Following up on this post for anyone currently experiencing concerns with local playback with plex.
This example is when using a pihole on the local network:
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SSH into your pihole
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nav to /etc/dnsmasq.d/
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open your 'custom'.conf
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add the following line
rebind-domain-ok=/plex.direct/
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save your config
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reboot pihole
This should resolve the concern with the 'insecure connection prompt' when playing plex on the LAN to a local device (chromecast, firestick, etc.)