Carving on an arched whiskey barrel stave

[WillAdams (William Adams (Carbide 3D))]

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Engraving on a curved surface - barrel stave

Hello - just wondering if any starting points for how to engrave on a curved surface - looking specifically how to say engrave circle pockets in a barrel stave - to make a beer/whiskey flight. Would I need CCPro for this? Thanks. Erik