I did a test with another email and it does not seem to be a general problem but rather related to specific emails from specific senders. The difference between a working email and a non-working Email:
Working Email sent with OS-X Mail and GPGTools with OpenPGP. The email headers from the working email include:
Content-Type: multipart/encrypted;
boundary="Apple-Mail=_5190EDB6-62A4-46DB-9236-629EB0945FD0";
protocol="application/pgp-encrypted"
X-Pgp-Agent: GPGMail 2.6b2
Content-Transfer-Encoding: 7bit
Content-Description: OpenPGP encrypted message
X-Mailer: Apple Mail (2.3124)
Non-Working Email was sent with MS Outlook via "SafeGuard MailGateway".The email headers from the non-working email include:
Content-Type: multipart/mixed;
boundary="-CM_GW:=GSjV6gJuKioe1e91NA6npXm7RLkl4rVQb4q"
X-MS-Has-Attach: yes
Any ideas?