> I just noticed, that the outlook plugin is german only, also if I switch kleopatras language. It would be a huge help if I could get a test account on your server, then I could try to figure out more what's going on using introspection tools and interactive debugging. The MIME Boundaries are not Boundaries that Outlook would generate and they contain the hostname of your Windows Server, so I guess the MAPI (Outlook's internal data format) to MIME (the internet transfer format) happens on your server and somehow it does not use the encrypted mail. From your mails I can at least take that there is something non standard going on. Still it would be surprising as I did not expect there to be a way for the server to get to the plain text if we encrypt on the Outlook client (without an addon). GFI Mailessentials might be the culprit as this is non standard and from the product description it supports introspection of outgoing mails. I installed Kaspersky Total security on one of my test systems and still can't reproduce the problem. Server Win 2012 R2 with Exchange Server 2013 and GFI Mailessentials. Win 10 Enterprise N en, Office 365 Pro Plus en, Kaspersky Internet Security. I sent it to a user on a different Mailserver.
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