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Does not for me, not even with busybox sh and no funky escape codes in PS1 at all. It does with cat or yes running, so just something being output is not the problem… Hm.
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It does not. open ssh linux to mac, typing ~ just types it on fish shell prompt. It works after`cat` followed by ENTER
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Just type <enter> without cat, your shell will show you another prompt, and the ssh escape command will also work.
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No they are correct, fish seems to intercept this or something like that. Only works with cat.
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In newer versions, it's disabled by default and you have to do something like this to enable in ~/.ssh/config:

    Host *
    EnableEscapeCommandline yes
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`EnableEscapeCommandline` only controls the <Enter>~C commandline.

The reason that is disabled in current OpenSSH by default is OpenBSD `pledge` support:

https://security.stackexchange.com/questions/280793/what-att...

On my Linux,

    cat<Enter>~.
closes the connection as expected, and no ~ is shown in the terminal.
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