@Gordon sounds like a fantastic plan! In regards to TLS/SSL, that is also an awesome idea to incorporate into the pico. A few days ago I stumbled across the stm32-cryp-lib found at: http://www.st.com/web/en/catalog/tools/PF259409 However, I'm not sure if that library supports TLS/SSL. I've been wanting to try and custom compile my own Espruino firmware to use AES encryption, but creating a custom linux environment to compile the Espruino firmware is out of my scope of know how. Also even if I successfully created the environment I still wouldn't be able to incorporate the lib because my programming know how is also limited.
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