To solve a Problem like your shift key is not working in Illustrator, you need to trash your illustrator preferences on your computer.
To do this you need to Quit Illustrator, this will help you make sure you have the right file because when you quit Illustrator the preferences will update.
To Locate the Illustrator preferences go to /Users/<username>/Library/Preferences/Adobe Illustrator CS4 Settings/en_US*/ This is for Mac OS, Illustrator CS4. Adobe Illustrator stores its preferences file in the following locations:
Once you have located your Illustrator preferences on your computer, trash it and hopefully this will solve the shift key not working.
You may want to restart your computer. Then re open Illustrator.
I hope this helps.
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