Outlook-iPhone sync doesn't work anymore

Long story short, I suddenly realized that my Outlook calendar doesn't sync with the iPhone anymore. I am not sure exactly when the problem started, but it's a fairly safe bet that it was caused by either the iTunes upgrade or the iOS update of my iPhone 4 to iOS5, both around Christmas time. Things were slow around the holidays, so I didn't realize the problem immediately.

The way things are now, if I add or delete or edit an appointment in Outlook (2010 version), the changes will not propagate to the iPhone. The only way I can get my new appointments on the iPhone is to uncheck the calendar sync box in iTunes, which causes the iPhone calendar to be erased on the next sync, then re-check the box, and sync again. Of course, that means that I can only one-way sync, apart from the fact that this procedure is a pain in the butt.

So, I have to admit that I was about ready to throw that Apple garbage out the window anyway, and I have pretty much decided to get myself a shiny new Windows Phone probably this summer, but in the meantime, does anybody have any idea how this could be fixed? And, yes, the iTunes plugin is installed in Outlook, and listed as active.

 

Some things to check.

On phone; Settings --> Mail, Contacts, Calendars. Select account with issue. Verify 'Calendars' and maybe also 'Reminders' are enabled/on.

Also for good measure set 'Mail Days to Sync' to 'No Limit'

On computer with iPhone connected check same under the device settings screen. Under 'Info' ensure 'Sync Calendars with Outlook' is selected and choose the Calendar from in the list if needed.

Then the obvious 'Do not sync events older than 30 days.' Use your own discretion there.

Scroll to the very bottom under the Advance section. Check that 'Calendars' is selected there.

Also, in your case to test. Under 'Edit' --> Preferences --> Devices. Take out the check for 'Prevent iDevices from syncing automatically....'

I'm not sure if you need to be on the same network for the syncing to work properly though. Never looked into that as I never had issues with such.

Also: http://support.apple.com/kb/ht1386

https://discussions.apple.com/thread/3395963?start=0&tstart=0

And lastly, apple and garbage don't go in the same sentence. Windows? pfffff!

I would agree though, that iTunes is a P.I.T.A sometimes. Had such an encounter last night myself.

 

Thanks for the advice. I fixed the issue this morning, it turned out that I need to run yet another stupid startup program (APSDaemon) now, which I had disabled after the latest iTunes install. With that present, the sync works fine.

Heheh, that's what the unwashed masses are being told these days, isn't it? Unfortunately, with a little more insight, it's fairly obvious that the team at Apple couldn't write decent code for Windows to save their lives. But that's a different topic.

Yeah, coming from a supposedly reputable shop, iTunes is probably one of the most badly written, unnecessarily bloated, slow pieces of crud I have seen in my career. Sheesh, it took them a couple of years in order to get their mouse-wheel support working! You know, at least in my case, I had a fairly positive opinion of Apple, before I got that iPhone, which forced me to install and deal with iTunes. Now, I won't touch anything coming from Apple with a ten-foot pole if I can avoid it.

Thanks again!