I did some more testing.

I unpacked the mails using munpack. I then analyzed the smime.p7m file
using dumpasn1.

I noticed that heirloom-mailx was not using the aes256 cipher even when
given the parameter "set mime-cipher=aes256". According to the manpage
the best thing it can do it triple DES so that's understandable.

So I configured s-nail to use mime-cipher des3 and
mime-sign-message-digest md5.

I compared the two smime.p7m files. They are almost identical.
One thing I noticed that in the last sequence (after object identifier
des-EDE3-CBC, the s-nail version has 2x16 bytes whereas the
heirloom-mailx version has 7x16 bytes.

Same result when using

openssl smime -pk7out -in file.eml | openssl asn1parse

However, Apple Mail on iOS still doesn't like the file.
I'll try to test it with another client.

-Sven

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