As far as I see this is intended behavior. You are telling it trigger once while the condition is true. You do the test 1 time, it is true. So the second time (for the second object) it doesn’t do it again.
Though I agree there should be a better way to do such a rudimentary task, but I can’t find a good solution on the top of my mind.
The only one I currently can think of is making the trigger once use a different uid on each iteration of the events, but it is problematic for many reasons (breaking change, breaks hot reload, potentially reusage of same UIDs causing very weird bugs, big occupation of memory for all UIDs to generate at runtime…)