I also wanted to use OpenSSL on Windows 10. An easy way to do it without running into the risk of installing unknown software from 3rd party websites and risking viruses, is by using the openssl.exe that comes inside your Git for Windows installation. In my case, I found the OpenSSL executable in the following location of the Git for Windows installation.

C:\Program Files\Git\usr\bin\openssl.exe

If you also want instructions on how to use OpenSSL to generate and use certificates, here is a write-up on my blog. The step by step instructions first explain how to use Microsoft Windows Default Tool and also OpenSSL and explains the difference between them.

Hello Jane,

Your case is not related to Windows for Business or Windows 365 Enterprise. What you are dealing with is an application dependency issue around OpenSSL versions on Windows. Winget installs the latest OpenSSL binaries into a system path, but applications do not automatically switch to using them. Each program either links statically to its own bundled OpenSSL libraries or dynamically loads them from a specific path. That means even if you have the newest OpenSSL installed globally, older applications may still be calling their embedded or outdated DLLs.

To verify which version is actually being used, you need to inspect the binaries that the application loads. On Windows, the most reliable way is to use Process Explorer from Sysinternals. Launch the application, open Process Explorer, and check the loaded modules under the process. If you see libssl-1_1.dll or libcrypto-1_1.dll, note the file path. That path tells you whether the program is using the system-installed OpenSSL or its own copy. You can also run openssl version from the command line to confirm the version of the OpenSSL binary you installed via Winget, but that only confirms the global installation, not what each application is consuming.

There is no single command line that forces all applications to use the new OpenSSL. Each application must either be updated by its vendor to link against the newer libraries, or you must replace the older DLLs in the application’s directory with the updated ones though this is risky and not recommended unless the vendor explicitly supports it. The best practice is to update the applications themselves to versions that are compiled against the latest OpenSSL.

I hope you've found something useful here. If it helps you get more insight into the issue, it's appreciated to accept the answer. Should you have more questions, feel free to leave a message. Have a nice day!

Domic Vo.

Yes. You can do one of two things:

1. Build it yourself

   You'll need a build environment (either Visual Studio or msys2 based), and a few other pre-requisites. Download the source from here:

   https://www.openssl.org/source/

   And (assuming you downloaded the 1.1.0 version), read the INSTALL notes here:

   https://github.com/openssl/openssl/blob/OpenSSL_1_1_0-stable/INSTALL

   There are also some Windows specific notes here:

   https://github.com/openssl/openssl/blob/OpenSSL_1_1_0-stable/NOTES.WIN

2. Download a pre-compiled version

   The OpenSSL project doesn't distribute pre-compiled binaries, but they do maintain a list of third-party provided binaries. The list is here:

   https://wiki.openssl.org/index.php/Binaries