Adventures in iTunes Fuckery: Holy Shit, It Actually Kinda Sorta Worked

Long-time readers are well aware that me and iTunes get along about as well as Kurds and Turks. And I'm far from the only person in this boat. To recap, though, I've been struggling since the day I bought my iPhone 6+ 128GB to get iTunes to reliably sync a big amount of music to my phone. 

I had recently gotten it to at least copy over a large-ish playlist, but it did so sans album art, which began to really chap my 'nads as of last week, so, over the weekend, I gave it One. Last. Shot.

And fuck me if it didn't actually sort of work okay.

I'm wondering if iOS9 (or 9.1, since I'm running that beta at the moment) introduced some fixes for syncing. Or if it was my decision to move my primary iTunes library back to a Windows machine and a local HDD that helped, though I had tried that ages ago and it didn't work for shit.

Whatever combination of factors was actually responsible, I was able, over the course of three syncs, the last of which actually worked over Wifi (a previous non-starter), to get about 9000 songs and associated album art and other metadata synced over to my phone.

Why three syncs?

Well, don't be silly; iTunes still sucks. The first sync kicked off fine and I left the phone wired to the PC overnight. Check in the morning, sync is complete, no errors. Yet only about 3000 songs had actually copied (you see a dashed-outline circle next to any song that didn't actually sync over if you examine your iPhone's library within iTunes in this case). I could almost have lived with that, but past experience shows that the iPhone will THINK that all of those songs synced over, and try to play them, and then freeze up when the song isn't actually available. That's beyond annoying to try and fix when you're doing 90 on the Tri-State and just want some goddamned jams.

So, I resignedly left my SIM in my Android phone for another day and kicked off another sync. Lo and behold, it reliably chugged along for a day and was still moving files over when I got home from work and needed to take the phone off the wire because Android phones have battery life better measured in nanoseconds than actual useful units of time.

I was happy to see that the syncing continued even off-wire, so I went about with my evening. The next morning, the syncing symbol was gone so I popped over to the PC and plugged the phone back in and, lo and behold, iTunes reported that everything had copied over.

Open Music on the phone, and yeah, everything's there, artwork and all.

Now, one shouldn't be happy with this (seriously, three sync cycles?) performance but compared to the last year of never-working half-assery I've dealt with with this phone and music, I'm beyond thrilled.