Forgot to mention that I am on an MBP 16" 2019

Ok - Here is what was happening. I have a Satechi USB-C hub connected on my MBP 16 and through HDMI a Dell U2415. I had a third party calibrated icc profile on it. Every time I was trying to login with the hub connected the laptop display would go out of sync resulting to the Windows server crashing and throwing me out in the login screen. Once I removed the relevant icc profiles from System preferences I was able to login normally

@rogerli05 could you please provide the relevant link?