Command Line – Modern File Encryption

If you encrypt, you are probably familiar with Pretty Good Privacy (PGP) [1] or its clone GNU Privacy Guard (GPG). Most likely, you have used one of these tools to generate public and private keys and to encrypt email and files. The Free Software Foundation explains these tools in its Email Self-Defense Guide as a first step towards privacy [2]. However, despite PGP and GPS being ubiquitous when it comes to privacy, some people believe that these tools are counter-productive and little more effective than the feeble default protection available for PDF files when it comes to modern computing. Ironically, as PGP and GPG become more widely used, some security experts are advocating for their replacement with Actual Good Encryption (age), at least for file encryption [3].

Why do some security experts claim that PGP and GPG are obsolete? To begin with, PGP and GPG have long public keys that can be difficult to work with when space is limited, and copying them accurately by hand is difficult. In particular, they can be difficult to configure, even when the simple configuration wizard is used (Figure 1). When generating a key, PGP and GPG require numerous choices, including the encryption method, the key size, and how long the key is valid. Even a moderately skilled user can be hard-pressed to answer such questions intelligently. As a result, users may simply fall back on the defaults, although ignorance and security are hardly compatible. Many users, too, complain about having to move the cursor around to generate sufficient randomness – and, the longer the key, the longer it takes to generate the randomness. To further add to the confusion, PGP and GPG do too many things, such as signing services and key management, that many users have no interest in, which can add to the confusion.

Figure 1: PGP can be difficult for non-cryptographers to configure intelligently.

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