Hello Everyone, I am having a hard time figuring this out and would appreciate any advise you can give me. I have setup my mail server (Postfix/Dovecot) to use the TLS protocol. I have the TLS working on both incoming and outgoing, but I also want to support ssl as Apple Mail is not working with pure TLS. I believe TLS is referring to the StartTLS, so I want to enable basic SSL as well. I have incoming working, but I can't get outgoing to access SSL instead of TLS. Outlook has a setting for SSL or TLS, so when I select ssl it says my server doesn't support that encryption type. Here is my main.cf: Code: # 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. #JMS biff is a unix command and does not need to be on # appending .domain is the MUA's job. # Uncomment the next line to generate "delayed mail" warnings delay_warning_time = 4h #JMS defines readme files so can be used with unix commands no real need for it. readme_directory = /usr/share/doc/postfix # TLS parameters smtpd_tls_cert_file = /etc/postfix/ssl/stephensdev.crt smtpd_tls_key_file = /etc/postfix/ssl/stephensdev.key smtpd_use_tls = yes #smtpd_tls_auth_only = no smtpd_tls_CAfile = /etc/postfix/ssl/stephensdev.ca-bundle smtpd_tls_loglevel = 1 smtpd_sasl_tls_security_options = noanonymous smtpd_tls_received_header = yes smtpd_tls_session_cache_timeout = 3600s tls_random_source = dev:/dev/urandom 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. #myhostname = stephensdev.com myhostname = localhost alias_maps = hash:/etc/aliases, hash:/var/lib/mailman/data/aliases alias_database = hash:/etc/aliases, hash:/var/lib/mailman/data/aliases myorigin = /etc/mailname #mydestination = stephensdev.com, localhost, localhost.localdomain mydestination = localhost, localhost.localdomain relayhost = mynetworks = 127.0.0.0/8 [::1]/128 mailbox_command = procmail -a "$EXTENSION" mailbox_size_limit = 0 recipient_delimiter = + inet_interfaces = all html_directory = /usr/share/doc/postfix/html virtual_alias_domains = virtual_alias_maps = proxy:mysql:/etc/postfix/mysql-virtual_forwardings.cf, proxy:mysql:/etc/postfix/mysql-virtual_email2email.cf, hash:/var/lib/mailman/data/virtual-mailman virtual_mailbox_domains = proxy:mysql:/etc/postfix/mysql-virtual_domains.cf virtual_mailbox_maps = proxy:mysql:/etc/postfix/mysql-virtual_mailboxes.cf virtual_mailbox_base = /var/vmail virtual_uid_maps = static:5000 virtual_gid_maps = static:5000 inet_protocols = all smtpd_sasl_auth_enable = yes smtpd_sasl_security_options=noanonymous broken_sasl_auth_clients = yes smtpd_sasl_authenticated_header = yes smtpd_recipient_restrictions = permit_mynetworks, permit_sasl_authenticated, check_recipient_access mysql:/etc/postfix/mysql-virtual_recipient.cf, reject_unauth_destination smtpd_delay_reject = yes smtpd_tls_security_level = encrypt transport_maps = hash:/var/lib/mailman/data/transport-mailman, proxy:mysql:/etc/postfix/mysql-virtual_transports.cf relay_domains = mysql:/etc/postfix/mysql-virtual_relaydomains.cf relay_recipient_maps = mysql:/etc/postfix/mysql-virtual_relayrecipientmaps.cf proxy_read_maps = $local_recipient_maps $mydestination $virtual_alias_maps $virtual_alias_domains $virtual_mailbox_maps $virtual_mailbox_domains $relay_recipient_maps $relay_domains $canonical_maps $sender_canonical_maps $recipient_canonical_maps $relocated_maps $transport_maps $mynetworks $virtual_mailbox_limit_maps smtpd_sender_restrictions = check_sender_access mysql:/etc/postfix/mysql-virtual_sender.cf smtpd_client_restrictions = check_client_access mysql:/etc/postfix/mysql-virtual_client.cf smtpd_client_message_rate_limit = 100 maildrop_destination_concurrency_limit = 1 maildrop_destination_recipient_limit = 1 virtual_transport = dovecot header_checks = regexp:/etc/postfix/header_checks mime_header_checks = regexp:/etc/postfix/mime_header_checks nested_header_checks = regexp:/etc/postfix/nested_header_checks body_checks = regexp:/etc/postfix/body_checks owner_request_special = no dovecot_destination_recipient_limit = 1 smtpd_sasl_type = dovecot smtpd_sasl_path = private/auth content_filter = amavis:[127.0.0.1]:10024 receive_override_options = no_address_mappings And my Master.cf: Code: # Postfix master process configuration file. For details on the format # of the file, see the master(5) manual page (command: "man 5 master"). # # Do not forget to execute "postfix reload" after editing this file. # # ========================================================================== # service type private unpriv chroot wakeup maxproc command + args # (yes) (yes) (yes) (never) (100) # ========================================================================== smtp inet n - - - - smtpd #smtp inet n - - - 1 postscreen #smtpd pass - - - - - smtpd #dnsblog unix - - - - 0 dnsblog #tlsproxy unix - - - - 0 tlsproxy submission inet n - - - - smtpd -o syslog_name=postfix/submission -o smtpd_tls_security_level=encrypt -o smtpd_sasl_auth_enable=yes -o smtpd_client_restrictions=permit_sasl_authenticated,reject # -o milter_macro_daemon_name=ORIGINATING smtps inet n - - - - smtpd -o syslog_name=postfix/smtps -o smtpd_tls_wrappermode=yes -o smtpd_sasl_auth_enable=yes -o smtpd_client_restrictions=permit_sasl_authenticated,reject # -o milter_macro_daemon_name=ORIGINATING #628 inet n - - - - qmqpd pickup fifo n - - 60 1 pickup cleanup unix n - - - 0 cleanup qmgr fifo n - n 300 1 qmgr #qmgr fifo n - n 300 1 oqmgr tlsmgr unix - - - 1000? 1 tlsmgr rewrite unix - - - - - trivial-rewrite bounce unix - - - - 0 bounce defer unix - - - - 0 bounce trace unix - - - - 0 bounce verify unix - - - - 1 verify flush unix n - - 1000? 0 flush proxymap unix - - n - - proxymap proxywrite unix - - n - 1 proxymap smtp unix - - - - - smtp relay unix - - - - - smtp # -o smtp_helo_timeout=5 -o smtp_connect_timeout=5 showq unix n - - - - showq error unix - - - - - error retry unix - - - - - error discard unix - - - - - discard local unix - n n - - local virtual unix - n n - - virtual lmtp unix - - - - - lmtp anvil unix - - - - 1 anvil scache unix - - - - 1 scache # # ==================================================================== # Interfaces to non-Postfix software. Be sure to examine the manual # pages of the non-Postfix software to find out what options it wants. # # Many of the following services use the Postfix pipe(8) delivery # agent. See the pipe(8) man page for information about ${recipient} # and other message envelope options. # ==================================================================== # # maildrop. See the Postfix MAILDROP_README file for details. # Also specify in main.cf: maildrop_destination_recipient_limit=1 # maildrop unix - n n - - pipe flags=DRhu user=vmail argv=/usr/bin/maildrop -d vmail ${extension} ${recipient} ${user} ${nexthop} ${sender} # # ==================================================================== # # Recent Cyrus versions can use the existing "lmtp" master.cf entry. # # Specify in cyrus.conf: # lmtp cmd="lmtpd -a" listen="localhost:lmtp" proto=tcp4 # # Specify in main.cf one or more of the following: # mailbox_transport = lmtp:inet:localhost # virtual_transport = lmtp:inet:localhost # # ==================================================================== # # Cyrus 2.1.5 (Amos Gouaux) # Also specify in main.cf: cyrus_destination_recipient_limit=1 # #cyrus unix - n n - - pipe # user=cyrus argv=/cyrus/bin/deliver -e -r ${sender} -m ${extension} ${user} # # ==================================================================== # Old example of delivery via Cyrus. # #old-cyrus unix - n n - - pipe # flags=R user=cyrus argv=/cyrus/bin/deliver -e -m ${extension} ${user} # # ==================================================================== # # See the Postfix UUCP_README file for configuration details. # uucp unix - n n - - pipe flags=Fqhu user=uucp argv=uux -r -n -z -a$sender - $nexthop!rmail ($recipient) # # Other external delivery methods. # ifmail unix - n n - - pipe flags=F user=ftn argv=/usr/lib/ifmail/ifmail -r $nexthop ($recipient) bsmtp unix - n n - - pipe flags=Fq. user=bsmtp argv=/usr/lib/bsmtp/bsmtp -t$nexthop -f$sender $recipient scalemail-backend unix - n n - 2 pipe flags=R user=scalemail argv=/usr/lib/scalemail/bin/scalemail-store ${nexthop} ${user} ${extension} mailman unix - n n - - pipe flags=FR user=list argv=/usr/lib/mailman/bin/postfix-to-mailman.py ${nexthop} ${user} dovecot unix - n n - - pipe flags=DROhu user=vmail:vmail argv=/usr/lib/dovecot/deliver -f ${sender} -d ${user}@${nexthop} amavis unix - - - - 2 smtp -o smtp_data_done_timeout=1200 -o smtp_send_xforward_command=yes 127.0.0.1:10025 inet n - - - - smtpd -o content_filter= -o local_recipient_maps= -o relay_recipient_maps= -o smtpd_restriction_classes= -o smtpd_client_restrictions= -o smtpd_helo_restrictions= -o smtpd_sender_restrictions= -o smtpd_recipient_restrictions=permit_mynetworks,reject -o mynetworks=127.0.0.0/8 -o strict_rfc821_envelopes=yes -o receive_override_options=no_unknown_recipient_checks,no_header_body_checks