Hallo.

Sven Neuhaus <[email protected]> wrote:
 |when switching from Ubuntu 14.04 to 16.04, heirloom-mailx got replaced
 |by s-nail. However, S/MIME encryption broke.
 |
 |Details are at
 |https://bugs.launchpad.net/ubuntu/+source/s-nail/+bug/1640190

I am not subscribed there.

 |Is anyone else able to reproduce this?
 |Has this issue already been fixed in the latest version of s-nail?

I don't think there is an issue on our side, S/MIME is tested via
cc-test.sh in the distribution.
I wouldn't exactly call the bug report detailed, your setup must
be different from what the bug report states, i.e., more complete.
Have you read the manual ("Signed and encrypted messages
with S/MIME")?

Compared to Heirloom mailx the S/MIME support has been actualized
a little bit regarding the standard RFC 5751.  E.g., if you
replace the line

  Content-Type: application/pkcs7-mime; name="smime.p7m"
with
  Content-Type: application/x-pkcs7-mime; name="smime.p7m"

then maybe that fixes the problem, though unlikely because other
MUAs use this one exclusively for some time.

More likely the culprit is the upgrade of the *smime-cipher*[1]
from des3 (DES EDE3 CBC) to aes128 (AES-128 CBC).  If i recall
correctly Heirloom used 3des for the name, so if you have set the
cipher to 3des then this could also be it.
You now can also fine-tune the message digest by setting the
*smime-sign-message-digest*[2] option, i.e., more backward
compatible:

  set mime-cipher=des3 mime-sign-message-digest=MD5

More forward compatible

  set mime-cipher=aes256 mime-sign-message-digest=sha512

  [1] https://www.sdaoden.eu/code-nail.html#429
  [2] https://www.sdaoden.eu/code-nail.html#_437

Hope this helps?!
Ciao!

--steffen

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