To change Outlook to be able to handle multiple signatures, you need to do the following.
Go to Tools-->Options and go to the Mail Format tab and UNCHECK the "Use Microsoft Office Word 2003 to edit e-mail messages"
To have the option to switch between email formats in Outlook, you will NOT be able to use MS Word as the email editor anymore.
After you change the default email editor, your email messages will have the option to select signatures within the message by going to Insert-->Signature-->Your desired Signature. From here you can select the signatures you've already setup.
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