Now that Google Chrome 68 is out, there is more of a focus on unsecured websites than ever before. Rather than highlight when a website is secure with a SSL cert, Google is taking the opposite approach and going off the basis that every site should have a SSL cert installed. Now when you browse to an unsecured site, .i.e. a normal http website, it will highlight that site as being unsecure.
A few years ago it was not unheard of for a SSL cert to cost you dearly every year. Luckily those times have changed and now you can get free SSL certs from a number of organizations. Let's Encrypt is one such authority offering free certs. As amazing as this service is, trying to get it setup can be a little bit daunting when you read over their integration guides. It appears to be very well setup for Linux admins but Windows Server admins are going to feel somewhat like a poor cousin.
Looking over the Github pages of many of the Client Implementations for Windows Server / IIS is more than a little depressing. A lot of these projects look to be failing nightly builds or haven't been updated in a while. As most of these offerings are open source there's nothing stopping you forking the repos and tinkering away to get it working but chances are you just want to get up and running as quickly as possible.
To that end, one of the choices on the list of solutions for Windows Server that stood out to me was Certify The Web. This tiny program has a pretty neat GUI that will guide you through the process of setting up your SSL cert, requesting it from Let's Encrypt and automating your cert renewals. It will even setup the correct bindings in IIS for you. Just download this program onto your web server, pick your existing IIS website from the dropdown and follow the onscreen instructions to generate the SSL from Let's Encrypt.
It is worth mentioning that this is not a completely free tool and the free community edition of Certify The Web only allows you to setup and maintain 5 ssl certs. If you want anymore then that you'll have to pony up around €50 for an 18month license but this is for an unlimited number of websites on 3 servers. As pricing goes I think this is very reasonable, especially for businesses. Also, as you might have gathered from this post, you will have to have rights to install programs on your server so this isn't a solution for most basic hosting providers.
So there you have it. Head over to Certify The Web, download the app onto your server and within around 5 minutes you'll have a valid SSL cert setup on your website. Perfect.