If you both are familiar with torrenting, make a torrent file, send the magnet link and then torrent the file.

No need for a central server.

Before that decrypt with gpg after over some other platform sharing your gpg public keys.

Is there a decent app for this?

It has been years since I used one, but back then Transmission was a good client.

It’s maybe sorta simple and lacking advanced features or even stuff like incremental file downloading in qbittorrent but on macos it feels like it’s the same app today that it was 15 years ago - it works and is stable and light on resources especially with modern systems. Hasn’t looked even a morsel different since I was in high school. Actually weirdly impressive especially considering changes to apple and macos apps over the years due to os changes some old apps just won’t launch on new macos versions

Nobody else could torrent the file without the magnet link, right?

That is the point of it, but if you are worried, grab 7-zip and make an mencrypted archive.

Wouldn’t the DHT scrapers still find it? Also what tracker do you guys use for this? I’ve thought about doing this but I am always worried it’ll get downloaded by unintended observers (regardless of how hard I PGP the contents.)

I am not really sure of how fast a DHT scraper works, but if you are worried, encrypt the file with VeraCrypt or 7zip before torrenting it.

It is a sensible precaution, since tge file is sent in clear over the interweb

Good to know, I was just double checking. Thanks!

Agreed. I recently did this (first time making a torrent-file) to transfer a set of 45 min videos to a friend, and will probably prefer this way of doing it in the future.

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