@Riot Concerning Diana Jungle (Currently) with Hunter's Talisman.
So, just to throw it out there. Hunter's Talisman's Unique does not proc on Diana's on-hit effect from her passive, but proc's on someone like Kayle E 100% of the time. (E.G to reproduce, go into custom, and fight any camp that has 2 or more creeps, and see that when Diana's 3rd hit proc's, it does not proc at all on the side creeps.)
I dont know if this is a bug, but, considering I noticed this whilst checking things, it needs to be fixed as it states "Damage against a monster" not specifically "Spell Damage" against a monster.
Unless it's been clarified to not work with, its a bug.