OK, unpacking the macro, there are some issues or misconceptions. Neither &{BOB|tracker} nor &{tracker|BOB} is a valid construction. There is the construction: @{tracker|Bob} This is a lookup, which returns the initiative value for "BOB" if it is a turn in the turn order., ex: "15" &{tracker} is just a command to "put this roll value on the turn tracker, using the selected token". It can receive a :+ or a :- to increment or decrement a value on the tracker for that token. example: [[1d0 + 5 &{tracker:+}]] will add 5 to the initiative value for a selected token that has a tracker entry. [[1d20 + @{selected|initiative_bonus} &{tracker}]] will roll a simple initiative for the selected character token. @{selected|wtype}&{template:simple} {{rname=^{init-u}}} {{mod=@{selected |initiative_bonus}}} {{r1=[[@{selected |initiative_style}+@{Kurtak|initiative_bonus}@{selected |pbd_safe}[INIT] &{tracker}]]}} {{normal=1}} @{selected |charname_output} Will roll a more robust initiative, taking into account more options. The character sheet has special built in code that looks for an associated token on the board and rolls initiative for that token. The base VTT has no such mechanism. There are reasons for this. Ex. If there are two goblin tokens on the board, but they both refer to the same character sheet, the tracker needs to have an entry for each token (assuming the GM isn't doing one initiative for all goblins). The turn tracker doesn't know anything about character sheets. It only knows tokens. TL;DR: Without a Mod script, and without rolling from the character sheet button, you need to physically select the token you want to send to the tracker.