I am using no gnus master on emacs23, with up to date gnupg1 and
gpg-agent, on NetBSD/i386 5.1ish.  I sign messages via:

  LT HASH secure method=pgpmime mode=sign RT

Usually all is well, but sometimes when I send a message I get "Sign
failed" and am left in the message buffer.  I then hit ^C^C again, don't
get warned about "already sent, resend?" and sending happens normally.
However, two signed copies of the mail go out.

So it seems like there is incorrect reading of status (or incorrect
status), but also that the marking of the buffer that the mail is sent
is more disconnected from sending than I would expect.

I'll look into this, but I wonder if anyone else is having this problem?