We spent the better part of three days trying to figure this out before finally stumbling across the rather simple solution. There didn't seem to be anything online pertaining to this exact problem, so we thought that we'd lay it out for the community.

Problem: Can't upload images correctly using Multiple File Upload, Gecko Uploadify, or Desktop Media Uploader. These packages will go as far as creating a URL for the image, but the actual file never gets uploaded and looks like this:

Situation:

• Images are still upload normally through the media tab
• The three packages above all work normally on our test server
• Consistent across all browsers

Errors:

• Desktop Media Uploader
  - didn't throw an error.
• Multiple File Upload
  There has been an I/O Error: Error #2038followed by
  There has been an HTTP Error: status code 500
• Uploadify
  

  An error occurred: Umbraco Exception (DataLayer): SQL helper exception in ExecuteNonQuery. Stack trace:    at umbraco.DataLayer.SqlHelper`1.ExecuteNonQuery(String commandText, IParameter[] parameters)
  An error occurred: Umbraco Exception (DataLayer): SQL helper exception in ExecuteNonQuery. Stack trace:    at umbraco.DataLayer.SqlHelper`1.ExecuteNonQuery(String commandText, IParameter[] parameters)
  
     at umbraco.cms.businesslogic.datatype.DefaultData.set_Value(Object value)
  
     at Gecko.Uploadify.MediaUtilities.SetCommonProperties(Media media, FileDetails file, String path)
  
     at Gecko.Uploadify.MediaUtilities.SetImageProperties(Media media, FileDetails file, Image image, String path)
  
     at Gecko.Uploadify.MediaUtilities.AddImage(FileDetails file, Int32 parentId)
  
     at Gecko.Uploadify.MediaUtilities.AddToMedia(FileDetails file, Int32 parentId)
  
     at Gecko.Uploadify.MediaUtilities.AddToMedia(HttpPostedFile file, Int32 parentId)
  
     at Gecko.Uploadify.UploadifyHandler.ProcessRequest(HttpContext context)
  

After lots of searching, this post about images seeming to upload correctly, but not really led us to look for 'orphan datatypes', which as I understand it, are data types that try to render a cotnrol that doesn't exist, probably because they were part of a package that uninstalled incompletely.

We didn't have any orphans as far as I could tell, but I thought it was a great idea and it got me thinking about the controls and settings that each datatype uses.

Finally I discovered that our label datatype had the wrong database datatype. It had been inadvertently set to Date rather than Nvarchar. Correcting this setting fixed it all, and suddently everything made sense (especially the values for image width and height shown in the first image).