@bjrohan, You are not alone. I too am seeing OTA upload error on one of my Oaks that may be the same thing you are seeing. This all started when I noticed this OAK was not publishing events to Particle. So I updated to version 1.0.5 and now cannot do OTA updates to this Oak even though it is claimed on Particle. The message is the same as your first post “Error : An error occurred while flashing the device:”. Interestingly I brought up a fresh out of the bag Oak today with no problems. Still trying to figure out what the issue is with the Oak that won’t OTA upload.
There is a thread on the Digistump forums here discussing the ongoing saga.
http://digistump.com/board/index.php?topic=2373.msg11226;topicseen#msg11226 (latest post by me).
I’ve created a custom CLI with debug to try and glean what the error may be. Here is what it reports…
“OakCLI tool version 1.0.2
Using config file at: C:\Users\Stephen\AppData\Roaming\oak\config.json
Sending file to cloud, to flash OAK_GD (Device ID: d9Removed for public consumption)
Get ready to flash C:\Users\Stephen\AppData\Local\Temp\build8316527855105053068.tmpBlinkTestPgm.cpp.bin
null
{ ok: false,
code: 200,
errors:
[ { id: ‘d9d9Removed for public consumption’,
status: ‘Update failed - File was too big!’ } ] }”
I think the error is being reported by a callback from the Particle side.
Like you, I am very anxious to have this understood and resolved.