__________________________________ GNUPG FREQUENTLY ASKED QUESTIONS Robert J. Hansen et al. __________________________________ 1 Foreword ========== Welcome to the GnuPG Frequently Asked Questions (FAQ)! Before we begin, there’s just a few things that need to be addressed. It’s regrettable these things have to be included, but society has become very litigious. 1.1 Trademark notice ~~~~~~~~~~~~~~~~~~~~ - Linux is a trademark of Linus Torvalds. - Macintosh, OS X and Mac OS X are all trademarks of the Apple Corporation. - PGP is a trademark of Symantec Corporation. - Solaris is a trademark of Oracle Corporation. - UNIX is a trademark of The Open Group. - Windows is a trademark of the Microsoft Corporation. - Some cryptographic algorithms mentioned in this FAQ may be trademarked. The use of these, or any other, marks is solely for identification purposes. 1.2 Licensing ~~~~~~~~~~~~~ This document is © 2012, Robert J. Hansen <[rjh@sixdemonbag.org]> and A.M. Kuchling <[amk@amk.ca]>. You are free to make use of this document in accordance with the [Creative Commons Attribution-ShareAlike 3.0 license], with the exception of Randall Munroe’s XKCD comic, which is released under terms of the [Creative Commons Attribution-NonCommercial 2.5] license; alternately, you may make use of it under terms of the GNU General Public License (version 3 or, at your discretion, any later version), again excepting Mr. Munroe’s works. [rjh@sixdemonbag.org] mailto:rjh@sixdemonbag.org?subject=The%20GnuPG%20FAQ [amk@amk.ca] mailto:amk@amk.ca?subject=The%20GnuPG%20FAQ [Creative Commons Attribution-ShareAlike 3.0 license] http://creativecommons.org/licenses/by-sa/3.0/ [Creative Commons Attribution-NonCommercial 2.5] http://creativecommons.org/licenses/by-nc/2.5/ 1.3 Disclaimer of liability ~~~~~~~~~~~~~~~~~~~~~~~~~~~ Although the contents of this document are believed to be correct, the author(s) cannot promise it is error-free and cannot assume liability for any errors. Table of Contents _________________ 1 Foreword .. 1.1 Trademark notice .. 1.2 Licensing .. 1.3 Disclaimer of liability 2 Welcome .. 2.1 What conventions are used in this FAQ? .. 2.2 Who maintains this FAQ? .. 2.3 Is this the official GnuPG FAQ? .. 2.4 When was this FAQ last checked for accuracy? 3 General questions .. 3.1 What’s GnuPG? .. 3.2 How do I pronounce GnuPG? .. 3.3 Is it compatible with Symantec’s PGP? .. 3.4 Which operating systems does it run on? .. 3.5 How much does it cost? .. 3.6 From where can I download it… .. 3.7 Is there source code available for it? .. 3.8 What’s Free Software, and why does it matter? .. 3.9 How can I donate money to the GnuPG project? .. 3.10 How can I help with GnuPG development? 4 Where can I get more information? .. 4.1 How can I spot the charlatans? .. 4.2 What are some useful mailing lists? .. 4.3 What are some useful webpages? 5 What email clients support GnuPG on… .. 5.1 … Microsoft Windows? .. 5.2 … Mac OS X? .. 5.3 … Linux or FreeBSD? 6 Is GnuPG available as a ‘portable app’? 7 What do all these strange words mean? .. 7.1 What’s ‘public-key cryptography’? .. 7.2 What’s ‘symmetric cryptography’? .. 7.3 What’s a ‘key’? .. 7.4 What’s a ‘certificate’? .. 7.5 What’s a ‘keyserver’? .. 7.6 What’s RSA? .. 7.7 What’s DSA? .. 7.8 What’s Elgamal? .. 7.9 What’s AES? .. 7.10 What are Twofish and Blowfish? .. 7.11 What’s 3DES? .. 7.12 What’s Camellia? .. 7.13 What are SHA-1, SHA-224, SHA-256, SHA-384, SHA-512 and SHA-3? .. 7.14 What’s MD5? .. 7.15 What are CAST, CAST5, and CAST5-128? .. 7.16 What are ZLIB, ZIP and BZIP? .. 7.17 What’s a ‘revocation certificate’? .. 7.18 What’s a ‘designated revoker’? .. 7.19 What does ‘validity’ mean? .. 7.20 What does ‘trust’ mean? .. 7.21 What does ‘ownertrust’ mean? 8 How do I start using GnuPG? .. 8.1 Does GnuPG need to be ‘tuned’ before use? .. 8.2 How large should my key be? .. 8.3 What algorithm should I use? .. 8.4 Why does it take so long to generate a certificate? .. 8.5 What should I do after making my certificate? .. 8.6 Where does GnuPG look for configuration options? .. 8.7 What options should I put in my configuration file? .. 8.8 Is there any particular keyserver I should use? .. 8.9 What’s the difference between an ‘option’ and a ‘command’? .. 8.10 What are the most commonly used options? .. 8.11 What are the most commonly used commands? .. 8.12 How do I use another person’s certificate? .. 8.13 Why can’t I read emails I’ve sent, and how do I fix it? .. 8.14 How do I encrypt a file for multiple recipients? .. 8.15 How do I sign a file with multiple certificates? .. 8.16 How do I combine encryption with signing? .. 8.17 How do I force GnuPG to make printable-text output? .. 8.18 How do I create an ‘inline signature’? .. 8.19 How can I use GnuPG in an automated environment? .. 8.20 I’m a programmer and I need a GnuPG library. Is there one? .. 8.21 I’m a programmer and I need a way to call GnuPG internals directly. Is there a library for this? 9 What common problems come up? .. 9.1 Why is GnuPG warning me this certificate might not belong to whom I think it does? .. 9.2 Why is GnuPG warning me about using insecure memory? .. 9.3 Why is GnuPG changing my message? 10 What are some common best practices? .. 10.1 How can I choose a strong passphrase? .. 10.2 How can I keep my revocation certificate safe? .. 10.3 How can I keep my computer safe from malware? .. 10.4 Should I use encrypted disk software like TrueCrypt, BitLocker or FileVault? 11 Advanced topics .. 11.1 Why does GnuPG default to 2048 bit RSA-2048? .. 11.2 Do other high-security applications use RSA-2048? .. 11.3 Why doesn’t GnuPG default to using RSA-4096? .. 11.4 Why do people advise against using RSA-4096? .. 11.5 Why does GnuPG support RSA-4096 if it’s such a bad idea? .. 11.6 Can any of the ciphers in GnuPG be brute-forced? .. 11.7 Has GnuPG ever been successfully attacked? .. 11.8 Should I use PGP/MIME for my emails? .. 11.9 What are the best algorithms in GnuPG? .. 11.10 Why is my DSA key limited to 3072 bits? .. 11.11 Why does my DSA-1024 key use a different digest algorithm than my DSA-2048 or DSA-3072 key? 2 Welcome ========= Welcome to the official GnuPG FAQ. This FAQ has been written from scratch and makes the old FAQ obsolete. Nevertheless this text is still incomplete but we believe it to be more accurate than the long outdated former FAQ. 2.1 What conventions are used in this FAQ? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ As is par for the course with everything involving computers, there are an awful lot of acronyms in this FAQ. For most of them, holding the mouse pointer over the acronym will reveal a tooltip containing the full expansion of the acronym. Hovering over the letters FAQ, for instance, will reveal the words “Frequently Asked Questions.” These acronyms are presented in a small-caps font in order to make them easier to recognize when reading. 2.2 Who maintains this FAQ? ~~~~~~~~~~~~~~~~~~~~~~~~~~~ [Robert J. Hansen]. Please feel free to contact me should there be an error in this FAQ, whether typographical, grammatical, or factual. When writing, the editorial “we” refers to the general consensus of the GnuPG community. This consensus is hammered out on the GnuPG-Users mailing list. All members of the GnuPG community are invited to participate. Individual people within the community may give their own editorial comments: these will be set off by square brackets, italicized, and initialed by their author. The different editors are: - wk: Werner Koch <[wk@gnupg.org]> - rjh: Robert J. Hansen <[rjh@sixdemonbag.org]> /[Do we have any other editors we need to add? — rjh]/ [Robert J. Hansen] mailto:rjh@sixdemonbag.org?subject%3DThe%20GnuPG%20FAQ [wk@gnupg.org] mailto:wk@gnupg.org?subject%3DThe%20GnuPG%20FAQ [rjh@sixdemonbag.org] mailto:rjh@sixdemonbag.org?subject=The%20GnuPG%20FAQ 2.3 Is this the official GnuPG FAQ? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Yes. 2.4 When was this FAQ last checked for accuracy? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ October 2012. 3 General questions =================== Since no company controls GnuPG, there’s really no single vendor for GnuPG. Instead, there’s a robust community surrounding GnuPG which has produced versions of it for several different operating systems. But first, let’s cover the basics. 3.1 What’s GnuPG? ~~~~~~~~~~~~~~~~~ GnuPG is cryptographic software that helps people ensure the confidentiality, integrity and assurance of their data. Let’s try that again: GnuPG is… - /Cryptographic./ The word “cryptography” is derived from two Greek words, κρυπτός (pronounced “kryptos,” meaning “hidden”) and γράφω (pronounced “graphein,” meaning “writing”). Cryptography is the mathematical study of codes and ciphers. - /Software./ This one should already be obvious. - /Confidentiality./ No one except authorized parties should be able to read your data. - /Integrity./ It shouldn’t be possible to tamper with a message unnoticeably. - /Assurance./ An assurance is not a guarantee. There are no guarantees in life, and software is no different. An assurance just means there is good reason to be confident of something — here, it means that when GnuPG is correctly used, people may be confident the data is confidential and/or possesses integrity. GnuPG may be used by itself as a command-line application (i.e., to be run at a Terminal prompt or a Windows command prompt), or integrated into popular email clients. It’s also used by some instant messaging clients, such as Psi. 3.2 How do I pronounce GnuPG? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ “guh-NEW-pee-gee.” 3.3 Is it compatible with Symantec’s PGP? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Largely, yes. It can be made to interoperate with anything from PGP 2.6 and onwards, and has excellent interoperability with the most recent releases. 3.4 Which operating systems does it run on? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Too many to list! It’s known to run on Microsoft Windows, Mac OS X, the various free Unixes, AIX, Solaris, HPUX, OpenVMS, and more. People are even working on porting it to smartphones such as Android. 3.5 How much does it cost? ~~~~~~~~~~~~~~~~~~~~~~~~~~ There is no fixed price. Many sites on the internet offer legal downloads of it for free. 3.6 From where can I download it… ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Lots of different places, but no one site hosts binaries for all operating systems. … for Microsoft Windows? ------------------------ A convenient Windows installer is available from [GPG4WIN]. [GPG4WIN] http://www.gpg4win.org … for Mac OS X? --------------- The [GPGtools project] has everything needed to get started. [GPGtools project] http://www.gpgtools.org … for Linux? ------------ The bad news is there is no single, consistent way to install GnuPG on Linux systems. The good news is that it’s usually installed by default, so nothing needs to be downloaded! * … for Debian GNU/Linux? GnuPG is installed by default with Debian GNU/Linux. If for some reason it is not, use the APT package manager to install the package “gnupg2”. * … for OpenSUSE? A recent version of GnuPG is part of the default OpenSUSE installation. * … for Fedora? See the [instructions for CentOS]. Typically, though, Fedora ships with a much more recent version of GnuPG, and as such you shouldn’t need to install anything. [instructions for CentOS] See section 3.6.3.4 * … for CentOS or RHEL? An older (but still secure!) version of GnuPG is part of every CentOS installation. To get the latest version, use the YUM package manager to install the package “gnupg2”. * … for Ubuntu? See the instructions for [Debian GNU/Linux]. [Debian GNU/Linux] See section 3.6.3.1 * … for Slackware? Install the `gnupg' package for GnuPG 1.4, or the `gnupg2' package for GnuPG 2.0. * … for Gentoo? To install GnuPG on Gentoo, run the following command as root: `emerge gnupg' The Gentoo documentation includes a [GnuPG User Guide]. [GnuPG User Guide] http://www.gentoo.org/doc/en/gnupg-user.xml … for FreeBSD? -------------- GnuPG is included in the ports collection. To install it, run the following commands as root: ,---- | cd /usr/ports/security/gnupg | make install clean `---- Alternatively, you can install GnuPG using a package manager: ,---- | sudo pkg_add -r gnupg `---- … for VMS? ---------- A port to *VMS* is maintained by Steven M. Schweda at [antinode.info]. [antinode.info] http://www.antinode.info/dec/sw/gnupg.html 3.7 Is there source code available for it? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Yes! The person, business or group that provided you with the GnuPG binary is required to give you the source code upon your request. 3.8 What’s Free Software, and why does it matter? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The word “free” should evoke ideas of liberty, not price. An awful lot of the software industry does not respect your freedoms: your freedom to use the software for any purpose, your freedom to study and learn from how it works, your freedom to share it with others who might benefit from it, and more. Free Software is the antithesis of this: Free Software is meant to respect your rights. You may use the software for any purpose: you may inspect and modify the source code: you may share the software and/or your modifications with others. 3.9 How can I donate money to the GnuPG project? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The best way is to visit the [g10 Code donation page]. [g10 Code donation page] http://g10code.com/gnupg-donation.html 3.10 How can I help with GnuPG development? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Development discussion takes place on the gnupg-devel mailing list. Go to the [GnuPG mailing list page] for links to subscribe and to the list's archives. The [GnuPG project's bug tracker] is also publicly available. [GnuPG mailing list page] https://www.gnupg.org/documentation/mailing-lists.en.html [GnuPG project's bug tracker] https://bugs.gnupg.org/gnupg/ 4 Where can I get more information? =================================== The good news is the internet is a treasure trove of information. The bad news is that the internet is a festering sewer of misinformation, conspiracy theories, and half-informed speculations all masquerading as informed commentary. The following mailing lists and web pages are generally known for having a strong signal-to-noise ratio. Despite this, we strongly urge skepticism. 4.1 How can I spot the charlatans? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ First, beware of all absolutes. Almost every question in either the fields of computer security or cryptography can honestly be answered with, “it depends.” Real experts will avoid giving blanket yes-or-no questions except to the simplest and most routine of questions. They will instead hem and haw and explain the several different factors that must be weighed. Hucksters will promise you absolute truth. Second, the experts really don’t care whether you take their advice. Hucksters often want to be seen as authorities, and if you fail to take their advice they may harangue you about how you’re taking chances with your data, how you’re acting irresponsibly, and so on. Third, experts genuinely don’t want you to trust them. An expert will instead point to the published literature (usually in a dead-tree edition with the imprimatur of a reputable publishing house) and tell you what the reference books say. They want you to trust the reference books, not them. Hucksters will go on about their extensive personal experience or refer to papers that have only ever been self-published on websites. Fourth, experts try not to scare people. The world is a scary enough place without it being made moreso. Hucksters will try to scare you, in order to keep you listening to them and dependent on them for information on how to be ‘safe.’ Fifth, experts will quickly admit when they are wrong and give credit to the person bringing the error to their attention. Hucksters tend to take challenges as personal affronts. 4.2 What are some useful mailing lists? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The good news is, there are many! The GnuPG-Users mailing list ---------------------------- Subscribing: visit the [GnuPG-Users webpage] Unsubscribing: see above List moderator: <[gnupg-users-owner@gnupg.org]> Supports PGP/MIME?: No Languages supported: English GnuPG-Users is home to the largest community of GnuPG users on the net. The list is very lightly moderated and somewhat freewheeling, but overall it has an excellent signal-to-noise ratio. The level of technical discussion is sometimes a little daunting for the newcomer, but on the whole it’s a wonderful resource. [GnuPG-Users webpage] http://lists.gnupg.org/mailman/listinfo/gnupg-users [gnupg-users-owner@gnupg.org] mailto:gnupg-users-owner@gnupg.org?subject%3DThe%20GnuPG-Users%20list The Enigmail mailing list ------------------------- Subscribing: Visit the [Enigmail mailing list page] Unsubscribing: See above List moderator(s): - John Clizbe <[john@enigmail.net]> - Olav Seyfarth <[olav@enigmail.net]> - Patrick Brunschwig <[patrick@enigmail.net]> - Ludwig Hügelschäfer <[ludwig@enigmail.net]> - Daniele Raffo <[daniele@enigmail.net]> - Robert J. Hansen <[rob@enigmail.net]> Supports PGP/MIME: Yes Languages supported: English, Deutsch, Schwyzerdütsch, Español Enigmail integrates GnuPG with [Mozilla Thunderbird] and/or [Mozilla Seamonkey]. It’s one of the most popular ways to use GnuPG, and the mailing list provides a friendly place to learn how it works and get started using it. The list is lightly moderated. [Enigmail mailing list page] https://admin.hostpoint.ch/mailman/listinfo/enigmail-users_enigmail.net [john@enigmail.net] mailto:john@enigmail.net?subject=The%20Enigmail%20list [olav@enigmail.net] mailto:olav@enigmail.net?subject=The%20Enigmail%20list [patrick@enigmail.net] mailto:patrick@enigmail.net?subject=The%20Enigmail%20list [ludwig@enigmail.net] mailto:ludwig@enigmail.net?subject=The%20Enigmail%20list [daniele@enigmail.net] mailto:daniele@enigmail.net?subject=The%20Enigmail%20list [rob@enigmail.net] mailto:rob@enigmail.net?subject=The%20Enigmail%20list [Mozilla Thunderbird] http://www.getthunderbird.com [Mozilla Seamonkey] http://www.seamonkey-project.org/ PGP-Basics ---------- Subscribing: visit the [PGP-Basics webpage] Unsubscribing: see above List moderator: Mike Daigle <[mdaigle@gswot.org]> Supports PGP/MIME: No Languages supported: English PGP-Basics was established over a decade ago specifically to provide a place where newcomers to GnuPG and PGP could learn about communications security. The list is low-volume, lightly-moderated, and remarkably friendly to new users. [PGP-Basics webpage] http://tech.groups.yahoo.com/group/PGP-Basics [mdaigle@gswot.org] mailto:mdaigle@gswot.org?subject=The%20PGP-Basics%20list PGPNET ------ Subscribing: visit the [PGPNET page] Unsubscribing: see above List moderator(s): Unknown Supports PGP/MIME?: No Languages supported: Unknown PGPNET exists to provide people with the opportunity to practice sending and receiving encrypted, signed, and encrypted-and-signed traffic in a group environment. [PGPNET page] http://tech.groups.yahoo.com/group/PGPNET 4.3 What are some useful webpages? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ As a general rule, the huckster quotient of webpages at-large is fairly high. That said, there are some web resources we recommend. They can be broken up into homepages for specific GnuPG-related projects, and sites of general interest. Where can I find the homepage for… ---------------------------------- Many of the projects associated with GnuPG maintain their own websites. If you have problems with an associated project, please check their website first: they might be able to give you faster and better help than the GnuPG community can. * … GnuPG? GnuPG’s homepage can be found at [[https://www.gnupg.org]]. It is also available in the [Tor] network as `ic6au7wa3f6naxjq.onion'. [[https://www.gnupg.org]] https://www.gnupg.org [Tor] https://torproject.org * … Enigmail? Enigmail, a plugin for Mozilla Thunderbird that adds strong GnuPG support, can be found at [[http://enigmail.net]]. [[http://enigmail.net]] http://enigmail.net * … GPGTools? Mac OS X users may wish to visit the GPGTools project at [[http://www.gpgtools.org]]. [[http://www.gpgtools.org]] http://www.gpgtools.org * … GPG4WIN? GPG4WIN, the Windows port of GnuPG, maintains a homepage at [[http://www.gpg4win.org]]. [[http://www.gpg4win.org]] http://www.gpg4win.org Where can I find webpages covering… ----------------------------------- Although the GnuPG community generally finds these websites to be useful, your mileage may significantly vary. There are wide differences of opinion about some of them. They’re worth visiting and worth reading, but make sure to read skeptically. * … an easy introduction to cryptography? There is no such thing as an easy introduction to cryptography. However, PGP Corporation has a well-regarded [/Introduction to Cryptography/]. [/Introduction to Cryptography/] http://www.cs.unibo.it/babaoglu/courses/security/resources/documents/intro-to-crypto.pdf * … the deeper mathematics of cryptography? The maintainer of this list also keeps a gentle(-ish) [introduction to the mathematics and computer science of cryptography]. [introduction to the mathematics and computer science of cryptography] http://keyservers.org/~rjh/cryptofaq.xhtml * … best practices for using GnuPG? At present, there are no reputable web pages detailing GnuPG best practices. * … the politics of cryptography? The inclusion of a site on this list is not an endorsement of that site’s political leanings. Probably the best-known organization is the [Electronic Frontier Foundation], which has been at the vanguard of electronic civil liberties for over twenty years. The [Free Software Foundation] is also deeply involved in these matters, although in a different way than the EFF. [Electronic Frontier Foundation] http://www.eff.org [Free Software Foundation] http://www.fsf.org 5 What email clients support GnuPG on… ====================================== Many email clients offer strong GnuPG integration. The column “Active” in the tables below indicate whether the software os actively developed. 5.1 … Microsoft Windows? ~~~~~~~~~~~~~~~~~~~~~~~~ Name Plugins GnuPG PGP/MIME Active see -------------------------------------------------------------- Thunderbird yes (Enigmail) 1.4, 2.0 yes yes (1) Kontact native 1.4, 2.0 yes yes (2) Claws-Mail yes (internal) 1.4, 2.0 yes yes (3) (1) With the Enigmail plugin, Thunderbird becomes one of the most popular GnuPG-aware email clients. it’s under active development and is compatible with the latest Thunderbird releases, with a friendly and welcoming user community. (2) Kontact is KDE’s integrated personal information manager of KDE. It runs anywhere that KDE does, and even on some mobile devices as Kontact Touch. (3) Claws-Mail for Windows is included in the [Gpg4win] installer. [Gpg4win] http://www.gpg4win.org 5.2 … Mac OS X? ~~~~~~~~~~~~~~~ Name Plugins GnuPG PGP/MIME Active see ---------------------------------------------------------------- Thunderbird yes (Enigmail) 1.4, 2.0 yes yes (1) Gnus yes ([EasyPG]) 1.4, 2.0 yes yes (2) Mutt native 1.4, 2.0 yes yes (3) Apple Mail yes ([GPGtools]) 2.0 no yes (4) (1) With the Enigmail plugin, Thunderbird becomes one of the most popular GnuPG-aware email clients. it’s under active development and is compatible with the latest Thunderbird releases, with a friendly and welcoming user community. (2) EasyPG is part of Emacs 23, proper. Thus there is no more need to install the plugin. See the Gnus manual for configuration hints. (3) For best experience make sure to put `set crypt_use_gpgme' in your `~/.muttrc' file. (4) PGP/MIME support in Apple Mail+GPGtools is not absent, just temporarily broken. [EasyPG] http://www.emacswiki.org/emacs/EasyPG [GPGtools] http://www.gpgtools.org 5.3 … Linux or FreeBSD? ~~~~~~~~~~~~~~~~~~~~~~~ Name Plugins GnuPG PGP/MIME Active see -------------------------------------------------------------- Thunderbird yes (Enigmail) 1.4, 2.0 yes yes (1) Gnus yes ([EasyPG]) 1.4, 2.0 yes yes (2) Mutt native 1.4, 2.0 yes yes (3) Kontact native 1.4, 2.0 yes yes (4) Evolution native 1.4, 2.0 yes yes Claws-Mail yes (internal) 1.4, 2.0 yes yes (1) With the Enigmail plugin, Thunderbird becomes one of the most popular GnuPG-aware email clients. it’s under active development and is compatible with the latest Thunderbird releases, with a friendly and welcoming user community. (2) EasyPG is part of Emacs 23, proper. Thus there is no more need to install the plugin. See the Gnus manual for configuration hints. (3) For best experience make sure to put `set crypt_use_gpgme' in your `~/.muttrc' file. (4) Kontact is KDE’s integrated personal information manager of KDE. It runs anywhere that KDE does, and even on some mobile devices as Kontact Touch. [EasyPG] http://www.emacswiki.org/emacs/EasyPG 6 Is GnuPG available as a ‘portable app’? ========================================= For Windows users, check [PortableApps.com]. To build you own portable application you may use the /mkportable/ tool which comes with [Gpg4win]. [PortableApps.com] http://portableapps.com/apps/internet/thunderbird_portable [Gpg4win] http://www.gpg4win.org 7 What do all these strange words mean? ======================================= Cryptography tends to use a whole lot of specialized language and jargon. In this section some of it will be deciphered. 7.1 What’s ‘public-key cryptography’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ In the 1970s new ideas came to the forefront of the cryptanalytic world. One of the most important was the development of asymmetric cryptography (also often called “public-key cryptography”). Asymmetric cryptography is built around problems that are very hard in one direction, and very easy in another. Consider the number 2,701. If you were to be asked for its prime factors, you would find it a daunting challenge. If you were to be given the numbers 37 and 73, though, it wouldn’t take but a minute to discover the answer was 2,701. Multiplying two numbers to yield a third number is easy: finding those two numbers, given the third, is hard. Asymmetric cryptography uses these asymmetric problems as the building-blocks of cryptography. It’s easy to create an encrypted message which neither you nor anyone else save the intended recipient can decrypt. To continue the metaphor, you and everyone else get to wrestle with the hard problem (“factor 2,701”). The intended recipient knows a secret piece of information which makes the problem easy (“factor 2,701, given that one of the factors is 73”). This manages to overcome the major flaw with symmetric cryptography. Your public key can be shared with the entire world, even your enemies, and your communications will still be secure. Compare this to symmetric cryptography, where as soon as the key became public knowledge the entire system was broken. 7.2 What’s ‘symmetric cryptography’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ One of the earliest ciphers was the shift cipher, which was allegedly used by Julius Caesar in his campaign against the Gauls. He took his plaintext and shifted each letter three positions up in the alphabet, wrapping around once he reached the end (so that ‘Z’ would become ‘C’). His correspondents would reverse the process: by moving each letter in the encrypted text down three letters the original message would be recovered. Knowing how to encrypt the text also gave the knowledge of how to decrypt the text: the process wasn’t identical (one shifted up, the other shifted down), but knowing one process the other one could trivially be discovered. This trait, that of encryption and decryption being two sides of the same coin, is the defining trait of symmetric cryptography. Modern-day symmetric ciphers are much more complex than Caesar’s scheme, but they still work in fundamentally the same way. Knowledge of how to encrypt reveals knowledge of how to decrypt, and vice-versa. The symmetry between those two operations leads to the name “symmetric cryptography”. Symmetric cryptography is fast, well-studied, and safe. It has one critical drawback, though: you have to have a secure communications channel by which you can share the key with someone. If you already have a secure communications channel, though, do you really need cryptography? 7.3 What’s a ‘key’? ~~~~~~~~~~~~~~~~~~~ The word ‘key’ is unfortunately ambiguous. It can either refer to the mathematical structures that allow encryption, decryption, signing and verification to occur, or to the rather large blobs of data that contain those mathematical structures as well as information about the person associated with it, additional subkeys, and so forth. With respect to the large blobs of data, it is preferable to call them ‘certificates’, so that the word ‘key’ may be unambiguously recognized as meaning just the mathematical structures. Unfortunately, this is a custom that seems to be honored mostly in the breach. 7.4 What’s a ‘certificate’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~ A certificate is a large data structure that contains one or more [keys], and optionally information that identifies the user, designated revokers, who has vouched for this certificate, and so on. [keys] Unknown reference 7.5 What’s a ‘keyserver’? ~~~~~~~~~~~~~~~~~~~~~~~~~ A keyserver is a service that publishes public-key certificates and makes them searchable. You can upload your certificate to a keyserver so that other users can find it. There are distributed networks of keyservers that share keys, so you only need to upload your key once to that network. One widely-used keyserver network is [sks-keyservers.net]. SKS stands for “Synchronising Key Server”. You can use this network by supplying the `--keyserver pool.sks-keyservers.net' option. [sks-keyservers.net] http://www.sks-keyservers.net/ 7.6 What’s RSA? ~~~~~~~~~~~~~~~ RSA is the world’s premier [asymmetric cryptographic algorithm], and is built on the difficulty of factoring extremely large composites. GnuPG supports RSA with [key] sizes of between 1024 and 4096 bits. [asymmetric cryptographic algorithm] See section 7.1 [key] See section 7.3 7.7 What’s DSA? ~~~~~~~~~~~~~~~ The United States’ National Institute for Standards and Technology ([NIST]) established the Digital Signature Algorithm (DSA) as a government standard for digital signatures. Originally, it supported key lengths between 512 and 1024 bits. Recently, NIST has declared 512-bit keys obsolete: now, DSA is available in 1024, 2048 and 3072-bit lengths. DSA belongs to the Elgamal family of algorithms, and is very well-regarded. [NIST] http://www.nist.gov 7.8 What’s Elgamal? ~~~~~~~~~~~~~~~~~~~ Elgamal may refer to either a family of cryptographic algorithms built around the difficulty of computing discrete logarithms in a finite field, or one particular [asymmetric encryption algorithm] based on that problem. The former is normally referred to as “the Elgamal family,” and the latter is normally referred to as simply “Elgamal.” GnuPG supports the Elgamal asymmetric encryption algorithm in [key] lengths ranging from 1024 to 4096 bits. There is also an Elgamal signature algorithm, which GnuPG no longer supports. [asymmetric encryption algorithm] See section 7.1 [key] See section 7.3 7.9 What’s AES? ~~~~~~~~~~~~~~~ Leading up to the year 2000, it was obvious that the old Data Encryption Standard (DES) was on its last legs and needed to be replaced. 3DES was available as a stopgap measure, but there was a lot of pressure to make a new encryption standard that made use of the last few decades of cryptologic research. The United States National Institute of Standards and Technology ([NIST]) held an open competition to select the new encryption standard. In the summer of 2000, a cipher named Rijndael (pronounced “RAIN-doll”) was selected as the new Advanced Encryption Standard, or AES. AES is a thoroughly modern cipher design and may be used with confidence. [NIST] http://www.nist.gov 7.10 What are Twofish and Blowfish? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Blowfish and Twofish are well-regarded symmetric ciphers. Blowfish should not be used to encrypt files larger than 4Gb in size, but Twofish has no such restrictions. These algorithms are modern, and may be used with confidence. 7.11 What’s 3DES? ~~~~~~~~~~~~~~~~~ In the 1970s, IBM developed a new symmetric cipher called the Data Encryption Standard (DES). They overdesigned it horribly: even after three decades, the only way to break DES is by brute force. Unfortunately, standard DES has a small enough keyspace to be susceptible to brute-forcing. A new variant of DES was needed. 3DES, which is made of three DES algorithms running together with three independent keys, was the result. 3DES is ungainly, ugly, slow, and has all the aesthetics of a Soviet workers’ housing bloc. It has also withstood three decades of cryptanalysis and is still going strong. Due to its 1970s-era 64-bit block size, it should not be used to encrypt more than about 4Gb of data. Beyond that, though, it is solid as a rock, and very few GnuPG users will ever notice a problem with it. Provided you’re not encrypting more than 4Gb of data you may use 3DES with confidence. 7.12 What’s Camellia? ~~~~~~~~~~~~~~~~~~~~~ During roughly the same time period that [NIST] was running the Advanced Encryption Standard trials, Japan’s [CRYPTREC] and the European Union's [NESSIE] were running their own similar trials. Camellia is the cipher that won the NESSIE and CRYPTREC trials, much in the same way that Rijndael won the United States’ AES trials. Camellia is a thoroughly modern cipher design and may be used with confidence. [NIST] http://www.nist.gov [CRYPTREC] http://www.cryptrec.jp/english/ [NESSIE] http://www.cryptonessie.org/ 7.13 What are SHA-1, SHA-224, SHA-256, SHA-384, SHA-512 and SHA-3? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The Secure Hash Algorithms are cryptographic hash functions originally devised by the United States’ National Security Agency. The algorithms have been made publicly available and have been subjected to an astonishing amount of peer review. - *SHA* and/or *SHA-0*: the original Secure Hash Algorithm, generating 160-bit outputs. Flaws were discovered in it almost immediately. SHA-0 never gained much traction in the cryptologic community, and it is not present in GnuPG. - *SHA-1*: This is SHA-0 with the flaws fixed, and not much else in the way of changes. It still generates 160-bit outputs. SHA-1 has not aged well. Although it is still believed to be safe, it would be advisable to use another, different hash function if possible. - *SHA-224*: This is a massively-overhauled SHA-1 which generates 224-bit outputs. It is believed to be safe, with no warnings about its usage. - *SHA-256*: This is a massively-overhauled SHA-1 which generates 256-bit outputs. It is believed to be safe, with no warnings about its usage. - *SHA-384*: This is a massively-overhauled SHA-1 which generates 384-bit outputs. It is believed to be safe, with no warnings about its usage. - *SHA-512*: This is a massively-overhauled SHA-1 which generates 512-bit outputs. It is believed to be safe, with no warnings about its usage. - *SHA-3*: SHA-3 is a completely new hash algorithm that makes a clean break with the previous SHAs. It is believed to be safe, with no warnings about its usage. At present, GnuPG does not support SHA-3. Support for SHA-3 is forthcoming: expect it soon. 7.14 What’s MD5? ~~~~~~~~~~~~~~~~ MD5 is a 128-bit cryptographic hash function invented by Ron Rivest (the ‘R’ of ‘RSA’) in the early 1990s. For many years it was one of the standard algorithms of the field, but it has not aged well and is widely considered to be completely obsolete. You don’t need to worry about MD5, though: although GnuPG can read MD5-based signatures, it will only generate MD5-based signatures if you jump through a lot of hoops. This is for your own safety, to prevent people from accidentally generating MD5-based signatures. 7.15 What are CAST, CAST5, and CAST5-128? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Carlisle Adams and Stafford Tavares (the “CA” and the “ST” in “CAST”) developed the CAST algorithm in 1996. It was later approved for Canadian government use. CAST has many names: CAST, CAST5, CAST5-128 and CAST-128 all refer to the same algorithm. Internally, CAST is distinctly similar to Blowfish, another well-respected algorithm. Like 3DES, its 64-bit block size means it should not be used to encrypt files larger than 4Gb in size. With that said, though, CAST is a modern cipher and may be used with confidence. 7.16 What are ZLIB, ZIP and BZIP? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ZLIB, ZIP and BZIP refer to different kinds of compression algorithms. GnuPG will use one of these three algorithms to compress your data before encrypting it, unless GnuPG can see the data is already compressed. 7.17 What’s a ‘revocation certificate’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ A revocation certificate is a [certificate] that possesses the information necessary to mark another certificate as unusable. This is called ‘revoking’ the certificate. Recommended procedure is to generate a revocation certificate immediately after generating a new GnuPG key. If the key is lost (say, if you have no backups of the key and you lose the smart card or laptop containing the key), you'll no longer be able to generate a revocation certificate. Consult [the FAQ instructions] on how to do this. [certificate] See section 7.3 [the FAQ instructions] See section 8.5.2 7.18 What’s a ‘designated revoker’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ A designated revoker is a person, identified by a certificate, that has the authority to revoke another certificate held by a different person. For instance, if you were using GnuPG in a corporate environment the IT staff might be listed as a designated revoker for your certificate, so that when you left the company the IT staff could revoke your certificate. 7.19 What does ‘validity’ mean? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Although a certificate makes certain assertions about identity, these assertions cannot be blindly trusted. (Consider, for instance, whether you should trust a certificate that claims to belong to `obama@whitehouse.gov'.) If you trust the certificate’s assertions, you are said to have ‘validated’ the certificate. Validation can be done by fiat or as the result of a process. For instance, you validate your own certificate by fiat: “this certificate says it belongs to me, and I trust it.” Validating other certificates, though, should probably have a little more rigor involved. How much rigor will depend entirely on your own particular needs and the threats you face. 7.20 What does ‘trust’ mean? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ‘Trust’ refers to how thoroughly a certificate has been [validated]. The terms are used somewhat interchangeably. [validated] See section 7.19 7.21 What does ‘ownertrust’ mean? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ If a certificate has been [validated], and if you trust the person owning that certificate to do proper validation of certificates, you can tell GnuPG “I am willing to trust this person’s validations as if they were my own.” /[For instance, I have fully validated John Hawley’s certificate. I further believe, based on my knowing John, that he will be as careful about validating a certificate as I would be. So if John validates your certificate, then if I pull your certificate down from the keyserver it will show up as a fully validated certificate. — rjh]/ [validated] See section 7.19 8 How do I start using GnuPG? ============================= The very first thing is to join the [GnuPG-Users mailing list]. You’ll find it to be a welcoming community that’s friendly to newcomers and is eager to help out. [GnuPG-Users mailing list] See section 4.2.1 8.1 Does GnuPG need to be ‘tuned’ before use? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ No. GnuPG has sensible defaults right out of the box. You don’t need to tune GnuPG before you can use it. 8.2 How large should my key be? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The overwhelming majority of users will be well-served by generating 2048-bit RSA keys. This is the default behavior for GnuPG. 8.3 What algorithm should I use? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The overwhelming majority of users will be well-served by generating 2048-bit RSA keys. This is the default behavior for GnuPG. 8.4 Why does it take so long to generate a certificate? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The short answer is, “your computer is doing a lot of work.” But don’t worry: although generating new certificates can take a while, actually using them once they’re made is quite fast. 8.5 What should I do after making my certificate? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Generate a revocation certificate, and store it in a safe place. Alternately, you may wish to appoint [a designated revoker]. [a designated revoker] See section 7.18 How do I appoint a designated revoker? -------------------------------------- A designated revoker is someone whom you trust to revoke your certificates on your behalf. This person may revoke your certificates without needing a revocation certificate. For instance, you may wish to appoint your lawyer as your designated revoker so that, in the event of your untimely death, your lawyer may revoke your certificates. To add a revoker, use the following command line: `gpg --edit-key' /[your key ID here]/ `addrevoker' When prompted, enter the key ID of the person whom you wish to appoint as a revoker. The revoker’s key must be fully validated. How do I generate a revocation certificate? ------------------------------------------- A [revocation certificate] marks another certificate as unusable. To generate a revocation certificate for your key, do: `gpg --armor --output revoke.asc --gen-revoke' /[your key ID]/ Copy `revoke.asc' to a safe place. [revocation certificate] See section 7.17 How do I send my certificate to the keyserver network? ------------------------------------------------------ `gpg --keyserver pool.sks-keyservers.net --send-key' /[your certificate ID]/ You should only upload your own certificates to the keyservers, or obtain the certificate holder's permission before doing so. In some circles it's considered rude to upload someone else's certificate; not everyone wants to publish their key publicly. 8.6 Where does GnuPG look for configuration options? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ GnuPG looks at a file called `gpg.conf' to determine various runtime parameters. On UNIX systems this file can be found in `~/.gnupg'. On Windows systems it’s a bit more difficult to predict, but try: Windows XP: FIXME Windows Vista: FIXME Windows 7: FIXME Windows 8: FIXME 8.7 What options should I put in my configuration file? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The good news is, you really shouldn’t need to. That said, the following is Rob Hansen’s `gpg.conf' file. The italicized text describes what each piece does: the monospaced text is the actual content of the file. /Ensure that all parameters are set for strict OpenPGP conformance. Later entries will override this, but setting ‘openpgp’ provides a really good baseline to start from./ `openpgp' /Make GnuPG a little quieter: don’t warn about insecure memory, don’t print a greeting message, don’t put comments in GnuPG’s output./ `no-greeting' `no-secmem-warning' `no-emit-version' `no-comments' /Since keyservers.org sits in my closet, I want GnuPG to always check it instead of going out on the network to ask another keyserver halfway around the globe. Most users don’t have a keyserver in their closet, and will want to substitute pool.sks-keyservers.net here./ `keyserver keyservers.org' /Whenever I sign a document, use certificate 0xD6B98E10/ `local-user 0xD6B98E10' /Whenever I encrypt a document, also include certificate 0xD6B98E10 as a recipient. This allows me to decrypt the messages I send./ `encrypt-to 0xD6B98E10' /In email, a line beginning with the word ‘From’ can be misinterpreted by the computer as the start of a new email message. Thus, whenever GnuPG sees a line starting with ‘From’, it will slightly mangle the line to prevent this bug from occurring./ `escape-from-lines' /Use SHA256 instead of SHA-1 for certificate signatures./ `cert-digest-algo SHA256' /Prefer these digest algorithms, in this order/ `personal-digest-preferences SHA256 SHA512 SHA384 SHA224 RIPEMD160' /Prefer these ciphers, in this order/ `personal-cipher-preferences TWOFISH CAMELLIA256 AES 3DES' 8.8 Is there any particular keyserver I should use? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Many people have had excellent luck with `pool.sks-keyservers.net'. 8.9 What’s the difference between an ‘option’ and a ‘command’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Commands tell GnuPG what to do: options tell GnuPG how to do it. For instance, `encrypt' is a command, and `armor' is an option that tells GnuPG to ensure the output contains only printable characters. 8.10 What are the most commonly used options? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Produce more output explaining what GnuPG is doing: `-v', `--verbose' Some of the most commonly used options are: Make no changes; this is useful for testing a command line that will modify keys or generate output: `-n', `--dry-run' Send output to the named file: `-o' /FILE/, `--output' /FILE/ Create ASCII-armored output that can be safely e-mailed, instead of binary output: `-a', `--armor' When encrypting a message, you will usually supply at least one recipient ID with the recipient option. This option can be supplied multiple times to encrypt a message to multiple recipients: `-r' /KEYID/, `--recipient' /KEYID=/ /specify a recipient ID/ 8.11 What are the most commonly used commands? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ GnuPG's primary functions are to encrypt and decrypt messages, and to sign and verify them. It's possible to sign without encrypting or encrypt without signing. Signing a file's content is done with the `-s' or `--sign' commands. A variation is `-b' or `--detach-sign', which produces a separate signature without including the file's content; this is useful for signing a software archive or other large file. The key to use for the signature can be specified with the `local-user' setting in your gpg.conf file, or with the `-u', `--local-user' options. Encrypting a file's content is done with the `-e' or `--encrypt' commands. Recipients are specified with the `-r' or `--recipient' options. GnuPG's default action is to decrypt and verify its input file, writing the contents to standard output or to the filename specified by the `-o' or `--output' options. The `--verify' command will only verify the signature without writing the file's contents anywhere. These commands are the most commonly used. GnuPG has many more commands, largely for managing your keyring containing your private keys and the certificates of others. 8.12 How do I use another person’s certificate? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ In order to send an encrypted message or verify a signature, you must obtain the certificate for the sender/signer's public key. Occasionally you might obtain the certificate physically, by meeting the certificate holder face-to-face and exchanging the certificate on some storage medium such as a USB stick, memory card, or portable disk. Or you might download a copy of the certificate from the holder's web site. Once obtained in one of these ways, you can add the certificate to your collection of public keys by doing: `gpg --import certificate.txt' More commonly, you'll download a correspondent's certificate from a keyserver. How do I search the keyserver for someone’s certificate? -------------------------------------------------------- There is also a network of public keyservers, accessible under the collective hostname `pool.sks-keyservers.net'. GnuPG users can upload their certificates to the keyservers, and other users can then search for and download them. `gpg --keyserver pool.sks-keyservers.net --search' /[email address, name, key ID, etc.]/ GnuPG will list matching certificates and prompt you to select which ones you wish to download and add to your keyring. People will obtain new signatures for their certificates from time to time. `gpg --refresh-keys' will recheck all of the certificates on your public key and download any new signatures for those keys. How do I retrieve a certificate if I already know its fingerprint? ------------------------------------------------------------------ `gpg --keyserver pool.sks-keyservers.net --recv-key' /[fingerprint]/ Why do I need to validate certificates? --------------------------------------- If you were to receive a letter in the mail that claimed to be from the President of the United States, would you believe it? Probably not, because anyone can put together official-looking letterhead: you’d insist on doing some kind of checking to make sure that no one was fooling with you. The same applies to email. A certificate can claim to be from anyone. You have to make sure that the certificate really belongs to whom it claims it belongs to. That process of making sure is called ‘validation’. How do I validate certificates? ------------------------------- *This advice is controversial.* It’s controversial for a simple reason: every Tom, Dick and Harry has their own idea about the “right way” to validate certificates. Some of these people are well-informed and some of them are just plain unhinged. In the end, you are responsible for making your own decisions. That said, the following is generally agreed upon as being a reasonable procedure: 1. Meet the certificate holder face-to-face. 2. Ask to see two forms of government-issued identification. 3. Upon verifying the person really is who they claim to be, ask this person to provide their certificate’s fingerprint, their email address, and where you can obtain a copy of their certificate. (Example: “My fingerprint is `4541 BB01 8EA4 8F99 19CA 3701 2380 6BE5 D6B9 8E10', and you can find it on `pool.sks-keyservers.net'.”) 4. On your own computer, retrieve the person’s certificate from the specified location. Check to make sure the email address they gave you is one that’s also listed on the certificate. Check to make sure the fingerprint of the certificate you’ve downloaded matches the fingerprint the person gave you. 5. `gpg --edit-key' /[their certificate ID]/ `sign' 6. Once signed, `gpg --armor --output signed_cert.asc --export' /[their certificate ID]/ 7. Send the file `signed_cert.asc' to the address they gave you By following this process you first ensure that you’re speaking to the right person. By comparing the fingerprints of the certificate you have against the fingerprint they specified, you’re ensuring that you have the right certificate. Checking to make sure the email address they gave you is also listed on the certificate is one more check to make sure. Once that’s done, presto, Bob’s your uncle: there’s nothing left to do except sign it and return the newly-signed certificate to the other person. 8.13 Why can’t I read emails I’ve sent, and how do I fix it? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ You encrypted a message to Alice, which means that it requires Alice’s private key to read it. Only Alice has her private key. That’s why you can’t read encrypted traffic you generated: only Alice can read it. To get around this, add yourself as a recipient (=--recipient = /[your certificate ID]/). 8.14 How do I encrypt a file for multiple recipients? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Use multiple `--recipient' options. Remember, options come before commands! 8.15 How do I sign a file with multiple certificates? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Use multiple `--local-user' options. Remember, options come before commands! 8.16 How do I combine encryption with signing? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ `gpg --armor --recipient' /[first recipient’s key ID]/ `--local-user' /[your key ID]/ `--sign --encrypt' /[filename]/ 8.17 How do I force GnuPG to make printable-text output? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Normally, computers use eight-bit binary code. This often presents trouble for email, which often requires that only printable (seven-bit) characters may be used. By using the `--armor' flag, GnuPG will generate output containing only printable characters. 8.18 How do I create an ‘inline signature’? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ An inline signature wraps a textual header and footer around the text to be signed, leaving the text readable without running GnuPG. This doesn't conceal the text at all and therefore provides no secrecy, but if someone edits the text GnuPG will report that the signature is bad. To generate an inline signature, run `gpg --armor --output signed_file.asc --local-user' /[your key ID]/ `--clearsign message_file.txt' To verify the resulting file, simply invoke GnuPG with the filename of the signed file: `gpg signed_file.asc' 8.19 How can I use GnuPG in an automated environment? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ You should use the `--batch' option. Don't bother to use a passphrase because there's usually no way to store it more securely than on the secret keyring itself. The suggested way to create keys for an automated environment is as follows. First, on a secure machine: 1. If you want to do automatic signing, create a signing subkey for your key. Use the interactive key editing menu by issuing the command: `gpg --edit-key' /keyID/ Enter "addkey" and select the DSA key type. 2. Make sure that you use a passphrase; this is required by the current implementation to let you export the secret key. 3. Run: `gpg --export-secret-subkeys --no-comment' /newsubkeyID/ `> secring.auto' 4. Copy `secring.auto' and the public keyring to a test directory. 5. Change to the test directory. 6. Run the command: `gpg --homedir . --edit' /newsubkeyID/ Use the sub-command `passwd' to remove the passphrase from the subkeys. You may also want to remove all unused subkeys by doing `key N' and then `delkey' for each subkey. 1. Copy `secring.auto' to the target box somehow. On the target machine, install `secring.auto' as the secret keyring and begin writing scripts that invoke GnuPG. It's a good idea to install an intrusion detection system so that you will get notice of a successful intrusion. If that happens, you can revoke all the subkeys installed on that machine and install new subkeys once the machine is secured again. 8.20 I’m a programmer and I need a GnuPG library. Is there one? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Check out [GPGME (GnuPG Made Easy)]. [GPGME (GnuPG Made Easy)] https://www.gnupg.org/related_software/gpgme/ 8.21 I’m a programmer and I need a way to call GnuPG internals directly. Is there a library for this? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ No, nor will there be. 9 What common problems come up? =============================== 9.1 Why is GnuPG warning me this certificate might not belong to whom I think it does? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ If you received an email claiming to be from a Nigerian oil tycoon, would you believe it? Or would you insist on doing some kind of verification first, in order to make sure that you’re not being scammed or swindled? The same principle applies here. If you’re using a certificate that claims to belong to Alice, but there’s no evidence it actually belongs to Alice, GnuPG will warn you that you’re using an untrusted certificate. You probably want to validate the certificate; see [this FAQ's instructions]. [this FAQ's instructions] See section 8.12.4 9.2 Why is GnuPG warning me about using insecure memory? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ GnuPG tries to lock memory so that no other process can see it and so that the memory will not be written to swap. If for some reason it’s not able to do this (for instance, certain platforms don’t support this kind of memory locking), GnuPG will warn you that it’s using insecure memory. While it’s almost always better to use secure memory, it’s not necessarily a bad thing to use insecure memory. If you own the machine and you’re confident it’s not harboring malware, then this warning can probably be ignored. 9.3 Why is GnuPG changing my message? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ GnuPG uses special lines to denote the beginning of a message, the beginning of a signature, and so forth. These lines start with “=----- BEGIN=…”. If your text contains a line beginning with a dash, that line will be slightly mangled in order to prevent GnuPG from misinterpreting your data as one of its special lines. 10 What are some common best practices? ======================================= It’s very hard to give advice on this subject, because everyone will have their own opinion. That said, here are some good guidelines: - *Join the community.* Join GnuPG-Users and get involved in the discussions. The conversation is wide-ranging and you’ll encounter a great variety of thoughts and opinions. Reading GnuPG-Users is one of the best ways to educate yourself. - *Practice.* If you don’t practice these skills before they become necessary, you won’t be able to use these skills effectively. - *Generate a revocation certificate and keep it safe.* - *Use a strong passphrase.* - *Keep your computer free of malware.* - *Validate certificates correctly.* 10.1 How can I choose a strong passphrase? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ If someone manages to obtain your secret key, the only thing protecting the key will be your passphrase. A passphrase should be 1) difficult to guess for someone who knows you, and 2) difficult to brute-force by trying every possible combination of characters. To meet requirement 1), the passphrase shouldn't be based on publicly-available information about you: your birthday, your spouse's name, your school's motto, a line of text from a book, etc. To meet requirement 2), the passphrase should be long: commercially available hardware can try 2.8 billion passwords in a day, which is sufficient to crack a 10-letter all-lowercase password. One simple approach that produces easy-to-remember passphrases is to generate four to six random words, as illustrated by the XKCD cartoon [“Correct, horse! Battery staple!”]. [“Correct, horse! Battery staple!”] http://xkcd.com/936/ 10.2 How can I keep my revocation certificate safe? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Good places include safe deposit boxes, kept on file with your lawyer, placed in a fireproof safe, and so forth. It should be treated as an important document that needs to be kept safe. 10.3 How can I keep my computer safe from malware? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Although there is no guaranteed way of keeping your system free of malware, you can reduce your risk quite a lot by following some basic rules. 1. Keep your system up-to-date. Always apply the latest patches. 2. Stop using old versions of Internet Explorer. If possible, use [Mozilla Firefox] or [Chromium]. 3. Don’t open email attachments unless they are expected and come from someone you know. 4. Don’t click on email links unless they are expected and come from someone you know. 5. Be suspicious of requests for personal information, especially if it’s more detail than is strictly necessary to solve a problem. [Mozilla Firefox] http://www.getfirefox.com [Chromium] http://download-chromium.appspot.com/ 10.4 Should I use encrypted disk software like TrueCrypt, BitLocker or FileVault? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ You can if you want, but it won’t make your private key any more secure. Your private key is already encrypted: your passphrase is the key used to decrypt your private key. 11 Advanced topics ================== These topics are ‘advanced’ in the sense that you really don’t need to understand them in order to safely and correctly use GnuPG. That said, if you have a more technical question about GnuPG, you may find some of the answers in this section. 11.1 Why does GnuPG default to 2048 bit RSA-2048? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ At the time the decision was made, 2048-bit RSA was thought to provide reasonable security for the next decade or more while still being compatible with the overwhelming majority of the OpenPGP ecosystem. Is that still the case? ----------------------- Largely, yes. According to NIST Special Publication 800-57, published in July 2012, 2048-bit RSA is believed safe until 2030. At present, no reputable cryptographer or research group has cast doubt on the safety of RSA-2048. That said, many are suggesting shifting to larger keys, and GnuPG will be making such a shift in the near future. What do other groups have to say about 2048-bit RSA? ---------------------------------------------------- In 2014, the German Bundesnetzagentur fuer Elektrizitaet, Gas, Telekommunikation, Post und Eisenbahnen recommended using RSA-2048 for long-term security in electronic signatures. In 2012, ECRYPT-II published their “Yearly Report on Algorithms and Keysizes” wherein they expressed their belief RSA-1776 will suffice until at least 2020, and RSA-2432 until 2030. In 2010, France’s Agence Nationale de la Securite des Systems d’Information stated they had confidence in RSA-2048 until at least 2020. Is there a general recommendation that 3072-bit keys be used for new applications? ---------------------------------------------------------------------------------- No, although some respected people and groups within the cryptographic community have made such recommendations. Some even recommend 4096-bit keys. Will GnuPG ever support RSA-3072 or RSA-4096 by default? -------------------------------------------------------- Probably not. The future is elliptical-curve cryptography, which will bring a level of safety comparable to RSA-16384. Every minute we spend arguing about whether we should change the defaults to RSA-3072 or more is one minute the shift to ECC is delayed. Frankly, we think ECC is a really good idea and we'd like to see it deployed as soon as humanly possible. I think I need larger key sizes. -------------------------------- By all means, feel free to generate certificates with larger keys. GnuPG supports up to 4096-bit keys. 11.2 Do other high-security applications use RSA-2048? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 2048-bit RSA is commonly used to secure SSL root signing certificates. It’s also used to sign operating system patches, Authenticode signatures, Java applets and more. RSA-2048 is believed to be safe against attack until at least the year 2030, so use it with confidence. 11.3 Why doesn’t GnuPG default to using RSA-4096? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Because it gives us almost nothing, while costing us quite a lot. Breaking an RSA-10 key requires you to try each prime number between two and one hundred. There are twenty-five of these, meaning RSA-10 is equivalent to about a 5-bit symmetric cipher. Breaking an RSA-20 key requires you to try each prime number between two and one thousand: there are 168 of them, meaning RSA-20 is equivalent to about an 8-bit cipher. Doubling the keylength (from RSA-10 to RSA-20) didn't give us the benefit that we naively expected. Each additional bit gives correspondingly less in the way of additional security, and we quickly reach a point of diminishing returns. That point of diminishing returns happens around RSA-2048. Once you move past RSA-2048, you’re really not gaining very much. At the same time, moving past RSA-2048 means you lose the ability to migrate your certificate to a smartcard, or to effectively use it on some mobile devices, or to interoperate with other OpenPGP applications that don’t handle large keys gracefully. If you really want a 4096-bit RSA key there’s nothing stopping you: but we sincerely believe the overwhelming majority of users will be well-served with RSA-2048. 11.4 Why do people advise against using RSA-4096? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Almost always when people use 4096-bit RSA they’re doing so because they believe RSA-4096 to be much stronger than it is. The United States’ National Institute of Standards and Technology ([NIST]) states that RSA-2048 gives roughly 112 bits of security and RSA-3072 gives roughly 128. There is no formal recommendation on where RSA-4096 lies, but the general consensus is that it would come in somewhere around 140 bits — 28 bits of improvement over RSA-2048. This is an improvement so marginal that it’s really not worth mentioning. If you need more security than RSA-2048 offers, the way to go would be to switch to elliptical curve cryptography — not to continue using RSA. [NIST] http://www.nist.gov 11.5 Why does GnuPG support RSA-4096 if it’s such a bad idea? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ RSA-4096 is not a bad idea: it’s just, generally speaking, unnecessary. You gain very little in the way of additional resistance to brute-forcing and cryptanalysis. 11.6 Can any of the ciphers in GnuPG be brute-forced? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ No. The laws of physics require that a certain amount of heat be used in computation. This is a consequence of the Second Law of Thermodynamics, and may not be violated under our current understanding of the laws of physics. Further, physics requires that a certain amount of time be used in computation. This is a consequence of the Heisenberg Uncertainty Principle, and may not be violated under our current understanding of the laws of physics. Using these two principles (the [Landauer bound] and the [Margolus–Levitin limit]), we can determine quite accurately how much heat would be released by a computer that brute-forced a 128-bit cipher. The results are profoundly silly: it’s enough to boil the oceans and leave the planet as a charred, smoking ruin. This is not to say that GnuPG cannot be successfully attacked. It is only to say that none of the ciphers in GnuPG are susceptible to brute-forcing. [Landauer bound] http://en.wikipedia.org/wiki/Landauer_bound [Margolus–Levitin limit] http://en.wikipedia.org/wiki/Margolus%E2%80%93Levitin_theorem 11.7 Has GnuPG ever been successfully attacked? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ This depends entirely on what is meant by “successful attack.” If you mean, “has GnuPG traffic ever been successfully cryptanalyzed?”, the answer is a flat ‘no’. We are unaware of any credible reports of any of the ciphers used in GnuPG having ever been successfully cryptanalyzed. If you mean, “have people figured out ways to obtain the plaintext anyway?”, the answer is an emphatic ‘yes.’ In [a 2007 Drug Enforcement Administration case], a keylogger was installed on a suspect's computer. GnuPG protects your traffic against cryptanalysis, but it is not magic fairy dust that can be sprinkled over your data to make it safe against all threats. [a 2007 Drug Enforcement Administration case] http://news.cnet.com/8301-10784_3-9741357-7.html 11.8 Should I use PGP/MIME for my emails? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ This is controversial, thus there are two commonly given answers. 1. Probably not. ---------------- PGP/MIME is the official, standardized way of using GnuPG with electronic mail. PGP/MIME packages the data up as encrypted attachments. This is the problem with it: attachments often get mangled, stripped, or otherwise tampered with. For instance, sending PGP/MIME traffic to the [PGP-Basics mailing list] will result in your email being completely blank. PGP-Basics is set up to drop all attachments from messages posted to the list, and that means your PGP/MIME attachments get dropped. For many years GNU Mailman would repackage attachments in ways that would break the PGP/MIME standard and result in unreadable traffic. These GNU Mailman installations still exist in the wild. For a long time both [GnuPG-Users] and [Enigmail] ran these buggy versions of GNU Mailman. Since PGP/MIME can't reliably be sent to the three largest GnuPG mailing lists, it’s hard to claim that PGP/MIME is ready for widespread usage. For now, it’s best to use inline traffic unless you can be certain that PGP/MIME messages will not be mangled in transit. [PGP-Basics mailing list] See section 4.2.3 [GnuPG-Users] See section 4.2.1 [Enigmail] See section 4.2.2 2. Yes, it is the safer solution. --------------------------------- The problems with the mailing list software are annoying but harmless. In most other cases PGP/MIME works very well and avoids a lot of semantic problems when sending signed mails. For example it is much easier for mail readers to indicate what parts of the mail are covered by the signature. Many mail readers have bugs pertaining to inline signatures which can be used to trick the user into assuming that some parts of a mail are covered by the signatures while in reality they are not. For encrypted and signed mails there are no problems with signature verification because almost all software uses the combined signature+encryption approach of PGP/MIME and thus GnuPG takes care of it in exactly the same way as it does with inline traffic. Non-ASCII character encoding is problematic with inline data. Although OpenPGP provides a way to specify the encoding, that feature is not widely supported. In good Unix tradition GnuPG does not try to interpret the data it signs or encrypts but relies on the peers to agree on a common encoding. PGP/MIME provides a well established and matured way of doing exactly that. Some plugins for Outlook do not support PGP/MIME but after all the OpenPGP support in Outlook is anyway quite limited. 11.9 What are the best algorithms in GnuPG? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ MD5 and SHA-1 should be avoided if possible. Beyond that, there is no “best algorithm” or “best algorithms” in GnuPG. It’s sort of like asking whether Godzilla or King Kong is better at terrorizing urban cities: there is no clear-cut winner. This is not to say you shouldn’t have preferences, though. It is only to say that GnuPG’s algorithms are so well-designed for what they do that there is no single “best”. There’s just a lot of personal, subjective choice. For instance: - /[I studied Twofish pretty intensively in graduate school, so I tend to prefer it. — rjh]/ 11.10 Why is my DSA key limited to 3072 bits? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The United States’ National Institute of Standards and Technology ([NIST]) is responsible for the DSA specification. NIST has not published a 4096-bit DSA variant, and thus GnuPG doesn’t offer it. [NIST] http://www.nist.gov 11.11 Why does my DSA-1024 key use a different digest algorithm than my DSA-2048 or DSA-3072 key? ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The DSA algorithm has gone through several revisions. GnuPG’s original implementation of DSA supported 1024-bit keys that used either SHA-1 or RIPEMD-160 as hashes. When the United States’ National Institute of Standards and Technology ([NIST]) revised the specification to support 2048- and 3072-bit keys, they also required longer hashes be used. DSA-2048 required a 224-bit hash (SHA-224, or a longer hash cut down to 224 bits), and DSA-3072 required a 256-bit hash (SHA-256, or a longer hash cut down to 256 bits). They also now allowed for stronger hashes to be used for DSA-1024: if they were more than 160 bits, they would simply be cut down. So, depending on how you have GnuPG configured, GnuPG might be forced to use SHA-1 and/or RIPEMD-160 with DSA-1024; GnuPG might be able to use any of the longer SHAs with DSA-1024; GnuPG might use SHA-224, -256, -384 or -512 for DSA-2048; GnuPG might use SHA-256, SHA-384 or SHA-512 for DSA-3072. [NIST] http://www.nist.gov