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Your certificate was properly refreshed. Excellent
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Your server is visible to Plex.tv
EventSource: Got event [data] '<Message address=“XX.XXX.XXX.XXX” port=“32400” asyncIdentifier=“12e37b76-ad99-42fa-9f76-0c3c1e6efd37” connectivity=“1”
Everything I see here looks like your machine is not openSSL v3.0.0 compliant.
It seems as if it’s v1.1.1 (now expired as of Sept 2023).
(35, SSL connect error) (OpenSSL/3.1.1: error:0A000410:SSL routines::sslv3 alert handshake failure)
Do you have openSSL v3.0.0 installed ?
Ref: Linux Tips - #25 by ChuckPa
The Linux Tip refers to custom certs but also requires openSSL v3.0.0 compliance.
Lastly, Are you attempting to use the ‘plex.direct’ URL to access the host ?