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Yes. You will need to temporarily deactivate your license before shutting down the Chariot server pre-upgrade. Next perform the server upgrade. Finally, activate your existing license by re-uploading and reactivating as shown here.

I have MQTT clients failing to connect over TLS/SSL with a "Handshake timeout, no data received" error. Can this SSL handshake timeout be increased?

Yes. Currently this configuration option is not available in the UI. First ensure you're running a Chariot version of 2.1.1 with a build date of 2021 May 13th or later. Next add the following line to the <Chariot_Install_Dir>/conf/com.cirruslink.chariot.server.config file.

sslHandshakeTimeout=I"2000"

This doubles the timeout from 1000 ms (1 sec) to 2000 ms (2 sec). Increase the timeout further if required.