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For the past 6 months or so, the snapping funcition while holding SHIFT doesn't work properly. In the video I took I am trying to rotate the rectangle for 90 degrees but I cannot do that - it always gets stuck at 45 degrees. The work-around is to not use SHIFT, and just rotate it until the smart guides appear, but this is both slower method and more prone to mistakes.
Does anyone know how to fix this?
Try Preferences > Smart Guides > Uncheck "Transform Tools" when you want to rotate with the Rotate Tool.
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I'm not experiencing this problem. You could try using the black Selection tool to rotate instead of the Rotate tool.
You might need to reset preferences, How to set preferences in Illustrator
If that doesn't fix it you may need to use the CC Cleaner Tool, Use the Creative Cloud Cleaner Tool to solve installation problems
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Thank you Barbara. Yes, with the standard Selection Tool the rotation works as it should. I was using the Rotate tool because I don't have to put the mouse close to the edge to rotate so it's a bit quicker (and an old habit). I even reinstalled Illustrator but it still had the same issue. Ton's tip solved the problem by unchecking the "Transform Tools" at the Smart Guides preferences.
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I'm glad the problem is solved. I've tried rotation with the Shift key and the Rotation tool with Transform Tools checked and with it unchecked. The Shift and rotate work for me in both cases. The rotation is easier with Transform Tools unchecked, but the only difference is that if Transform Tools is checked the position of the cursor becomes more critical and seems that the cursor needs to be inside the shape in order to work.
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Barbara, I see, it works only inside the objects.
I wonder why.
Not very intuitive.
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Try Preferences > Smart Guides > Uncheck "Transform Tools" when you want to rotate with the Rotate Tool.