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!