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In Illustrator, on a curve anchor point, sometimes rotating 1 handle also rotates the other, keeping them in a straight line. But sometimes 1 handle moves but not the other. Why? Can I can a setting to also rotate both when rotating just 1?

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If one handle doesn't move, then it's a corner anchor point.

You can convert a corner anchor point to a smooth anchor point by clicking on the "Convert selected anchors to smooth" icon in the tool options.

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