Looks like the issue occurs when using TextScaled. (It’s just assuming that the actual size of your font is Size96, and it doesn’t account for the size scaling)
Yeah, TextScaled unfortunately messes things up. You need to either manually edit the text size using textbounds or use a consistent size. This same problem occurred in Heist for me.
I was able to fix this problem by making the GUI huge momentarily and then checking the TextBounds value. It appears that the value doesn’t work if the text doesn’t fit.