I have logged a support to Sitecore, and the solution that they provided, which was
setting "Upload.Classic" = true in web.config is the solution
Tuesday, January 26, 2010
SSO enabled Sitecore interfere with uploading of media into library
Recently, I faced with an issue whereby when SSO (single sign on) is enabled on Sitecore website and try to upload media onto library, it will prompt for username and password and when valid username and password is entered, it will hang. strangely, it happens for IE7 only. I have tested on IE8 it works fine!
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