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Install OpenSSL on Windows server 2016 A Step-by-Step Guide

OpenSSL stands as an all-encompassing encryption toolkit that leverages the TLS protocol, and it’s freely available as open-source software. Initially launched in 1998, it supports a range of operating systems including Linux, Windows, macOS, and BSD. OpenSSL empowers users to perform various SSL-related tasks such as generating a Certificate Signing Request (CSR), creating private keys, and installing SSL certificates. In this guide, we’ll walk you through the process of configuring OpenSSL on a Windows Server 2016. For those in need of a Windows VPS server, Eldernode offers suitable packages for purchase.

Setting Up OpenSSL on Windows Server 2016: A Beginner’s Tutorial

OpenSSL is a powerful, industrial-strength toolkit designed for implementing the Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols. In the following segments, we aim to familiarize you with the basics of OpenSSL. After that, we’ll guide you through the installation process of OpenSSL on Windows Server 2016. To conclude, we’ll show you the steps to properly configure OpenSSL. Make sure to follow along for a comprehensive walkthrough.

Getting Started with OpenSSL: A Beginner’s Guide

OpenSSL stands as a pivotal tool in the realm of SSL technologies, with SSL certificates now more crucial than ever. The push for encryption took a significant leap forward with the “HTTPS Everywhere” initiative, fundamentally altering how online security is viewed. Initially, the introduction of SEO benefits for sites using digital certificates nudged website owners towards adoption. Subsequently, browsers like Chrome mandated HTTPS for all sites, marking unsecured sites as “not secure” in popular browsers like Chrome and Firefox.

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The role of SSL in ensuring a website’s security and credibility cannot be overstated. Despite many site owners only recently becoming acquainted with SSL, they must have access to the right tools for implementation. OpenSSL is one such indispensable tool.

OpenSSL facilitates a range of SSL management tasks, from certificate requests to installation and format conversion, alongside various authentication processes. Mastering a few basic OpenSSL commands can significantly streamline the certificate installation and configuration process. This is especially true for operating systems or server environments lacking a graphical interface for SSL management, where OpenSSL might be the sole method for certificate handling.

Continue with us as we delve into a step-by-step guide on installing OpenSSL on Windows Server 2016, simplifying the process for beginners and seasoned users alike.

Easy Steps to Install OpenSSL on Windows Server

Ready to get OpenSSL up and running on your Windows Server 2016, 2019, or 2012? Just follow these straightforward steps to ensure a smooth installation.

Kick things off by navigating to the OpenSSL download webpage. Once there, select the most recent OpenSSL version compatible with your server’s operating system. Alternatively, you can download OpenSSL directly using PowerShell with the command below:

curl.exe -L -o Win64OpenSSL.exe

Once the download is complete, you’re ready to start the installation. Launch PowerShell and execute the command:


A setup window will pop up. Here, you’ll need to agree to the license terms by choosing the “I accept the agreement” option, then proceed by clicking “Next.”


Moving forward, the next step involves choosing where OpenSSL should be installed on your Windows Server. Simply enter or confirm the desired installation path and click “Next.”

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Next, decide on a location for the OpenSSL application shortcuts. This step helps you quickly access OpenSSL from your desktop or start menu.


Finally, it’s time to select any additional tasks you want to perform during the installation. Review the options presented in the following screen, make your selection, and then proceed by clicking “Next.”


To wrap up the OpenSSL setup on your system, simply hit the “Install” button:


After the installation process has concluded, click “Finish” to finalize everything:


Important Reminder: After installation, remember to add the OpenSSL directory to your Windows environment PATH. Use C:\OpenSSL-Win64 for the 64-bit version or C:\OpenSSL-Win32 for the 32-bit version. This ensures that OpenSSL commands can be run from anywhere in the command prompt.

Setting Up OpenSSL on Your Windows Server 2016

Now that you’ve successfully installed OpenSSL, let’s move on to configuring it for your system. To test your installation and create a sample SSL certificate, use the command below:

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

Next, it’s crucial to set up the necessary environment variables for OpenSSL to function correctly on your system. These include OPENSSL_CONF and Path. Apply the following commands to adjust these settings conveniently:

set OPENSSL_CONF=C:\OpenSSL-Win32\bin\openssl.cfg

set Path=%Path%;C:\OpenSSL-Win32\bin

To make the OPENSSL_CONF and Path variables a permanent part of your system’s environment, here are the steps to follow:

– Begin by pressing the Windows+R keys together to launch the Run dialog box.

– Enter `sysdm.cpl` into the dialog box and hit Enter:


Continue by navigating to the “Advanced” tab, then select “Environment Variables” to proceed:

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This part will guide you through setting up the OPENSSL_CONF variable:


Lastly, we’ll show you how to correctly adjust the Path Variable for complete integration:


We kicked off this guide by giving you a rundown of what OpenSSL is all about. Following that, we walked you through the installation process of OpenSSL on Windows Server 2016. To cap it off, we’ve shown you the steps to properly configure OpenSSL to ensure it’s set up correctly on your system.

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