hasta la vista, microsoft entourage

I’ve been an Entourage user for probably about eight years or so, after ditching the (terrible) Outlook 2000 for Mac. It was a great improvement on Outlook for Mac, but always had its limitations. I’ve noted in the past (in my old blog) about some annoying quirks, and many others have written extensively about these as well. But it generally worked, and worked fine. Looming in the background, however, was always the threat of catastrophic data loss. Not just data loss, but the whole thing. That’s because Microsoft took the bad approach of storing everything in a single, and generally bloated, database file. All one’s calendar entries, e-mail, notes, tasks and contacts reside in that one file. I’ve had several times where out of nowhere, Entourage would quit and the MS Database Utility would startup, all to have me waste about 15-20 minutes having it rebuild my database.

I put up with this, as do many others, because overall, Entourage works, and provides one-application access to a calendar, e-mail, contacts, etc. I’ve been running Entourage 2008 mostly fine for the past few months and it was syncing to my iPhone via iCal and Address Book thanks to Apple’s Sync Services. All was well…

Until about two months ago, when I had major problems with syncing. I got that all resolved after too many hours, and things were very good. If I created a calendar event in either Entourage or on the iPhone, it was all passed very quickly to iCal and everything would sync up just fine. But this past weekend, I noticed that a few upcoming calendar events were missing on my iPhone. Looking at my MacBook Pro, the events in question were correctly situated in Entourage, where I had created them, but never synced to iCal. And nothing I did would get them to sync. At one point, I disabled syncing between Entourage and iCal and then deleted the Entourage calendar in iCal, which proceeded to sync anyway (I had disabled syncing in the Entourage prefs), wiping out everything in both calendars. Nice. I had a backup, but I was in Mexico for work at the time.

I got back, restored from a backup and proceeded to follow the official advice on how to rebuild SyncServices and have all Entourage data go to iCal and Address Book. Note that syncing between Entourage and Address Book has always been flawless. The problem is with the calendar entries. Unfortunately, while I was able to get my calendar onto iCal and then my iPhone, nothing would sync in either direction. Redoing the whole SyncServices rebuild ended up triplicating Entourage calendars in iCal. Something was screwed up, and nothing would work.

So I now am up and running with Mail, iCal and Address Book. I don’t have these sync issues so far. That said, I’m still not entirely sold on this. For starters, iCal now hangs after a few minutes, perhaps as a result of importing my tasks. Who knows. Also, Mail takes literally just under five minutes to open. Five minutes—I’ve clocked it. No idea why. I used a Unix command (sqlite3 ~/Library/Mail/Envelope\ Index vacuum) to try to optimize it, but that hasn’t led to any speed increase, nor should it, since the Envelope database is brand new. So I’ve got some troubleshooting still to do. But at least I don’t have to worry about all this syncing stuff. Now there are some things I miss about Entourage, for sure. But I think I can live without it. We’ll see…

Update: The Mail hang was due to many, many old completed To Do items that were automatically imported from Entourage. Took a while to get rid of them, but they’re gone and Mail and iCal are behaving themselves.