On Thu, Oct 07, 2021 at 06:01:45PM +1300, Andrew Hardy wrote: > The core of my issue is that the sending MTA receives the 250 STARTTLS > from the receiving MTA but never replies with STARTTLS. The sending > MTA has smtpd_tls_security_level = may defined.
There's you problem "smtpd_tls_security_level" is for receiving email (via smtpd(8)). The corresponding parameter for sending email (via smtp(8)) is: smtp_tls_security_level. -- Viktor. P.S. 1. ESMTP feature advertisements in the EHLO response are not "headers", they are "keywords" that advertise ESMTP "service extensions". 2. Postfix receives SMTP email via the smtpd(8) program, many of whose particular tunable parameters start with "smtpd_". 3. Postfix sends SMTP email via the smtp(8) program, many of whose particular tunable parameters start with "smtp_".