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I am using Photoshop CS4, and the file windows do not resize to fit when I zoom in or out, even though that option is checked. I am not using tabbed windows (each document window is floated). Similarly, when I double click on the Hand Tool, the image resizes to fit but the window does not.

How do I fix this?

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Holding Shift causes the window not to resize. In my experience modifier keys sometimes become "stuck" so I would try pressing and releasing each Shift key several times to see if that fixes it. If not, it might be a corrupted preferences file. –  Mr.Wizard Jul 29 '12 at 10:44
@Mr.Wizard- I tried your suggestion and it didn't help. I also deleted the preferences file and that didn't help either. –  dmr Jul 30 '12 at 17:00
Sorry, I'm out of ideas. :-/ –  Mr.Wizard Jul 30 '12 at 17:19

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