We have kind of a crazy bug that is showing up in our environment specifically with Outlook 2011 users.  We use Exchange 2010 sp3.

Sometimes when our users save multiple saved drafts in Outlook for Mac, and then later on send one of those drafts, their client will merge two drafts together and end up sending Draft B, with all of the content of Draft B, but to the recipients specified in Draft A.  In this situation both drafts disappear completely , and as far as Exchange is concerned, only one email is submitted which is the strange merged version, which is then routed as you would normally expect it to be.

The other odd part of this bug is, when we later take a look at these merged messages, the headers look correct, as in the headers of Draft B show the originally intended recipients of that Draft B, and make no reference to the mistaken recipients that are 'borrowed' from Draft A.  We obviously can't do any analysis of Draft A in these situations as Draft A disappears completely.

So if I have two emails in my drafts folder:

Draft 1:

To: Todd

Subject: Hey Todd

Body: Hey Todd

Draft 2:

To: Andy

Subject: Hey Andy

Body: Hey Andy

When I send the first draft in this example, I will end up sending an email to Todd, but it will be an email with the subject line, body and headers of the other draft originally addressed to Andy.  The hybrid email will make its way into the "Sent Items", the other draft will disappear completely.

It's almost as if the client is combining these two drafts together and then submitting a merged copy to Exchange.

So far it has impacted around 14 people in our environment, all using Outlook for Mac and all using drafts.  Other common factors seem to include time and travel, as in these drafts would be created while on a plane, and then sent when landed, or created a few days prior to being sent, or created offline, and then sent later when online.

Microsoft is aware of this and working with us to try and figure out what is going on here, but as it stands we have been unable to repro this in any kind of controlled environment, and I was hoping that someone else may have come across a similar issue?

Thanks!

Andy