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Slamming Spam: A Guide for System Administrators Paperback – Dec 20 2004

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From the Inside Flap

Slamming Spam: A Guide for System AdministratorsPreface

This book is meant to be a reference for the email system administrator who has been asked to implement an anti-spam solution for their organization. This is an administrator's "how to" stop spam book. It is very hands on, with none of the "why people spam" or other topics which are usually only peripherally interesting or useful to a mail administrator.

Fighting spam is a complex problem, with many potential technical, legislative, and social solutions. No book could ever hope to cover them all in a reasonable amount of space. In fact, when considering only the possible technical spam-fighting solutions, it isn't possible to give them all the coverage they require. Our focus in this book is on the widely used open source anti-spam solutions available for major mail transfer agents (email servers).It has all the latest information on the book, including updated URLs, errata, and other useful information in the fight against spam.

Who This Book Is For

The reader is assumed to have a limited knowledge of Linux/Unix. In most cases, step-by-step instructions are provided for the covered package or approach. These "cookbook" examples are meant to work for most installations, with minimal changes and/or customizations. While some knowledge is assumed of the mail-transfer agent software used (such as Sendmail), the administrator doesn't need to be a mail server expert or Linux guru to implement the solutions outlined here.

You will learn about the best current anti-spam methods and software available. Most of the methods are open source and freely available (as in free beer). These open source solutions offer the "best of breed" anti-spam solutions available today. Implementing open source solutions requires more work than commercial solutions, but often the administrator ends up with a more flexible, better solution than is otherwise available.

We initially thought we would discuss anti-spam services such as Postini and Symantec's Brightmail in the book. However, we found that most of the commercial anti-spam solutions (such as anti-spam firewalls) and services were documented quite well and didn't require additional coverage. As a result, most commercial solutions are only mentioned in the Introduction. The only non-open source anti-spam solution covered here (McAfee SpamKiller) is directly related to the commercial mail servers covered—IBM/Lotus Notes/Domino and Microsoft Exchange.

The IBM Lotus Domino and Microsoft Exchange administrator has a choice. An anti-spam solution can be implemented directly as part of the mail server, since both IBM Lotus and Microsoft Exchange support plug-ins. To supplement or as an alternative to a tightly integrated solution (like McAfee SpamKiller), additional open source email servers can be deployed specifically to perform spam filtering or virus checking. These anti-spam/virus servers would process the message before sending it on to the Domino/Exchange server for delivery to the recipient.

While adding to the "box count" an administrator needs to manage, this approach does enable an open source best-of-breed solution to these otherwise "closed" commercial email servers. A hybrid approach can reduce the out-of-pocket cost while giving the administrator much flexibility in tweaking the anti-spam solution.

What You Will Need

The solutions in this book focus on Linux, on the server side. There is some coverage of the client side, but primarily the client coverage is meant to complement the server implementations we examine. Although the solutions presented here have been tested on Debian and/or Fedora Core Linux, they should work on almost every version of Linux available without too many modifications.

The covered mail transfer agents (MTAs) are Sendmail, Postfix, qmail, IBM Lotus Domino, and Microsoft Exchange. We assume the reader has a previously installed and working MTA, as the task of installing and configuring a single MTA can be a book unto itself. SMTP authentication support for Postfix, Sendmail, and qmail may require the recompilation of the MTAs in order to implement. Having a previously installed compiled and working MTA makes SMTP AUTH much easier.

We assume the reader has root access to the machine(s) they want to implement the anti-spam solutions covered here. Although many of the solutions do not require root access and can be installed and run as a "regular" user (though sometimes this requires configuration changes), we assume root access in our examples. You will see the use of root only when absolutely necessary. You won't see us compiling or installing anything as the root user, unless there is no other way to do it.

Often, we use the sudo command in order to run privileged commands which otherwise would require the root password. sudo is potentially a better way of giving out root access, without disclosing the root password. The commands prefixed by sudo could just as easily be run as root, assuming the root user's path is identical to the unprivileged user's path. For many examples, we assume the user performing the installation tasks has write access to /usr/local.

A few notes regarding other Linux/Unix command assumptions. We presume the reader has access to and knowledge of the following Linux utilities:

  • tar for tar formatted archives

  • gzip for GNU zip formatted archives

  • zip for the Info-zip formatted archives

  • bzip2 for bzip2 formatted archives

  • wget, lynx and/or ftp for retrieving source archives

We presume you have a recent version of gcc on the system to build the anti-spam utilities outlined here. Some of the packages covered here specifically require GNU make. Most Linux distributions come with GNU make. If you are building these solutions on a BSD derivative such as FreeBSD, or another platform such Sun Solaris or HP-UX, you may need to install GNU make for the spam-fighting utilities that require it.

In this book, we often mention maildir and mbox (or mailbox) formatted files. You should be aware which type of mailbox your email server software uses. The configuration for many anti-spam utilities covered in this book will vary depending upon which mailbox format is used. (Lotus Domino and Microsoft Exchange use their own internal format, so the mailbox format doesn't apply to those email servers.)

The mbox format stores the messages for a particular user in one file per folder. Because mbox was the original (and at one time only) mailbox format, it has wide support. Sendmail and Postfix use mbox formatted mailboxes by default. Mailboxes in the mbox format work fine in many installations, but can pose problems for some administrators in some cases. For example, mbox formatted mailboxes on NFS-mounted filesystems have locking issues that can result in mailbox corruption.

Maildir stores each message as individual files, with unique names in a directory structure with a directory for each folder. In many cases, a "/" after a filename parameter will indicate maildir formatted message directory, and the lack of a "/" will indicate that a mailbox is in mbox format. qmail uses maildir formatted mailboxes by default. Postfix can be configured easily to use maildir formatted mailboxes. If Procmail is used as the mail delivery agent, Procmail can easily be configured to use maildir format by specifying the folder name with a trailing "/".

How This Book Is Organized

This book can be read cover to cover in order to give the reader a hands-on view of the many methods to fight spam. However, the individual chapters are self-contained, so if there are specific anti-spam solutions you want to implement, you can just skip to those particular chapters.

Chapter 1, "Introduction," is an overview of some of the currently available major anti-spam technologies. It is useful for putting the solutions provided in the rest of the book in context. The focus is designing an anti-spam infrastructure for an organization's network, walking through policy, information gathering, design questions, and goals. If you are interested in designing an anti-spam architecture from scratch, Chapter 1 is an excellent starting point.

Chapter 2, "Procmail, " is a tool often used as a mail-delivery agent by anti-spam software to complete the job of fighting spam. For example, many statistical analysis tools depend upon procmail to perform the filtering of messages into the spam or non-spam folders. If the anti-spam tools of interest require the use of procmail, this chapter should be read if the reader is not familiar with the procmail utility.

Chapter 3, "SpamAssassin," covers the widely known and used spam classifier program. This chapter contains a treatment of the popular anti-spam scoring program, from installing the required packages to configuring SpamAssassin, and ruleset (scoring) creation. If the reader is planning to utilize a general purpose anti-spam filter, SpamAssassin is an excellent choice.

Chapter 4, "Native MTA Anti-Spam Features," covers the native anti-spam capabilities included with the covered open source MTAs. Topics covered here include whitelisting/blacklisting, blackhole listing services, tweaking the MTA to help block spam, and other functions native to the modern MTA. If you wonder what the access database is, or how to tweak Postfix's configuration to block the PIPELINE command, then this is a good chapter for you.

Chapter 5, "SMTP AUTH and STARTTLS," shows how to secure the covered MTA's from sending unwanted outbound spam. Cyrus SASL is used as the basis of SMTP AUTH and STARTTLS functionality for the Sendmail and Postfix MTAs. Installation and configuration of Cyrus SASL for Sendmail and Postfix is covered, as well as the netqmail-1.05 distribution of qmail, which includes patches providing SMTP AUTH and STARTTLS functionality.

Chapter 6, "Distributed Checksum Filtering," covers the Distributed Checksum Clearinghouse (DCC) and Vipul's Razor protocols for exchanging email checksums to identify bulk emailings. Distributed Collaborative (or Checksum) Filtering is an excellent way to help determine whether a message is spam by querying other servers and seeing the number of times a particular message has been processed by other servers.

Chapter 7, "Introduction to Bayesian Filtering," gives the reader a working knowledge behind the most efficient spam-fighting technology to date, Bayesian analysis. Written by Rob Kolstad, it gives an accessible treatment of how the Bayesian analysis algorithms are implemented in the covered applications as well.

Chapter 8, "Bayesian Filtering," covers installation and configuration of a number of the more popular Bayesian filters available, including bogofilter, ASSP, and CRM114.

Chapter 9, "Email Client Filtering," walks the reader through the built-in anti-spam capabilities in Microsoft Outlook, Microsoft Outlook Express, and Mozilla Messenger. It also covers POPFile, one of the Bayesian filters available for any POP3-compliant email client platform.

Chapter 10, "Microsoft Exchange," covers the basic anti-spam capabilities in this popular email server, including the Intelligent Message Filter, Microsoft's anti-spam solution based upon its Smartscreen technology. Chapter 10 also covers McAfee SpamKiller for Exchange 2.1.1, which is an implementation of SpamAssassin tightly integrated into Exchange.

Chapter11, " Lotus Domino and Lotus Notes," walks the reader through the built-in anti-spam capabilities in this popular enterprise email server, Domino, and associated email client, Notes. McAfee SpamKiller for Domino 2.1, a SpamAssassin-based implementation tightly integrated into Domino, is also covered. In addition, how to set up Lotus Domino for use with SMTP AUTH/STARTTLS is detailed.

Chapter 12, "Sender Verification," covers some of the lesser known open source products available in the areas of challenge response and one-time use email accounts (Active Spam Killer and Tagged Message Delivery Agent). Also covered is a sender compute implementation with very nice CRM114 integration known as Camram.

Appendix A covers Sender Policy Framework, a relatively new method for determining the validity of sending email messages by domains publishing "reverse mail exchanger" (MX) records, and recipient email servers enforcing those SPF records published by domain owners.

Appendix B shows the reader how to read email headers, and covers tools associated with spam fighting including SpamCop. It uses an example spam message to show how spammers try to obfuscate their intentions.

Appendix C explains the SpamAssassin default ruleset as it is shown on the SpamAssassin web site.

Appendix D covers SpamAssassin utilities command line interface options.

Appendix E shows SpamAssassin configuration file keywords.

Appendix F covers DSPAM, a Bayesian classifier designed for speed and accuracy, aimed squarely at the organization with thousands of email boxes.

Appendix G contains a list of resources the spam fighting reader should find useful.


No project like this occurs without the assistance of numerous people, some of whom are listed here.

First of all, we would like to thank Rob Kolstad for contributing Chapter 7, "Introduction to Bayesian Analysis". This is an accessible and thorough treatment of the theory behind what we consider the most important spam-fighting technique available today.

We owe a great debt of gratitude to all the people from Pearson: Mary Franz, Noreen Regina, Jim Markham, and Lori Lyons.

The following people reviewed the entire manuscript, for which we are greatly indebted: Fredrick M. Avolio, Eric S. Johannson, and Sarah Ratta. The following individuals reviewed pieces of the manuscript under very short notice, for which we are very grateful: Tim Speed, Henrik Walther, Lars Powers, and Pete Moulton.

We would like to thank all the authors of open source packages used in this book, along with the many people who have devised (and shared) their anti-spam solutions through web sites, email lists, and other avenues. Without people like you, our inboxes would be even more flooded with spam! We truly stand on the shoulders of giants.

The Resources appendix lists many of the URLs we used in building the software components listed in this book. In particular we would like to thank the following people for allowing us to use portions of their web sites in parts our coverage.Mastaler.

From Microsoft's public-relations firm of Waggener Edstrom, we would like to thank Tina Austinson and Amy Petty. From IBM/Lotus, we thank Erica Topolski and Edmund "Ted" Stanton. From McAfee Inc., we thank Tracy Ross, Zoe Lowther, Tim Smithson, and Brian Barnes. From Microsoft support, we thank Fred Wander.

Robert Haskins thanks: Jim Markham of Pearson for his very able assistance in manuscript preparation; my employer, Renesys Corporation (especially Todd Underwood, Andy Ogielski, Jim Cowie, BJ Premore, Rob Bushell, Eric Smith, and Joe Edelman) for their ideas, feedback, and support; David Webster of Computer Net Works for his support and the use of CNW facilities; and most importantly, to my spouse Mary and children Claire and Peter for their encouragement, patience, and understanding during this project.

Dale Nielsen thanks: My partners at Avacoda, LLC, Daniel Dee and Scott Reed, for the use of the Avacoda computing lab facilities as test beds for the software described herein; and especially my wife Janice and my daughter Crystal, for their willingness to have their email put through experimental anti-spam configurations, but most of all for their patience and support over the months that were spent on this project.

© Copyright Pearson Education. All rights reserved.

From the Back Cover

Real Anti-Spam Help for System Administrators

In Slamming Spam, two spam fighters show you how to fight back—and win. Unlike most spam books, this one is written specifically for in-the-trenches system administrators: professionals who need hands-on solutions for detecting, managing, and deterring spam in Unix/Linux and/or Microsoft Windows environments.

The authors offer deep, administrator-focused coverage of the most valuable open-source tools for reducing spam's impact in the enterprise—especially SpamAssassin. Drawing on their extensive experience in developing and implementing anti-spam tools, the authors present expert insights into every leading approach to fighting spam, including Bayesian filtering, distributed checksum filtering, and email client filtering.

Coverage includes

  • Step-by-step junk mail filtering with Procmail

  • Protecting Sendmail, Postfix, qmail, Microsoft Exchange, and Lotus Domino servers from spam

  • Making the most of native MTA anti-spam features, including whitelists/blacklists, DNS black hole services, and header checking

  • Distributed checksum filtering solutions, including Vipul's Razor and Distributed Checksum Clearinghouse

  • McAfee SpamKiller for Lotus Domino

  • McAfee SpamKiller for Microsoft Exchange

  • Implementing and managing SpamAssassin

  • Implementing SMTP AUTH, providing effective outbound SMTP authentication and relaying with any mail client; and STARTTLS, encrypting outbound mail content, user names, and passwords

  • Sender verification techniques, including challenge/response, special use addresses, and sender compute

  • Anti-spam solutions for Outlook, Outlook Express, Mozilla Messenger, and Unix mail clients

Whatever your IT environment and mail platform, Slamming Spam's defense in-depth strategies can help you dramatically reduce spam and all its attendant costs—IT staff time, network/computing resources, and user productivity.

© Copyright Pearson Education. All rights reserved.

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4 of 5 people found the following review helpful
Nice Read May 2 2005
By Niloufer Tamboly - Published on
Format: Paperback
I was naive to believe that stricter laws would decrease spam. Now I think that while stricter laws may not decrease the amount of spam that spammers send, they can certainly help filters to decrease the amount of spam that recipients actually see.

The Bayes theorem used to fight spam by most of the spam filters of the day finds its roots in 1763 when a year after his death the work of Thomas Bayes was published. The development of probability theory in the early 18th century arose to answer questions in gambling, and to underpin the new and related ideas of insurance. A problem arose, known as the question of inverse probability: the mathematicians of the time knew how to find the probability that, say, 4 people aged 50 die in a given year out of a sample of 60 if the probability of any one of them dying was known. But they did not know how to find the probability of one 50-year old dying based on the observation that 4 had died out of 60.

Like many educated men of his time, Bayes was both a clergyman and an amateur scientist/mathematician. His solution, known as Bayes' theorem, underlies, and gave its name to, the modern Bayesian approach to the analysis of all kinds of data.

A nice read to understand the ongoing battle against spam.

Niloufer Tamboly, CISSP
lacks perceptive analysis Jan. 15 2005
By W Boudville - Published on
Format: Paperback
The book gives a description of the main types of antispam methods available to system administrators, at the end of 2004. As such, it is a good summary of the state of the art at that time.

However, the book does not help sysadmins by providing an understanding of the limitations of the methods mentioned. In this sense, the book is more of a simple description of how to use those methods, rather than an independent analysis of their efficacies.

Consider the methods for finding and comparing checksums or hashes of messages. The basic idea is valid. But more detail about how the methods act against spammers who introduce random variations into their messages might have been useful. The book only says that such steps are taken in the methods. Examples please? Also, the book says that the methods generate one checksum or hash per message. Limited. Far better is to make several. And I'm not referring here to when a method might make two checksums per message, where each sum is taken over the entire message and the difference is that the methods to find each sum are different. Regardless of the specific checksum or hashing method, one should make several per message, for more robustness.

Plus, the methods use what they call greylisting. Done at the system level. No suggestion that it might be better to also let each user make her own greylist.

SpamAssassin gets the most coverage in the book. But not mentioned is that it can use a blacklist against domains in body links. A vital improvement against merely using it against the purported sender domain or against possibly fake relays in the header. Much time is spent in the book explaining Bayesians. But little about how they are very computationally intensive, compared to applying a blacklist against body links. And that Bayesians are inherently probabilistic. So one technique by spammers is simply to send more, so that enough of an absolute number of spam gets through a Bayesian. And, it is manually intensive on the part of a sysadmin and users to have to continually retrain a Bayesian, to ward off deliberate poisoning by spammers.

This is compounded by the descriptions of how qmail and sendmail can use blacklists against where the message purportedly comes from. This is of limited use. For some reason, there is a persistent mindset, as evidenced by what you can read in the book, about this usage. Yes, it works, sometimes. But spammers often forge header information.

In any event, the book's authors do not point out - why do you [the sysadmin] care where a spam comes from? Far better to ask is where it goes. That is, where its links go to. I have criticised other antispam books for not doing this. I was hoping when I read this book that it would be more perceptive. Unfortunately not.
Good reference for any messaging system administrator Nov. 1 2005
By Ben Rothke - Published on
Format: Paperback
Be it inane e-mails with topics such as "retention bobble cicada emanuel," attempts to pitch 21st century snake oil, or incessant pleas to refinance your mortgage or find a date online, we've all received our share of spam. And as antispam software develops, mass marketers get ever more crafty in defeating these programs. Spam is truly overwhelming today's workplaces, and systems administrators are in dire need of effective solutions.

One place to turn is Slamming Spam, a systems administrator's and messaging administrator's guide to reducing spam. With its hands-on, high-level approach for detecting, managing, and eliminating spam, the book is not for beginners. Readers are expected to be comfortable with UNIX and Windows system administration and be familiar with core concepts of messaging and messaging protocols.

Thankfully, the authors don't delay in providing helpful information. By chapter two, the book is already in the solutions phase of how to harden a system against spam. Besides covering SpamAssassin, a popular open-source antispam tool, the book shows how to protect messaging systems, such as Microsoft Exchange and Lotus Domino, and messaging clients including Outlook Express and Mozilla Messenger.

Alternative solutions to junk e-mail are provided as well, including Sender Policy Framework (which identifies spoofed mail) and DSPAM (an open-source statistics-based spam filter), as well as commercial solutions. Whitelists and blacklists, DNS black-hole services, header checking, and other antispam niceties are explained as well. The result is a book that will help any organization substantially reduce its spam intake.
4 of 7 people found the following review helpful
Good book for admins Feb. 9 2005
By Dr Anton Chuvakin - Published on
Format: Paperback
When opening the book, I was convinced that spam doesn't really deserve a book. However, I enjoyed scanning through this "Slamming Spam" and picked up an idea or two from it.

I liked the chapters on Bayesian methods, and I think that this book contains one of the clearest explanations on how they work and how to make them work for you.

Overall, the book is very practical and will be great for people configuring mails servers for spam-fighting on a daily basis. However, this is not an in-depth review, since I am not tasked with fighting spam (and SpamAssassin does a fine job on my mail account).

Anton Chuvakin, Ph.D., GCIA, GCIH, GCFA is a Security Strategist with a major security company. He is an author of the book "Security Warrior" and a contributor to "Know Your Enemy II". In his spare time, he maintains his security portal
1 of 3 people found the following review helpful
More practical than theoretical... Feb. 23 2005
By Thomas Duff - Published on
Format: Paperback
Another book to add to your spam prevention arsenal... Slamming Spam - A Guide For System Administrators by Robert Haskins and Dale Nielsen (Addison-Wesley).

Chapter List: Introduction; Procmail; SpamAssassin; Native MTA Anti-Spam Features; SMTP AUTH and STARTTLS; Distributed Checksum Filtering; Introduction to Bayesian Filtering; Bayesian Filtering; Email Client Filtering; Microsoft Exchange; Lotus Domino and Lotus Notes; Sender Verification; Sender Policy Framework; Reporting Spam; Default SpamAssassin Ruleset; SpamAssassin Command Line Interface Reference; SpamAssassin Configuration File; DSPAM; References; Index

I'll say right up front that this book gets bonus points for covering Notes/Domino, as most books ignore the fact that it is the leading corporate messaging system. :-) The book doesn't focus much on theoretical discussions of spam, what it is, and why it's bad. It just digs into hands-on scenarios using various spam-prevention options on different system platforms. They cover platforms such as Sendmail, Postfix, qmail, Microsoft Exchange, and Notes/Domino, so somewhere in that list you should find your mail system. Being the book is more practical in nature, it should probably be coupled with another title that's more general in nature so that you gain a complete understanding of the subject coupled with how spammers work. But for someone who's already covered those basics and is now ready for implementation, this is a good addition to the bookshelf.