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OpenSSL is an open source library that provides a full-featured toolkit and APIs for secure computer network communication over Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols on Linux and other Unix-like systems
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The source code of the project lives on GitHub and is managed by a worldwide community of software engineering volunteers with over 300 contributors.
Most network communication apps, personal computers, web servers, cell phone and tools that use TLS/SSL protocols have a version of OpenSSL installed on them.
The default toolkit of OpenSSL that comes with Ubuntu isn’t the latest. To get the latest, you must download it yourself and install. An older version will work with the tutorial as well. You do not need to upgrade to follow this tutorial.
Just as mentioned in the title, in this tutorial we will be using OpenSSL in a slightly unusual way, we will be using it to encrypt and decrypt a file on our computer.
Since OpenSSL allows us to specify the encryption algorithm to use, we’ll use the des3 encryption algorithm, which in simple terms means a complex encryption algorithm is applied three times to each data block, making it difficult to crack through brute force methods or other computer hacking methods.
While we will be focusing on Mac OS X and Ubuntu in this article, these commands will work anywhere that OpenSSL is installed, including older versions of OS X, CentOS, and all other Linux variants.
How to install OpenSSL on a Ubuntu
Most versions of Ubuntu come with OpenSSL installed, it is usually not the latest version but just as mentioned above it you can use it for this tutorial. If you want to verify which version of OpenSSL you have installed, you can do that easily by typing the command below in your terminal.
This should display all information related to the version of OpenSSL you have installed on your computer, it should be similar to the output below:
If you don’t have it installed, you can just use the commands below to install it and all it’s associated development libraries.
How to install OpenSSL on a Mac
To install OpenSSL on a Mac we will be using homebrew. By running the commands below you will have OpenSSL installed and linked correctly on a Mac
How to Encrypt Files with OpenSSL
With OpenSSL installed and verified on our system, we can so ahead and use it to encrypt and decrypt individual files.
The syntax for using OpenSSL is pretty basic: It starts with the commandopenssl and you specify the type of encryption, and then you add the file that needs to be encrypted. Below is a template of the command used.
We’ll be using the des3 encryption algorithm for this example, and we’ll be using a text file as the input. We’re also going to specify a different output file to prevent any errors.
Here is what the command would look like:des3 which is short for Triple Data Encryption Standard (DES) is a type of computerized cryptography where block cipher algorithms are applied three times to each data block.
You will be asked to set and confirm a password before the encryption is complete, do not lose this password or you will lose access to the file.
Additionally, you can also just use an input file within filename, but that may cause issues. To prevent any unexpected problems, do not specify the same file as the input and output. This means the original file will stick around either before or after encryption, and you will want to deal with that file individually, preferably through a secure delete method.
Decrypting Files with OpenSSL
In the previous section, we set password will be required to decrypt the file. Once you execute the command above, you will be asked for the password you used. Other than switching the placement of the input and output, where again the original file stays put, the main difference here is the -d flag which tells OpenSSL to decrypt the file.
If you are wondering what happens when the password is invalid, you’ll get an error message, but if you force open the file with something like TextEdit, you’ll see the text encrypted version followed by a bunch of gibberish like so:
The file will remain unreadable until it has been decrypted through OpenSSL again. For more about file security follow us on Twitter, Facebook and sign up for our newsletter.
OpenSSL provides support for the TLS and SSL protocols and also includes various tools used in cryptography. Note that OpenSSL is officially available only as source, so you must manually compile and install the software on your Mac.
Deploy the OpenSSL toolkit via the command line
To install the OpenSSL toolkit and library on your Mac, you must open the Terminal application, go to the OpenSSL source folder, and follow the instructions from the INSTALL file included in the archive.
For short, you must run the './config', 'make', 'make test', and 'make install' commands, and then type openssl in the Terminal. If you need to see what OpenSSL release you are using, you can use the 'version' argument.
Note that you must make sure you are using the correct PATH to reach the latest OpenSSL installation. When you install OpenSSL, you get to see the output location, and you can check the path used by default with the 'which openssl' shell command.
Older OpenSSL versions are delivered with the system by default, and the old link will most likely be preserved. This means that you must configure the shell to use the correct path on your own.
Worth mentioning is that you can also install the toolkit using a package management solution such as Homebrew.
Quick access to SSL and Crypto libraries
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While in OpenSSL's command line interface, you get to see all the standard, message digest, or cipher commands supported by OpenSSL, but you do not get usage instructions.
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Make sure to check the online documentation to read extensive descriptions and learn about configuration options for each of the included commands.
OpenSSL's developers also provide a Frequently Asked Questions section where you can get details about the latest version, about how you can use the commands, and so on.
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To conclude, the OpenSSL software package offers you the possibility to work with the SSL and TLS protocols or to access cryptography tools, as long as you are willing to work with the command line.