A little further testing has shown something interesting. I created a duplicate of an old Player Character, to see what would happen. The duplicate did function properly. It stayed on top of unassigned/unsighted/uncontrolled tokens. So then I started messing around with that duplicate and its token. If I choose "Represents Character" on the duplicate characters token, and set it to any controlled Player Character (including the new PC 'Girtha') the token does properly always go in front! (and vice versa - selecting it to represent an NPC immediately stops it appearing in front) This makes me think that the problem cannot be in the Character settings. This made me think, perhaps I could try and sneakily alter this duplicate of the original character... Somehow refashion it into the new character. ...But the problem seems to come when removing or replacing the Default Token (which is pretty necessary, because the old character is a big spiky Tortle, and the new one is a Dwarven woman!) As soon as I remove the Default Token, no replacement token properly stays on top. I then tried messing around with the other old characters tokens. Just like the duplicate, their tokens do actually accept that representing a controlled Character is a valid reason to stay on top of unassigned tokens. ....However, I cannot recreate this willingness to stay on top in any other tokens. Only the tokens that come from the old Player controlled characters (or duplicates of them) are actually appearing in front when representing Controlled Characters! Other things I've tried: Changing old NPC tokens to have Sight & represent Controlled characters - still refuse to appear on top properly. Using the old characters original art upload in a new token - still refuse to appear on top properly. ....there is something about the tokens that belong to the old characters that is different. Something that actually makes the intended Z-Ordering of sighted controlled tokens work properly. But I'm damned if I know what. Sorry for the peculiarly formatted info dump. This is driving me a bit nuts! I swear, these tokens are Sighted. They are Controlled. I am testing them against unsighted tokens. They should appear on top!!