Can not send email through mail server

I have started hosting a friends site as well as their email. They are receiving mail through their client (Outlook express) but they can not send. When sending they are getting the following error:

The connection to the server has failed. Subject ‘test’, Account: ‘mail.mydomain.com’, Server: ‘mail.mydomain.com’, Protocol: SMTP, Port: 25, Secure(SSL): Yes, Socket Error: 10060, Error Number: 0x800CCC0E

I have tried using authentication in the mail client (outlook ) but this did not help.

My virtualmin is using the Postfix mail server.

I am not very comfortable with ‘mail’ issues so I was hoping someone could point me in the right direction.

Protocol: SMTP, Port: 25, Secure(SSL): Yes, Socket Error: 10060, Error Number: 0x800CCC0E

Unless you have a non-default Postfix configuration, you’re trying to connect using SSL on a port that does not accept SSL. Either turn off encryption in the client, or setup Postfix to accept SMTPS connections (or “submission”), and configure the client to connect on either the smtps or submission ports.

I am not sure why it says I am trying to connect using SSL…I am not. I tried connecting using Thunderbird mail as well and it says the server is not allowing SMTP connections.

I am using a hardware firewall and Port 25 is open. Yet I try to telnet on port 25 and it is not connecting. Any idea where I can start to troubleshoot. Is there documentation on the site for setting up SMTP connections.

Here is my postfix config file…anything look odd.

command_directory = /usr/sbin
daemon_directory = /usr/libexec/postfix
#myorigin = $myhostname
#myorigin = $mydomain

mydestination = $myhostname, localhost.$mydomain, localhost, localhost.localdomain
unknown_local_recipient_reject_code = 550
mynetworks = 192.168.1.0/24, 127.0.0.0/8, MY IP HERE

alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
recipient_delimiter = +
home_mailbox = Maildir/

#header_checks = regexp:/etc/postfix/header_checks

smtpd_banner = $myhostname ESMTP $mail_name

sendmail_path = /usr/sbin/sendmail.postfix
newaliases_path = /usr/bin/newaliases.postfix
mailq_path = /usr/bin/mailq.postfix
setgid_group = postdrop

html_directory: The location of the Postfix HTML documentation.

html_directory = no

manpage_directory = /usr/share/man

sample_directory: The location of the Postfix sample configuration files.

This parameter is obsolete as of Postfix 2.1.

sample_directory = /usr/share/doc/postfix-2.3.3/samples

readme_directory: The location of the Postfix README files.

readme_directory = /usr/share/doc/postfix-2.3.3/README_FILES
virtual_alias_maps = hash:/etc/postfix/virtual
sender_bcc_maps = hash:/etc/postfix/bcc
mailbox_command = /usr/bin/procmail-wrapper -o -a $DOMAIN -d $LOGNAME
home_mailbox = Maildir/
smtpd_sasl_auth_enable = yes
smtpd_sasl_security_options = noanonymous
broken_sasl_auth_clients = yes
smtpd_recipient_restrictions = permit_mynetworks permit_sasl_authenticated reject_unauth_destination

I am using a hardware firewall and Port 25 is open. Yet I try to telnet on port 25 and it is not connecting.

Sounds like your ISP is blocking port 25.

Can you connect from localhost to port 25?

I can’t make any sense out of configuration file settings. The maillog entries from failed connection attempts would be far more useful.

It appears Port 25 is being blocked. I can not telnet to it remotely. On my local network I can send through mail server from mail client.

Where do I change the port number? Is this all that has to be done and then the new port is specified in the mail client?

Thanks

A simpler way may be to enable SMTPS and/or Submission, which allows you to securely access your SMTP server using SSL or TLS – and they use ports 465 and 587.

If you change your SMTP port from 25, no one would be able to send you mail.

To enable those, go into Webmin -> Servers -> Postfix -> SMTP Authentication And Encryption, and make sure "Enable SASL SMTP authentication" and "Enable TLS encryption" are enabled.

Then you’d just configure your email client to use it.

For example, you could configure it to authenticate using SSL, and use port 465.
-Eric