Hi RobbAlarcon,
That sounds really weird. My school has over 300 Surface Pro 6 , 7 and 7+. Updates are pushed out regularly and I've never heard of an update affecting a genuine Microsoft Active USBC-HDMI adapter. My school Surface Pro 7+ had massive issues with two brand new top-of-the-line HP 27" monitors when I first installed them. After firmware for the 7+ and all Windows updates and genuine MS adapters, everything worked well (that was in March I think). Since then I've applied all Windows updates and update the firmware for the SP7+ regularly (they constantly update their firmware download).
If the updates are the cause then the problem may be your individual device; possibly worth opening a ticket with MS.
If you can prove that the monitors worked before the update but not after, you might be up for a replacement device. We do replace the SPs regularly - common faults include battery failure or inability to boot to Network drives for imaging.
Good luck.
Regards
Scott