Lessons from 30 years of Sendmail
lwn.net
lwn.net
I'd love to see retrospectives and lessons-learned on BIND, awk, perl, ssh, the Linux kernel, PostgreSQL etc.
One of the noteworthy points is that Eric Allman really does skim over the unbelievably crappy model for managing security problems in the code and in configurations (understandable of course, for the time, but a retrospective on how that can be/is better now would be fascinating), the guru-level fragility and bizarreness of configuration (the implementor and administrator use-cases).
And also, more than a line in passing about sendmail.com, one of the first semi-open source startups.