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OpenSSL Cookbook  3rd Edition

The definitive guide to using the OpenSSL command line for configuration and testing. Topics covered in this book include key and certificate management, server configuration, a step by step guide to creating a private CA, and testing of online services. Written by Ivan Ristić.


1.1 Getting Started

If you’re using one of the Unix platforms, getting started with OpenSSL should be easy; you’re virtually guaranteed to have it already installed on your system. Still, things could go wrong. For example, you could have a version that’s just not right, or there could be other tools (e.g., LibreSSL) configured to respond when OpenSSL is invoked. For this reason, it’s best to first check what you have installed and resort to using a custom installation only if absolutely necessary. Another option is to look for a packaging platform. For example, for OS X you could use Brew or MacPorts. As always, compiling something from scratch once is rarely a problem; maintaining that piece of software indefinitely is.

In this chapter, I assume that you’re using a Unix platform because that’s the natural environment for OpenSSL. On Windows, it’s less common to compile software from scratch because the tooling is not readily available. You can still compile OpenSSL yourself, but it might take more work. Alternatively, you can consider downloading the binaries from the Shining Light Productions web site.1 If you’re downloading binaries from multiple web sites, you need to ensure that they’re not compiled under different versions of OpenSSL. If they are, you might experience crashes that are difficult to troubleshoot. The best approach is to use a single bundle of programs that includes everything that you need. For example, if you want to run Apache on Windows, you can get your binaries from the Apache Lounge web site.2


1

Win32/Win64 OpenSSL (Shining Light Productions, retrieved 19 July 2020)

2

Apache 2.4 VS16 Windows Binaries and Modules (Apache Lounge, retrieved 18 September 2021)

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