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A word of caution when doing serial uploads: Serial uploads always go to memory slot 0 of your Oak - no matter what is in that slot. A factory Oak boots to 0 looking for the system firmware, so if you upload via serial, you essentially wipe the ability for your Oak to do natively do OTA updates and firmware updates. If you want to restore that ability, you'll need to use follow the instruction on how to restore your Oak to factory defaults.