Ask the iTunes Guy: Manage your iTunes music library

This week, I look at a few questions about managing an iTunes music library, dealing with liner notes, album artwork in WAV files, and correcting capitalization in song titles. I also suggest a way to download music from the iTunes Store with an old Mac.

DIY digital booklets

Q: I’ve been ripping my CD collection and I’d like to add liner notes to my iTunes library. I’m happy to scan the CD inserts but what’s the best way to add these files so I can easily access them?

Read more »


Ask the iTunes Guy: Help for old-school iPod problems

The popularity of the iPhone and iPad mean that most people who use iTunes have iOS devices. But we shouldn’t forget that there are still millions with non-iOS iPods, such as the classic, nano, and shuffle. In this week’s column, I address a couple of questions sent in by readers who use these “legacy” devices. I also look at questions about gaps not playing between songs, and devices authorized to download iTunes content.

Deleting phantom podcasts

Q: I have a podcast episode stuck on my iPod classic. I have deleted it in iTunes, and I have tried unsubscribing to the podcast. I don’t know what else to try. Do you have any ideas?

Read more »


Ask the iTunes Guy: Cleaning up your iTunes library

Like children, or weeds, an iTunes library has the tendency to grow and grow. Your Mac’s internal storage does not. iTunes 12 segments your media in a way that makes it easy to forget you have a bunch of audiobooks, podcasts, or old TV shows in your library that probably don’t need to be there anymore. But iTunes also makes it easy to back that media up in another location, so it’s safe to delete and free up space on your Mac.

Offloading audiobooks

Q: I have so many audiobooks that I’m wondering if I could remove some of them from my iTunes library and hold then in a folder somewhere on my iMac?

Read more »


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.

Read more »


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.

Read more »


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?

Read more »


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?

Read more »