Ask the iTunes Guy: Naming live sets, syncing old-style iPods with iTunes Match

Apple may have sold gazillions of iPhones in the latest quarter, but the questions about iTunes are still coming strong. This week, I look at three interesting questions. How can you label live recordings by date and set? How can you sync from iTunes Match to a non-iOS iPod? And what are those mystery columns that show up in the iTunes library?

Live sets

Q: I have a live recording of a band’s entire run from one venue. This is a multiple disc set. I would like to break the shows down by date and then set, but all iTunes offers is “Disc 1,” “Disc 2,” and so on. I can re-tag the files so that each set or night is a disc, but they will still be labeled with this “Disc 1” scheme. Is there a way I can present the discs as they are actually named—“Night One-First Set” and “Night One-Second Set”—in Albums view, rather than the way iTunes names them now?

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Ask the iTunes Guy: Joining tracks, iOS and Apple Lossless

For the first column of 2015, I look at a few interesting questions. I show a couple of ways to have two songs always play together in shuffle mode; look at a question regarding high-resolution files, Apple Lossless, and iOS devices; and I field two questions about adding information to the Lyrics tag of audiobooks files (and how to export text from that tag).

Keep it together

Q: When I play music in shuffle mode, how do I keep two songs together so they always play back to back?

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Ask the iTunes Guy: Of missing genres and artist sorting

In this week’s column, I examine a host of iTunes questions. I look at a bug in iTunes 12, where deleting the genre tag creates a blank genre. I discuss an issue where a reader couldn’t import AAC files into iTunes. I explain how to combine a pre-ordered single with an album. And I show how to sort artists by their last name.

Editing genre tags

Q: I’ve noticed a new behavior with editing the Genre tag in iTunes 12. Previously, when I wanted to remove a Genre tag and not reassign it (keep it blank), deleting the genre tag from the Info window worked just fine—there was no genre assigned. Now, when I delete the genre, the track has a blank genre. Is there any way to fix this?

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Ask the iTunes Guy: Missing ringtones and explicit radio

Another iOS update, another round of bugs. This time, a recent update to iOS 8 deleted ringtones and alert tones. I explain how to get them back. I also look at using multiple Apple IDs in the iTunes Store and App Store, discuss not being able to block iTunes Radio, and look at a question about moving an iTunes library to a new Mac while retaining metadata.

Lost ringtones

Q: All my ringtones are missing from my iPhone and I can’t find any way to re-download them. What can I do?

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Ask the iTunes Guy: Ripping CDs in 2014, streaming music from Mac to stereo

I’ve received lots of interesting questions in the last couple of weeks, and here are four of them. I address the increasingly common problem of ripping a CD when your Mac doesn’t have an optical drive. I discuss two ways of streaming music from a Mac to a stereo. I examine the quirky way iTunes Match won’t let you sync music files from your iTunes library. And I look at an issue with playback options for TV shows in iTunes 12.

No more CD drive

Q: I bought an audio CD that I want to add to my iTunes library, but neither of my Macs have CD drives. I am also an iTunes Match subscriber. My girlfriend has a MacBook Pro with a CD drive, however. Can I log into my iTunes account on her computer and add the CD that way, or will that affect my authorized computers? I really don’t want to buy an external CD drive just for one CD and I can’t use her drive remotely since it is a music CD.

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Ask the iTunes Guy: Missing artwork, shuffling iTunes 12, and gifting movies

It’s time for a grab-bag column. Some of this week’s questions deal with iTunes 12: What do you do when album art disappears? How do you mark TV shows as watched? And how do you play music in shuffle mode in iTunes 12? I also look at a question about gifting a movie you’ve purchased from the iTunes store, and an app-updating problem with iOS 8.

Disappearing album artwork

Q: I’ve noticed in iTunes 12 that some of my albums don’t display artwork, even though I’ve manually added album art to all my music. I also found this with some of my movies. Is there any way to get the artwork back?

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Ask the iTunes Guy: Demystifying artwork, wish lists, and alerts in iTunes 12

With more and more users updating to iTunes 12, I’ve been getting a huge number of questions about how to use this new version. In this week’s column, I look at more questions about iTunes 12. (The last column was a Special iTunes 12 edition.) I discuss adding artwork to files, deleting artwork, and changes to the iTunes Store’s Wish List and My Alerts section.

Adding artwork

Q: I’m confused by iTunes 12. How do I add album art to my music and movies?

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