Hello Jason,
First please follow the next steps to update the firmware of the LPC-Link2 :
Download and install the newest version of LPCScypt 2.0, you can download it from the next link.
Put your board in DFU mode by removing JP1. Once you remove JP1 from your board do a power cycle to reset the board.
Go to the following path on your PC and open the script: <LPCScrypt Install Dir>\scripts\program_JLINK
Press any key to run the script. Please refer below image to see the results when the script runs successfully.

Once the script runs successfully install JP1 on your board and do a power cycle.
Before trying to debug again please erase the old debug files on MCUXpresso IDE as shown below.

Once you delete the debug files and flash the new firmware please try to debug again.
Hope it helps!
Victor.
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