In my case, all STARTTLS commands fail. Delivery succeeds after re-connecting
with plaintext.
Apparently, not all connections are retried in plaintext.
To work around one could say:
smtpd_discard_ehlo_keyword_address_maps = cidr:{
{188.68.34.52 starttls}
{2a03:4000:10:51d:b8ce:63ff:feca:a5a0 starttls}}
I'll reach out to sys4.de people.
Wietse
SMTP server logging shows that all STARTTLS commands fail (starttls=0/1)
and that plaintext succeeds (no starttls= logging).
$ grep 'disconnect from list.sys4.de' /var/log/maillog
Sep 17 01:58:07 spike postfix/smtpd[53249]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 01:58:08 spike postfix/smtpd[53249]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 02:07:57 spike postfix/smtpd[53309]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 02:07:58 spike postfix/smtpd[53309]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 mail=1 rcpt=1 data=1
quit=1 commands=5
Sep 17 08:27:52 spike postfix/smtpd[56501]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 08:27:53 spike postfix/smtpd[56501]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 08:37:49 spike postfix/smtpd[56537]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 08:37:50 spike postfix/smtpd[56537]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 mail=1 rcpt=1 data=1
quit=1 commands=5
Sep 17 09:08:54 spike postfix/smtpd[56707]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 09:08:55 spike postfix/smtpd[56707]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:19:01 spike postfix/smtpd[56772]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 09:19:02 spike postfix/smtpd[56772]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:22:12 spike postfix/smtpd[56805]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:22:13 spike postfix/smtpd[56805]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 mail=1 rcpt=1 data=1
quit=1 commands=5
Sep 17 09:25:49 spike postfix/smtpd[56825]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 09:25:50 spike postfix/smtpd[56825]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:27:01 spike postfix/smtpd[56825]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:27:04 spike postfix/smtpd[56825]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 mail=1 rcpt=1 data=1
quit=1 commands=5
Sep 17 09:37:30 spike postfix/smtpd[56866]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:37:31 spike postfix/smtpd[56866]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 mail=1 rcpt=1 data=1
quit=1 commands=5
Sep 17 09:49:18 spike postfix/smtpd[56909]: disconnect from
list.sys4.de[2a03:4000:10:51d:b8ce:63ff:feca:a5a0] ehlo=1 starttls=0/1
commands=1/2
Sep 17 09:49:19 spike postfix/smtpd[56909]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 09:57:20 spike postfix/smtpd[56945]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 starttls=0/1 commands=1/2
Sep 17 09:57:22 spike postfix/smtpd[56945]: disconnect from
list.sys4.de[188.68.34.52] ehlo=1 mail=1 rcpt=1 data=1 quit=1 commands=5
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