How would I make the player take damage as he goes up?

Nope, here is the error:
https://gyazo.com/0635f264b0f61a61ada8dd6c615000e7

Ah, silly mistake on my part! The local keyword should not be in that line, Iā€™ve removed it in the original reply

Changed it, and thereā€™s a new mistake -_-

For some reason, the

  head:GetPropertyChangedSignal("Position"):Connect(function()

function workā€™s only twice, Iā€™ve checked it with a print.
It only prints twiceā€¦

Changed some typos, try it again

Still doesnā€™t workā€¦ (30 charsssssssss)

Iā€™ll see if I can give it a look soon, but I canā€™t properly test it atm Iā€™m afraid. The logic should still be there though