Installing OpenSSL in Windows 8.1

Windows doesn’t have a good tool for manipulating SSL certificates.  So, if you want to do anything serious with SSL, you need to grab yourself a copy of OpenSSL.  I’m installing the Windows x64 version of OpenSSL provided by Shining Light Productions.

First, you’ll need to download and install the Microsoft Visual C++ 2008 Redistributable Package (x64) from Microsoft.  Just accept all of the defaults for the installation.  (If you’re running a 32-bit version of Windows, you’ll need to install 32-bit versions of everything.  This example is for 64-bit.)

Once you have that installed, download the latest “Light” version of OpenSSL.  If you’re not developing software, you don’t need the full versions; the “Light” version is intended for end-users.

Accept the defaults for the installation until you come to the “Select Destination Location” window.  Figure out where you want OpenSSL to be installed.  I like to keep everything in my Program Files directory, so that’s where I’m putting mine:

Destination

I don’t worry too much about Start Menu locations, but the “Select Additional Tasks” window is important:

DLL Location

Wherever you put the DLLs is up to you, but I put them in their own directory rather than the System directory.  It just makes more sense to me.

Once you complete the installation wizard, you’ll end up at the following window:

Donation

Whether you donate or not is up to you, of course.  You can simply clear the check box and hit “Finish” and the software will work fine.  I’d like to encourage you to make a donation, though.  Everyone thinks open source software is “free”.  In actuality, it’s extremely expensive in time and resources and if you benefit from its use, please support the developers by donating when you can.

The last thing to do is to modify the Path system variable so you can launch the OpenSSH shell from anywhere at a command prompt:

1. Right-click the Windows icon and select “System”

Start Menu

2. Select “Advanced System Settings”

System

3. On the “Advanced” tab, click the “Environment Vairables…” button

Advanced

4. Find the “Path” variable in the “System variables” selection window and click on “Edit…”

Find Path

You’ll have a “Edit System Variable” dialogue box appear.  Append “;C:\Program Files\OpenSSL-Win64\bin” to the end of the path information and click “OK”.  Notice there is a semi-colon at the start of the string.  This is a delimiter which tells Windows that this location is a separate location and not part of the path immediately before it.

Edit System Variable

Click “OK” a few times and you’re done.

Once you’ve completed the installation and path configuration, you can launch OpenSSL from a command prompt window:

OpenSSL CMD

For more information about how to use OpenSSL’s commands and syntax, refer to the official documentation.

I hope this helps someone and saves some time.  If you see anything wrong, please let me know.

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