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Software Entropy and the Strangler Fig: Surviving a 20-Year-Old Codebase

Right now, I find myself fighting a three-front war. Front one is keeping a 20-year-old behemoth of a B2B application alive. We are talking about decades of legacy ASP.NET and VB.NET where two decades of tweaks, patches, and "temporary fixes" have become permanent, load-bearing pillars of the architecture. Every time I touch it, it feels like playing Operation with oven mitts on—spending 90% of my week untangling logic just so a simple bug fix doesn’t cause a ripple effect that crashes a critical service. Front two is modernizing the architecture. I am actively trying to implement a rudimentary Strangler Fig pattern—slowly carving out legacy functionality and pushing it into a clean, testable shared library project so we can actually run proper unit tests and stop the bleeding. Front three is modernizing the team. While keeping the lights on and quietly rebuilding the engine, I am also pushing a retraining effort to get my peers up to current framework versions and embracing ...
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