content: For simplicity purposes they expect me to run a Web service in my web server  So like Jenkins, cPanel, CMS, any daemons tied to a cloud service?  Most people are ok with installing an administrative panel on their web server.  Yes, when you get to the point that you are handling credit card data directly you want your only interface to be ssh but considering the effort of implementing code complaint with PCI regulations if you've reached that scale you probably aren't using letsencrypt. Administrative panels and their background processes have their place in the process of launching a prototype to being a major website.  If you want to get a cert off of letsencrypt you can do it with just some http requests if you want to just use a terminal.  That's what they were doing for their alpha before they had the python out. But in linux style the thing really should be c and distributed through a package manager. Edit: Also, how are you going to show ownership without running some sort of service on the server.  I'm sure he'd rather just serve a static item from nginx but the point is for it to be dead simple.