Is it possible to add a token more than once to the Turn Tracker

I want to be able to add the same token twice on the turn tracker due to a specific homebrew game mechanic.  Is that even possible?

I don't believe so. But an easyish workaround would be to make a copy of the token you want to have twice on the turn tracker and simply move it off to the side of the map and add the duplicate to the turn tracker.  With the API (Pro subscription) that could be automated. I swear I tried adding additional entries for a single token before and it didn't work... but trying it out right now and it does.  I must have had a script or something that was preventing multiple entries. Thanks, Kraynik!

Right click on the token and select "Add Turn".  You can add as many entries for that token as you want.  You can only have one rolled initiative entry (as far as I know) without the api, because each additional roll entry will replace the previous.  I don't think there is a limit to manually added entries though.

Hmm, well that sort-a works, but I really want two different rolled values per token.  I like to use an idea called Combat Awareness where each player declares action from the least combat aware to the most BEFORE the actual action is performed.  I wonder if there is an API that would help me with that.... hmmmm