So I have just discovered that the windows installer sets the certbot renewal task to only run when a user is logged in. It hadn't run since August and I got an email that some certs were going to expire. Worked just fine when I logged in and manually triggered the task. The machine is installed on a virtual machine that really never has a user log into it as it is dedicated to certbot.
Before I create a new task to run always on my own, I wanted to see if there was an important reason for this? I figure it looks like an automatically created task so when I make changes to it they might be overwritten on update?