The 250 - STARTTLS is just a server option, it is listing the available functions of the server if you actually respond using that it will say that the TLS session is already started.

Right now I am working with VB to try and write a mIRC dll that when you can use to send the variables
%emailSMTPserv
%emailSMTPport
%emailAUTHlogin
%emailAUTHpass
%emailMailFrom
%emailRcptTo
%emailTo
%emailFrom
%emailSubject
%emailMessage
to it using the /dll command and it will interface with the OpenSSL dll's to open the connection using TLS automatically and then have it send the email. I am not very good with VB so this may take me a bit of time. But I am thinking its about the only way to do a secure connection to a SMTP server.

I already tried having mIRC write a .bat file and running it but as soon as the OpenSSL command is run it doesn't parse any other commands until the OpenSSL ends. Also using the -e switch with sockopen doesn't do the handshake either so don't think its possible using sock mSL commands.

If the DLL doesn't work out the only other way I can see is possibly using Stunnel to negotiate the TLS handshake.

Last edited by Demonlord; 22/11/08 02:26 AM.