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Everytime I try to start drawing a line/any shape with the paintbrush tool, it brings up the option bar with the "undo calligraphy?" and "show guide" and etc., or at the very least starts to. This only happens when I use my stylus and tablet, and not my mouse. Is it the tablet's problem? Is there someway I can make that menu not show up? Or is there a way to stop Illustrator's hold and bring up menu thing?
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Can you screenshot the menu? I'm not sure what you mean.
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I think it tablet problem. Try to reinstall tablet driver. What is your tablet? Wacom?