Hello @brandonProgramming
I don't think problem is CMSIS-DAP firmware 3.133. I test this firmware with LPC55s36-evk, there is no issue. While I have MCU-LINK_installer_2.250.exe, you can test if need. Can not find 2.245.
Recommend you enter ISP mode, then use GUI Flash tool inside MCUXpresso IDE (or blhost tool) erase flash all. then Remove ISP jumpers. Create a new IDE workspace, import LED demo. Debug again.

BR
Alice