Siri, sync my sh*t.

Siri, sync my sh*t.

I was a relatively early adopter of the Cult of iPhone. Grant bought me a first-gen model a few months after it was released, and I’ve been an addict ever since. (I’m sure there are some fantastic other smartphones out there, but my 1st gen, 3GS and now 4S have never made me want to switch, even with some minor AT&T frustrations.) I have been using the sync functionality for a certain, limited number of podcasts since the first time I set up my first iPhone in 2007. I like sync. Sync used to like me back. So why, all of a sudden, does sync now suck?

Ever since I set up the 4S (as a brand new phone and not from a backup, just to be extrasupercareful not to import any glitches of yore) my sync functionality has been broken. iTunes regularly tries to load podcasts that I manually added once for a trip and then intentionally manually removed. This kicks me over the space limit and thus screws up some other syncery. It also attempts to sync to my phone even when I haven’t asked it to, even though I have all the relevant options un-checked. It thinks my phone is plugged in when it isn’t and thinks it isn’t when it is. It repeatedly says “The sync session failed to finish because the sync failed to start.” after I select the option to, ya know, sync. Half my podcasts that I do try to sync show up as greyed-out not-really-present content, which seems to mean they helpfully take up space but aren’t actually available for listening. If I then try to download one of these greyed-out podcasts that didn’t actually make it onto the phone via the iTunes app, the app frequently thinks the content is already downloaded and won’t let me grab it. When the app does allow me to download content that appears greyed-out on the phone,  iTunes on the PC then freaks out the next time I sync, as if it can’t handle this alternative reality in which its process didn’t work the first time around and there are now two copies of the same content. I’ve memorized the slightly obscure process to manually delete the phone’s last backup, but it never seems to help. I restart my computer more than ever now in order to try to combat these Appley problems, but to no avail. I’ve become familiar with error messages I’ve never seen before in my life, and I’m now accustomed to each sync attempt taking 45 minutes and at least three tries. I’m considering actually restoring my phone over this — yes, my approximately two and a half week old phone.

WTF? Where did sync go so very wrong? (And before Merlin Mann can get preachy about it, I should add that I don’t use iCloud, largely thanks to his prescient observations about its limitations.) I wonder how many other fairly savvy users are running into new glitches with old processes like I am. Siri doesn’t seem to understand my frustration, but at least I’ve trained her to curse on my behalf about it.