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PGP & GPG

Ben Rothke writes "PGP (Pretty Good Privacy), as most Slashdot readers know, is one of the most popular software encryption programs ever. It is so good and so effective that in the early 1990s the FBI launched a multi-year investigation against Phil Zimmerman, the creator of PGP, for possible violation of federal export laws, especially ITAR (International Traffic in Arms Regulation). After many years of investigation, the FBI ultimately dropped its case against Zimmerman. Even though PGP is synonymous with end-user encryption, there have only been a few books written on the subject. Jump to 2006, and PGP & GPG: Email for the Practical Paranoid is a welcome title." Read the rest of Ben's review. PGP & GPG: Email for the Practical Paranoid author Michael Lucas pages 216 publisher No Starch Press rating 8 reviewer Ben Rothke ISBN 1593270712 summary Pretty good overview of PGP & GPG

On page 167 in Appendix A of the book, the author candidly writes that PGP "comes with a very good and complete manual at over 300 pages". With that, one may question why one would spend $24.95 on a book which covers much of the same information as the bundled documentation.

The reality is that there is a large class of people that will simply not read any form of documentation. Rather, they prefer something with an ISBN number. Such people are a boon to authors (of which I am one) and publishers. For that group, PGP & GPG: Email for the Practical Paranoid provides a pretty good overview of how to use PGP.

The book is written for an end-user who, while comfortable with the workings of technology, is new to the sometimes strange world of public key cryptography. The author writes in an easy-to-read style and, through repetition, inculcates the principal ideas of encryption and cryptography to the reader.

The introduction and first chapter provide a good presentation of the concepts of encryption, cryptography and public-key cryptography. The idea of public-key cryptography, on which PGP is based, is not so intuitive, and many people struggle with the basic concepts. The first chapter, appropriately titled 'Cryptography Kindergarten' is a good read for those who are public-key cryptography challenged.

On a side note, the notion that even smart end-users can be intimidated by public key cryptography was detailed in a now seminal research paper 'Why Johnny Can't Encrypt: A Usability Evaluation of PGP 5.0.'

The premise of the paper is that user errors cause or contribute to most computer security failures, yet user interfaces for security still tend to be clumsy, confusing, or near-nonexistent. The authors argue that effective security requires a different usability standard, and that it will not be achieved through the user interface design techniques appropriate to other types of consumer software. The authors conclude that PGP 5.0 is not usable enough to provide effective security for most computer users despite its attractive graphical user interface. Even though PGP is in version 9.x, it still suffers from usability flaws.

Cryptography purists may recoil when the author repeatedly uses the term 'military-grade encryption.' Military-grade encryption and military-grade cryptography are overused terms, most often by marketing departments, but there is no real definition of 'military-grade encryption' -- and even if there were, it would be classified. Most people use 'military-grade encryption' to mean really strong crypto, much like those who use the term 'Olympic-size swimming pool' to refer to a really large pool. But the term 'military-grade encryption' is so misused by so many people that it is a lost cause to try to fight it.

In the rest of the book, chapters 2 - 11, the author details the varied usages of PGP & GPG. The book also details the differences between OpenPGP, PGP and GPG.
The difference between them is that PGP is a commercial piece of software, GPG (Gnu Privacy Guard) is open source, and OpenPGP is a protocol that defines a standard format for encrypted messages, signatures, and certificates for exchanging public keys.

The author astutely writes that while PGP provides really strong security, this is only if, and this is a huge if, it is implemented correctly. Chapter 11 notes that although OpenPGP provides a reliable method of authentication and encryption, it is also not unbreakable. OpenPGP can be vulnerable to many different types of attacks and weaknesses, including poor implementation, hardware or software compromise, fake keys and more. It is important to realize that OpenPGP provides significant, but not unbreakable security.

At 180 pages and priced at $24.95, PGP & GPG: Email for the Practical Paranoid is an excellent book that shows the end-user in an easy to read and often entertaining style just about everything they need to know to effectively and properly use PGP and OpenPGP.

For those that want to save money and perhaps save a few trees, the free documentation that comes along with the product is similarly worth reading.

You can purchase PGP & GPG: Email for the Practical Paranoid from bn.com.

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4 of 157 comments (clear)

  1. Should rename the book by Rosco+P.+Coltrane · · Score: 5, Interesting

    PGP & GPG: Email for the Practical Paranoid

    title soon to become "PGP & GPG: encryption for the practical suspicious target of the homeland security dept."

    --
    "A door is what a dog is perpetually on the wrong side of" - Ogden Nash
  2. S/MIME by Lord+Ender · · Score: 4, Interesting

    When people say "X.509" when talking about email security, what they mean is S/MIME. It is pretty clear S/MIME is going to win the battle to be the most common form of email security on the Internet. It has built-in support on Outlook, Thunderbird, hell--even mutt.

    If people CHOOSE to trust a PKI, S/MIME works WAY better than PGP because key distribution is much easier. If they don't want to do a PKI, they can still trust individual certificates, just like PGP. They can verify certificates by reading thumbprints over the phone, if they like.

    Basically, S/MIME can do everything PGP/MIME can do except the "web of trust." And WoT is just WAY too much work for 99.9% of the population. PGP will eventually vanish.

    --
    A slashdotter who didn't build his own computer is like a Jedi who didn't build his own lightsaber.
  3. Re:So What Does It Mean? by sahuaro · · Score: 5, Interesting
    Mod this poster up! The inventors of public key encryption envisioned a future where encrypting email would be as common as stuffing a letter in an envelope. Phishing would be unheard of since a digital signature would prove that the mail came from who it said it did.

    The US government, of course, didn't want this future to come about and put roadblocks in place to prevent it. So, today we have phoney email scams and unencrypted personnel data that gets scattered to the winds on unsecured government and private sector computers. Encrypt your email? Why you must be doing something illegal!

    Dennisk

    --
    Phoenix Linux Users Group
    Penguins in the desert
  4. Re:I wish security were more accessible to the mas by smoker2 · · Score: 3, Interesting
    Add to that the number of web sites using an aging perl shopping cart system whereby half the credit card number is immediately emailed to the admin and the rest is stored as plain text on the server. Also the web sites who claim that your numbers are perfectly safe as they are using 128 bit encryption and the data is not decrypted until it reaches their [colocated, probably virtual] server. I had an argument with some previous employers when they insisted on calling their colocated RAQ3 a "secure server". I pointed out that they had never even seen the facility that it was housed in, and the private data was freely accessable using telnet, because it wasn't encrypted once ssl had done with it.

    Just as a an example, I set up a shopping cart of the type I mentioned and they thought it was the mutts nutz until I showed them that I was receiving both parts of the credit card numbers by email at a private email account. Even then I don't think they thought it was a problem. I left shortly afterwards.

    I wonder whose harvesting those numbers now...

    BTW, I deleted that shopping cart, so I am not guilty of abusing the system. It was done to prove a point.