So I use Microsoft Entourage as my main email client, and had been wanting for some time to get my messages exported out of my local drive. As much I trust my laptop and my backups, one good earthquake later and all of that would be futile.
Getting my message archives preserved (with all metadata intact, like Sent and Received dates, etc) was the easy part. Grabbing all future messages was the hard one. Of course, Microsoft, in its infinite wisdom, didn’t include an auto-bcc for Entourage.
I had this setup going on to automatically redirect most messages I send to a repository for later search and retrieval. I had a process set up where, except for select messages that I mark as confidential, the above rule gets triggered.
A month later, by pure chance, I realized that Entourage wasn’t quite deactivating the CC field on the redirect for archival. There is a bug that resends the message to all CC’ed emails on redirect. For example, if I were sending to email@example.com, cc’ed to firstname.lastname@example.org, and redirecting to email@example.com:
1. the first copy goes out to a and b.
2. Then, the redirected copy will be sent to archive and b, as b appears on the CC list.
3. End result: a receives 1 copy, b receives 2 copies, and archive receives 1 copy.
In essence, all the people I cc’ed on anything got spammed with a duplicate every time I sent a redirected copy via Entourage’s Outgoing rule. This is stupid, and Microsoft’s website doesn’t warn you about this. Try it for yourself if you don’t believe me.
Had I been more diligent at searching the web or even just testing out this archival strategy, this wouldn’t have happened. Plus, I would have noticed one fellow complaining that all contacts on the CC list, for every email, received a copy of his archived messages. Ouch. I’m glad I didn’t try redirecting all of my sent box (there is another strategy, which I will outline sometime, is far easier – but it can’t do real-time, auto-bcc).
To all the people whom I inadvertently spammed, I’m awfully sorry. This won’t happen again.