Hi Jack,
Thanks for your feedback.
As Nancy mentioned, is there any error message in office2010 or upload center? If yes, please provide them to us for further troubleshooting. Except that, could you please describe the detailed steps that you upload the files? Here is an article about Save a document to SharePoint from Office 2010 for your reference.
In addition, please remove the failed file from the upload center queue first and “Delete cached files” under Microsoft Office Upload Center settings, and then try again.
Thanks,
Eben Liu