Headless Chromium usually runs WebGL on SwiftShader, a CPU renderer. It never runs out of video memory and never times out a draw call, so context loss simply does not happen there.
For performance and stability, run headed with the real driver:
--use-angle=d3d11 --ignore-gpu-blocklistKeep SwiftShader for visual regression; use the real GPU for "does it survive on an office PC".