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Kitty is not able to open external applications after a connection is established, nor can it confirm the existence of a tunnel by giving some kind of signal.
I would make a script using plink . It will run invisibly, work in the background.
If it returns 0 on startup, then start an RDP connection.
True, you need to figure out how to then nail plink.exe from processes. It might even be better to always leave it in the background.
Several well-known programs for Windows work on this principle (for example, HeidiSQL).
Be careful: the first time you connect, plink will ask for an interactive confirmation of the key fingerprint (y/n). Theoretically, you can hide through -batch.
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