Apparently the command “do-release-upgrade” is not advisable over SSH:
Continue running under SSH?
This session appears to be running under ssh. It is not recommended to perform a upgrade over ssh currently because in case of failure it is harder to recover.
If you continue, an additional ssh daemon will be started at port ‘1022’.
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That warning is simply letting you know that if you update SSH while you are connected, you might lose your connection. If that happens, a second ssh session has been opened on another port that you can connect to using:
ssh -p 1022 user@your.ip.address
Additional, the console in the DigitalOcean control panel connects to the droplet directly. If you lose connectivity over the network, you can always fall back to the console.
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