[...]... V3 - 03/26/2008 5:05pm Contents Acknowledgments xv Part I Email and Security Background Chapter 1 Introduction How This Book Is Organized Part I: Email and Security Background Part II: PKI Basics Part III: Secure Email Part IV: Tokens Part V: Case Studies Part VI: Expectations for the Future Appendices Who Should Read This Book Chapter 2 Understanding Email History and Evolution Internet Email Wow! Email. .. technical parts of email in two manageable byte-sized pieces The first is the process and format of email, and the second is the system that moves the email Wow! Email Is Just Like Snail Mail With a name like email, you shouldn’t be surprised that email is a lot like regular postal service mail The process, formats, and commands for email have postal service analogies Process To email or not to email: that... standards for details on the syntax and semantics of email- related protocols and PKI-related protocols You are presented with many choices when implementing an email security system We hope that this book will help you wade through these options and achieve the benefits of secure email 5:15pm Page 6 Turner c02.tex V3 - 03/26/2008 5:19pm CHAPTER 2 Understanding Email Before you can run, you have to walk, and... revocation lists structures produced by a PKI Part III: Secure Email Part III contains two chapters, both detailing the ins and outs of email security Chapter 6, ‘‘Protecting Email Message Contents,’’ provides a history of email security mechanisms and explains the most common mechanism to protect your emails’ contents, whereas Chapter 7, ‘‘Protecting Email Passwords, Message Headers, and Commands,’’ explains... Certificates Security Labels Equivalent Labels Secure Mail Lists Algorithms Generating an S/MIME Message Chapter 7 Protecting Email Passwords, Headers, and Commands Password Scramble Connection Security Transport Layer Security Handshake Protocol Record Protocol IPsec Security Associations Authentication Header Encapsulating Security Payload Internet Key Exchange (IKE) Part IV Tokens Chapter 8 Tokens and... free webmail Combine free email with the spread of wireless technologies to laptops, PDAs, and cell phones, and you have a recipe for an almost viral-like growth of email Now people give out email addresses instead of phone numbers, put email addresses on their business cards, and send billions of emails every year Life has changed Internet Email As we mentioned earlier, email has many moving parts... providing these protections In this book, we explain security tools, including cryptography, security protocols, tokens, and hardware security modules to protect your email You do not need to be an expert in these technologies to secure your email Products are available that can help you This book provides the information needed to first select wisely from these security offerings and then successfully deploy... and Pat can compose an email together during one of their arduous retreats in Palm Springs, and then they get Doug to send it to Bob 11 Page 11 Turner 12 Part I ■ c02.tex V3 - 03/26/2008 Email and Security Background Table 2-2 Snail Mail and Email Process Similarities STEP SNAIL MAIL EMAIL Compose Alice pulls out pen and paper and writes her letter Alice either starts a dedicated email application or... this field to add words she thinks Bob might find useful; in this case there are none Resent-Date:, Resent-From:, Resent-Sender:, Resent-To:, ResentCc:, Resent-Bcc:, and Resent-Message-ID: These fields are added by Alice if she has to resend the message to Bob and Matt These fields are almost always filled in by Alice’s email program when she hits send Body The body, which is optional, is either a text message... the trans- mission channel Date: Mon, 11 Feb 2008 09:57:06 -0 400 From: Bob To: Alice Cc: Matt Subject: Re: Meeting Date and Time Message-ID: In-Reply-To: MIME-Version: 1.0 Content-Type: multipart/mixed; boundary="notice the boundry" notice the boundary Content-type: text/plain; . alt="" Turner ffirs.tex V2 - 03/26/2008 5:00pm Page iv Turner ffirs.tex V2 - 03/26/2008 5:00pm Page i Implementing Email Security and Tokens: Current Standards, Tools, and Practices Sean Turner Russ. Housley Wiley Publishing, Inc. Turner ffirs.tex V2 - 03/26/2008 5:00pm Page ii Implementing Email Security and Tokens: Current Standards, Tools, and Practices Published by Wiley Publishing, Inc. 10475. ftoc.tex V3 - 03/26/2008 5:05pm Page xiii Contents xiii Choosing Smart Cards 154 USB Tokens 155 Software Tokens 156 iButton Tokens 156 Embedded Tokens 157 Hardware Security Modules 158 Network-Attached