Install OpenSSL in Windows Server 2025 | Best Guide Steps

In this guide, you will learn to Install OpenSSL in Windows Server 2025, add it to the system path for command line access, and generate a test SSL certificate. OpenSSL is a free tool that helps protect data by using SSL and TLS security. It is mostly used on Linux, but it also works on Windows Server 2025 to add security features to apps.

To install OpenSSL on Windows Server 2025, you need to download the right files and set up the system settings. To do this, follow the steps below on the Orcacore website.

Install OpenSSL, Add to System PATH & Create SSL Certificate on Windows Server 2025

To complete OpenSSL Setup on Windows Server 2025, you must log in to your Windows Server and follow the steps below. Let’s see how we can set up OpenSSL easily.

Also, if you looking for a Video Tutorial, you can check this video guide on OpenSSL Setup on Windows Server 2025:

1. Download OpenSSL for Windows Server 2025

First, you must visit the Win32/Win64 OpenSSL Downloads Page and get the latest version Exe package of OpenSSL that matches your CPU architecture.

Once your download is completed, open your OpenSSL download file. This will open a setup wizard for you. Then, proceed to the next step to complete the OpenSSL Setup on Windows Server 2025.

Note: To install OpenSSL Windows, you need Visual C++ Redistributables. Ensure that you have these installed. During the setup, it will ask you to download it by default.

2. Install OpenSSL on Windows Server 2025

First, you must accept the agreement and click Next.

Then, you must select the Destination Location for OpenSSL in Windows Server 2025. Here we choose the default path and click Next.

Now you can select the Additional Tasks for OpenSSL setup. You must copy OpenSSL DLLs to the Windows System Directory and click Next.

Finally, review your settings and click the Install button to set up OpenSSL on Windows Server 2025.

Once your OpenSSL installation is completed, click the Finish button.

Next, proceed to the next step to add OpenSSL in the system path for command line access.

3. Add OpenSSL to Windows Server 2025 System Path

From your search bar, type Environment and open Edit the system environment variables.

From the System Properties Advanced Tab, open Environment Variables.

Under System Variables, find the Path variable and click the Edit button for it.

From there, click on the New and Browse option to add the OpenSSL path.

This will open a new pop-up window. From there, search for the OpenSSL Bin Path and click Ok. In my case, it is:

C:Program FilesOpenSSL-Win64bin

You should see that the OpenSSL path has been added to the system variables in Windows Server 2025. Click Ok.

Again click on Ok to close the Environment Variables Window.

Finally, close the System Properties to apply the changes. Simply click Ok.

You can now verify your OpenSSL command line access. Open your command prompt on Windows Server 2025 and confirm your OpenSSL version:

openssl version

4. Generate a Test SSL Certificate with OpenSSL on Windows Server 2025

Now you are ready to use OpenSSL on Windows Server 2025. First, you must export the OPENSSL_CONF file. To do this, open PowerShell as an administrator and run the command below:

set OPENSSL_CONF=C:OpenSSL-Win64binopenssl.cfg

Then, create a test SSL certificate to validate your installation. To do this, you can run the command below:

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

That’s it, you are done with OpenSSL Setup on Windows Server 2025.

Conclusion

At this point, you have learned to Install OpenSSL in Windows Server 2025 by downloading the latest Exe package and then adding OpenSSL in your system variables for command line access and generating a test SSL certificate with it.

Hope you enjoy OpenSSL Setup on Windows Server 2025. Please subscribe to us on Facebook, YouTube, and X.

Also, you may like to read the following articles:

OpenSSL Setup on Windows Server 2019

Configuring OpenSSL in Windows Server 2022

Install FTP on Windows Server 2025

Improve Security with TLS 1.3 on Windows Server 2022

FAQs

Alternative Solutions for Installing OpenSSL on Windows Server 2025

While the above method outlines a common approach to installing OpenSSL on Windows Server 2025, there are alternative methods that might be preferable depending on your specific needs and environment. Here are two such options:

1. Using Chocolatey Package Manager

Chocolatey is a package manager for Windows, similar to apt on Debian/Ubuntu or yum on CentOS/RHEL. It allows you to install, update, and manage software packages from the command line. Using Chocolatey simplifies the installation process and ensures that you receive updates automatically. This is a streamlined approach to Install OpenSSL in Windows Server 2025.

Steps:

1. Install Chocolatey: If you don’t already have Chocolatey installed, open PowerShell as an administrator and run the following command:

   Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))

2. Install OpenSSL: Once Chocolatey is installed, use the following command in an administrative PowerShell or command prompt to install OpenSSL:

   choco install openssl

   Chocolatey will download and install OpenSSL, configuring the system PATH automatically.

3. Verify Installation: Open a new command prompt or PowerShell window and run:

   openssl version

   This will display the installed OpenSSL version, confirming the successful installation.

Advantages:

• Simplified Installation: The installation process is reduced to a single command.
• Automatic Updates: Chocolatey can be used to easily update OpenSSL to the latest version.
• Dependency Management: Chocolatey handles any dependencies automatically.

Code Example (Update OpenSSL):

choco upgrade openssl

2. Using WSL (Windows Subsystem for Linux)

The Windows Subsystem for Linux (WSL) allows you to run a Linux environment directly on Windows, without the need for a virtual machine. This provides a convenient way to leverage Linux’s native package management and command-line tools, including OpenSSL. This is another valid method to Install OpenSSL in Windows Server 2025.

Steps:

1. Enable WSL: Open PowerShell as an administrator and run the following command:

   Enable-WindowsOptionalFeature -Online -FeatureName Microsoft-Windows-Subsystem-Linux

   You may need to restart your server after enabling WSL.

2. Install a Linux Distribution: After restarting, visit the Microsoft Store and install a Linux distribution of your choice (e.g., Ubuntu, Debian).

3. Launch the Linux Distribution: Launch the installed Linux distribution. This will open a terminal window.

4. Install OpenSSL: Use the distribution’s package manager to install OpenSSL. For example, on Ubuntu or Debian, run:

   sudo apt update
   sudo apt install openssl

5. Access OpenSSL: You can now use OpenSSL from within the WSL terminal.

Advantages:

• Leverage Linux Tools: Provides access to a full Linux environment and its rich set of tools.
• Clean Installation: OpenSSL is installed within the WSL environment, keeping your Windows system clean.
• Version Control: You can manage different versions of OpenSSL within WSL if needed.

Code Example (Generate a Self-Signed Certificate in WSL):

openssl req -x509 -newkey rsa:4096 -keyout key.pem -out cert.pem -days 365

This command generates a self-signed certificate valid for 365 days, storing the private key in key.pem and the certificate in cert.pem.

By understanding these alternative methods, you can choose the installation approach that best suits your requirements and technical preferences for OpenSSL on Windows Server 2025. The initial method involving manual download and PATH configuration works, but package managers and WSL offer streamlined and potentially more robust solutions.