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Does anyone have any idea how to make a rounded dotted border like in the empty TextMate project drawer?

I really have no idea where to begin.

Review NSBezierPath for drawing any path including a rounded rectangle as well as -setLineDash:count:phase:.

Review path drawing in general at In particular, look at the section and example for “Line Dash Style”

This sample code includes a category on NSBezierPath specifically for drawing rounded rectangles:

Also see HowToCreateWalkingAnts