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Boot 3.0 USB on Surface Go 3 works with adapter but not with USB hub

I’m trying to boot a permanently installed Linux from a portable SSD on my Surface Go 3.

The SSD has GRUB installed on it and basically works just line any other portable Linux. I have confirmed that it definitely boots.

I currently use it with a direct USB-C to USB-A Adapter (that supports 3.0) and it “works”. It boots as it should, but the Surface Go 3 only has one single USB-C port and therefore I can’t use any external devices (e.g. USB peripherals).

Now, I’ve tried it with a USB hub that also supports USB 3.0 but can’t get the drive to boot. In theory, it should work just fine, as it boots with a direct adapter using 3.0 as well.

The Surface Go has all the latest firmware updates installed.

Does anyone have any idea why this might be and how I can try to fix it?