I have tried uploading files from 450mb to 1.6gb and can't get any of them to finish uploading. I haven't used handbrake. I didn't see a limit on file size for dtube so I never even considered it. To you think file size is the issue?
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I am not certain but with Handbrake I got the file for my two hour radio show down from 507MB to 197MB and that loaded okay to DTube. Before I used Handbrake I couldn't get the bigger files to load.
The other factor that might come into play is your internet upload (rather than download) speed. Mine is quite good at the moment at about 10MB. That might help with a quicker upload in case their is any time limit?
What sort of upload speed have you got?