The Architecture of Open Source Applications: Sendmail (2011)
aosabook.org
aosabook.org
Full marks to anyone who can look back and honestly say as much. I went in skimming to see if there would be discussion of the security and correctness issues that sendmail became unfortunately infamous for, and I really appreciate them being discussed at reasonable length. (And I say that without judgment; I've certainly shipped enough things that lasted long enough for me to realize the errors that I had made in their design and/or implementation.)
"The case of the 500-mile email"
But I’d rather swallow my own tongue than use it to configure Sendmail again. Postfix had many compelling features that made me want to switch to it. None were as insta-buy as comparing its configuration language to Sendmail’s.