I have 180 or so websites that all run of a single MVC app. 

The app runs on a domain, which is not accessible directly by the public, and each of the 180 public facing sites are set up as domain aliases of this.  

I have always put off using `https` because the cost of 180 certs was prohibitive.  But recently I started using [Let's Encrypt][1] for some other sites and now I want to try it on these.  

The problem is, there is a [maximum domain alias limit of 100][2]. As Stephen pointed out, I'd like to cover the www and non-www versions, so that's really 360!

Until now I have only used the [plesk plugin][3] which makes it REALLY easy. So now when I want to go beyond the 'default' usage, I have absolutely NO idea where to start.  I am worried that in my ignorance I will spend days persuing a solution that it was never suitable in the first place!

So I have 3 questions: 

 1. What is the easiest / simplest approach for me to get certification
    for 180 domain aliases with LE?
    
 2. It appears that I will need to install an ACME client on the server,
    is that correct?
    
 3. If so, a [Rick Strahl blog post][4] led me to [Win Acme][5]. Is this
    a suitable tool for the job?


We're using Win Server 2012.




  [1]: https://letsencrypt.org/
  [2]: https://community.letsencrypt.org/t/limit-on-domain-aliases/66136
  [3]: https://www.plesk.com/blog/product-technology/lets-encrypt-plesk/
  [4]: https://weblog.west-wind.com/posts/2016/feb/22/using-lets-encrypt-with-iis-on-windows
  [5]: https://github.com/PKISharp/win-acme/releases