Hi,
Ok, you should never work with the 2d option checked in... your trigger is in -10 in z so looking front it seems to pass trhough it but if you look from above...
once you have them truly aligned it will be better but still not enough
collisions and trigger MUST have rigidbodies, else it doesn't work. so add rb2d to your player and trigger, set the constraints etc so that they behave how you want it and triggers will be performed properly
also, please do not share PlayMaker dlls when you zip your project, prefer creating a package of your scene, and make sure you uncheck anything inside the PlayMaker folder and it will be safer.
Bye,
Jean