Found something promising: mutt has been ported to cygwin
. It works out of the box, too, with cygwin's gpg. The only security problem present appears to be that the submission agent, ssmtp
, does not do TLS out of the box and the source code won't build:
ssmtp.o(.text+0x1c01): In function `smtp_open':
/usr/src/ssmtp-2.60.9-1/ssmtp.c:1119: undefined reference to `_X509_free'
collect2: ld returned 1 exit status
make: *** [ssmtp] Error 1
Looks like it might be a SSL version problem.