Im validating with Windows Live Mail and Microsoft Office.
Chances are small that 2 of microsoft's validation tools are "defective".

However, it seems that the problem solved when I switched to djignz (a central S/MIME open source solution for signing, decrypting, verification and encryption. Djignz seems to be able to cope with really bad MIME without generating bad signatures which is good.

-----Ursprungligt meddelande----- From: Wietse Venema
Sent: Thursday, March 05, 2015 7:11 PM
To: Postfix users
Subject: Re: Have tested lots of solutions now with signing-milter. What is the problem?

Wietse Venema:
How many other milters are there after the signing milter?
If there are none, then your signing milter is defective
(produces an incorrect signature).

Another possibility is that your validation tool is defective.

Wietse

Attachment: smime.p7s
Description: S/MIME Cryptographic Signature

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