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Secure File Transfer for Windows with Cerberus by Redwood
Protect and share files over FTP/S, SFTP, HTTPS and SCP with the #1 rated Windows file transfer server.
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SubSet is a small file management tool that creates a random subset of files from a large collection and copies them to a target location. It is intended to fill a small MP3 player with random files from a much larger collection.
If you create a playlist on a pc, you may want to listen to that playlist on a portable player. This copies the playlist and all files it refers to, preserving the dir tree. Use the gui or cli or create shortcuts to drop files on. M3U only for now.