Of the 20+ users of Enigmail at our shop, a quarter sporadically
experience a peculiar problem when sending PGP encrypted 
email.   At unpredictable times, outgoing encrypted email 
will be transmitted in a form that cannot be decrypted by 
the intended recipients. This happens about once or twice
a month per affected user.  The sender eventually hears
about it, and resends: it is nearly always sent correctly encrypted
the second time.

Three affected users have Enigmail 1.5.1 in Thunderbird 17.0.5 on
MacOS-X 10.7, gpg (GnuPG/MacGPG2) 2.0.17. Two other users 
observe identical symptoms on Windows 7 (with the same versions 
of Thunderbird, GPG and Enigmail).

Symptoms:

The outgoing message, as encrypted for the intended recipients,
appears to get wrapped in another layer of encryption, keyed only for
the sender.  The recipients get the error "secret key needed to
decrypt message".  The recipients will see PGP/MIME headings.  This is
curious since PGP/MIME was NOT selected or intended (inline is still
the standard here). Affected senders are not using any per-recipient
rules.

If viewed by the sender in his Sent folder, the sender just sees
another block of encrypted armor message.  Since Enigmail 1.5, this at
least can be Forwarded, and the original message will be decrypted and
pasted inline.

This problem (or one that from a user perspective looks exactly
like it) was noted in the support forum on 2012-10-28
under the title "sent mail sporadically double encrypted?"
A lot of time was spent collecting and examining debug logs from
Enigmail, but no definitive cause was diagnosed.  An Enigmail developer
suggested this problem was likely a setup issue on our side, and
perhaps someone on this forum has seen this and solved it.  We've
struggled to find anything common in the setups of affected parties
that is not present in those of other users. No luck so far. 

Fresh suggestions on how to fix, work-around, or debug would be welcome.



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