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In my CC Illustrator, the text box won't allow me to turn on its side/rotate, every time I try to turn, the text stays horizontal and moves within the box. It is acting like text in indesign. Is there a setting I can change?

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The behavior you're seeing is because you're actually rotating a text frame...much like InDesign, as you said. You can rotate the object the way you want using the Rotate Tool (R) or the Free Transform Tool (E).

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    This seems to be a new behaviour in the most recent version of CC. Apparently if you 'free rotate' by dragging the corners of a text box now, it rotates the frame but not the text, and as you've said, you have to use the Rotate tool (R) if you want to rotate the text itself. – Alex May 10 '16 at 21:43
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This use to happen to me on Photoshop. Try deleting the layer. Making a new text box and turn off caps lock if you have it on. Then click the word that you are trying to rotate while holding command. Also make sure you are using the pointer that has the black outline and not the solid pointer.

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