, when is a movie a Movie, and gapped playback.

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How to sync both ringtones and iTunes Match music

iTunes syncing can be confounding, particularly when some media is from an iTunes library and the other from iTunes Match. Here's a bit of clarity.

Ask the iTunes Guy: Changing tags and missing movies

Our own iTunes Guy, Kirk McElhearn, returns to discuss the changing nature of some media tags, iOS backups, and movies here but not there.

Ask the iTunes Guy: When iTunes Match doesn't match

Kirk McElhearn offers advice for convincing iTunes Match to show your music, creating playlists of playlists, and making a USB stick full of music work in your car.

Ask the iTunes Guy: Locating unique playlist tracks and the perils of the 25K track limit

In this edition of Ask the iTunes Guy, Kirk McElhearn teaches you how to find unique tracks within two playlists, eyeballs the downside of a too-large music library, and puts the kibosh on cross-border gifting.

Ask the iTunes Guy: Glitchy tracks, numbers game, and too-large libraries

iTunes Guy Kirk McElhearn addresses issues of tracks that aren't all what they should be, unwanted track numbers, and libraries that are bigger than iTunes prefers.

iTunes Radio: Poor reception

Music lover Chris Breen understands that iTunes Radio is designed with the "good enough" listener in mind. Still, he mourns what might have been.