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For with anonymity: OnionShare . For automated sync of huge datasets: Syncthing . For quick CLI transfers between two trusted parties: Magic Wormhole .

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Uses browser-based AES-256-GCM encryption so the key never leaves your device; supports up to Cloud Storage Solutions

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If you are comfortable with a command-line interface, Croc allows you to transfer files of any size directly between two devices. Instant streaming

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or RAR5 with Recovery Volumes