X World 2025

Legacy.exe - The Story of an App that Refused to Die

What do you do when your organisation has a mission-critical Windows app from 2009, no source code, and zero chance of migrating away? You run it natively on macOS — obviously. This session explores how Apple’s Game Porting Toolkit (GPTK), originally intended for gaming, can be repurposed to run legacy Windows applications directly on macOS. We’ll walk through real-world examples where GPTK was used to resurrect EXEs from the grave, sidestep infrastructure constraints, and delay costly Windows upgrades. You’ll learn how to configure GPTK, manage application quirks, and decide when this approach is viable — and when it’s a terrible idea. Whether you’re supporting a university with ancient lab software or an enterprise that refuses to let go of Access 2007, this talk will give you practical tools and unhinged inspiration. Expect chaos. Expect hacks. Expect results.

About the presenter

An Apple Systems Architect with a background in automation, governance, and large-scale deployment, this speaker has delivered outcomes for organisations like NSW Government, Vodafone, Macquarie University, and Allianz. With a passion for solving legacy tech challenges in unconventional ways, they specialise in high-impact initiatives that reduce technical debt and modernise IT environments. Known for platform optimisation, workflow automation, and strategic leadership, they bring a blend of enterprise experience and creative problem-solving — occasionally powered by GPTK, Python, or pop punk.