I can't attach a pdf to an email but can attach a saved pdf to an email?

So, I can open a new email and click the paperclip and attach a pdf with no problem but when I open a pdf and click file/attach to an email it fails. Why? is three a setting in 9.0 that I need to change? This is using Outlook 2007.
Thanks,
Ken

Fails how?  Is Outlook running when you try the attach?

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