Surprises, Bugs, and Deep Dives: Lessons from a Python Upgrade

Yonatan Bitton Yonatan Bitton
Language: Hebrew
The presentation was given on 2025.07.27 at PyWeb in July 2025 at NymHealth in Tel Aviv.

Upgrading a large production system to a new Python version always sounds simple—until it's not. In this talk, I’ll share a series of real and surprising bugs we encountered right after upgrading to Python 3.12.

These weren’t obvious issues. They involved silent crashes, confusing errors, and subtle behavior changes in libraries we didn’t even touch. Instead of focusing on one root cause, the talk highlights the debugging mindset, the investigation process, and how we handled uncertainty in complex systems.

You’ll leave with practical insights on preparing for upgrades, debugging across layers (from Python to native code), and how to stay sane when the unexpected happens.