I successfully published our exchange server 2007 over the Sophos utm (compare https://community.sophos.com/products/unified-threat-management/astaroorg/f/57/t/50159).
Two of our teachers connected Apple Mail at home with our Exchange Server. If I’m right, this doesn’t work over Outlook Anywhere but over EWS. With the most mails that worked. But three times there was a mail, where the sender address wasn’t the sending teacher himself but a randomly other person in our institution. The main problem with that is, that this randomly other person finds this mail in his sent item folder so he can read the mail. We sent hundreds of mails since we replaced our ISA server with the Sophos utm, but this happened only 3 times, and every time it was from outside with an Apple Client. So that is the reason I suspect WAF making this problem and not the exchange server itself. It is very difficult for me to reproduce the behavior as I don’t have a Mac Client myself and because it doesn’t happen every time. I recommended to use Outlook Web Access instead until I have more information.
Is there anybody who has detected the same behavior? Maybe this is a bug in WAF for Exchange.
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