(WIP) OpenSSL for Windows

Synopsis: Notes on OpenSSL install and setup for Windows

Published October 15th, 2025
Last Modified: October 23rd, 2025

Intro: I normally use IIS for attaching keys to .cer files, but needed to use a specific tool for a client with an infrastructure less environment. I will hopefully expand this document with notes as I continue to use the tool. This is a bit of a learning document.

Quick Run Down

1.) Downloading OpenSSL

2.) Updating System Path

3.) Scripts

Downloading OpenSSL.

OpenSSL can be downloaded from several sources. Note that some installs won't update the %PATH% variable for OpenSSL. This can be mitigated by calling the command with the full file path of the utility.

The utility is not packaged conveniently for use, but a windows version can be found here: Downloaded and installed from :https://slproweb.com/products/Win32OpenSSL.html

Updating System Path

Updating the system PATH environment variable. (This is so you can run openssl from the command line.)
Find the 'bin' folder location, which is probably C:\Program Files\OpenSSL-Win64\bin .

To modify the path variable, search for "Environment Variables" and launch the windows utility.
Then edit the "Path" variable to include the bin folder location noted above.

Scripts

• Using OpenSSL to create the required certificates for an AzureVPN deployment: GitHub
  

Newest Post