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My Emails sometimes stop correcting misspelled words. I can resolve the issue by going to

File | Options |  Mail (Left Tab) | Spelling and Auto Correct 

I uncheck "Check spelling as you type", click OK out of all the dialog boxes to apply the change, go through again, and readd the check-mark. This immediately resolves the issue.

This is crazy, why do I have to do this every other day, and how can I resolve it?

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Look at your Add-Ins under word options:

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Choose Disabled Items from the Manage drop down menu at the bottom. Then click the Go button. Make sure that Proofing is not disabled

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