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Hello Vanguard,

I will just drop them into the new email to attach them via the
embedded Outlook interface.

What happens when you use the Insert menu to attach the .pdf file(s)?

I have business contact manager installed (this is the office addon
product)

I attempted to update office via the microsoft website and it failed so
I'm at a loss if its a patch fix.

Have you scanned for malware (which often blocks Windows Update)?

For add-ins:
Chapura (for my TREO 600)
Windows CE Support
Exchange extendsion property pages

What happens when you start Outlook in its safe mode ("outlook.exe /safe")?
The add-ons do not get loaded in safe mode.

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