Hej Brent,
the tutorial page https://learn.adafruit.com/adafruit-airlift-featherwing-esp32-wifi-co-processor-featherwing/upgrade-external-esp32-airlift-firmware says Make sure to solder all three of these pads together. You will not be able to upload firmware to your ESP32 if they are not connected. This is somewhat misleading, because many students literally solder all three pads together (so that all three pads are interconnected!) instead of bridging each pad with solder. Maybe that should be changed?
Thanks!