Can't upload a compiled sketch to Nano IOT

I can use the Arduino IDE just fine with my Nano 33 IOT. But when trying the example cloud project (https://docs.arduino.cc/arduino-cloud/guides/arduino-c/), I can compile but it will not upload the image to my device. I know this because the power light is on, but the activity light never blinks and the cloud IDE outputs text that the code is verified and compiled. But then after a very long time it says it uploaded the image to the device but I think that is just a timeout

Things I have tried:

  • updated the firmware
  • re-installed the Cloud Agent
  • signed up for a paid Arduino cloud subscription
  • disconnected all other USB devices from my laptop
  • deleted all things, devices, and sketches from my cloud account and then walked through the example again (several times)
  • monitored the Serial Monitor. It connects but sends nothing. If I disconnect the USB cable (Power it off and on) and then reconnect it it ask me if I want to create a certificate and I choose 'n'. I have also tried walking through the steps to create the cert.

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