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I generally just wrap a piece of copy paper around the thing and then draw a line where I want it to be straight. Unwrap and voila you have something you can scan in and use to warp/bend your text or graphic to meet the curve. sometimes takes some tweaking if there are compound curves. Every cup is different it seems.

After a bit more thinking I don't think this is as complicated as I thought it might be. Dusting off my high school geometry I think the following will give the width you'd need to stretch an image to get it to appear at the correct aspect ratio. Stretch Width = arcsin(image width/Diameter of cylinder) Need to experiment, but I believe if I stretch the image as specified by the equation and then run it through the cone correction tool when applied to a glass it should be straight and have the desired appearance.

Not doable in CUT (basic) version. (it's part of Artistic Text, but that feature is available only in LTR and PRO versions) Here is a little trick I learned years ago --- install and run SignBlazer Elements, just create your arc text (or Arched text, or anything else in SBE) and then simply Export as .eps and bring that into VinylMaster.

is this what you're looking for 65bt_zps4f0b4d99.eps dwz4_zpsbeaa0b86.eps