I just tripped over this app while looking for something else

and
find it was recommended a while back by Mightly Kitten (in a "Greeware
again" -> Greenware thread). Perhaps of interest?
Program: Secure Email Attachments
Company: iOpus
Ware: (Freeware)
http://www.iopus.com/freeware/
http://www.iopus.com/secure-email.htm
http://www.iopus.com/download/index.htm
http://www.iopus.com/download/iOpus-SEA-setup.exe
iOpus Secure Email Attachments (SEA) V1.0 (only 559 KB)
Windows® 95, 98, Me, NT4, 2000 and XP!
"Let's face it, in the real world many people simply aren't willing to
buy and install a specific encryption package just to be able to read a
couple of files you send them. With iOpus Secure Email Attachments (SEA)
they don't have to, because you can send them self-decrypting archives
that "unpack" themselves. The recipient just double clicks on the file
and enters the password at the prompt displayed. The original files are
then decrypted, extracted and written to your disk automatically."
"iOpus SEA uses the Blowfish encryption algorithm with a key length of
up to 448 bits. Blowfish encryption is so strong that it has never been
cracked yet. In fact, most experts agree that it cannot be cracked with
current computer technology and that includes supercomputers!"
More info on the site.
Susan