iPhone will not sync to Outlook 2007 after 2.0 & iTunes 7.7 update!

I only have 1 calendar (called 'Calendar') in Outlook. When I first sync'd (after upgrading to 2.0 and 7.7) it created a 'Home' calendar. I deleted 'Home' and reset the synch history. Now there are two behaviors...

1. When I set iTunes to push my Outlook calendar to my iPhone (not trying to take entries made in my iPhone to the Outlook calendar) it works. But...this is inadequate because I often make my calndar entries in the iPhone...and with this process they get wiped out.

2. When I let my Calendar synch (two-way sync) it throws a mesage saying 'more than 5% of my calendar has changed (stating 100+ entries will be modified)...do I want to continue?' I haven't modified 100 entries in my calendar so I aborted to avoid potentially wiping out my Outlook calendar. I have no idea why it thinks all these entries have changed in some way, obviously something introduced in 2.0 and/or 7.7 is causing the conflict. And, to make matters worse, I've had a few conversations with Apple support and they frankly don't understand this problem at all and suggest steps that we've all already gone through.

Help!

Is the setting in iTunes set to sync with All Calendars rather than "Selected Calendars?" Even with only 1 calendar, the sync from the phone to Outlook didn't work with my 1 calendar identified in Selected Calendars.

I've set iTunes to synch with 'Selected Calendar' and then I have the 'Calendar' box checked. Since I deleted the 'Home' calendar, I only have one in Outlook at the momement, but I've still stuck with 'Selected Calendar' rather than 'All Calendars'. But note the only way I've gotten it to synch is if I go to the bottom of the same iTunes menu and check the box to have Outlook overwrite the phone (one-directional sync). It works, but only in terms of putting what's on my Outlook calendar onto my iPhone. If I entered something onto my iPhone calendar it doesn't move to Outlook and it's wiped off the iPhone after the sync. Not a good long term solution obviously...

I am having a similar issue--tried syncing a brand new iPhone 3G w/Outlook 2007, and contacts sync but no calendar. I have tried, in the following order:
1. Reset sync history in iTunes & sync...no dice
2. Remove "annual events" from Outlook calendar & sync...nope
3. Remove all "events" from Outlook calendar & sync...nothing
4. Reinstall iTunes & Apple Mobile Device support, re-sync...nada
5. Restore iPhone (reset) without restoring backup, re-sync...nope
6. Restore iPhone & restore backup, re-sync...nope!

Talk about frustrating, and what a waste of time! A co-worker running last year's model iPhone also recently upgraded to 2.0 software and iTunes 7.7, and he is having exactly the same problem. I am hoping for an update from Apple very soon!

Until a proper solution to this problem is identified/released, here's the best I have come up with. It allows me to sync Outlook to my iPhone, but not the other way around. But at least I can make entried in Outlook and then sync them to my iPhone. First, make sure you only have one Calendar in Outlook (if you see 'Home', delete it. Then reset sync history. Then, in iTunes, check the box that pushes data from Outlook to the iPhone (rather than two-way sync). Then sync. Again, it's a marginal work around - not great, but something.

Ok, now I know there must be a bug (or I'm going nuts or maybe both!). I am able to successfully get calendar entries that I make on the iPhone to sync with Outlook but after a few additional syncs, the iPhone entries on my Outlook Calendar are all WIPED OUT even though they remain on my iPhone. As long as an event starts on my PC, it stays on the PC and on the iPhone. But, after a few syncs, the entries that started on the iPhone are erased from Outlook even though they remain on the iPhone. I think I'm going to give up. My work around will be to enter appointments as Notes on my phone while I'm away from my computer and then re-enter them on my laptop in Outlook when I'm back at my desk. In all of my tests, as long as a calendar event started in Outlook, it was never erased by a two-way synchronization. The only events that got erased from Outlook were those that originated "offline" in the iPhone. They appeared in Outlook for a while, and then they disappeared.

Just an update from me as well - from the guy with one of the above "fixes."

Arriving home... some appointments landed in Outlook from the phone, but others didn't. Upon either a second look (or second sync) they've vanished from outlook. To say this is odd is understating it. I do, now, as per my fix last night, have only 1 calendar on outlook and itunes. Still, as the kitty pictures on the Internet say, "I'm doin' it wrong."

Help me, Apple Tech Support - you're our only hope.

Not only do none of my Outlook Calendar items show up... but the sync process takes forever and the hard drive reads constantly, even the portion of the process when iTunes says it is syncing Contacts. The Contacts sync, but it never took 30 minutes to an hour to sync before!

THIS IS OBVIOUSLY A HIGH PRIORITY PROBLEM - PEOPLE ARE LOSING DATA!

Current config:
iPhone 2.0
Windows Vista
Outlook 2007
iTunes 7.7

I am also in the same boat.
I am running Windows XP with Office 2007 and iTunes 7.7. I have updated my iPhone to 2.0. I have been syncing my outlook calendar with my iPhone since Nov when I bought my iPhone. As of Friday's update, all meeting requests are disappearing when their time is up. For instance, an meeting made for 1-2 pm, will disappear at 2:05. Now I suppose it shouldn't matter after the fact, however, I need them for reporting.

I disabled syncing the iPhone to outlook, created a new appointment and waited for the time to expire and it's still there. When I go back and accept the meeting invite from the past, it will show up in the calendar, then disappear.

Please Help - my IT guy is at a loss as am I.

In case this helps anyone, I was on the phone with Level 2 tech support at Apple (really nice guy) for 219 minutes this afternoon and I was able to replicate the sync problem for him. We did a really interesting test where I set up a new user on my PC and then tried syncing with the iPhone. Everything worked on a couple of syncs until I imported my original Outlook calendar. In a totally bizarre occurrence, some of the calendar entries that "disappeared" from Outlook but remained in the iPhone actually showed up when I imported the calendar data (it had been exported as a .csv file) into the new user account. We've basically isolated the problem and my new best friend at tech support is taking all my logs and case write up to the Apple engineering team (along with a link to this entire discussion thread). He promised me some feedback in 3-5 days so I hope to be able to report a resolution by the end of the week.

Cute.. I AM an IT guy... and I'm at a loss too. This isn't a tech issue we can solve - it's a programming problem.

We need a tourniquet to stem the bleeding... My life is slipping away...

...okay, maybe just my calendar, but in a figurative sense, it could be construed as the same thing...

Hanley -

You are my new best friend.

Kudos.

Me Too
woo hoo

Hanley - thanks for all the effort, I really hope Apple follows through and delivers a solution to this problem quickly! Between your 219 minute investment and this thread, they should have a lot to work with.

I'm having the same problem with Outlook 2003.