How to Install OpenSSL on Windows 10 & 11: A Complete Guide

If you’re a developer, system administrator, or cybersecurity enthusiast, having OpenSSL on your Windows system is almost indispensable. Whether you’re managing SSL/TLS certificates for your website or using encryption for secure communications, OpenSSL remains a trusted tool behind the scenes. In this guide, we dive deep into two main methods to install OpenSSL on Windows 11 or 10—using Windows’ built-in package manager, Winget, for quick and hassle-free installation, and building OpenSSL from source for those who need a more customized setup.
Whether you’re a command-line wizard or much more comfortable with a graphical interface, we’ve got you covered.

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Why OpenSSL Matters in the Windows Ecosystem​

Before we delve into installation procedures, let’s take a moment to appreciate what OpenSSL does. At its core, OpenSSL is a robust toolkit used for implementing SSL/TLS protocols. This means it’s key to encrypting data over networks and ensuring the integrity and security of information transmission. Although OpenSSL is most commonly associated with Unix-like systems, Windows users—especially those building and testing secure applications—also benefit significantly from this toolkit.

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Method 1: Installing OpenSSL Using Winget​

For most Windows users, simplicity is king. Windows 11 and 10 include a handy package manager called Winget that makes installing OpenSSL as easy as typing a few commands. Follow these steps to get up and running:

Step-by-Step Installation via Command Prompt or PowerShell​

• Open the Terminal with Administrative Privileges
  Right-click the Start button and select “Terminal (Admin)” from the Power User menu. This ensures you have the necessary permissions.
• Verify Winget Availability
  To check if Winget is already installed on your machine, execute:
  

  shell
  
     winget -v

  If you see version details or a help message, you’re good to go!
• Search for OpenSSL Package
  Before installation, confirm the right package name by searching for OpenSSL:
  

  shell
  
     winget search openssl

  The package should show up, most commonly listed as something like ShiningLight.OpenSSL.Light.
• Install OpenSSL Using Winget
  Now, install the package:
  

  shell
  
     winget install ShiningLight.OpenSSL.Light

  This command downloads and installs a precompiled binary for OpenSSL on Windows.

Graphical User Interface (GUI) Option​

Not too keen on using the command line? No problem. You can also install OpenSSL using a GUI installer:

• Download the Installer
  Visit a trusted website that provides OpenSSL binaries for Windows (such as "sl proweb"). Choose the installer based on your system architecture:
• Win64 OpenSSL v3.x.x (EXE) for 64-bit systems
• Win32 OpenSSL v3.x.x (EXE) for 32-bit systems
• Run the Installer
  Double-click the downloaded .exe file to launch the installation wizard. Follow the prompts, accept the license agreement, and select the default installation path (typically C:\Program Files\OpenSSL-Win64 for 64-bit systems).
• Choose to Copy DLLs (Optional but Recommended)
  When prompted, opt to copy the OpenSSL DLLs to the system directory. This step simplifies access to OpenSSL commands from any command line window.

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Configuring Your System: Adding OpenSSL to the PATH​

Even after the installation, one more critical step remains. Without proper configuration of the system PATH environment variable, Windows won’t recognize OpenSSL commands in Command Prompt or PowerShell.

Updating the PATH Variable​

• Open Environment Variables Window
  Press Win + R, type sysdm.cpl, and press Enter to open the System Properties window. Navigate to the Advanced tab, then click Environment Variables.
• Edit the System PATH
  Under the System Variables section, locate and select the Path variable, then click Edit.
• Add OpenSSL’s Bin Directory
  Click New and enter the path to OpenSSL’s bin folder (for example: C:\Program Files\OpenSSL-Win64\bin). Click OK to save the change.
• Verify Installation
  Open a new Command Prompt or PowerShell and type:
  

  shell
  
     openssl version

  If the installation is successful, you should see the version details of OpenSSL displayed in the terminal.

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Method 2: Building OpenSSL from Source (For Advanced Users)​

For tech enthusiasts who prefer absolute control over their software environment, building OpenSSL from source can be an attractive option. This method allows for custom configurations tailored specifically to your development needs. Here’s a brief rundown of the process:

Prerequisites: Installing Dependencies​

• Visual Studio (with C++ Build Tools)
  Download and install from Visual Studio: IDE and Code Editor for Software Developers and Teams. During installation, select “Desktop development with C++”.
• Perl (Preferably Strawberry Perl)
  Install Strawberry Perl from Strawberry Perl for Windows or use Winget:
  

  shell
  
     winget install StrawberryPerl.StrawberryPerl

• NASM (Netwide Assembler)
  Download the installer from NASM or install via Winget:
  

  shell
  
     winget install NASM.NASM

• Git
  To download the latest OpenSSL source code, install Git using:
  

  shell
  
     winget install Git.Git

Building OpenSSL from Source​

• Clone the OpenSSL Repository
  Open Command Prompt, navigate to your preferred folder (e.g., the root directory), and run:
  

  shell
  
     cd \
  
     git clone https://github.com/openssl/openssl.git
  
     cd openssl

• Configure the Build
  Run the configuration script:
  

  shell
  
     perl Configure VC-WIN64A

• Compile and Install
  Build and install OpenSSL using Microsoft's build tools:
  

  shell
  
     nmake
  
     nmake install

  Voilà! You now have a custom-built version of OpenSSL tailored for your Windows system.

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Frequently Asked Questions (FAQs)​

• How do I check if OpenSSL is installed?
  Simply open Command Prompt and type:
  

  shell
  
     winget search openssl

  0000000
  This command should display the installed version if OpenSSL is correctly set up.
• How do I update OpenSSL on Windows 11?
• Step 1: Uninstall the current version via the Control Panel.
• Step 2: Reinstall the latest version using the method of your choice.
• Step 3: Restart your PC to ensure all changes take effect.
• How do I generate SSL certificates using OpenSSL?
  To generate basic SSL certificates, use:
  

  shell
  
     winget search openssl

  1111111
  Replace mycert.pem and mykey.pem with your desired names.

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Final Thoughts​

Whether you’re a beginner or an advanced user, installing OpenSSL on Windows 11 or 10 doesn’t have to be a daunting task. With the convenient Winget method, even users who are not comfortable with the command line can quickly get the precompiled binaries installed. On the other hand, those looking for a high degree of customization will appreciate the ability to build OpenSSL from source.
By following this comprehensive guide, you can ensure that your Windows system is well-equipped with a powerful tool essential for secure communications and modern development practices. So, why wait? Take control of your encryption needs today and see firsthand how OpenSSL can empower your projects with robust security capabilities.
Happy encrypting, and may your keys always be secure!

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Source: H2S Media How to Install OpenSSL on Windows 11 or 10 via Command or GUI