Pfthb

I am currently trying to set up postfix on RHEL as an SMTP Relay for our internal ticketing system.

The basic configuration is running and working fine; mails get send and recieved. We do alter some headers to secure our internal networks, but that's about it.

Trying 10.71.17.107...
Connected to mail-gw.doma.in.
Escape character is '?'.
220 mail-gw.doma.in ESMTP Postfix
STARTTLS
220 2.0.0 Ready to start TLS

Similary, I am able to ask the GMail-Server for STARTTLS, so I presume that firewalls are not an issue:

Trying 108.177.15.26...
Connected to gmail-smtp-in.l.google.com.
Escape character is '?'.
220 **************************************************
EHLO mail-gw.doma.in
250-mx.google.com at your service, [91.198.93.107]
250-STARTTLS
STARTTLS
220 2.0.0 Ready to start TLS

I have acquired a free SSL Certificate for this mail-gw, and it seems to be valid. However, whenever I relay a message to GMail, it shows me that the message has not been encrypted.

Not secure according to google

Here is my master.cf

smtp inet n - n - - smtpd -v
submission inet n - n - - smtpd -v
 -o smtpd_tls_security_level=encrypt
 -o smtpd_sasl_auth_enable=yes
 -o smtpd_reject_unlisted_recipient=no

And here is my main.cf

smtp_sasl_auth_enable = no
smtp_sasl_password_maps = hash:/etc/postfix/relay_passwords
smtp_tls_CAfile = /etc/pki/tls/certs/mail-gw_doma_in.ca-bundle
smtp_tls_cert_file = /etc/pki/tls/certs/mail-gw_doma_in.crt
smtp_tls_key_file = /etc/pki/tls/private/prv.key
smtp_tls_loglevel = 1
smtp_tls_note_starttls_offer = yes
smtp_tls_security_level = may
smtp_tls_session_cache_database = btree:/var/lib/postfix/smtpd_cache
smtp_use_tls = yes

smtpd_tls_CAfile = /etc/pki/tls/certs/mail-gw_doma_in.ca-bundle
smtpd_tls_cert_file = /etc/pki/tls/certs/mail-gw_doma_in.crt
smtpd_tls_key_file = /etc/pki/tls/private/prv.key
smtpd_tls_loglevel = 1
smtpd_tls_received_header = yes
smtpd_use_tls = yes
tls_random_source = dev:/dev/urandom

I am all out of ideas, especially since all solutions in the internet are smtp_tls_security_level = may.

Any help would be appreciated.

e: As per the comments, here is my connection log with Google.

Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: < gmail-smtp-in.l.google.com[173.194.76.27]:25: 220 **************************************************
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: name_mask: disable_esmtp
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: name_mask: delay_dotcrlf
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: 14ED21038196: enabling PIX workarounds: disable_esmtp delay_dotcrlf for gmail-smtp-in.l.google.com[173.194.76.27]:25
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: > gmail-smtp-in.l.google.com[173.194.76.27]:25: HELO mail-gw.doma.in
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: < gmail-smtp-in.l.google.com[173.194.76.27]:25: 250 mx.google.com at your service
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: server features: 0x31000 size 0
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: smtp_stream_setup: maxtime=300 enable_deadline=0
Nov 15 07:06:44 atdc1-proxy01 postfix/smtp[26878]: > gmail-smtp-in.l.google.com[173.194.76.27]:25: MAIL FROM:<dct_test_it@doma.in>

Is it supposed to be this way? When I debug incoming connections, I see my server responding with all SMTP options (including STARTTLS)? Even more confusing since telnetting onto the google host also offers me STARTTLS.

I finally found the solution.
For some reason - I am not sure how - my Postfix thought that our Firewall was doing SMTP Inspection, and enabled the PIX workaround "disable_esmtp"

Thus, my Postfix only started a connection with a HELO, and didn't get the option to STARTTLS.

Solution:
In your main.cf, only enable the other workarounds. For the sake of brevity, I did it like this for now:

smtp_pix_workarounds = delay_dotcrlf

Hard for me to believe that I haven't found anything about this.