Issues running headless

I am currently on the latest stable release.
I still experience issues trying to run headless via SSH, namely the connection cutting out, especially when using commands such as sudo apt-get install python3-pip
Whenever I install any package, or sudo apt-get upgrade, it tends to really like to shut off the connection forcing me to unplug and replug the dragonboard. Any ideas as to why this is if the internet issue has already been resolved?

Is it an internet issue or simply that the ssh server gets restarted as part of the upgrade process (any C library upgrade often offers to restart services)? When upgrading any Debian system through an SSH connection you need to use a tool that preserves the session through a disconnection (tmux is a good solution for this).

I’m afraid right now “latest stable release” is ambigious (19.01 has not been announced but it is what the documentation points too). What was the version numbers on what you installed.