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 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. 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 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 led me to Win Acme. Is this a suitable tool for the job?

We're using Win Server 2012.

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 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. 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 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? Is it even possible?

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 led me to Win Acme. Is this a suitable tool for the job?

We're using Win Server 2012.

Update

Stephen also suggested splitting up the sites into groups of 50. This is do-able but it would require maintaining a number of code bases, which I would prefer not to do, if possible.

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 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.

Until now I have only used the plesk plugin 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 led me to Win Acme. Is this a suitable tool for the job?

We're using Win Server 2012.

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 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. 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 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 led me to Win Acme. Is this a suitable tool for the job?

We're using Win Server 2012.