status of S/MIME and interoperability?

[Greg Troxel]

I am using gnus/epg/gpgsm (emacs 24, gpgsm 2.0.29, on NetBSD 6 i386) to
do S/MIME.  Yes, I know why I should use OpenPGP instead, and the entire
issue of X.509 trust anchors with S/MIME in practice has been an
adventure.

Generally, I find that gnus/gpgsm works well.  I can process on receive
pretty much all S/MIME messages I receive.

Sending, my impression is that users of Thunderbird and Mail.app
following can receive my encrypted messages, at least without large
attachments.  But Outlook users appear not to be able to process
encrypted messages from gnus/gpgsm.

I wonder if anyone has done a more thorough investigation of MUA
interoperability, and if it is known whether the gnus/gpgsm->Outlook
lack of interop can be fairly pinned on Outlook, or whether it is a bug
on the free software side and should be fixed.

I have had no issues with OpenPGP.  However it appears that OpenPGP
tends to leave out Outlook users :-)
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