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

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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.

Ah, the old problem of physical and digital not co-existing very well. Your question reminded me that there’s only one Mac sold with an optical drive—the entry-level, non-retina 13-inch MacBook Pro. And you’d be hard pressed to find any mention of that drive on Apple’s website.

So, to resolve your problem, you could log into your account on your girlfriend’s computer, rip the CD, and then add it to your iTunes library. You’d have to create a new user account so that the contents of her iTunes library aren’t added to your iTunes Match library. It would affect your authorized computers, as you say, but that’s only a problem if you’re approaching the five-computer limit.

It wouldn’t take too long to do it, but there’s a much easier way. Rip the CD on her computer, then connect to yours over a network. (Go to the Sharing preference of System Preferences on both Macs and turn on File Sharing to enable this.) In the Finder on her Mac, click on your Mac in the sidebar, enter your user name and password, and then copy the tracks to your Mac. Go back to yours and add the files to your iTunes library.

Barring that, good old sneaker-net would also work. Rip the CD, copy the files to a USB flash drive, insert the drive in your Mac, and copy them.

How can I stream from Mac to stereo?

Q: My iMac is in the study and my audio gear is in the living room. How do I stream music from one to the other?

There are two Apple-focused ways you can do this, and each has advantages and disadvantages. The two devices you can use are an AirPort Express or an Apple TV, and each costs $99. Here are the pros and cons of each.

If you use the AirPort Express, not only can you set it up to extend your Wi-Fi network (and thus provide a better Wi-Fi signal to another part of your home), but you can also stream music through it via AirPlay. Just connect a cable from its audio output to your stereo.


AirPort Utility lets you turn on AirPlay streaming so you can send music to an AirPort Express.

The Apple TV doesn’t allow you to extend your network, but it can be used to stream media from your iMac or iOS device, as well as fetch content from the iMac’s iTunes library (and, of course, from supported online services when you control it from your TV). And, unlike the AirPort Express, it supports both audio and video. The AirPort Express offers only audio streaming, though its 3.5mm jack supports both analog and digital output.

iTunes Match and syncing locally stored music

Q: I have a 128 GB iPhone, so I should be able to put most of my iTunes library on it. But when I try to manually sync music to it from iTunes on my Mac, it says I can’t because I have iTunes Match enabled. Is it really an either/or choice? If I want to sync a bunch of music to my phone manually, do I have to give up being able to copy songs I haven’t synced from the cloud?

Yes, that’s correct. It’s one or the other, not both. Which means that if you have iTunes Match enabled and you want to fill your iPhone with music, you need to download all that music to the device. You can’t even drag music files from iTunes to the device, which would save a lot of time. And if you sync the music first and then turn on iTunes Match, the iPhone deletes all the music on the device.

What I think iTunes should do is offer to copy music that is physically on the computer you sync with to the device, up to a limit of the available space (minus a few gigabytes). Expecting us to download many gigabytes of music is unrealistic, especially since many people have broadband contracts that limit the amount of data they can download each month (and, in some cases, limited bandwidth that can make this a long, complicated process). And if you ever have to restore the device, you have to start all over.

Missing playback options

Q: I’ve noticed that, in iTunes 12, the Skip when Shuffling option is no longer available for TV shows and movies. I also don’t see the Remember Playback Position option any more. I like having TV shows in a playlist and shuffling them. Is there any way I can do this in iTunes 12?

This one was a bit of a conundrum. The reader sent me a screenshot showing that, indeed, neither of those options were available for a TV show. When I checked my iTunes library, however, I found that the Remember Playback Position option is available. The reader said it was only available on TV shows he had imported before iTunes 12. I haven’t imported any since the release of iTunes 12, but I have downloaded some from the iTunes Store and I see the Remember Playback Position option.

Nevertheless, there is a way to access those options, even in iTunes 12. Press and hold the Option key, click on an item, and select Get Info. You’ll see an Info window similar to what was used in older versions of iTunes.


Using the secret Info window, you can get access to these options.

Click the Options tab and you’ll see (and have the opportunity to enable) each of these options.

Have questions of your own for the iTunes Guy? Send them along for his consideration.

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