When I had a BlackBerry, I relied on PocketMac’s free sync tool that enabled me to sync my Entourage calendar, notes and address book with the BlackBerry. Since moving to the iPhone, I rely on the sync services built into Entourage, which also interacts with OS X’s sync services. Until recently, it worked ok—new events got synced from Entourage to iCal within seconds, and then to my iPhone over a USB sync (or vice-versa, since new events on the iPhone would make it to Entourage).
Then came Apple’s change to MobileMe. Dorky name, but whatever. It held the promise of push e-mail as well as push contacts, push calendar events and push bookmarks. Sounded great. And initially, once some bugs were worked out on Apple’s end, it seemed to work ok. Certainly, the push e-mail works perfectly. However, “pushing” to and from my MacBook Pro would take much, much longer. True, the MobileMe sync preferences are set to sync at 15-minute intervals (a number easily changed, mind you, but in the end that doesn’t help much—trust me). That I could have lived with, since all I’d have to do is hit the Sync Now button in iSync on my menu bar, and that would be that. However, syncing this way takes forever. The sync would keep going and going for 30 minutes or more, even if hardly anything had changed on my iPhone or laptop.
I reset sync services, restarted, repaired permissions, etc. but that didn’t make the “push” syncing any faster. So I disabled push on my iPhone except for e-mail, and that’s when the real troubles started. As expected, the calendar, contacts and bookmarks on my iPhone were now blank, but one sync with my MBP over a USB cable would do the trick. And it did. Except that with all the sync services nonsense I went through, my iCal calendar wouldn’t sync within any reasonable timeframe with my Entourage calendar. I had read an article on MacFixit about how to solve these issues by deleting several preference files, and that made things worse. I no longer had any Entourage calendar within iCal, nor was it being recreated by deactivating then reactivating sync services in Entourage. And when I finally had some success, everything was duplicated on both ends. Fortunately, I had a backup of my Entourage database (several, actually, all taking up 2+ GB of space), and reverted to that one, but now iCal only showed all my old recurring events ad nauseum. I even went into the terminal and tried the following:
rm -rf ~/Library/Application\ Support/SyncServices/*
(note: in general, I never recommend using any rm -rf Unix commands, since it can end up irrevocably trashing unintended files, but in this case it was worth a shot.). Unfortunately, this didn’t work. Apple does mention never to delete anything in the SyncServices folder, but deleting the entire folder in the expectation that it would be recreated later on seemed reasonable.
To make a long story short, after two days and many hours of dealing with this issue, here was the fix, at least on my system, which I found in a support article from the Entourage Help Page:
Turn OFF all sync services in Entourage preferences
Quit ALL Office applications (including Daemon—a script to do this is here)
Quit Safari, Address Book & iCal and all applications synching through .Mac (Transmit, Yojimbo…)
Use Activity Monitor to quit Sync Services
Delete the contents of ~/Library/Application Support/SyncServices/
Optionally: if you want to replace all data in the system Address book and iCal with Entourage data, delete all iCal & Address Book Data Files:
Open the .Mac System preferences and make sure .Mac synching is enabled
Restart all applications that sync to .Mac (Safari, Address Book, iCal, etc…. and Entourage).
Turn ON Sync Services in Entourage preferences.
- ~/Application Support/iCal/*~/Application Support/AddressBook/*
I should also add that I used iSync to reset the sync history. How much that helped is hard to say, but Apple also suggests going into Terminal.app and typing:
I didn’t need to try that one, which probably does what I did with resetting the sync history anyway. In any event, I now can sync perfectly over USB again. However, I strongly recommend not enabling push for contacts, calendar and bookmark synchronization. It’s slow, unpredictable, and the fact that I usually cannot load the calendar page in MobileMe doesn’t make me very confident in Apple’s servers these days. Until they really have their act together on the MobileMe front, I’m keeping push off except for e-mail. The whole MobileMe push thing is what got me into this nonsense, anyway. It cost me much of my weekend, and had I not been careful, could have lost data as well.
UPDATE 3/30/09: Well, I think Apple has finally gotten its act together on the MobileMe front. I’ve been using MobileMe sync for weeks now and it’s been great. I no longer use Entourage at all, but use Mail/iCal/Address Book, so my sync problems have been gone for many months, and the addition of syncing through the cloud only makes this better. But if I were still using Entourage, I’d be leery, mainly because SyncServices and MS Sync is not great.