status of S/MIME and interoperability?

Ed Finnerty edfinnerty at
Tue Feb 2 17:58:59 CET 2016

On 02/02/2016 06:56 PM, Ed Finnerty wrote:
>>> Sending, my impression is that users of Thunderbird and
>>> 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.
>> For this particular interop issue, I am curious what is causing the
>> difference.  S/MIME encrypted messages are typically in the
>> enveloped-data format, which means that the encrypted content is simply
>> treated as an attachment.
>> If you have access to an MUA interoperable with Outlook, could you
>> compare the message structures for the success/failure cases?
> I've actually logged the problem here and even attached a script that
> easily tests for the issue and can be modified to produce trivial test
> output for comparison purposes.
> Nobody seemed to really care. So if you do S/MIME with GPG, and use
> Thunderbird, every once in a while you'll get an undecryptable message
> that you have to save to disk and try to deal with in some way with GPG.

Of course, I forgot to add the link:

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