Connecting to smtp.gmail.com via command line

Question

I am in the process of writing an application that sends mail via an valid GMail user ID and password.

I just wanted to simulate the SMTP connection on my Windows XP

Answer 1

tcp/465 was initially intended for establishing the SSL(and newer TLS) layer first, and inside doing cleartext or plain old protocols (smtp here)

tcp/587 was intended as a replacement to default tcp/25 port initially when spammers and mass mailing attacks commenced like a decade or more ago, but also during those infamous AOL ages, when some funny ISP had some blocks on default ports outbound (such as that tcp/25) for denying their own customers (AOL) to mass-send emails/spam back then, but AOL-customers needing to use alternative mail-accounts and mail-providers still needed to send their mails from AOL-internet connections, so they could still connect to tcp/587 and do simple smtp on it back then.

The deal with the STARTTLS way to do smtp is to use the two well known originally plain-text tcp/25 and tcp/587 ports, and only when the initial clear-text connect suceeded, to then START the TLS layer (thus STARTTLS) from there on, having a secured connection from that point onwards.

As for debugging these kind of things maybe via command-line tools, for example for windows there is the historical blat command line mailer (smtp), which up till today cant do TLS (STARTTLS) so it can only use plain-text smtp to send its mails.

http://www.blat.net/

Then there are numerous projects freeware and open source software that have more capabilities and features, such as

smtp client: mailsend @ googlecode http://code.google.com/p/mailsend/

smtp client: msmtp @ sourceforge (related to mpop below) http://msmtp.sourceforge.net/

pop3 client: mpop @ sourceforge http://mpop.sourceforge.net/

Answer 2

Try this:

telnet smtp.gmail.com 587

Answer 3

For OSX' terminal:

openssl s_client -connect smtp.gmail.com:25 -starttls smtp 

Answer 4

Jadaaih, you can connect send SMTP through CURL - link to Curl Developer Community.

This is Curl Email Client source.