[Analemma_]

Seconded, Normal Accidents is one of the best books I've ever read. In addition to the maritime accidents, there are chapters on nuclear plants, chemical plants, and dams. It is a great discussion of how modern industrial accidents rarely have a single cause but instead are cascade failures of systems whose complexity has evolved beyond what we can handle, and presaged many of the messes we've got into with hyper-scale software projects before those ever existed.

Is there a "sequel" to Normal Accidents about software? Because I'd buy that in a heartbeat.

[QuarterReptile]

There's a book that seems similar to what you've described, called Atomic Accidents. It's a compelling narration of many notable mishaps in nuclear power, weapons,and research. Needless to say, it won't scratch the software itch.

[dredmorbius]

Comp.risks has a lot of raw source material, and its moderator, Peter G. Neumann, has published a few books.

Ex-Goggler Yonatan Zunger has had some really good recent essays at, variously, Medium, Twitter, the Boston Globe, and Google+ (for which he was chief architect, and despite its general lack of widespread success, I consider his contributions and lessons-learned experience quite positively).

And he's a fan of Perrow.

Bruce Schneier's work is somewhat more focussed on crypto and security, but covers much this ground, especially later works.

Shoshana Zuboff also addresses social impacts of computers and data systems in her work.

[MarkMMullin]

Check out stuff that Betrand Meyer, Eiffels dad, has written - he pretty much beat hell out of software mishaps to show how he'd tried to compensate for those issues in Eiffel. -- here's one of the best known -- https://archive.eiffel.com/doc/manuals/technology/contract/a...

[lazyant]

Somehow related, "Command and Control" is an excellent read.