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iPhone Sent Items Issue with Entourage 2008 July 2, 2009

Posted by bigmaconcampus in Mac Tech.
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UPDATE 8-20-2009:
Seems that the iPhone OS 3.1 update fixed this issue. So the following info might be moot at this point.

Ever since using my iPhone with Exchange (since the iPhone 2.0 Beta program), I’d had an issue with how the Sent Items from the iPhone device show in the Exchange Sent Items when viewed from Entourage 2008 (think it’s a problem with Entourage 2004 also, if I’m remembering correctly). Messages that are sent, show with no subject and the message content displays in HTML code or MIME encoded making it unreadable by the user.

After originally blaming the iPhone for this new behavior at the time (issue wasn’t present when connecting to Exchange via IMAP), I narrowed it down to an issue between ActiveSync and Entourage (wonderfully, both being Microsoft Products). I’ve since seen the issue with a Palm Treo running Windows CE that also uses ActiveSync to connect to Exchange and the user uses Entourage 2008.

Anyway, never having seen the problem fixed, about a year ago I came up with a work-around to make Entourage at least ‘seem’ to behave as you’d expect. A couple of Exchange Rules can be created to manipulate the messages around to end up doing what you’d expect.

This relies on having some unique text in your iPhone signature to identify emails coming from the device. Something like “Sent via iPhone” would do the trick. Also, the iPhone (or other device) should be set to BCC all sent messages to your email address. Entourage will then be able to determine which messages come from you from the device and move the appropriately using the following two rules:

ActiveSync Sent Items Fix

ActiveSync Sent Items Fix

ActiveSync Sent Items Cleanup

ActiveSync Sent Items Cleanup

Make sure that the rules have been added to the Exchange tab in the Entourage Rules section and are enabled and that should do it. Keep in mind that this is a local client rule and won’t take affect until the messages are downloaded onto the Mac running the rules. The side-effect of this is that you’ll receive a copy of all sent emails on your iPhone if your Mac is not open and able to apply the rules, but once you open Entourage, it will move everything around to its proper place and everything will eventually work out.