I had this setup going on to automatically redirect most messages I send to a repository for later search and retrieval…A month later, by pure chance, I realized that Entourage wasn’t quite deactivating the CC field on the [redirected] archival email. In essence, all the people I cc’ed on anything got spammed with a duplicate every time I sent a message…
And now, the continuation…
So Google finally enabled IMAP for my accounts on thallos.org, which allowed me to test a new strategy for archiving sent mail. Again, the goal is to have a copy archived straight from Entourage, whenever I send a new email, to my mail repository. With proper IMAP access, however, this became much easier.
First, configure Entourage for IMAP access to Gmail / Google Apps. This is surpisingly non-trivial, since Entourage is not a supported client as of the time of this post. Rather strange, considering that Entourage must be at least second or third place in terms of install-base for Mac email clients. Follow the generic instructions for IMAP setup, and you should do okay. If you’re on Google Apps, the username is your_name@your_domain.tld, as per this configuration instruction.
You should have an IMAP structure for your Gmail boxes once this is complete. Simply set a rule in Rules -> Outgoing, for all messages, to copy the message to the Gmail/Sent Mail folder. In fact, this is the exact same approach if you were backing up to an IMAP-enabled mail server.
Unfortunately, It broke for me on a couple of messages. Gmail servers reported inconsistent failure messages, such as “Connection to the server failed or was dropped” and “The message could not be copied.” Some message headers also seemed to be mangled in transit, with the sender’s name dropped and so forth. The messages themselves were innocuous, text-only messages with no attachments, HTML, or any other random nonsense, so I find it very curious to be failing on these messages. Will have to look into it a bit more.
UPDATED Nov 22, 2007
See the exciting (yet depressing) episode 3 of my adventures in email archival.