SharePoint 2010 Unable to Upload Multiple Documents (End User Device Issue)

Environment

SharePoint 2010 Enterprise running on SSL

Windows 7 64BIT/Office 2010

This is a weird one, so hoping maybe someone can point me in the right direction.

End User called stating they cant upload multiple items(doesnt matter the file type) to their library, Only single items. So I created a new library ensuring they had full control (to see if it was a permission issue), they still got the same error "Failed".  So I tried to upload multiple documents to the same libraries and that worked.  Had the user come down to my office and logged him into a newly imaged computer and he could upload multiple documents with success. So theres a disconnect between his computer and the SharePoint portal.

I am also having the same problem with a computer in my office.  So Created a new web app that runs on port 8089 and I can upload multiple documents successfully to the SharePoint site on port 8089, but once I go to the SharePoint site that is on 443, I get the failed message.  Its sporadic, some computers work great, some just get failed when they try to upload multiple documents.

Fiddler is stating 403 forbidden error

I tried to use Explorer view to copy multiple documents over and I get this error, "there is already a folder with the same name as the file name you specified.  Now I know there isnt a folder or anything else with the same name as I named these test documents 90099988.docx

I just imaged a new machine and it has none of these issues.  So I am really not sure where the disconnect is.