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iPhone calendar sync issues with Outlook

I have a problem with syncing my iPhone calendar with my Outlook 2003 calendar.

For example, let's say I had a 12pm appointment today displaying both in my outlook and iPhone. However, when I sync my iPhone after the event e.g. at 3pm, the appointment entry in the Outlook is removed, whilst the appointment entry on my phone remains. I did not edit either of the appointment entries. Even if I re-sync my phone, the 12pm appointment still remains in my phone whilst it's missing in my Outlook.

Are there others encountering the same problem as well? Any ways to fix this problem? Thanks

3G iPhone, Mac OS X (10.5.4)

Posted on Jul 24, 2008 4:05 AM

Reply
24 replies

Jul 29, 2008 8:39 AM in response to Ivan C

I had the same problem, and spent DAYS on it. Here are the details:

I could sync Outlook contacts with no issues, but no matter what I tried I could not get one calendar appointment to show up on the iPhone. Itunes would sync, and even take a while processing "Syncing Calendar", but display no errors.

* This is an iPhone 3g, firmware 2.0.5A347
* Itunes 7.7.043
* I am a Microsoft Exchange client, so do NOT use PST files to store my mail
* Would not work with Outlook 2003 SP3 -or- Outlook 2007 SP1, -or- Entourage 2008 (Mac)
I tried everything I could find on the forums, including:
* full iPhone restore,
* Creating new Outlook profiles
* Creating new Windows User profile
* Clearing Sync History
* Uninstall / Reinstall Itunes
* Disable all third-party plug-ins in Outlook
* Set outlook security to none
* I had the appropriate plug-ins for Outlook
* Tried this all on a separate PC as well - no joy

What turned out to be causing the issue were Outlook recurring appointments which had atypical characters in the name: example

JESICA'S B-DAY<<Free>>
Steve's B-day<<Free>><<Free>><<Free>><<Free>>

I have been using some sort of PDA for around a decade, and carrying a lot of these recurring appointment over for almost as long. Somewhere along the way whatever sync software (ActiveSync, PalmSync) changed the formatting of the appointment itself and generated the symbols. When I deleted these recurring appointments and re-synced I saw all appointments show up.

Here is what I recommend:
1. First, if you are having your mail delivered to a .PST file then please ensure that you have followed the procedure to properly format/replace your PST, along with all of the other easy suggestions related to this issue.

2. Back up your entire calendar before doing this. The easiest way for me in 2007 was to highlight the calendar in the left-pane in Outlook, click File - Save As and choose .ics as the format.
3. Click More Options. For Date Range, select Whole Calendar. For detail, select Full Details. Click the Show button and check both boxes, and save this someplace you won't lose it.
4. In your Outlook Calendar, sort the entries by clicking View - Current View - By Category. Expand as necessary and sort the entries by the "Recurrence Pattern" column. Look for any entries that contain alphanumerics or other novel characters in the titles. Delete all of these odd (remember, you have a backup) entries.
5. Open up Itunes, access Preferences - Sync tab. Click the button to reset sync history, then try to sync your iPhone again.

Any calendar entries show up? If not, delete ALL reccuring appointments and try the sync again this time. If this works, you'll need to do some more analysis on those specific appointments to see which ones are causing the issue.

Good Luck

Jul 29, 2008 8:40 AM in response to Ivan C

I had the same problem, and spent DAYS on it. Here are the details:

I could sync Outlook contacts with no issues, but no matter what I tried I could not get one calendar appointment to show up on the iPhone. Itunes would sync, and even take a while processing "Syncing Calendar", but display no errors.

* This is an iPhone 3g, firmware 2.0.5A347
* Itunes 7.7.043
* I am a Microsoft Exchange client, so do NOT use PST files to store my mail
* Would not work with Outlook 2003 SP3 -or- Outlook 2007 SP1, -or- Entourage 2008 (Mac)
I tried everything I could find on the forums, including:
* full iPhone restore,
* Creating new Outlook profiles
* Creating new Windows User profile
* Clearing Sync History
* Uninstall / Reinstall Itunes
* Disable all third-party plug-ins in Outlook
* Set outlook security to none
* I had the appropriate plug-ins for Outlook
* Tried this all on a separate PC as well - no joy

What turned out to be causing the issue were Outlook recurring appointments which had atypical characters in the name: example

JESICA'S B-DAY<<Free>>
Steve's B-day<<Free>><<Free>><<Free>><<Free>>

I have been using some sort of PDA for around a decade, and carrying a lot of these recurring appointment over for almost as long. Somewhere along the way whatever sync software (ActiveSync, PalmSync) changed the formatting of the appointment itself and generated the symbols. When I deleted these recurring appointments and re-synced I saw all appointments show up.

Here is what I recommend:
1. First, if you are having your mail delivered to a .PST file then please ensure that you have followed the procedure to properly format/replace your PST, along with all of the other easy suggestions related to this issue.

2. Back up your entire calendar before doing this. The easiest way for me in 2007 was to highlight the calendar in the left-pane in Outlook, click File - Save As and choose .ics as the format.
3. Click More Options. For Date Range, select Whole Calendar. For detail, select Full Details. Click the Show button and check both boxes, and save this someplace you won't lose it.
4. In your Outlook Calendar, sort the entries by clicking View - Current View - By Category. Expand as necessary and sort the entries by the "Recurrence Pattern" column. Look for any entries that contain alphanumerics or other novel characters in the titles. Delete all of these odd (remember, you have a backup) entries.
5. Open up Itunes, access Preferences - Sync tab. Click the button to reset sync history, then try to sync your iPhone again.

Any calendar entries show up? If not, delete ALL reccuring appointments and try the sync again this time. If this works, you'll need to do some more analysis on those specific appointments to see which ones are causing the issue.

Good Luck

Jul 29, 2008 9:24 AM in response to Ivan C

*I have solved this problem.* I have had the same issue since upgrading to iTunes 7.7. Immediately after the upgrade, there was a new calendar named "Home" on the iPhone. I deleted it. I experienced the same problems with the calendar not syncing (however it really is). When I synced, and opened Outlook, on the main page, it showed the event I had just entered on the iPhone but when I went to the calendar, it was gone.

Thursday, I created a new folder within the Calendar folder with the name of my iPhone. If you did not name your iPhone, then it shows up on iTunes as "iPhone". This is the name.

Now, all the calendar entries I make on the iPhone are appearing properly in Outlook. I have entered events for 3 days and all the events sync perfectly back to Outlook.

You do not need to ever display the "Named" calendar on the iPhone, you can select "Calendar" and all the events will show just fine.

This has been a royal pain in the arse trying to figure out why it appeared they did not sync.

Jul 29, 2008 9:25 AM in response to Ivan C

I'm afraid I don't know how link to an existing post but I've come up with one solution to this. (There are also other suggestions in this thread http://discussions.apple.com/thread.jspa?threadID=1595598&start=150&tstart=0)

Here's my solution: (sorry for cut and paste)

Outlook 2003 connected to an Exchange Server. Windows XP SP3. iTunes 7.7.

Despite my post back on page 3 claiming my appointment 'categories' were causing my issues it transpired eventually that they were not.

A curious thing got me thinking... when I edited a missing appointment (I had an easy one to locate on my Today screen) and then went to the month view calendar it was not there. However clicking off the calendar and back onto it (causing a refresh) made it appear. Doing the same thing again caused it to disappear again. This was if I got the timing right - after much playing it seemed as if the appointment existed for about 20 seconds but only about 10 seconds after I'd saved it. (I should note that all this time the iPhone was not plugged in and I did not try to Sync and that this was all done with an appointment that iTunes/iPhone/Outlook had damaged previously.)

So why would an appointment only exist in a viewable state for a short while with no other interaction? Hmmm perhaps it's because I'm at work and Outlook is syncing with an Exchange server? It's doing stuff without my involvement? I turned off Cached Exchange Mode and lo and behold - all my missing appointments came right back.

To do this go to Tools/Email Accounts/View+Change/Next/Select the correct account/Change/Untick 'Use Cached Exchange Mode'/Next/Finish/Close Outlook+iTunes. Give it 30 seconds to close the datafiles. Restart Outlook.

Hopefully this should fix it for some of you that sync Outlook on Exchange.

Jul 29, 2008 10:50 AM in response to Guesswho369

After reading thru these threads I have finally tried and found a solution that worked 100%. Thanks to Guesswho369 for the post that helped.

Im using an old iPhone, software v2.0 Itunes 7.7 sncing to outlook 2007 on WinXpPro.

*The issue was with recurring appointments.*
1. I created a new calendar in Outlook called Birthdays and moved all recurring birthdays to that calendar. I did not give them an end date.
2. I gave all remaining work related recurring appointments an *End Date*
3. I disabled all MobileMe sync my control panel (this feature was added in Itunes 7.7 and I had also been trying it out).
4. I restarted my PC
5. when I opened outlook I now had 4 calendars; Calendar (my main), Work, Home and Birthdays.
6. I Set my iPhone to sync only calendars I select and chose Calendar and Birthdays.
7. My iPhone synced in about 1 min vs 10 mins previously and all appointments are confirmed and available.

I hope this helps. This has truly been a frustrating few days since upgrading to v2.0 and itunes 7.7!

Peace -

Jul 29, 2008 12:17 PM in response to kk5do

Honestly I am not sure whether creating a new calendar with my iPhone's name did the trick, or fixing the recurring appointments did it, but I FINALLY got the bloody iPhone to sync! This is beyond acceptable. I have a 1G iPhone and am using XP SP3.

What also occurred is that all of my appointments appear in at least duplicate form. Since this is better than no appointments appearing on my phone, I will leave well enough alone.

Don't get me started on MobileMe' inability to sync with my Outlook 2007 calendar, and how it totally scrambled my contacts.

Aug 2, 2008 12:18 AM in response to Guesswho369

I'm new to the iPhone and this support page, but this sounds like the right place.

When I first synced my iPhone with Outlook 2002 (directly to the computer - no exchange server) it proceeded to delete a bunch of recurring appointments from the Outlook and didn't bring any of them to the phone. Have you all been articulating a solution to this problem and I'm too dense to see it on the screen? (Forgive me - it's late).

Aug 2, 2008 10:39 AM in response to SEP1234

I gave up trying to sync my 3G phone to Outlook 2007 using iTunes and the direct USB connection but was successful syncing via Microsoft Exchange.

The problem now is that events entered into Outlook calendar appear as invitations on the iPhone. As such, you can only respond using accept, decline or maybe instead of being able to edit the event, i.e, to change the time or day, etc. I'm convinced that this is a fundamental incompatibility with 2.0 firmware and Outlook preventing a seamless integration of the pst entries.

I have spoken to Apple tech support severaal times and even to a specialist -- they don't have a solution and try to blame this on Microsoft -- not a bad idea generally but entirely unfair in this case (I scolded them for trying).

I have not usedApple products since the late '80s when my workplace required conversion to PCs. This is really a disappointment!

iPhone calendar sync issues with Outlook

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