If you get the above when inspecting the putput from your SMTP server then you most likely have something inspecting your SMTP or ESMTP traffic. In my case it was a CISC0 851 router. I believe a most CISCO gear especially PIX firewalls are culprits for this. Below is what I was getting:
250-SIZE 52428800
250-PIPELINING
250-AUTH PLAIN_TEXT LOGIN
250-XXXXXXXA
250 XXXB
starttls
500 unrecognized command
If you want to see a genuine output from a server try the following.
debian:~# telnet YOURSERVER.COM 25
Trying 8.8.8.9…
Connected to YOURSERVER.COM.
Escape character is ‘^]’.
220 YOURSERVER.COM ESMTP Exim 4.5 Sun, 21 Jan 2007 19:16:18 +0000
When you see the above, enter:
EHLO [10.10.10.8]
and the following will be the output.
250-YOURSERVER.COM Hello me.org [81.107.112.224]
250-SIZE 52428800
250-PIPELINING
250-AUTH PLAIN_TEXT LOGIN
250-STARTTLS
250 HELP
Then type:
STARTTLS
to see.
220 TLS go ahead
This means your encrypted link to the server is working.
Have fun.