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Connectivity checker causes further "port already in use" issue #2090
As mentioned in #2038 (comment), there's still an issue with the connectivity checker causing "port already in use" issues on server startup.
The problem can only be observed on Windows (for Linux/Unix the intermediary server is now started in a way that it no longer inherits its socket to subprocesses - sadly that is not an option for Windows). It's caused by the connectivity check triggering an event during runtime of the intermediary server that in turn can trigger several subprocesses in the Software Update Plugin (for checking pip). If the timing is just right that causes the same "port already in use" issue on startup that was reported in #2035 and caused there by the file analysis.
Current idea to solve: Do not start connectivity check until after the actual tornado server runs. Additionally limit event propagation to plugins that have already been initialized (that was also a problem observed while debugging this further).
In the long run maybe look into reusing the same listening socket for both the intermediary server and tornado (might not be possible however and also feels like a hack).
Solved differently than originally anticipated: