thanks for reporting this - we will look into it and provide feedback here as soon as possible.
Cheers
Tim
Update: We indeed identified an issue with the checklist “Any is before” match type. A fix is already in the pipeline and will be live soon. I will notify you here when the fix is live.
Update #2: The fix was just deployed and should resolve the inconsistent behaviour you reported. Kindly check and confirm that this is fixed now, and do reach out to me directly if you have any further questions here regarding this issue.