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I have a unique problem and I am hoping someone may have some direction to provide me.

We have a Windows environment with an Exchange 2007 Server. For some reason when a user sends an email from Outlook to a destination, it finds its way into the SPAM box of the recipient. Now, I know there could be a 100 reasons why this is happening, but I have found a resolution to the problem and it is the resolution that is confusing me..

If I remove the mailbox profile from the user's computer, then re-add the mailbox profile, the mail is no longer sent to the recipient's Spam folder.

This also means that if I find a user that is having this issue but log into OWA with their account, the email does NOT go to the recipient's Spam box, but if I send an email from their computer using Outlook, it DOES go to the recipient's Spam box.

To test this, I am having users send email to my private Gmail account. This has been the main form of testing that I have been using. I should specify that if I look at the original message (headers of the message) sent from the user, there is no indication that the message should be treated as Spam.

We changed our self-signed certificate yesterday so I am assuming it has something to do with that, but now I am just trying to figure out why exactly this is happening and how to resolve it (other than going around to EVERY computer and re-adding the mailbox profile for their computer). Does anyone have any suggestions?

Any help or information is greatly appreciated!

burmat
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My guess based on what you are saying would be that something in their original profile had a plug-in/add-in that was causing the email headers to tag it different than would be with OWA or the new profile.

The cert shouldn't matter, unless you are using it for TLS and even then it shouldn't work for TLS if it is self-signed. Plus, OWA would be using that same cert.

If you can compare the message headers of one that doesn't go to the spam box vs. one that does, that would probably tell you where the difference lies. I know you said you have looked at the original message header but did you compare a good vs. spam one?

TheCleaner
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  • I will re-compare tomorrow. The OWA access (IIS) uses a wildcard certificate while our Exchange services (currently) utilize the self-signed one. I just don't understand how removing and re-adding the mail profile triggers a fix to this problem. – burmat Apr 22 '13 at 01:34
  • If the mail profile was associated with a certain add-in...but that's the only thing I can think of as well. – TheCleaner Apr 22 '13 at 13:02