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The fact that macOS doesn't have a built in history for the clipboard is the problem there imo. I use pasteBot and I think macOS is broken without it (which of course means iOS is broken and cannot be fixed by a third party).

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I use JumpCut. I still don't want my stuff on one machine erased via the other unless i specifically connect them via vnc.

It can. In the EU. AltStore -> Clip. No jailbreak, clipboard manager.

The blog post about it seems to imply you have to do an extra swipe down to put it in the clipboard manager for every copy...

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