I have been working on the same thing currently I have a work around with sending to gmail but it requires installing an SMTP server on my system, socket connecting to it and having in the RCPT TO:Whoever@gmail.com
and then setting a filter inside gmail to check for the subject to be IRC Text Message and From to be from what ever I setup in the MAIL FROM:.

I am using my own custom script to connect and currently I have found a way to use MS-DOS to connect correctly to gmail and send an email log file shown below.

I am working on a way for a TLS connection through mSL code currently and will keep you updated on my progress (just started all of this about 25 hours ago and have spent about 18 or so hours total towards learning SMTP protocol, AUTH, TLS connections, and writing my script.



This is the command entered with openssl installed in C:\Windows\System32
Code:
C:\Documents and Settings\User>openssl s_client -connect smtp.googlemail.com:25 -starttls smtp -crlf

*Notes for command above
s_client - Used to establish that you are the client
-connect - Connect to proceeding server:port
-starttls - Automatically start a TLS connection simliar to a telnet connection
smtp - telling the -starttls that this is a smtp server
-crlf - Changes normal LF or linefeed (next line) into CR LF or Carriage return Line Feed (which is required for SMTP)

*Note S> = server notice C> = Client typed. Added Blank Lines for easier Readability. Only S> and C> are actual communication all * are notes. Edit - All commands sent to openSSL should be lowercase. If you try and use an uppercase R or Q it will not send the command but be interpreted as either renegotiate or quite respectively.
Code:
S>250-mx.google.com at your service, [71.53.76.253]
*servers Welcome after the TLS handshake

S>250-SIZE 35651584

S>250-8BITMIME

S>250-STARTTLS

S>250-ENHANCEDSTATUSCODES

S>250 PIPELINING
*servers modes available

C>ehlo Demonlord.Haxx
*ehlo to tell server that we want enhanced SMTP

S>250-mx.google.com at your service, [71.53.76.253]

S>250-SIZE 35651584

S>250-8BITMIME

S>250-AUTH LOGIN PLAIN

S>250-ENHANCEDSTATUSCODES

S>250 PIPELINING
*New server modes presented

C>auth login
*Tell the server we want to login

S>334 VXNlcm5hbWU6
*Server asking for username VXNlcm5hbWU6 stands for username in *Base64

C>RXhhbXBsZQ==
*Client Username changed to Base 64 in this case it means Example

S>334 UGFzc3dvcmQ6
*Server Asking for password UGFzc3dvcmQ6 = Password in base 64

C>R21haWw=
*Client Password in Base 64 in this case it means Gmail

S>235 2.7.0 Accepted
*Server accepts Login

C>mail from:<fad2007@gmail.com> auth=fad2007@gmail.com
*You *MUST* add the AUTH like this to make it work correctly!

S>250 2.1.0 OK 28sm2010271qbw.11

C>rcpt to:<relayirc@gmail.com>

S>250 2.1.5 OK 28sm2010271qbw.11

C>data

S>354  Go ahead 28sm2010271qbw.11

C>from:irc@irc.com

C>to:relayirc@gmail.com

C>subject:text

C>
*MUST INCLUDE BLANK LINE THERE

C>Test123 123 12345

C>
*MUST INCLUDE BLANK LINE THERE

C>.
*PERIOD ENDS EMAIL

S>250 2.0.0 OK 1227251631 28sm2010271qbw.11
*Message Being sent

C>QUIT
*Ends openssl connection

S>DONE
*openssl connection closed successfully

Last edited by Demonlord; 21/11/08 08:07 AM.