Software updates for sleeping devices

Could you just try a longer wake periode e.g. once per day or once every ten wakes?
If you are still in the middle of development, you might be able to accept a bit more power consumption, just for the sake of shorter dev cycles, and once you got a stable state, having a once in a while check cycle might still be acceptable.

Since we don’t know your code I’d have to guess, but if you were using SYSTEM_THREAD(ENABLED) you must be aware of the asynchronous nature of your code and the cloud tasks. The cloud tasks might be aware of the pending update, but might not have the time to pull the breaks before you cut the connection.

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