Hi, I was wondering if someone else has encountered this issue before whats odd its at time i get that error and the mail gets stuck on the Queue. This is my main: Code: # See /usr/share/postfix/main.cf.dist for a commented, more complete version # Debian specific: Specifying a file name will cause the first # line of that file to be used as the name. The Debian default # is /etc/mailname. #myorigin = /etc/mailname smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu) biff = no # appending .domain is the MUA's job. append_dot_mydomain = no # Uncomment the next line to generate "delayed mail" warnings #delay_warning_time = 4h readme_directory = no # TLS parameters smtpd_tls_cert_file = /etc/ssl/certs/server.crt smtpd_tls_key_file = /etc/ssl/private/server.key smtpd_use_tls=yes smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache # See /usr/share/doc/postfix/TLS_README.gz in the postfix-doc package for # information on enabling SSL in the smtp client. smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination myhostname = mail.mydomain.com.co alias_maps = hash:/etc/aliases alias_database = hash:/etc/aliases myorigin = /etc/mailname mydestination = mydomain.com.co, mail.mydomain.com.co, localhost.mydomain.local, localhost relayhost = mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128 192.168.0.0/24 mailbox_size_limit = 0 recipient_delimiter = + inet_interfaces = all inet_protocols = ipv4 home_mailbox = Maildir/ smtpd_sasl_type = dovecot smtpd_sasl_path = private/auth smtpd_sasl_local_domain = smtpd_sasl_security_options = noanonymous broken_sasl_auth_clients = yes smtpd_sasl_auth_enable = yes smtpd_client_connection_count_limit = 10 smtpd_client_connection_rate_limit = 30 disable_vrfy_command = yes smtpd_recipient_restrictions = permit_sasl_authenticated,permit_mynetworks,reject_unauth_destination smtp_tls_security_level = may smtpd_tls_security_level = may smtp_tls_note_starttls_offer = yes smtpd_tls_loglevel = 1 smtpd_tls_received_header = yes sender_bcc_maps = hash:/etc/postfix/sender_bcc recipient_bcc_maps = hash:/etc/postfix/recipient_bcc virtual_alias_maps = hash:/etc/postfix/vmaps milter_default_action = accept milter_protocol = 2 smtpd_milters = inet:localhost:8891 non_smtpd_milters = inet:localhost:8891 maximal_queue_lifetime = 1d and this is a snip of a log im getting alot of these Code: auto eth0 iface eth0 inet static address 192.168.0.203 netmask 255.255.255.0 network 192.168.0.0 gateway 192.168.0.1 dns-nameservers 8.8.8.8 also I was reading could be also a firewall issue but i dont think so running pfSense and check the NAT rules and everything seems good i can telnet to the gmail servers Code: root@mail:~# telnet aspmx.l.google.com 25 Trying 74.125.141.26... Connected to aspmx.l.google.com. Escape character is '^]'. 220 mx.google.com ESMTP w131-v6si7023891vkh.19 - gsmtp So its very odd. Thank you