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#architecture #dotnet #continuousdelivery #genai #data 

Bad architecture decisions don't just slow you down - they destroy business value. Poor coupling means you can't add the features customers are asking for.

Data model mistakes mean you don't have the information to answer your questions, and a lot of your decisions can't be easily reversed. You know the problems are there. You've known for years. But there's never time to fix it properly - you're too busy keeping the lights on.

Then one day, the stars align. You finally have time to tackle it. You open the codebase, ready to make things right - and realize you have no idea where to start. Everything is wrong. Every fix breaks something else. The whole thing feels impossible.

I'm a business owner. I had full authority to prioritize this rewrite. No one to convince, no budget to fight for. I still couldn't make it happen for five years - even while watching money walk out the door.

This is the story of how we finally completed that rewrite. You'll learn:

- Why we abandoned a full rewrite and pivoted to strategic refactoring instead
- How to assess whether your legacy system is salvageable (ours barely was)
- The architectural patterns - including the actor model - that would have prevented this mess
- How we used AI to accelerate the work (spoiler: it wasn't vibe coding)
- The management failures that let this happen, and how to avoid them

This isn't a talk about how smart we are. It's about how we recovered from one of my biggest failures as an engineering leader - and what you can learn from our five-year journey through hell.

NDC Conferences

A CEO and software developer shares a candid postmortem of a five-year technical disaster building SDK Cabin, a NuGet package fulfillment platform. The story covers a series of catastrophic architectural decisions made by an unsupervised developer: a generic repository pattern causing N+1 queries and Cartesian explosions, seven microservices for a two-person startup, untestable Razor Pages, billing bugs that gave away free product, and a test suite covering dead code paths. The talk walks through the gradual recovery using a strangler fig refactoring pattern, CQRS, architecture decision records, actor-model-based billing with Akka.NET, and AI-assisted code migration — while sharing hard lessons about management, architecture reviews, and the cost of not looking early.

Completing the Rewrite from Hell: Five Years of Technical Debt and How We Escaped - Aaron Stannard