Fun with Mail (part 1)

A description of switching around with email clients, and writing some IMAP code in Smalltalk.

I've been a Eudora user for many years. I started using it back when I was a student, and mostly stuck with it, with a bit of time off using VM in Emacs as my primary client. I never liked Outlook, but was able to so I just kept using Eudora in preference to that for corporate email. One of the very nice things in the later versions of Eudora was the search system. The UI was slightly awkward, but it was fast and gave good results. And I keep a lot of email, so that's important to me. I'm at about 5GB right now, with some of it going as far back as 1990.

Unfortunately, Eudora has been abandonware for quite a while now. I resisted switching for a long time, but there were starting to be enough problems that it had to happen.

I wasn't sure what client I'd end up with. The various webmail solutions seemed to be out because none of them seemed to have ways for me to upload huge archives of old mail. So I figured I'd end up with an actual mail client on my machine. In order to be able to try out different ones, and also because I thought it'd be fun, I set up a small Linux server with IMAP (using dovecot) and had it fetch the messages from my various accounts to one location.

Getting the email over was a bit of an adventure. It was possible, in Eudora, to set up an account on the IMAP server, and then to drag folders over onto it, copying their contents. But that was very slow, and tended to crash. Eventually I found a Mac called Eudora Mailbox Cleaner that can also convert the format, and I was able to use that to import both my old Eudora mail, and some other stuff that wasn't in Eudora, but was saved in more or less Unix mailbox format. It crashed a couple of times part-way through, but with a bit of babysitting I got it all converted into local folders in Thunderbird. Thunderbird would let you move stuff from local folders into IMAP as well, and it wasn't quite as slow and didn't crash quite as often.

So ultimately I had my mail converted, and was able to try out some clients. Apple's mail was the main other one I tried, but it missing features I wanted, so I ended up mostly using Thunderbird, particularly with the QuickFolders and Archive This extensions, which were helpful for quick filing and finding folders. But Thunderbird had some problems. The search was not particularly fast, at least not on the kind of volume of mail that I had. Worse, the filters didn't seem to work reliably. I don't know if that was just an issue with Thunderbird and IMAP, but the spam filtering wasn't moving things out of the Inbox reliably, and mailing list messages weren't reliably going into the right folders.

I decided to take this as an opportunity to write some Smalltalk code, and made myself a little cron job that would run a Smalltalk program to filter the messages. Along the way, I learned a bit about IMAP and the VisualWorks libraries for using them. So in part 2, I'll talk about some of the code that I ended up with.