on Windows... I got things working by creating certbot-update.bat like this. certbot certonly --standalone -d <domain> -n copy /y C:\Certbot\live\<domain name>\fullchain.pem %APPDATA%\deluge\ssl\daemon.cert copy /y C:\Certbot\live\<domain name>\privkey.pem %APPDATA%\deluge\ssl\daemon.pkey