Using the Kensington SD5600T with Boot Camp

I recently got a Kensington SD5600T as a dock for my 2019 16″ MacBook Pro. It’s a solid dock that provides 100W of power through the main Thunderbolt port, so it even charges the greedy beast. But, when I went to use it within Boot Camp, nothing. I could get power, but that was it. The Kensington site says basically, it should just work sans drivers.

IMPORTANT NOTE: IF YOU ARE NOT FAIRLY EXPERIENCED WITH NON-STANDARD WINDOWS INSTALLS, OR NON-STANDARD BOOT CAMP INSTALLS, PLEASE FIND A FRIEND WHO IS AND HAVE THEM DO THIS FOR YOU. PAY THEM. IT ISN’T *HARD*, BUT THIS IS EASY TO MESS UP, AND IT TAKES A WHILE.

So after a lot of playing around, as near as I can tell, the main Thunderbolt drivers weren’t really working. No idea why, although the fact I’m using Boot Camp on an USB-attached SSD may have something to do with it. Anyway, I thought I’d write up how to deal with this so it’s out in the great search engine support database.

First, install the Boot Camp drivers onto a USB stick. This is well-documented about everywhere.

Next install Windows on the SSD. This is a bit tricky, but basically, you use WinToUSB from within a windows VM to install windows from an ISO. There’s a number of sites documenting it, this one: https://www.pcworld.com/article/3185777/how-to-install-windows-on-an-external-drive.html worked well for me.

With modern Apple hardware and either Catalina or Big Sur, to boot windows off of an external drive, you have to shut off boot security in the Mac firmware and enable external drive booting. That’s a risk you have to decide on your own. In any event, you have to make a trip into recovery mode to do this, and change the settings in the Startup Security Utility to “No Security” and “Allow Booting from External Drive”. https://osxdaily.com/2020/12/09/allow-t2-mac-boot-external-startup-disk/ for useful screen shots.

Okay so once that’s done, make sure the drive is plugged into the computer directly, not into the dock. You’ll get “inaccessible boot media” errors if you have the drive plugged into the dock. Yeah, annoying, but minor.

Boot into windows, and you’ll hit a couple things until you run the Boot Camp driver install on that USB stick. First, the laptop keyboard and mouse won’t work. You have to plug at least an external keyboard into the laptop to install the drivers. Fortunately, Windows is keyboard friendly, so the mouse isn’t needed. Do the Windows first run steps, then run the boot camp installer, and reboot.

Okay, so now we can use the trackpad and keyboard. Cool, but the dock may not show up. If it doesn’t, go into Device Manager, and look for items that show as having no driver. If you hit what I did, you’ll see some system devices, mass storage, PCI, about 4-5 things. Starting at the topmost one, and with that USB stick with the Boot Camp drivers still attached and visible in windows, install the drivers one at a time, taking the option to use drivers you have a “disk” for.

Point the installer at the $WinPEDriver$ folder on the USB stick and tell it to search subfolders. You’ll have to repeat this for each device, but the Device Manager does a solid job of finding and installing the correct drivers for the device(s). Once that’s done, you’ll want to reboot (if you haven’t already. one of the driver installs may just reboot for you. Fun times.) Then go and check for updates, you’ll find quite a few there. Install and reboot as necessary, and now your SD5600T Dock should be working fine for you. I did let Kensington know about my solution, so they should be able to help you.

Note that even with the drivers, you still can’t boot into windows if the drive is attached to the dock. It can’t find the drive. If there’s a way around it, someone let me know and I’ll add it in here. But, if it’s a SATA SSD and you’re using a fast USB 3.1/C connection, you literally can run as fast as SATA bandwidth allows, so the slowdown should be minor.

Hope this helps someone!