Free SSL Certificates with Let's Encrypt on IIS



Last updated: January 28th, 2024

Why Use An SSL?

The use of an SSL (secure socket layer), which results in websites being prefixed with "https" instead of "http" has many benefits.

Using an SSL enables a secure connection from your broswer to the server. The benefit of this is that your connection is encrypted, making it very difficult for an attacker to steal your form data while in transit. When you sign into a website, without an SSL, your information is at risk.

Additionally, Google has been using an SSL on a website as a ranking factor since 2014. You can read more about the use of an SSL for SEO reasons here. Google Chrome also displays messages about insecure forms when a website doesn't have an SSL.

Quick and Free Solution on IIS

Until recently, having an SSL meant going through 3rd party companies like GoDaddy which charge $50 or even hundreds of dollars per year to have an SSL. The process was manual, expensive and error prone.

Today, Let's Encrypt offers free certificates that you can generate yourself. If you are on IIS and want to use the fastest solutoin, download Let's Encrypt Win Simple from GitHub.

All you need to do is run the program on the server which hosts IIS and type the website number from the list they display. After you run the program, you will see a list of all websites on the computer and then you can select the website by number and press enter.

Let's Encrypt will add files to the directory with the website and confirm the SSL. After that, it will add a binding for the website. You need to do this for all alternatives of your site, such as www and non-www bindings.

The Let's Encrypt utility for Windows also adds a scheduled task which will renew your certificate for you. The certs expire in 90 days and attempt to renew after 60 days, giving you time to confirm they renewed.

Read all of the messages from the command prompt as you go through it! You may need to adjust your SNI/ SSL settings so that a single IP address can be used for multiple SSLs. This feature, should you need it, is only available on Windows 2012 and up.

Other Options

I found out about the Let's Encrypt Win Simple program from this blog post by Rick Strahl. He provides more detail about Let's Encrypt as well as other options available for IIS. I suggest visiting his post for more details about Let's Encrypt on IIS.

Also win-acme (which is what Let's Encrypt Win Simple became), it allows creating new certificates and automatically renewing them through a command prompt.


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ryan
About Me

With 15 years in tech, I've excelled as a senior software engineer, specializing in ASP.NET, C#, SQL, Azure, and front-end technologies. I've led diverse projects across various sectors, from startups to global corporations, particularly during my decade in the San Francisco Bay Area.


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