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Install OpenSSL on Windows with Cygwin

This how-to will step you through installing OpenSSL on Windows with Cygwin. OpenSSL is a very useful open-source command-line toolkit for working with SSL/TLS certificates and certificate signing requests (CSRs). With OpenSSL you can easily:

Windows 10 users can now easily use OpenSSL by enabling Windows 10’s Linux subsystem. The official cURL binaries for Windows also include OpenSSL.
Note: If you are using a Unix/Linux-based OS such as Ubuntu or macOS, you probably have OpenSSL installed already. You can confirm this and check your installed version with the command openssl version. Linux distributions will probably display something like OpenSSL 1.1.1 11 Sep 2018. macOS uses OpenBSD’s forked version, LibreSSL, so you will probably see something like LibreSSL 2.6.5.

Install Cygwin and OpenSSL

Cygwin offers a simple way to install a large collection of free and open-source software (including OpenSSL) on Windows. To install Cygwin with OpenSSL:

  1. Visit https://cygwin.com/install.html and download the appropriate installer for your OS (32- or 64-bit).

    Cygwin packages

  2. Open the installer .exe file and click the Next > button on the window that appears. (You may have to click through a User Account Control warning to run the installer.)

    Cygwin Setup

  3. Make sure that Install from Internet is selected, then click the Next > button.

    Install from Internet

  4. Leave Root Directory and Install For at their default settings (unless you know that you have some reason to change them), then click the Next > button.

    Choose Installation Directory

  5. Select a local package directory, then click the Next > button. (Again, the default is probably fine.)

    Select Local Package Directory

  6. Choose your appropriate setting for connecting to the Internet, then click the Next > button.

    Select Connection Type

  7. Choose a download site from the list, then click the Next > button.

    Choose a Download Site

  8. The installer will download the setup application, then launch it.

    Downloading Cygwin Setup

  9. Type “openssl” into the Search field, then navigate to All > Base in the Package column.

    Navigate to All > Base

  10. Find the line with openssl, then select the most recent version from the drop-down menu on the right side of the New column.

    Select Version

  11. At this point you can continue searching for and selecting packages you would like to install, or just continue with the installation (you can always re-run the application to install or remove individual packages). When you are ready, click the Next > button.

    Click the Next button

  12. Click Next > again.

    Click the Next button

  13. Cygwin Setup will start downloading the necessary files for the installation. There are a lot of files in the base Cygwin install, so it may take awhile to finish.


  14. Select if you would like to create icons on the Desktop and/or Start Menu, then click the Finish button.


  15. Verify that you have installed OpenSSL by opening the Cygwin terminal application and typing openssl version at the command prompt. You’re all done!

    Command prompt

OpenSSL Tutorial Videos

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