Sven Neuhaus <sven-launch...@sven.de> wrote:
 |Thanks. I wrote "mime-cipher" and "mime-sign-message-digest" but I
 |actually had it correctly with an "s" in front.
 |
 |It gets weirder and weirder then. 
 |There must be something subtle that Apple Mail on iOS doesn't like.
 |I verified that the problem remains even with cipher DES3 and digest MD5.

Well, your problem report isn't very detailed, i don't know.
I don't have Apple Mail around, let alone on iOS.  Could very well
be an Apple Mail bug, then?  I really cannot tell you, i even use
my own CA storage when i can, and never touched KeychainAccess.app
or whatever the name was/is.  Yes, i have imported certificates
into Firefox once.

Of course there could be a S-nail bug: can you use the shown
openssl smime(1) commands on your target platform and re-verify it
is all working also there?  Maybe we find something subtle, then
i would like to fix it?  Otherwise i am out of ideas -- except
there were quite some fixes since v14.8.9, not to talk about .6,
what you say.  Not directly OpenSSL related, but of course
indirectly content could be different, and possibly Apple Mail
doesn't like what it sees when it decodes the content, though
i personally never have seen any message which would trigger those
problems (thinking about commit [ba29651], for example).
Would you be willing to check against v14.8.14, whether the
problem is solved there?  Download from

  https://www.sdaoden.eu/downloads/s-nail-latest.tar.xz

for example, simply "make all" and then use ./s-nail from within?
That would be nice.

Thank you, and ciao

--steffen

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https://bugs.launchpad.net/bugs/1640190

Title:
  S/MIME encryption broken

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