Rebuilding My Music Library Part 2: Back to iTunes

I was never fully satisfied with Rhythmbox as my new music player. It gets the job done, but it isn’t iTunes. What can I say? I’m set in my ways. Since I’m also a glutton for punishment, I refused to give up until I found a way to get iTunes back despite the fact that my main laptop, Envy, is running Ubuntu instead of Windows now.

Thankfully, my stubbornness paid off. I eventually managed to get both Windows and iTunes back…though neither are in quite the same form as they were before.

Installing Windows

As I’ve already established, I had problems installing Windows directly on Envy and my netbook Bluebell, which meant that I couldn’t install iTunes. Thus, the only option left was to try installing the program with some of the usual Linux workarounds. Spoiler alert: none of them worked.

PlayOnLinux came the closest. It installed iTunes on Ubuntu with no problem. However, iTunes couldn’t get past the license agreement screen without crashing. I traced the possible origin of the crash to a 32-/64-bit issue with PlayOnLinux through a Make Use Of article, but I wasn’t Linux-savvy enough to make the suggested fixes work. Even if iTunes had worked perfectly, PlayOnLinux made it abundantly clear that I wouldn’t have been able to sync my iPad with the program. That would have been a total bummer, but not a complete dealbreaker.

A week or two later, I decided to try directly installing Windows on a computer again. Envy was out of the question. I didn’t want to mess up its working Ubuntu setup or entrust my music library to its failing hard drive. Bluebell, however, was free for experimentation. I had to use Windows 7 because Bluebell isn’t compatible with Windows 10. Yes, Windows 7 is no longer supported, but the computer would only be running iTunes.

The installation went smoothly. My finicky external DVD drive didn’t give me grief about the Windows 7 disc. Moreover, I correctly formatted the hard drive for Windows this time, which is what had caused the previous installation attempts on the netbook to fail. The only snag was that I couldn’t get Windows 7 to activate online. I had to call Microsoft’s automated activation service to work that out.

Installing iTunes

Then it was time to install iTunes. I still had a copy of the most recent 32-bit version of the program for Windows (12.11 at the time) from when I had tried to use it with PlayOnLinux. I transferred the .exe file from my external hard drive to Bluebell and fired it up. The installation failed straight out of the gate. Like when I tried to use WINE, iTunes took issue with the fact that I wasn’t running Windows 10. Fine.

From there, I visited the iTunes download page, which hosts older versions of the program. I downloaded the second most recent version available (12.10.11). It didn’t work either. It only supports Windows 7 if the OS has the first service pack installed. Unfortunately, the download page for the service pack doesn’t exist anymore and Windows Update wouldn’t run, presumably because, again, Windows 7 is discontinued. Okay then.

The only other Windows version left to try was 12.1.3. If you don’t remember that version, it’s the one when iTunes had the red and silver logo. I copied my entire iTunes folder to Bluebell’s music folder. Even though it was technically made for Windows XP and Vista, it worked perfectly on Bluebell. Mission accomplished. More or less.

Working With Old iTunes

I should have known that Apple wouldn’t make running this old version of iTunes (which I call “Old iTunes”) easy for me.

I ran into several stumbling blocks with the program:

1. It couldn’t read the newer format of my original library’s .itl file. I got an error message every time I tried to launch the program until I deleted the file.
2. It wouldn’t let me sign in with my Apple ID or authorize the computer to validate my DRM-ed songs.
3. It couldn’t see the apps, music videos, or TV shows that were also in my library.

I was disappointed. Yes, I had iTunes back. Sort of. Being on familiar ground again eased some of my anxiety. Yet, I was essentially in the same situation as I had been with Rhythmbox without my play counts or playlists. After some thought, I made that work to my advantage.

I deleted the iTunes folder from Bluebell and replaced it with the music files from Envy. The changes I had made with Rhythmbox—removing the music videos, adding the DRM-free songs, and importing the new songs—made its version of my library both the most current and the most streamlined. I was up and running in no time.

With iTunes back in the mix, I stopped adding new stuff to my Rhythmbox library. Having to organize music in so many places, making sure that all of the tags and titles were identical, was too much work.

Regaining iPad Syncing

The good news is that Old iTunes recognized my iPad mini. That one thing gave Old iTunes the ultimate win over Rhythmbox. Of course, this had downsides too. Two of them.

One, Old iTunes required too many steps to sync the iPad:

• Plug the iPad into Bluebell.
• Unlock the iPad with my passcode.
• Confirm that I “trust” Bluebell by hitting the “Trust” button in the dialogue box.
• Put my passcode code in again.

That song-and-dance got old real quick.

Two, I had to erase the music that was already on the tablet. That wasn’t a big deal—I had already recreated most of my old playlists. The only thing I would lose was the Newly Added smart playlist from my original library. Newly Added is my go-to playlist, a timeline of sorts that shows what I’ve bought and discovered over the past three years. It’s the closest thing I had to a purchase record without my metadata.

I spent two hours adding those 500+ songs to a new, regular playlist in Old iTunes. I put them in the exact order they were in on my iPad to mimic the date I added them to my original library. I named the new playlist “Old Faves” so it wouldn’t conflict with Old iTunes’ own Recently Added smart playlist.

Old iTunes briefly gave me grief about the iPad’s storage being full when I synced for the first time. I unchecked all of the playlists from the sync list except one small one. Once that playlist synced, the rest of the music on the iPad was deleted and I was able to sync the stuff from my new library.

Getting Some Upgrades

I was happy with Old iTunes. It did everything I needed it to do, in the ways that I was used to doing them. But I couldn’t shake the feeling that there was a way to get that first service pack for Windows 7—and thus, a more recent version of iTunes—that I hadn’t considered.

During my research, I learned that Windows 7 had some kind of second update that came out after the first service pack. Since it was a cumulative update, I thought it might be possible to use it to bypass the first service pack altogether. I was wrong there, but a How-To Geek article I found on the subject showed me how to get that first service pack after all. In a nutshell, I was able to download an .exe from the Microsoft Update Catalog, a site that contains all of the updates for various Windows versions in case Windows Update isn’t working on your computer. I had forgotten about that site! Thanks for the assist, How-To Geek!

Now that I had the service pack, iTunes 12.10.11 installed with no problems. But could it read my original library? That was the million dollar question. I logged into a second user account on Bluebell, plugged in my external drive, and loaded my original library into a clean copy of iTunes. YES!! SUCCESS!! There she was, my beloved library, exactly as I remembered her. I almost cried.

When I logged back into my main user account, I erased my new library’s iTunes folder and replaced it with my original library’s folder. I signed in with my Apple ID and authorized the computer, because that worked again. Then, as I had planned, I copied all of the new songs I had collected since I lost access to iTunes from my “iTunes New Music” folder into my original library.

I had to do a bit of clean-up after the installation. None of the new songs had any of the edits I had made to the genres, artist names, etc. in my new library. I also had a lot of duplicates to delete for some reason. I’m sure I’ll find other things to fix too. In the meantime, I’m just going to bask in my victory.

Conclusion

I appreciate Apple making previous versions of iTunes available. Not to shade Rhythmbox, which was there for me in my time of need, but even the oldest version of iTunes is better than almost everything else out there. I’m going to keep the setup files for those old iTunes versions in case a situation like this pops up again.

Running my music library on a different computer than the one I work on is a new experience. I’m used to having everything in one place. On one hand, I like the compartmentalization. My music library is safe from everything that’s ailing Envy. On the other hand, it can be inconvenient. If my iPad and phone are both charging (like they are as I write this), I have to pull a separate table up to my desk to sit Bluebell on so I can fire up my library.

Most importantly, I learned that I need to do better about backing up my library. I know how to make an index of my entire library and playlists now, so I won’t be caught without that data again. There will probably come a time when I’ll have to switch to another music player permanently, so I need to keep better records.