Kragger
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Kragger's post in Plex Container Execution Error was marked as the answerYeah, it was a port issue. Having it in bridge mode I added 100 or 1000 to the various default Plex ports. Apparently something else started wanting to use one of those.
Frustratingly, the only place to see that this is a problem is if you edit and save the config and then watch the output as it does the setup.
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Kragger's post in External USB drive suddenly 130 PB was marked as the answerThanks. Fortunately a reboot of the USB box fixed the issue. I'm migrating drives out of it and into my case so this shouldn't be a possible issue for much longer.