Help setting up Let's Encrypt on multiple server configurations


I have two production servers that are running Windows 2008 R2 and IIS, one server running Windows 2008 R2 with Tomcat (Percussion CMS), and a Windows XP box running Tomcat (JIRA).

Right now I’m trying to figure out how I can install Let’s Encrypt to issue an SSL certificate for my two servers using Tomcat and how to import the SSL’s on Tomcat as I’m not that familiar with it.

I would also like to figure out how to install Let’s Encrypt certificates on my two IIS boxes. They are redundant servers that are mirrored every few minutes.

I really appreciate any help anyone can give me.


For the Tomcat bit, you’ll need to do some additional processing after handling the cert bit. Tomcat uses Java Keystores, and you can find some directions at this post.

For IIS, there are some tools that can automate the process. I suggest searching the community forum as it’s been discussed quite a bit.


Well I migrated over to my mac hoping I could create the certs with it and then move them to my servers but my version of the OS is to new for the Certbot method.

As for Windows, I tried to compile the code for generating the SSL’s but it failed every time so after an hour I just gave up and moved to my mac with zero success as well.


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