Complete Guide: How to Install & Use OpenSSL on Windows Server 2025

OpenSSL is a powerful open-source toolkit used for Secure Sockets Layer (SSL) and Transport Layer Security (TLS) encryption. If you're running Windows Server 2025, installing and configuring OpenSSL is essential for managing secure communications, creating SSL certificates, and encrypting data.

This guide will walk you through the installation, configuration, and usage of OpenSSL on Windows Server 2025.

Why Install OpenSSL on Windows Server 2025?

Installing OpenSSL allows you to:
Generate and manage SSL/TLS certificates
Secure server-client communications
Encrypt and decrypt sensitive data
Validate certificate chains and keys

Whether you're setting up a secure web server, VPN, or email encryption, OpenSSL is a must-have tool.

Step 1: Download OpenSSL for Windows Server 2025

  1. Visit the official OpenSSL website – Open your browser and go to OpenSSL.org.
  2. Choose the Windows version – OpenSSL is not officially provided as a Windows installer, but you can download a precompiled version from trusted sources like Shining Light Productions.
  3. Select the right package – Choose the latest OpenSSL 64-bit (light) MSI installer for Windows Server 2025.
  4. Download the file – Save the OpenSSL installer to your server.

Step 2: Install OpenSSL on Windows Server 2025

Once the download is complete, follow these steps:

  1. Run the OpenSSL Installer – Double-click the .exe file.
  2. Choose Installation Directory – It’s recommended to install OpenSSL in:
  3. C:\Program Files\OpenSSL-Win64 
  4. Select Components – Choose Full Installation to get all OpenSSL features.
  5. Set Environment Variables – During installation, select the option to add OpenSSL binaries to the system PATH.
  6. Finish Installation – Click Install and wait for the setup to complete.

Step 3: Verify OpenSSL Installation

To ensure OpenSSL is properly installed:

  1. Open Command Prompt (cmd) or PowerShell.
  2. Type the following command:
  3. openssl version
  4. You should see output similar to:
  5. OpenSSL 3.x.x  (Library: OpenSSL 3.x.x)

This confirms that OpenSSL is successfully installed on your Windows Server 2025.

Step 4: Generate an SSL Certificate Using OpenSSL

  1. Open PowerShell and navigate to OpenSSL’s installation directory:
  2. cd C:\Program Files\OpenSSL-Win64\bin
  3. Generate a private key:
  4. openssl genpkey -algorithm RSA -out privatekey.pem
  5. Create a certificate signing request (CSR):
  6. openssl req -new -key privatekey.pem -out request.csr
  7. Generate a self-signed certificate (for testing purposes):
  8. openssl req -x509 -days 365 -key privatekey.pem -in request.csr -out certificate.crt

Now you have a valid SSL certificate that can be used for secure connections.

Step 5: Configure OpenSSL for Automatic Use

To make OpenSSL accessible from anywhere in the command line:

  1. Open System Properties → Advanced System Settings.
  2. Click Environment Variables → Find Path under System Variables.
  3. Click Edit → New → Add the OpenSSL bin directory path:
  4. C:\Program Files\OpenSSL-Win64\bin
  5. Click OK and restart your server.

Now, you can run OpenSSL commands from any command line interface without navigating to its installation directory.

Final Thoughts

By following this guide, you’ve successfully installed and configured OpenSSL on Windows Server 2025. OpenSSL is a vital tool for securing your server, encrypting sensitive data, and managing SSL certificates.

Source: orcacore.com/install-openssl-in-windows-server-2025/

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