I seem to have a similar problem like in https://forum.howtoforge.com/threads/server-ssl-did-not-auto-update-expired.89225/ but on Debian 9. I followed the tutorial at https://www.howtoforge.com/tutorial...-9-stretch-apache-bind-dovecot-ispconfig-3-1/ to set up the server. Certbot is installed The server is used as a mailserver mainly, Outlook complains about expired certificates that expired July 27th 2022 and the ISPConfig control panel website shows a valid certificate which is valid from June 27th 2022. So it seems the Let's encrypt renewal works, but the newly issued certificates are not properly distributed to the mailserver. Test script output: Code: ##### SERVER ##### IP-address (as per hostname): ***.***.***.*** [WARN] could not determine server's ip address by ifconfig [INFO] OS version is Debian GNU/Linux 9.13 (stretch) [INFO] uptime: 09:02:31 up 63 days, 17:56, 1 user, load average: 0,15, 0,10, 0,09 [INFO] memory: total used free shared buff/cache available Mem: 11G 2,3G 1,4G 156M 8,1G 9,0G Swap: 3,7G 23M 3,7G [INFO] ISPConfig is installed. ##### ISPCONFIG ##### ISPConfig version is 3.2.8p1 ##### VERSION CHECK ##### [INFO] php (cli) version is 7.0.33-0+deb9u12 [INFO] php-cgi (used for cgi php in default vhost!) is version 7.0.33 [WARN] Your php-cgi in ' . /usr/bin/php-cgi . ' seems to be outdated and might contain known exploits. ##### PORT CHECK ##### ##### MAIL SERVER CHECK ##### ##### RUNNING SERVER PROCESSES ##### [INFO] I found the following web server(s): Apache 2 (PID 17364) [INFO] I found the following mail server(s): Postfix (PID 1483) [INFO] I found the following pop3 server(s): Dovecot (PID 835) [INFO] I found the following imap server(s): Dovecot (PID 835) [INFO] I found the following ftp server(s): PureFTP (PID 1808) ##### LISTENING PORTS ##### Server) () Local (Address) [anywhere]:993 (835/dovecot) [anywhere]:995 (835/dovecot) [localhost]:10023 (755/postgrey) [localhost]:10024 (1821/amavisd-new) [localhost]:10025 (1483/master) [localhost]:10026 (1821/amavisd-new) [localhost]:10027 (1483/master) [anywhere]:587 (1483/master) [localhost]:11211 (785/memcached) [anywhere]:110 (835/dovecot) [localhost]:783 (3926/perl) [anywhere]:143 (835/dovecot) [anywhere]:465 (1483/master) [anywhere]:21 (1808/pure-ftpd) ***.***.***.***:53 (779/named) [localhost]:53 (779/named) [anywhere]:22 (860/sshd) [anywhere]:25 (1483/master) [localhost]:953 (779/named) *:*:*:*::*:993 (835/dovecot) *:*:*:*::*:995 (835/dovecot) *:*:*:*::*:10023 (755/postgrey) *:*:*:*::*:10024 (1821/amavisd-new) *:*:*:*::*:10026 (1821/amavisd-new) *:*:*:*::*:3306 (938/mysqld) *:*:*:*::*:587 (1483/master) [localhost]10 (835/dovecot) *:*:*:*::*:783 (3926/perl) [localhost]43 (835/dovecot) *:*:*:*::*:80 (17364/apache2) *:*:*:*::*:8080 (17364/apache2) *:*:*:*::*:465 (1483/master) *:*:*:*::*:8081 (17364/apache2) *:*:*:*::*:21 (1808/pure-ftpd) *:*:*:*::*:53 (779/named) *:*:*:*::*:22 (860/sshd) *:*:*:*::*:25 (1483/master) *:*:*:*::*:953 (779/named) *:*:*:*::*:443 (17364/apache2) ##### IPTABLES ##### Chain INPUT (policy ACCEPT) target prot opt source destination f2b-postfix-sasl tcp -- [anywhere]/0 [anywhere]/0 multiport dports 25 f2b-dovecot tcp -- [anywhere]/0 [anywhere]/0 multiport dports 110,995,143,993,587,465,4190 f2b-pure-ftpd tcp -- [anywhere]/0 [anywhere]/0 multiport dports 21 f2b-sshd tcp -- [anywhere]/0 [anywhere]/0 multiport dports 22 Chain FORWARD (policy ACCEPT) target prot opt source destination Chain OUTPUT (policy ACCEPT) target prot opt source destination Chain f2b-dovecot (1 references) target prot opt source destination ##### IPTABLES ##### Chain INPUT (policy ACCEPT) target prot opt source destination f2b-postfix-sasl tcp -- [anywhere]/0 [anywhere]/0 multiport dports 25 f2b-dovecot tcp -- [anywhere]/0 [anywhere]/0 multiport dports 110,995,143,993,587,465,4190 f2b-pure-ftpd tcp -- [anywhere]/0 [anywhere]/0 multiport dports 21 f2b-sshd tcp -- [anywhere]/0 [anywhere]/0 multiport dports 22 Chain FORWARD (policy ACCEPT) target prot opt source destination Chain OUTPUT (policy ACCEPT) target prot opt source destination Chain f2b-dovecot (1 references) target prot opt source destination RETURN all -- [anywhere]/0 [anywhere]/0 Chain f2b-postfix-sasl (1 references) target prot opt source destination REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable RETURN all -- [anywhere]/0 [anywhere]/0 Chain f2b-pure-ftpd (1 references) target prot opt source destination RETURN all -- [anywhere]/0 [anywhere]/0 Chain f2b-sshd (1 references) target prot opt source destination REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable REJECT all -- ***.***.***.*** [anywhere]/0 reject-with icmp-port-unreachable RETURN all -- [anywhere]/0 [anywhere]/0 ##### LET'S ENCRYPT ##### Certbot is installed in /usr/bin/letsencrypt
