Funny that mailers should come up here today. I went on holidays for a three-day weekend, which meant that I had approximately 300 critical, must-answer mails waiting for me after I got in last night and downloaded my mail (I get about 75 critical mails/day on weekends and about 150 on weekdays; it's kinda gross, actually).

So just before I went to bed, I decided to file my sent mail (I file all my mail into 50+ folders, by hand), but there was a weird display-bug, some of the messages weren't showing up. When I tried to select them, Entourage crashed. It did this repeatedly, so I decided to rebuild my mail-database, using the Advanced Rebuild.

Now, I have a lot of archived messages in Entourage: Over 100,000. My mail-database is edging up on 1.5GB, and a rebuild takes about an hour. So I went to bed. When I got up this morning, I checked my mail, pruned out 200+ spams, and started to go through the prioritized inboxes (High, Medium, Low, Rock-Bottom) that I use to keep track of what I need to do.

They were empty. Nearly 300 critical messages, vanished. Panic set in.

I opened up my Microsoft User Data folder and checked out my Main Identity dir. There was the new database (1.45GB) and my database (which Entourage had backed up to a file called "Old Database") (1.5GB). 50MB of mail was gone. Some of that was reclaimed empty space, but also gone were my 300 messages.

So I did the logical thing. I quit Entourage. I renamed the Database file to "Database.bak" and the Database Cache file to "Database Cache.bak." I renamed Old Database to "Database" and "Old Database Cache" to "Database Cache." I relaunched Entourage.

I was looking at the same view I'd seen the last time I'd launched it. My inboxes were empty and the new messages were there. OK, I thought, Entourage is still looking at the rebuilt database and cache. Must be referring to them by alias instead of pathname. Fine. I tarred the rebuilt files, trashed them, and relaunched.

Same goddamned thing. I was definitely looking at the original database file, but all the messages from the night before were gone and all the new messages I'd fetched this morning were there, having magically leapt from one file into another.

I started to hyperventilate. I called MSFT support and waited to get it fixed.

They couldn't fix it. But the CSR I talked to told me a couple things:

• If you want to archive 100,000 messages, don't use Entourage. Run Outlook under OS9 (ugh, you're kidding me, right?). Entourage isn't intended for heavy use.
• The behavior Entourage exhibited is totally inexplicable.
• Before rebuilding a database in Entourage, duplicate your Main Identity dir and throw out the Database Cache file. That way, you can switch between the two spools using "Switch Identity."
• Your most recent messages are the most likely source of sudden corruption in your mail database, and therefore most prone to being deleted during a rebuild

The story has a happy ending: After quitting and relaunching Entourage dozens of times, all my missing messages came back. I dragged them to the desktop, switched to the rebuilt database and dragged them back in.

But now I'm thinking that Entourage and me aren't long for this world. I'm thinking I'm going to switch to something like mutt or pine, which store their messages in good, old-fashioned ASCII files. I hate Eudora's UI, but I have a feeling that Eudora can read the mbox files that mutt and pine use, so I can switch to a GUI app when I want to use a windowed mailer instead of a command-line utility. I'll miss some of Entourage's features (especially the automatic linking of messages, threads and address-book records), but my mail is far, far too important to trust to a crash-prone mailer that eats recent messages when it dies.