"It requires an Enterprise Support Agreement to ask that kind of questions to the IIS / Azure Web App product team and I do not have that."Sounds like you're running the wrong web server for your needs, then. Every OSS web server has several methods for getting LE certificates implemented mostly by volunteers (my company implemented it in Virtualmin, both the OSS projects and commercial products, within a couple days of it being available, maybe even during the beta I don't recall exactly, and we're just a couple of developers), and you don't have to have an enterprise contract to make suggestions.
