Asif Iqbal wrote:
On Fri, Dec 19, 2008 at 4:41 PM, Victor Duchovni
<victor.ducho...@morganstanley.com> wrote:
On Fri, Dec 19, 2008 at 04:32:55PM -0500, Asif Iqbal wrote:

How do I test the SSL ?

I go this with openssl

iqb...@ghar:~$ openssl s_client -connect smtp.gmail.com:587
You forgot "-starttls smtp". But gmail's SSL works, you don't really

Just for the sake of some troubleshooting tips really. I tried with
-starttls smtp

 (iqbala)@scrub:~$ openssl s_client -starttls smtp -connect smtp.gmail.com:587
CONNECTED(00000004)
14859:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown
protocol:../../../../common/openssl/ssl/s23_clnt.c:567:
(iqbala)@scrub:~$ openssl s_client -connect smtp.gmail.com:587
CONNECTED(00000004)
14862:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown
protocol:../../../../common/openssl/ssl/s23_clnt.c:567:
(iqbala)@scrub:~$ openssl s_client -connect smtp.gmail.com:587 -starttls smtp
CONNECTED(00000004)
14863:error:140770FC:SSL routines:SSL23_GET_SERVER_HELLO:unknown
protocol:../../../../common/openssl/ssl/s23_clnt.c:567:

And same result

I can cut-n-paste the command you show above and it works here. Either your OpenSSL is broken or something (firewall, proxy, ...) is interfering with the TCP stream.

What if you
telnet smtp.gmail.com 587
and type  EHLO somename

From here:
$ # telnet smtp.gmail.com 587
Trying 66.249.93.111...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.
220 mx.google.com ESMTP i30sm4121152ugd.30
ehlo testing
250-mx.google.com at your service, [65.83.58.34]
250-SIZE 35651584
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
starttls
220 2.0.0 Ready to start TLS

(after this nothing will work since you aren't speaking TLS - they will disconnect after several seconds.)

Maybe a broken firewall is eating the EHLO command or STARTTLS.


--
Noel Jones

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