Ask the iTunes Guy: Solving all your playlist problems in iTunes 12

Playlists are one of the best, and most creative ways to organize music in iTunes, and to listen to music on your iOS devices. But sometimes, it can be hard to figure out how to make complex playlists. In this week’s column, I look at three questions about playlists, both standard and smart. And I also look at an issue where album art, for some albums, changes on iOS devices.

Playing multiple playlists in order

Q: Is there a way to play several playlists in sequence? Placing them in a folder doesn’t retain the song order.

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Ask the iTunes Guy: Deleting iTunes Radio, death of the old Info window

iTunes, like most software, requires that you do things in a certain way. It isn’t very flexible for users who think differently. For example, why would anyone want to get rid of iTunes Radio? Why would iTunes users wish to sort their music by artists’ last names, then first names? And why would you want to use a more capable Info window to tag files? Because that’s the way you prefer to work? Let’s explore.

Deleting iTunes Radio

Q: Is there a way to disable iTunes Radio? I don’t use it and I sometimes click it by accident. It also pops up every time I launch iTunes, asking me for my iTunes password, which is driving me mad.

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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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