Certainly that was the case for me, a music-school student in the late 2000s. In the waning hours of a camp or festival, you’d squat with the other kids on the carpet, set up Firewire cables between everyone’s laptops and hard drives, and move music files back and forth. (I still have a DRM-locked copy of Candide in my library that will forever require Will Carmichael’s iTunes password, which I do not know.)

But as streaming services have flooded out MP3s, the situation worsened. Apple, which long paid classical more mind than other big tech companies, debuted Apple Music with dismal classical options, as NPR’s Anastasia Tsioulcas and The New Yorker’s Alex Ross have documented.

And even beyond the streaming service, the new version of Apple’s signature music software seems especially broken. In the name of creating a “complete thought around music,” iTunes 12 has crammed a streaming service and a media library and a recommendation service and a file store and a device manager into one interface. The sum is that nothing “just works”—and MP3s especially don’t work well. I wondered: How were professional musicians handling the change? And how did they organize their music in the first place?

After all, their job requires them to have quick and fluent access to a library of working recordings.

I had another interest here. Earlier this month, Apple released the new and likely final versions of its iPod Nano and iPod Shuffle. They shipped with interfaces that looked more than three years out of date. The blogger John Gruber said that this was because “what remains of the iPod software team” had been absorbed by the Apple Watch division. Apple has already discontinued its iPod Classic, the last media player that could conceivably let you tote around your entire music library in one device. The company is floating to a streaming model.

If classical listeners are ill-served by streaming services, though, they will stick with music files; and that means they represent, as a bloc, the set of listeners who will continue to maintain personal libraries of owned music even as the larger public rents their digital music instead. How are they adapting?

* * *

As it turns out: poorly.

First, the bugs. The new version of iTunes disappears music. It confuses live tracks and studio versions. And its search bar cannot even find songs which it contains in its library.

“To give you a really specific situation, there are two settings of the Te Deum text by Benjamin Britten. And it would seem to me that if you type in ‘Britten’ and ‘Te Deum,’ you would see some of them,” the composer Nico Muhly told me. “But it says, ‘no results found.’”

I want to submit to the record here that Muhly’s hard drive contains seven different files that could be reasonably called the Britten Te Deum. In fact, it contains more than 2,000 files, or 11.9 gigabytes, of music by Benjamin Britten. It also contains 97 different settings of the Te Deum text.