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Windows only updates the bootloader, it doesn't touch Linux partitions. After an update you just have to fix the bootloader again which isn't too hard if you know how it works.
I'd argue one shouldn't even be messing with dual booting if they don't understand much about the bootloader.
My counterpoint would be how does one best learn about anything if not by messing with it
As in tradition - mindset. Getting on Linux requires a certain mindset, and this gets more and more true the weirder and more involved whatever it is that you are planning to do gets.
The best way to learn how it works is to mess with it. I have reinstalled my Surface Go 2 numerous times because I messed something up. After leaving Windows I have used dual boot with Arch and Chrome OS for a while, and now I just use Arch including secureboot enabled.
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I'm sure it varies a lot, but you should be able to enter bios setup and add a boot option. There may be a file browser type popup and you can add the known file as a boot option. Right now it may be looking for the old file location on the current windows boot option you have.