Cannot Send Email - timed out while receiving the initial server greeting

[hyerk]

Good Morning,

What I'm posting I don't believe to be a problem with Zentyal, but who knows.  I'm using the following Zentyal version.

Core version    3.0.3
System load    0.35, 0.19, 0.10

I have configured the mail module in Zentyal and can receive email fine, but receive the following when I attempt to send a message outside of my network, to gmail for example.

"conversation with outbound.mailhop.org[204.13.248.72] timed out while receiving the initial server greeting"

I am using Dyn.com.  I am using a dynamic external IP, but that is being taken care of by Dyn DNS standard and also Dyn Standard SMTP.  I have outbound.mailhop.org setup as the smarthost (dyn's email server) but I get the error seen above.  I'm using port 10465 to authenticate with my username and password.  If I set it up any other way I get authentication errors, so I think I have it setup correctly. 

I have emailed Dyn support who said to post in their forum (sum support eh?).  I intend to do so, though I though I'd post here to see if anyone might know if the problem has to do with other postfix settings that I could possibly modify.  I have searched the internet and found various things to try, but non have worked. 

http://www.linuxquestions.org/questions/linux-server-73/timed-out-while-receiving-the-initial-server-greeting-722722

Any help would be appreciated.

Thanks,

[Marcus]

Hello,

(according to your logs) It looks like it is either:
a) the remote server that is quite slow
b) your server is too much impatient

Try this:
Log to your server by ssh and execute those two cmd:

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sudo echo smtp_connect_timeout = 120s >> /etc/postfix/main.cf

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sudo /etc/init.d/postfix restart
Now send an email.

Is it working now ?

Best,

Marcus

[hyerk]

Thanks for the tip Marcus.  I did add that line to the main.cf file and restarted postfix but the symptoms have not changed.  I still get that same message (I'm finding the message in the Mail Queue Management).

[christian]

Did you check that you do not face error with route (I mean at network level, from Zentyal server, are you sure you can resolve and reach external servers) ?

[hyerk]

Christian,

I did verify that from my zentyal mail server I am able to ping outbound.mailhop.org.

Thanks for the input.

[christian]

OK, you can ping but can you reach it on port 25?

Try something like:

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telnet outbound.mailhop.org 25
What I mean is that your ISP may, e.g. block outgoing flow on port 25 except for ISP's MTA. In such case, you lay have to use smart relay.

[hyerk]

Christian,
Thanks for sticking with me on this one (Sorry for the late reply)!

Actually if I use the following command

telnet outbound.mailhop.org 10465

It says connected to outbound.mailhop.org so I think everything is working.  I just don't know why things aren't sending!

[christian]

so I suppose you already had a look at this page.

[hyerk]

I have many times in fact.
I've posted in the dyn forms. I'll post here if I get any input!

[hyerk]

So, this "Mega Bytes"! HaHaHa

Well, I posted in the dyn forums, and they told me that I need to get help here since can telnet to the outbound server on the desired port. 
http://www.dyncommunity.com/questions/29532/cannot-send-email-timed-out-while-receiving-the-in.html

Thanks for the help guys.  If anyone else has any input it's greatly appreciated. I'll post back once I finally find a solution!

[thorsten]

Christian,

I got a similar problem using the smtp relay service provided by Dyn.com. Just a little background:
I used just Zentyal as the SMTP relay - Not entering anything in those fields above - everything works almost perfect: I can receive E-Mail but when sending, 85 % of recipient servers do not accept my e-mails at all. Usually dynamic IP ranges are blacklisted. The other 15 % consider my E-Mails as spam. So I decided for a SMTP relay, e.g. provided by dyn.org. What are the settings to be entered in the dialog as described here?

http://doc.zentyal.org/en/mail.html#general-configuration

My entries are as follows

smarthost: outbound.mailhop.org:465
smarthost authentification: Login
user name: my_Dyndns_name
user password: my_dyndns_password

Derived from your quote:

so I suppose you already had a look at this page.

What are the correct entries?

Most confusiong: I do not see any option to set TLS / SSL or not - is zentayl capable of doing this




Thanks
Thorsten

[christian]

I can't really comment about smarthost (smtp relay) because configuration really depends on your provider (ISP or service provider).

Let me explain further:
I currently rely on 2 different ISPs. Both allow outgoing mail (on port 25 BTW  ) so that I can reach external MTA directly from Zentyal. With one of these ISPs, if I want to use its MTA as a relay, I don't need any authentication because control is IP based. This ISP will only allow its MTAs to accept relay from IP addresses that are in range he manages.

Some other service providers may have different constraints, like authentication using login/pwd (e.g. pop3 login before sending) or even SSL based connection. In such case, one may pay attention to certificate exposed by remote MTA. Is this certificate signed by CA that is trusted by Zentyal ? This doesn't prevent to establish tunnel but may explain why client 'here Zentyal) is waiting for trust approval (since I don't remember having faced such issue with SMTP)

At least these are the directions I would look at if I was facing such problem