Catalina Security Update 2021-002 broke my Mac

Last night I took the plunge and installed the April 2021 security update to Catalina on my Mac, which didn’t go so well. After several reboots my Mac got stuck on this screen:

Somehow I was able to power cycle the Mac and it seemed to come back and complete the install.
This morning when I tried to boot the Mac, it was continuously wedging with this black screen of death.
The pattern went something like this:

  • Power on Mac
  • Get to FileVault login boot loader
  • After entering the password, change to a black screen with the Apple logo and boot progress bar
  • Get to 60% and then black screen of death
  • Lather, rinse and repeat

Eventually I had the idea to perform a PRAM reset (which reminds me, I must go and disable the startup chime again) and finally my Mac booted normally.

Alas a utility that I use, TotalSpace2 would fail to load because SIP was enabled now.
When I next had a chance to debug the situation, I booted into Recovery Mode and tried to minimally disable SIP so I could get TotalSpaces2 working again using:

csrutil enable --without debug --without fs

This was accepted, I rebooted and **** **** the machine would refuse to boot once more until another PRAM reset.
I decided to try one more time from Recovery Mode:

csrutil disable

… close down terminal window, ask for a reboot and …. hey that worked.
Now I’m pretty sure that before Security Update 2021-002 I was running SIP in the first mode (without debug and fs), however that combination no longer seems to work.