How do I fix postfix TLS?

Posted by Savanni D'Gerinel on Ask Ubuntu See other posts from Ask Ubuntu or by Savanni D'Gerinel
Published on 2013-11-06T02:25:37Z Indexed on 2013/11/06 4:18 UTC
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STARTTLS was working with my system earlier today. Without me altering the system in any way, it spontaneously broke. I've now been trying to fix it for a couple of hours, to no success.

When I connect to the server, this is what I get:

savanni@Orolo:~$ telnet apps.savannidgerinel.com 25
Trying 129.121.182.135...
Connected to apps.sasavanni@Orolo:~$ telnet apps.savannidgerinel.com 25
Trying 129.121.182.135...
Connected to apps.savannidgerinel.com.
Escape character is '^]'.
220 ***********************************************
ehlo dude
250-apps.savannidgerinel.com
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-XXXXXXXA
250-AUTH PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
^]close

telnet> close
Connection closed.

Okay, obviously STARTTLS isn't present in this list. So I've been digging through my configuration files and working through the tutorials again, and that has done me no good at all. Here's my tls-related configuration:

smtp_tls_CAfile = /etc/ssl/certs/savannidgerinel_com_CA.pem
smtp_tls_cert_file = /etc/ssl/certs/apps.savannidgerinel.com.pem
smtp_tls_key_file = /etc/ssl/private/apps.savannidgerinel.com.key.pem
smtp_tls_security_level = may
smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_tls_CAfile = /etc/ssl/certs/savannidgerinel_com_CA.pem
smtpd_tls_cert_file = /etc/ssl/certs/apps.savannidgerinel.com.pem
smtpd_tls_key_file = /etc/ssl/private/apps.savannidgerinel.com.key.pem
smtpd_tls_loglevel = 3
smtpd_tls_received_header = yes
smtpd_tls_security_level = may
smtpd_tls_session_cache_database = btree:${data_directory}/smtpd_scache

tls_random_source = dev:/dev/urandom

All of the certificate files are present, the server private key is present, the server CA is present, and the smtpd_scache.db and smtp_scache.db files are both present. All are accessible to the postfix user. Speaking of which, here are the processes running:

savanni@apps:/var/lib/postfix$ ps aux | grep postfix
root      3525  0.0  0.1  25112  1680 ?        Ss   20:19   0:00 /usr/lib/postfix/master
postfix   3526  0.0  0.1  27176  1524 ?        S    20:19   0:00 pickup -l -t fifo -u -c -o content_filter= -o receive_override_options=no_header_body_checks
postfix   3527  0.0  0.1  27228  1552 ?        S    20:19   0:00 qmgr -l -t fifo -u
postfix   3528  0.0  0.4  46948  4144 ?        S    20:19   0:00 smtpd -n smtp -t inet -u -c -o stress= -s 2
postfix   3529  0.0  0.1  27176  1628 ?        S    20:19   0:00 proxymap -t unix -u
postfix   3530  0.0  0.3  38212  3176 ?        S    20:19   0:00 tlsmgr -l -t unix -u -c
postfix   3531  0.0  0.1  27176  1516 ?        S    20:19   0:00 anvil -l -t unix -u -c
postfix   3535  0.0  0.1  27188  1544 ?        S    20:20   0:00 trivial-rewrite -n rewrite -t unix -u -c

The log files say absolutely nothing related to TLS except for this:

Nov  6 02:19:45 apps postfix/master[3525]: daemon started -- version 2.9.6, configuration /etc/postfix
Nov  6 02:19:49 apps postfix/smtpd[3528]: initializing the server-side TLS engine
Nov  6 02:19:49 apps postfix/tlsmgr[3530]: open smtpd TLS cache btree:/var/lib/postfix/smtpd_scache
Nov  6 02:19:49 apps postfix/tlsmgr[3530]: tlsmgr_cache_run_event: start TLS smtpd session cache cleanup
Nov  6 02:19:49 apps postfix/smtpd[3528]: connect from unknown[204.16.68.108]

Neither syslog nor mail.err shows any indication of a problem. As far as the whole system is concerned, all is well. But there is no STARTTLS and so I suddenly can't send any email at all.

Help???

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