So it seems the choice of upload control was based on some hasty testing and it turned out my implementation of Plupload did not fix the large file issue (files were transferred but server-side messed up, and no files were saved).
I tried troubleshooting Plupload, but in the process stumbled upon the updated AjaxControlToolkit. Supplied as a NuGet package with excellent setup guide made it hard to resist.
This also forced a update from .NET 3.5 to .NET 4.5, as the updated toolkit requires 4.5. That was merely a symbolic update tho, and no code had to be changed.
As per this commit everything should be functional, i even did some deployment testing this time, and at least a 2.1GB movie transferred without issues.
Project is hosted at github:
The code still contains the legacy Plupload JS, it will probably be removed during the next commit-session.
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