I was just able to troubleshoot this successfully, so in case it's helpful to others, let me document my situation. First of all, I should note that I was able to use my exact hub/dock and external monitors without issue on my MacBook Pro (M1 Pro chipset) until about 2-3 months ago. I don't know what OS X version it was running at that time, but that's when I noticed that one of my USB-A devices connected to the hub (a Leopold mechanical keyboard) could no longer be detected by my computer until I connected it (via an adapter to make it USB-C) directly to the machine. Then suddenly, my other USB-A accessory (Razer Kiyo Pro webcam) and my external displays (see below for makes and models) also were no longer detected. I have since verified the failure on another hub (Anker 777 Thunderbolt Docking Station) as well as my wife's work hub (model info not available at this time, but it was a third manufacturer).
My home setup (where problems were first discovered)
The setup that allowed me to successfully fix the problem
- Same Kensington hub and M2 Max Macbook Pro
- LG 27BL85U-W external display (HDMI plug)
- 1x of the Anker adapters mentioned above for the external monitor connection
I'm still not *exactly* sure what fixed it all, but the problem seemed to be that, upon plugging my hub into the Macbook Pro (via a USB-C cable), an Allow/Deny dialog was popping up saying something like "Would you like to allow this Kensington hub access to your computer?" However, on my home setup, this dialog was popping open and immediately closing itself before I could even read what it said. When I went to my local Apple Store for a Genius Bar appointment to troubleshoot it though, and used their external test monitor (the LG one I mention above), the dialog didn't auto-close for some mysterious reason. So I was able to Allow the hub on my machine and, when I got back home, it worked flawlessly with my home setup!
What is super puzzling about all of this is that I had already tested the hub at home with no monitor plugged in at all, which I assume would have triggered the Allow/Deny dialog properly, but it didn't. It's possible that the dialog won't trigger without a device attached to the hub that you're trying to connect, but I'm not sure. Ultimately, the most likely explanation to me is that my HP monitors weren't communicating through the hub in a way that Ventura/Sonoma OS X could understand to properly trigger the Allow/Deny dialog and using the LG monitor worked better.
I hope this helps those of you still struggling out there! The key takeaway: try a bunch of different external displays to see if this confirmation dialog is the real culprit. Once you Allow, you should be able to switch back to your preferred setup and have it all work again.