How to install OpenSSL on Windows Server 2019?, How to use OpenSSL on Windows server 2019?. OpenSSL is an open source library that provides cryptographic protocols used to secure applications and transfer of information between systems. Management of OpenSSL is under volunteers all around the worldwide.

In a nutshell, OpenSSL toolkit implements the Secure Sockets Layer (SSL v2/v3) and Transport Layer Security (TLS v1) protocols with full-strength cryptography. This guide will show you how to install OpenSSL on Windows Server 2019.

Install OpenSSL on Windows Server 2019

Head over to OpenSSL downloads page and grab the latest build of OpenSSL that matches your CPU architecture. For me I’ll download 64-bit version. You have an option of choosing the Light version or full version.

You can also use curl.exe command to download from command line.

curl.exe -L -o Win64OpenSSL.exe

See screenshot below.

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Once the installation is complete, run the installer by double-clicking on .exe file or from PowerShell.


Accept Software license Agreement and click “Next”.

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Select destination folder where OpenSSL will be installed.

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Select directory for Application shortcut.

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Select additional tasks to be performed.

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Click “Install” to start installation of OpenSSL on Windows Server 2019.

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Give installation few minutes to complete.

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Click “Finish” to end successful installation.

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Lastly add C:\OpenSSL-Win64 to the Windows environment PATH.

$userenv = [System.Environment]::GetEnvironmentVariable("Path", "User")
[System.Environment]::SetEnvironmentVariable("PATH", $userenv + "C:\OpenSSL-Win64\bin", "User")

For a 32-bit system, replace OpenSSL-Win64 with OpenSSL-Win32.

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Generate Certificates with OpenSSL on Windows Server 2019

You are now ready to use OpenSSL on Windows Server 2019 to generate certificates. Start by exporting OPENSSL_CONF.

set OPENSSL_CONF=C:\OpenSSL-Win64\bin\openssl.cfg

For a 32-bit system, replace OpenSSL-Win64 with OpenSSL-Win32. Let’s create a test SSL certificate to validate our installation.

openssl.exe req -new -nodes -keyout server.key -out server.csr -newkey rsa:2048

Also read:

How to run Linux on Windows Server 2019 with WSL

How to enable Remote Desktop Protocol (RDP) on Windows Server 2019

Install and Configure DHCP Server on Windows Server 2019

How to Install Active Directory Domain Services in Windows Server 2019

Easy Way To Install Windows Terminal on Windows 10 / Server 2019

How To Install SSL Certificate on Windows IIS Server

How To open a port in Windows Server Firewall

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