Sending files to devices using another OS is still complicated. Pairdrop solves this by using WebRTC and p2p networking to send files from your browser. It’s opensource and self-hostable, so you don’t need to trust anyone else.
What tools do you use to send files?
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KDE connect. You need to install it on all devices you own but it hasn’t let me down. these WebRTC based websites are always wonky.