PGP & GPG: EMAIL FOR THE PRACTICAL PARANOID

By JAMES HARRIS

CONTENTS IN DETAIL INTRODUCTION THE STORY OF PGP OPENPGP HOW SECURE IS OPENPGP? TODAY’S PGP CORPORATION WHAT IS GNUPG? PGP VERSUS GNUPG EASE OF USE SUPPORT TRANSPARENCY ALGORITHM SUPPORT OPENPGP AND THE LAW WHAT THIS BOOK CONTAINS STOP WASTING MY PRECIOUS TIME WHAT DO I NEED TO READ? CRYPTOGRAPHY KINDERGARTEN WHAT OPENPGP CAN DO TERMINOLOGY PLAINTEXT AND CIPHERTEXT CODES CIPHERS HASHES CRYPTANALYSIS GOALS OF PGP’S CRYPTOGRAPHY CON?DENTIALITY INTEGRITY NONREPUDIATION AUTHENTICITY ENCRYPTION ALGORITHMS SYMMETRIC ALGORITHMS ASYMMETRIC ALGORITHMS PUBLIC-KEY ENCRYPTION DIGITAL SIGNATURES COMBINING SIGNATURES AND ASYMMETRIC CRYPTOGRAPHY PASSPHRASES AND PRIVATE KEYS CHOOSING A PASSPHRASE UNDERSTANDING OPENPGP SECURITY AND OPENPGP WEB OF TRUST TRUST IN OPENPGP WHERE TO INSTALL YOUR KEYPAIR KEY LENGTH KEY EXPIRATION DATE NAME, EMAIL, AND COMMENT REVOCATION CERTI?CATES STORING YOUR KEYPAIR STORING YOUR REVOCATION CERTI?CATE PHOTO IDS AND OPENPGP KEYS KEY DISTRIBUTION KEYSERVERS INSTALLING PGP DOWNLOADING PGP INSTALLING PGP KEY TYPE KEY SIZE EXPIRATION PGP KEY BACKUPS IMPORTANT INSTALLATION LOCATIONS REVOCATION CERTI?CATES AND PGP DISABLING KEYSERVER UPDATES REVOKE THE KEY RE-IMPORT YOUR PRIVATE KEY KEY PROPERTIES USING THE REVOCATION CERTI?CATE KEYSERVERS AND PGP INSTALLING GNUPG DOWNLOADING GNUPG CHECKING CHECKSUMS CALCULATING CHECKSUMS UNDER WINDOWS CALCULATING CHECKSUMS UNDER UNIX GNUPG HOME DIRECTORY GPG CONF INSTALLING GNUPG ON WINDOWS COMMAND-LINE GNUPG WIN32 INSTALLATION GRAPHICAL GNUPG INSTALLATION WINPT CREATING KEYPAIRS IN WINPT KEY MANAGER WINPT REVOCATION CERTI?CATE SENDING YOUR KEY TO A KEYSERVER INSTALLING GNUPG ON UNIX-LIKE SYSTEMS RANDOMNESS AND GNUPG BUILDING FROM SOURCE CODE INSTALLING GNUPG CON?GURATION OPTIONS SETUID ROOT GNUPG DON’T RUN GNUPG AS ROOT COMMAND-LINE GNUPG KEYPAIRS GNUPG REVOCATION CERTI?CATES PUBLICIZING YOUR KEY TEXT EXPORTS WEB FORMS THE WEB OF TRUST SUBKEYS PGP NET KEYSERVER PGP COM SEARCHING FOR KEYS SIGNING A KEY SIGNING KEYS OF FRIENDS AND FAMILY SIGNING STRANGERS’ KEYS WHAT TO DO WITH SIGNED KEYS WHEN YOU GET NEW SIGNATURES KEYSIGNING PARTIES KEY TRUST AVOIDING THE WEB OF TRUST PGP KEY MANAGEMENT ADDING KEYSERVERS ADDING KEYS TO YOUR KEYRING SEARCHING KEYSERVERS IMPORTING FROM A FILE FINGERPRINT COMPARISONS RETURNING THE SIGNED KEY VIEWING SIGNATURES UPDATING SIGNATURES ADDING PHOTOS TO YOUR KEYS MANAGING GNUPG KEYS KEYSERVER OPTIONS KEYSERVERS AND WINPT COMMAND-LINE KEY FETCHING COMMAND-LINE KEY VIEWING WINPT KEY VIEWING AND FETCHING COMMAND-LINE KEY IMPORTS WINPT FILE IMPORTS CHECKING FINGERPRINTS SIGNING KEYS ON THE COMMAND LINE SIGNING KEYS IN WINPT VIEWING KEY SIGNATURES COMMAND-LINE EXPORTS WINPT EXPORTS IMPORTING NEW SIGNATURES PUSHING SIGNATURES TO KEYSERVERS UPDATING KEYS DELETING PUBLIC KEYS FROM YOUR KEYRING GNUPG AND PHOTOS ADDING PHOTOS TO YOUR KEY VIEWING PHOTOS WITH GNUPG WINPT AND PHOTOGRAPHS BUILDING THE WEB OF TRUST WITH GNUPG PGP GNUPG COMMAND-LINE TRUST CON?GURATION WINPT TRUST CON?GURATION OPENPGP AND EMAIL MESSAGE ENCODING INLINE ENCODING PGP/MIME EMAIL CLIENT INTEGRATION PROXIES PLUG-INS SAVING EMAIL—ENCRYPTED OR NOT? SAVING UNENCRYPTED EMAIL ENCRYPT TO SELF EMAIL FROM BEYOND YOUR WEB OF TRUST EXPANDING YOUR WEB OF TRUST TRACING THE WEB OF TRUST REPEATABLE ANONYMITY UNPROTECTED EMAIL COMPONENTS PGP AND EMAIL PGP AND YOUR EMAIL CLIENT IDENTIFYING OPENPGP MAIL EMAIL STORAGE PGP POLICIES OPPORTUNISTIC ENCRYPTION REQUIRE ENCRYPTION MAILING LIST SUBMISSIONS MAILING LIST ADMIN REQUESTS CREATING CUSTOM POLICIES SAMPLE CUSTOM POLICY: EXCEPTIONS TO DEFAULT POLICY SAMPLE CUSTOM POLICY: OVERRIDING THE DEFAULTS CUSTOM POLICIES ORDER AND DISABLING POLICIES GNUPG AND EMAIL MICROSOFT MAIL CLIENTS AND GNUPG OUTLOOK EXPRESS AND GNUPG CON?GURING OUTLOOK EXPRESS FOR OPENPGP SENDING OPENPGP MAIL RECEIVING AND VERIFYING SIGNED AND ENCRYPTED MAIL OUTLOOK AND GNUPG INSTALLATION CON?GURING THE PLUG-IN RECEIVING OPENPGP MAIL DECRYPTING PGP/MIME MESSAGES WITH MICROSOFT MAIL CLIENTS THUNDERBIRD AND GNUPG INSTALLING THE THUNDERBIRD GNUPG PLUG-IN CON?GURING ENIGMAIL READING OPENPGP MAIL UPGRADING THUNDERBIRD AND ENIGMAIL OTHER OPENPGP CONSIDERATIONS WHAT CAN GO WRONG? POOR USAGE POOR SIGNING HARDWARE COMPROMISE SOFTWARE COMPROMISE PEOPLE COMPROMISE FAKE KEYS OPENPGP INTEROPERABILITY TEAMS AND OPENPGP OPENPGP AND SHARED SYSTEMS OTHER SOFTWARE FEATURES PASSPHRASE CACHING SHREDDING