I wanted to automate some reminder emails I send out every week (because I always forget to send them), and thought I’d give Automator a try. The experience wasn’t that great. It launches OS X’s Mail application and, for whatever reason, doesn’t send anything. The message just sits in the Outbox. I think it’s a known bug in Automator, but it was sort of a letdown for something as simple as auto-sending email.
So instead, I adapted a short python script that sends email via the smtplib and email modules, and used Automator to run the script via an iCal plug-in (File>Save As Plugin). Creating a plugin creates an Automator calendar in iCal where your scheduled script resides. All you have to do is set the timing. I know the command-line folks probably use cron to schedule scripts like this, but I like seeing the scheduled script on my calendar. I also like the script approach because I don’t have to launch any other applications (e.g., Mail). The script also works for those of you using google apps (just use your google apps email address).