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I'm aware that you can stream files to a video server using FFMPEG - something like the following.

fmpeg -re -i localFile.mp4 -c copy -f flv rtmp://server/live/streamName

Is anybody aware of whether FFMPEG can be setup to stream whole playlists or folders of videos, preferably on shuffle?

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I don't think so. Certainly not on shuffle... FFMPEG is not built for that sort of thing. You would have to script it. Your question is essentially identical to this: Now, if you script it, the server will likely just stream the data continuously. If your format, codec, and resolution were all the same, you might be able to get away with just running FFMPEG back-to-back. – Brad Dec 16 '12 at 6:25

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