Le 10/03/2014 10:38, soumya tr a écrit :
Thanks James and Yves. I tried connecting using openssl command [tried
connecting to smtp.gmail.com], and that was successful. Now I tried to use
the normal command which I use in SMTP transactions:

---------------------
220 mx.google.com ESMTP gg3sm63604270pbc.34 - gsmtp
EHLO abc.com
250-mx.google.com at your service, [X.X.X.X]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
250-ENHANCEDSTATUSCODES
250 CHUNKING
MAIL FROM: [email protected]
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 
http://support.google.com/mail/bin/answer.py?answer=14257gg3sm63604270pbc.34
- gsmtp
-------------------

Its doesn't allow me to send out mail without authenticating. Does that
mean using port 465 we will have to authenticate all the time before
sending out mail?

I'm not sure what you mean... There is no automagical behaviour associated with the number 465. This port, like any other, behaves like you tell it to. Google configured its 465 port to require authentication. You are under no obligation to do the same, although doing so is sensible, in my opinion.

Quoting from Wikipedia [ https://en.wikipedia.org/wiki/Smtps ]:

-------------
*SMTPS* refers to a method for securing
SMTP<https://en.wikipedia.org/wiki/Simple_Mail_Transfer_Protocol>with
transport
layer security <https://en.wikipedia.org/wiki/Transport_layer_security>. It
is intended to provide
authentication<https://en.wikipedia.org/wiki/Authentication>of the
communication partners, as well as data
integrity <https://en.wikipedia.org/wiki/Data_integrity> and
confidentiality<https://en.wikipedia.org/wiki/Confidentiality>
.
-------------

I suppose "authentication" there refers to server authentication (which SMTPS does provide), not user authentication (which SMTPS does _not_ provide). Destination server authentication is taken care of. Source server authentication is up to you (eg. DKIM check). User authentication is also up to you (eg. password).

Or am I going in wrong track?

Thanks in advance


On Mon, Mar 10, 2014 at 2:55 PM, Yves <[email protected]> wrote:

Le 10/03/2014 10:06, soumya tr a écrit :

  Hi,

I am using 465 as SMTPS
-----------------
daemon_smtp_ports = 25 : 465 : 587
tls_on_connect_ports = 465
-----------------

I was trying to send mail via port 465 with/without authentication.

But telnet <hostname> 465 just quits when I enter EHLO:

$ telnet <hostname> 465
Trying X.X.X.X...
Connected to <hostname>.
Escape character is '^]'.
EHLo abc.com
Connection closed by foreign host

How can I try to send out mails via port 465. Please assist.


I might be wrong, but it seems to me that tls_on_connect_ports' purpose is
"legacy" SMTPS, with SSL first, then SMTP inside the SSL tunnel (just like
HTTPS). So you should talk SSL to the 465 port configured this way, not
SMTP. Use eg. openssl instead of telnet.

You probably wanted to use STARTTLS instead, which is TLS (aka "SSL")
inside an SMTP negociation, instead of the reverse. In this case, you don't
need tls_on_connect_ports.

Yves.

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