Hi @Jseiler
If we can trouble you, p lease flash the DeviceOS manually to the latest v2.0.0-rc.3 then do a Cloud Debug again:
You can manually flash the DeviceOS of your choice by following the instructions here (link).
Do not : do so without reading the instructions very carefully. Please keep track of which firmware parts should be flashed via DFU ( --usb ) and those which should be flashed via Serial ( --serial ). Under no circumstances should you have to use the --force argument.
Instructions: Releases · particle-iot/device-os · GitHub
Sample response from forum for your reference, please be cautious as the error reported is similar but situation might not be totally same as yours.