Using gmail as a SMTP Server

Firstly you will not be able to do a direct telnet as gmail using secure connections so there is a free utility that you can use it is called OpenSSL and works pretty much the same as telnet however you will have to enter your username and password in 64 bit MIME (Multipurpose Internet Mail Extensions) based content transfer encoding with base64

Dont worry if didnt quite understand the last bit :-) this encoding is just a standard used to encode non-text 8 bit and binary data. Sometimes used for text data that frequently uses non-US-ASCII characters. There is an internet site which can encode your text data into MIME base64 using this free online utility http://base64-encoder-online.waraxe.us/

1. To begin with download the OpenSSL for windows from http://code.google.com/p/openssl-for-windows/downloads/list
2. Encode your gmail username and password using the encoding utility
3. Go to the DOC command prompt and start the OpenSSL utililty
openssl s_client -ssl3 -connect smtp.gmail.com:587 -starttls smtp -crlf
Loading 'screen' into random state - done
CONNECTED(0000015C)
depth=1 /C=US/O=Google Inc/CN=Google Internet Authority
verify error:num=20:unable to get local issuer certificate
verify return:0
---
Certificate chain
0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
i:/C=US/O=Google Inc/CN=Google Internet Authority
1 s:/C=US/O=Google Inc/CN=Google Internet Authority
i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority
---
Server certificate
-----BEGIN CERTIFICATE-----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=
-----END CERTIFICATE-----
subject=/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
issuer=/C=US/O=Google Inc/CN=Google Internet Authority
---
No client certificate CA names sent
---
SSL handshake has read 1932 bytes and written 337 bytes
---
New, TLSv1/SSLv3, Cipher is RC4-SHA
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
SSL-Session:
Protocol : SSLv3
Cipher : RC4-SHA
Session-ID: F08336D4E6FBF5787A197A46D52333B1B2F19B1DA908C213184DD4797B92E60A

Session-ID-ctx:
Master-Key: 18C7490AA3E755D0BCE0EFB80CF99FD0D245A0C6FE58F4D1AD0176E0D826667B
CB8B5ECCE9AA6C67FE680139FF3C771D
Key-Arg : None
Start Time: 1324960518
Timeout : 7200 (sec)
Verify return code: 20 (unable to get local issuer certificate)
---
250 ENHANCEDSTATUSCODES
AUTH LOGIN
334 VXNlcm5hbWU6
c2hhaUBzaGFpLWFydml4ZS5jb20=
334 UGFzc3dvcmQ6
bjw1JWptPm5+OWtjVjdpRi9IIl5HcEhnaHMwN
235 2.7.0 Accepted
mail from:<snk@ae.columbusit.com>
250 2.1.0 OK b20sm85444224ibj.7
rcpt to: <snk@ae.columbusit.com>
250 2.1.5 OK b20sm85444224ibj.7
data
354 Go ahead b20sm85444224ibj.7
subject:Hello
Hello World from gmail SMTP
.
250 2.0.0 OK 1324960636 b20sm85444224ibj.7
quit
221 2.0.0 closing connection b20sm85444224ibj.7
read:errno=0