Thanks, the way it was worded “failed” made me think it was an error. Now I understand it simply means a condition went the false route, not a failure at all: in fact, completely as designed.
I have solved my issue, turns out I had accidentally pasted the dev URL for a webhook in Square for production.
This log happened to be showing this seeming error on the exact action that wasn’t working so the language really tripped me up. I hope they make that more clear in the future, or at least if anyone searches the forum in the future, they can see this and learn that it’s not actually an error.