I'm building a new server to replace an old one in production. I've never had trouble in the past, but it's been a while and it is not going smoothly this time. I've spent a week trying and not getting it going. I gave up getting Cyrus-sasl to work, moved to Dovecot. Got farther but stuck now. Eyes crossed. :)
This is on Centos 7, Postfix 2.10.1 from stock rpm, Dovecot 2.2.10. I have my self signed certificates made and entered in main.cf and /etc/dovecot/conf.d/10-ssl.conf I am no certificate guru, I think I have them right. I've checked everything best I can figure out how: ----- test tunneled TLS connections to port 465 openssl s_client -connect tn2.myserver.com:465 Appears to work ----- >From remote server test STARTTLS connections on port 25 or 587 with: openssl s_client -connect tn2.myserver.com:587 -starttls smtp appears to work, shows a bunch of info and the certificate text. Nothing that looks like errors except a line that says: verify error:num=18:self signed certificate verify return:1 ----- >From remote server Tested my cacert.pem certificate with openssl x509 -in cacert.pem -inform pem -noout -text It did not ask for a PW, displayed contents, so I think that' s good (happy to post output if it helps) ----- checked if the cert and key match (openssl x509 -noout -modulus -in /etc/certs/tn2.myserver.com.crt | openssl md5 ;openssl rsa -noout -modulus -in /etc/certs/tn2.myserver.com.key | openssl md5) | uniq I only get one match so I think that' s good. ---- Telnet to the server and STARTTLS seems happy: 220 tn2.myserver.com ESMTP Postfix ehlo sample.com 250-tn2.myserver.com 250-PIPELINING 250-SIZE 10240000 250-ETRN 250-STARTTLS 250-AUTH PLAIN LOGIN 250-AUTH=PLAIN LOGIN 250-ENHANCEDSTATUSCODES 250-8BITMIME 250 DSN STARTTLS 220 2.0.0 Ready to start TLS --------------- My postfix config is: alias_database = hash:/etc/aliases alias_maps = hash:/etc/aliases broken_sasl_auth_clients = yes command_directory = /usr/sbin config_directory = /etc/postfix content_filter = smtp-amavis:[127.0.0.1]:10024 daemon_directory = /usr/libexec/postfix data_directory = /var/lib/postfix debug_peer_level = 2 debugger_command = PATH=/bin:/usr/bin:/usr/local/bin:/usr/X11R6/bin ddd $daemon_directory/$process_name $process_id & sleep 5 disable_vrfy_command = yes home_mailbox = Maildir/ html_directory = no inet_interfaces = $myhostname, localhost inet_protocols = ipv4 local_recipient_maps = hash:/etc/postfix/local_recipient mail_owner = postfix mail_spool_directory = /var/spool/mail mailq_path = /usr/bin/mailq.postfix manpage_directory = /usr/share/man mydestination = $myhostname, localhost.$mydomain, localhost, $mydomain mydomain = tn2.myserver.com myhostname = tn2.myserver.com mynetworks = localhost, $mydomain, xx.xx.xx.xx/32 myorigin = $myhostname newaliases_path = /usr/bin/newaliases.postfix queue_directory = /var/spool/postfix readme_directory = /usr/share/doc/postfix-2.10.1/README_FILES relay_domains = mlec.com relay_recipient_maps = hash:/etc/postfix/relay_recipients sample_directory = /usr/share/doc/postfix-2.10.1/samples sendmail_path = /usr/sbin/sendmail.postfix setgid_group = postdrop smtpd_data_restrictions = reject_unauth_pipelining, permit smtpd_helo_required = yes smtpd_recipient_limit = 2500 smtpd_recipient_restrictions = reject_invalid_hostname, reject_non_fqdn_hostname, reject_non_fqdn_sender, reject_non_fqdn_recipient, reject_unknown_sender_domain, reject_unknown_recipient_domain, permit_sasl_authenticated, permit_mynetworks, reject_unauth_destination, check_recipient_access pcre:/etc/postfix/recipient_checks.pcre, check_helo_access hash:/etc/postfix/helo_checks, check_sender_access hash:/etc/postfix/sender_checks, check_client_access hash:/etc/postfix/client_checks, check_client_access pcre:/etc/postfix/client_checks.pcre, check_recipient_access hash:/etc/postfix/access, reject_rbl_client zen.spamhaus.org reject_rbl_client psbl.surriel.com, reject_rbl_client bl.spamcop.net, check_policy_service unix:postgrey/socket, permit smtpd_sasl_auth_enable = yes smtpd_sasl_local_domain = smtpd_sasl_path = private/auth smtpd_sasl_security_options = noanonymous smtpd_sasl_tls_security_options = $smtpd_sasl_security_options smtpd_sasl_type = dovecot smtpd_tls_CAfile = /etc/postfix/certs/cacert.pem smtpd_tls_cert_file = /etc/postfix/certs/tn2.myserver.com.crt smtpd_tls_key_file = /etc/postfix/certs/tn2.myserver.com.key smtpd_tls_loglevel = 2 smtpd_tls_received_header = yes smtpd_tls_session_cache_timeout = 3600s smtpd_use_tls = yes soft_bounce = no tls_random_source = dev:/dev/urandom unknown_local_recipient_reject_code = 550 ------------------ MS Outlook is happy using port 587 (SASL only I think) I can deliver a test message. POP also works and it will retrive same. But with Outlook set to use port 465 it will not work. Times out. ---------------- The maillog for the timed out test shows below. It gets to that last line and just hangs. Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: connection established Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: master_notify: status 0 Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: name_mask: resource Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: name_mask: software Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: connect from yy-yy-yy-yy.lightspeed.nsvltn.sbcglobal.net[yy-yy-yy-yy] Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: match_list_match: yy-yy-yy-yy.lightspeed.nsvltn.sbcglobal.net: no match Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: match_list_match: yy-yy-yy-yy: no match Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: match_list_match: yy-yy-yy-yy.lightspeed.nsvltn.sbcglobal.net: no match Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: match_list_match: yy-yy-yy-yy: no match Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: smtp_stream_setup: maxtime=300 enable_deadline=0 Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: setting up TLS connection from yy-yy-yy-yy.lightspeed.nsvltn.sbcglobal.net[yy-yy-yy-yy] Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: yy-yy-yy-yy.lightspeed.nsvltn.sbcglobal.net[yy-yy-yy-yy]: TLS cipher list "aNULL:-aNULL:ALL:!EXPORT:!LOW:+RC4:@STRENGTH" Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: auto_clnt_open: connected to private/tlsmgr Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: send attr request = seed Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: send attr size = 32 Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: private/tlsmgr: wanted attribute: status Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: input attribute name: status Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: input attribute value: 0 Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: private/tlsmgr: wanted attribute: seed Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: input attribute name: seed Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: input attribute value: vyQmNnun9ko49YWyusMMmpdLoWMD3oF6j6MJwcWHXrs= Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: private/tlsmgr: wanted attribute: (list terminator) Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: input attribute name: (end) Jul 23 16:09:27 tn2 postfix/smtps/smtpd[10110]: SSL_accept:before/accept initialization Can someone see what I'm doing wrong? How to fix it? Hoping it's a config error. Please let me know if I've missed some piece of information. I'm a novice, I'll be grateful if you temper your replies so I can take advantage of them. Thanks very much