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.