I've seen a "don't ask again" checkbox a few times, it's not consistent. Personally, I'm not too bothered by it asking if I want to enable Link. Sometimes I want Link on right away, other times I was just plugging in the headset to charge it while watching Pluto TV or chatting with friends in Alt Space. What bugs me more is it asking if it's okay to allow my PC access to my Quest 2 Every Single Time I plug it in.
For everyone still struggling with this: here's my solution to get rid of this repeating message.
The problem is that you have to authorize your Oculus with ADB, and once that is done you can simply switch off the usb message and a new world order of rest and peace will settle upon your soul.
1) First you should install the Oculus ADB Drivers 2.0 and add the platform tools:
2) Unplug your Quest from your PC's USB. Wait 3.14159265359 seconds precisely (just kidding). Plug your Quest back in again.
3) Now enter 'adb devices' in your command line prompt. It should show your device and behind it 'unauthorized'.
4) Mount your Quest (put it on your head). Now you should see that other message that allows you to ALWAYS access your Quest through your PC's USB connection.
5) For the second message (which you have been seeing thousands of times until now and which drove you to near insanity) just click 'Don't show again'.
6) Now enter 'adb devices' again and if correct, your Quest is now 'authorized'.
7) Unplug your Quest and plug it in again. You should get no prompt in your Quest and 'adb devices' should still should your Quest as a registered and authorized device.
8)) If any of this fails, reboot your Quest and try again.
9) If it still doesn't work for you then this tutorial doesn't work for you, sorry.