Hammer Editor trigger_remove not outputting

[Frank The Duck]

To put it simply in hammer I have a section of a map where a trigger_remove is meant to destroy physics props and spawn a can from an env_entity_maker elsewhere. After some fiddling around I've found a couple things:
1) The trigger remove is enabled
2) The entity maker does work when given input from a button
3) A test light didn't turn on from any outputs of the trigger remove

So I'm asking if anyone knows why the trigger remove won't output or if there's another way to trigger an output when a physics prop gets passes through an area before it reaches the trigger remove.