Outlook will not attach using Send To Feature

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bpuddy

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Outlook 2010 64 bit
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I have a user who is trying to attach a file using the send to feature in MS Office or Adobe Reader and when pressing the button it will bring up a new outlook message but will not attach the file. It will attach files manually. I have already tried re-installing Office, repairing it and re-doing local windows profile. I am just thinking that it may be an outlook issue?
 
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