In Illustrator 10 on Mac OSX, my option and shift key constraints are not longer working, as if this option was turned off, and I cannot figure out how to turn it back on.
Somebody else has had this problem recently. Try scrolling down the Illustrator forum for "Shift Key doesn't work".
Try to remember if you made any changes to your system lately - like OS update, etc. that can always cause some problems. If you reinstall AI, make sure that you trash your AI prefs before reinstalling, as corrupted prefs are a major problem with all apps on all OS's.
Are the handles available for you to resize the objects? If not, you need to turn the bounding box back on, either by hitting apple+shift+B or going to View>Show Bounding Box.
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