Help & troubleshooting for channels on your Roku device, including adding/removing channels, logging in to, authenticating, or activating a channel, channel-specific playback issues, assistance contacting channel publishers to report issues, and adjusting channel-specific settings.
That's usually the job of the server streaming the video. Of course, if you're playing them from a USB drive, there is no server. But I believe that RMP will recognize a JPG image that is named to match the video and use that for the icon. But the image file and media file names must be identical.
Dan Roku Stick (3600), Ultra (4640), Ultra (4670), Premiere (3920), Insignia 720p Roku TV, Sharp 4K Roku TV, Nvidia Shield, Windows 10 Pro x64 running Serviio and Plex on a wired Gigabit network.