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The sendmail book from O’Reily is considered by most to be the definitive book on sendmail. It is often called the "bat book" because of the flying fox (a species of fruit bat) depicted on the cover. The fourth edition, released in October 2007, was written by Bryan Costales, George Jansen & Claus Assman with Gregory Neil Shapiro and covers through version 8.14.
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Sendmail Theory and Practice from Digital Press, Authored by Frederick M. Avolio and Paul A. Vixie, emphasizes how sendmail fits into the mail system in general without going into the deep technical details.
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sendmail Performance Tuning, by Nick Christenson, is a practical guide to building, tuning, and testing email servers based on sendmail. Featuring sendmail 8.12 (and earlier versions), the book begins with an introduction to sendmail and performance tuning. Author Nick Christenson then describes best practices for building, installing, and maintaining a system and details proven techniques for tuning email relaying, reception, and sending.
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sendmail Milters: A Guide for Fighting Spam, by Bryan Costales and Marcia Flynt, is the first in-depth guide to writing powerful Milters to block even the cleverest spammers.
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A completely updated twentieth anniversary edition (July 2010) of the UNIX and Linux System Administration Handbook, by Evi Nemeth, Garth Snyder, Trent R. Hein, Ben Whaley. The book includes a few chapters on open source MTAs, including sendmail.
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Linux Sendmail Administration, authored by Craig Hunt, describes sendmail configuration under Linux but most of the material applies to non-Linux systems. A user friendly comprehensive book about sendmail for people who find the sendmail book (bat book) to daunting. Covers sendmail 8.11 including SMTP authentication and STARTTLS.
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