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This is probably the most painful bug report I've ever read, describing in glorious technicolor the steps leading to Knight Capital's $465m trading loss due to a software bug that struck late last year, effectively bankrupting the company.
The tale has all the hallmarks of technical debt in a huge, unmaintained, bitrotten codebase (the bug itself due to code that hadn't been used for 8 years), and a really poor, undisciplined devops story.
Read more here.