I used this guide: https://www.howtoforge.com/tutorial/securing-ispconfig-3-with-a-free-lets-encrypt-ssl-certificate/ For some reason the script at the end was not recreating the FTP correctly. I changed it to this: Code: #!/bin/sh ### BEGIN INIT INFO # Provides: LE ISPSERVER.PEM AUTO UPDATER # Required-Start: $local_fs $network # Required-Stop: $local_fs # Default-Start: 2 3 4 5 # Default-Stop: 0 1 6 # Short-Description: LE ISPSERVER.PEM AUTO UPDATER # Description: Update ispserver.pem automatically after ISPC LE SSL certs are renewed. ### END INIT INFO cd /usr/local/ispconfig/interface/ssl/ mv ispserver.pem ispserver.pem-$(date +"%y%m%d%H%M%S").bak cat ispserver.{key,crt} > ispserver.pem chmod 600 ispserver.pem cd /etc/ssl/private/ rm pure-ftpd.pem ln -s /usr/local/ispconfig/interface/ssl/ispserver.pem pure-ftpd.pem chmod 600 /etc/ssl/private/pure-ftpd.pem service pure-ftpd-mysql restart service postfix restart service dovecot restart service nginx restart and it seemed to work fine now.