Death to Failing Tests: A Hands-On Debugging Bootcamp

David Ingraham

13:30 - 17:00 CEST, Monday 15th June

There are few things that slow teams down more than failing tests. Sometimes it’s a true defect in the application. Sometimes it’s a misconfigured environment. Sometimes it’s your own brittle test code. And sometimes…it’s the dreaded flake. Regardless of the cause, failing tests erode confidence, block pipelines, and burn engineering hours.

This hands-on bootcamp is designed to change how you approach them. Over three hours, we’ll roll up our sleeves and work through the full lifecycle of debugging — building the right mindset, applying best practices, and then diving into real-world failures until you can tackle them with confidence.

We’ll begin with the troubleshooting mindset — what to think about before touching a line of code.

You’ll learn how to slow down, gather evidence, and avoid jumping to conclusions that waste time. Next, we’ll cover debugging best practices, including how to use artifacts and result visibility effectively, how the “where and when” of your tests influences outcomes, and what high-level setup decisions can make or break stability. We’ll also touch on where AI can assist as a debugging companion.

From there, we’ll dig into the four core categories of test failures — Test Code, Application, Environment, and Flake. For each, we’ll break down how failures manifest, why they happen, and the strategies that actually work to resolve them.

Flakiness will get special focus, since few things frustrate engineers more than a test that passes one moment and fails the next.

Finally, you’ll put your skills to the test in a debugging challenge using Playwright. Using a deliberately failing repo, you’ll investigate and repair a mix of application bugs, environment misconfigurations, brittle tests, and flaky runs. The goal isn’t just to fix them, but to practice thinking like a debugger — gathering clues, forming hypotheses, and narrowing down root causes.

By the end of the workshop, you’ll leave with more than just fixes: you’ll have a debugging framework and a reusable checklist to take back to your team, helping you transform failing tests from blockers into opportunities for stronger, more reliable automation.

What you will learn

A structured debugging mindset – know what to check first, how to gather evidence, and how to avoid wasting time chasing the wrong problem
Proven strategies for stabilizing failing tests – practical techniques to fix issues across application code, environments, test code, and flakes
A reusable debugging checklist and framework – a playbook you can take back to your team to quickly diagnose and resolve future failures with confidence

Session Details

Introductory
3hrs
Interactive Tutorial
Testing methods for continuous improvement

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Session Speakers

David Ingraham

Matium, USA

I’m a Senior SDET and QA leader who has built and scaled automation frameworks for organizations ranging from 15-person startups to Fortune 100 enterprises.

I’ve specialized in turning fragile test suites into reliable sources of truth, leading teams through the challenges of automation maturity, and championing “Shift Left” practices that make quality everyone’s responsibility.

As a Cypress Ambassador and active contributor to the testing community, I’m passionate about making testing approachable, innovative, and fun. I love sharing not only frameworks and strategies, but also the stories, struggles, and lessons learned that resonate with testers at every stage of their careers.

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