@Bryan
Load the sketch from the wifi101 examples into the board called "FirmwareUpdater"
The board may (not always) now appear on a new com port that will be OK.
Select the WiFi101 Firmware Updater option and in there select the correct COM port and then TEST CONNECTION.
It should now work and you can update the firmware from there
It was mentioned that the latest firmware can only be uploaded with IDE 1.8.2 and that not all boards can accept the very latest depending on board revisions.