My email server died last week (hardware) so I took the opportunity to
move the system (Postfix) to a different version of Linux (Debian).
Everything is working fine and all users are 100% happy with the new
machine / Postfix install except I have one web server on my LAN (DMZ)
which is unable to send / relay messages out using my SMTP server. The
web server and mail server are completely different machines:

web - 192.168.1.92 /16
mail - 192.168.0.76 / 24

*both machines are on the DMZ interface*

This partnership of being able to send mail from the web server using
my SMTP server worked perfect before the change over and the only
thing that is different is the mail servers subnet mask. It was /16
which matched the web servers mask however I don't understand why
someone had a class b on a 192.168.x.x address so I simply changed it
to the traditional class c. I also copied over the /etc/hosts.allow
entries over from the old email server to the new one. The old mail
server was not relaying and hosts or domains for this to work in the
main.cf so I don't think that is the cause.

Here is the old mail servers "hosts.allow" file:

ALL: localhost
ALL: 192.168.0.76
ALL: 216.242.0.
ALL: 169.254.0.
ALL: 10.10.0.
ALL: 192.168.0.
ALL: 10.1.1.13
ALL: 192.168.0.100

I copied that to my new email server and the web server (192.168.1.92)
still is unable to send messages out for whatever reason.

I attached the output of postconf -n

alias_database = hash:/etc/aliases
alias_maps = hash:/etc/aliases
append_dot_mydomain = no
biff = no
config_directory = /etc/postfix
content_filter = smtp-amavis:[127.0.0.1]:10024
home_mailbox = Maildir/
inet_interfaces = all
mailbox_size_limit = 0
mydestination = $myhostname, $mydomain, localhost.$mydomain, localhost
myhostname = mail.*******.org
mynetworks = $config_directory/mynetworks
myorigin = *********.org
readme_directory = no
recipient_delimiter = +
relayhost =
smtp_tls_session_cache_database = btree:${queue_directory}/smtp_scache
smtpd_banner = $myhostname ESMTP $mail_name
smtpd_recipient_restrictions = permit_mynetworks,
permit_sasl_authenticated,        reject_unauth_destination,
reject_non_fqdn_sender,        reject_non_fqdn_recipient,
reject_unlisted_recipient,        reject_unlisted_sender,
reject_invalid_hostname,        reject_non_fqdn_hostname,
reject_rbl_client zen.spamhaus.org,        reject_rbl_client
bl.spamcop.net,        reject_rbl_client safe.dnsbl.sorbs.net,
reject_invalid_hostname,        reject_non_fqdn_hostname
smtpd_tls_cert_file = /etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file = /etc/ssl/private/ssl-cert-snakeoil.key
smtpd_tls_session_cache_database = btree:${queue_directory}/smtpd_scache

I also attached below the log entries from the web server trying to
send emails out:

AssemblyVersion: 04.05.05
PortalID: 0
PortalName: LT2 Portal
UserID: 370
UserName: ******
ActiveTabID: 16
ActiveTabName: Host Settings
RawURL: /Host/Host Settings/tabid/16/portalid/0/Default.aspx
AbsoluteURL: /Default.aspx
AbsoluteURLReferrer:
https://********l.org/Host/Host%20Settings/tabid/16/portalid/0/Default.a
spx
UserAgent: Mozilla/4.0 (compatible; MSIE 7.0; Windows NT 5.1; .NET CLR
2.0.50727; .NET CLR 1.1.4322; .NET CLR 3.0.04506.30; .NET CLR 3.0.04506.648;
.NET CLR 3.5.21022; .NET CLR 3.0.4506.2152; .NET CLR 3.5.30729)
DefaultDataProvider: DotNetNuke.Data.SqlDataProvider,
DotNetNuke.SqlDataProvider
ExceptionGUID: bde87654-b6f4-40fc-97f4-91c8be753286
InnerException: Unable to connect to the remote server
FileName:
FileLineNumber: 0
FileColumnNumber: 0
Method: System.Net.Sockets.Socket.DoConnect
StackTrace:
Message: System.Net.WebException: Unable to connect to the remote server
---> System.Net.Sockets.SocketException: A connection attempt failed because
the connected party did not properly respond after a period of time, or
established connection failed because connected host has failed to respond
192.168.0.76:25 at System.Net.Sockets.Socket.DoConnect(EndPoint
endPointSnapshot, SocketAddress socketAddress) at
System.Net.Sockets.Socket.InternalConnect(EndPoint remoteEP) at
System.Net.ServicePoint.ConnectSocketInternal(Boolean connectFailure, Socket
s4, Socket s6, Socket& socket, IPAddress& address, ConnectSocketState state,
IAsyncResult asyncResult, Int32 timeout, Exception& exception) --- End of
inner exception stack trace --- at
System.Net.ServicePoint.GetConnection(PooledStream PooledStream, Object
owner, Boolean async, IPAddress& address, Socket& abortSocket, Socket&
abortSocket6, Int32 timeout) at System.Net.PooledStream.Activate(Object
owningObject, Boolean async, Int32 timeout, GeneralAsyncDelegate
asyncCallback) at System.Net.PooledStream.Activate(Object owningObject,
GeneralAsyncDelegate asyncCallback) at
System.Net.ConnectionPool.GetConnection(Object owningObject,
GeneralAsyncDelegate asyncCallback, Int32 creationTimeout) at
System.Net.Mail.SmtpConnection.GetConnection(String host, Int32 port) at
System.Net.Mail.SmtpTransport.GetConnection(String host, Int32 port) at
System.Net.Mail.SmtpClient.GetConnection() at
System.Net.Mail.SmtpClient.Send(MailMessage message)
Source:
Server Name: WWW

I can't find anything relivant in my postfix /var/log/mail.log or
/var/log/mail.err.

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