In Which I Fail

to update my phone.

Ages ago I stopped updating the OS on my iPhone. I have an older one and everyone that did it had a crappy experience. It was even in the news at the time that the OS really wasn't working correctly with the older models. So although I had diligently updated from purchase until then I gave up.

Not so long ago I stopped really syncing my iPhone to my computer because it started to crash out saying I was missing a .dll file. I know this is probably one of the many downsides to inter-operating windows and apple products but up until then it had worked ok. Eventually I discovered if I told it not to sync the address book that the process would complete. Although I'm not so much certain what I am syncing if I'm not syncing the address book. I manually sync music, I don't view videos on my phone, I manually sync photos. I guess it is syncing apps, but I really don't know why.

Pretty recently I even stopped the no-contact syncing. The process was taking literally hours. For what little benefit I could discern it seemed like a very long process with very little payout.

Recently I've started to notice my phone crashing a lot. I mean it's old and the apps coming out recently aren't really optimized for this phone, and certainly not this OS so it's understandable that there might be problems. I've lived with it a while but the loginess and the crashing have started to get to "irk" on the irritation scale. I think it is time to bite the bullet and upgrade the OS.

I've been thinking about how long it takes to sync and wonder if the cable or the port might have something to do with it. I did a bunch of plugging and replugging and cable swapping to no improvement. I remember a co-worker telling me once he couldn't get his device to work because his iTunes was out of date, so I upgraded that.

When I went to upgrade the OS it told me there are unsynced purchases on my phone and that I should sync first. So I did. That took that whole evening. When I came back a second time to sync the thing it said there were unsynced purchases on my phone and I should sync first. Deja vu. It's at this juncture that I remember that I have only once actually paid for an iPhone app. So I guess there might be unsynced apps, but none that actually cost money - and frankly a few I wouldn't actually mind losing. I've never purchased music with my phone. In light of that realization I just clicked through and started the upgrade process.

Of course the first thing that happens in this process is backing up the phone. That took the better part of an hour and at the end it announced that there were 500+ sync discrepancies. I could go through them now or later. I picked later. I'm guessing this has something to do with the non-syncing of the addressbook. But truthfully in hindsite I don't think I have that many contacts, certainly not that many that have changed much. Maybe there's an iPhone, Outlook, Thunderbird, Plaxo problem here. One more thing for the list.

After clicking through the upgrade started, but after 30 minutes there was only one little nub in the progress bar, so I aborted. So that's two attempts, North of five hours, and no dice.

Any ideas?