Recent Files Not Updating when Using Insert Hyperlink in Outlook 2013

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Outlook version
Outlook 2013 64 bit
Email Account
I am using Outlook 2013 in a Windows 8.2 environment and the Recent Files list when using the Insert Hyperlink function is no longer working. It's worked for and think it still works sporatically but the list is not up to date. In the past it would update if I downloaded a file to my hard drive and saved it say in MS Word or Adobe Acrobat. Now the list is still there but it's all old stuff.

Is there something I need to do to get it to start work again? Ideas?
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