I can confirm that the issue appeared in a recent change to Plex.
I was trying to migrate a plex server with a working custom cert setup on version 1.21.3.4014 to a new server, on the latest version 1.21.3.4046.
I spent hours trying to understand why I couldn’t get the custom certificate to work on the new server, while it was working perfectly before. The symptoms were as described here, which is that plex is serving content with its own plex.direct certificate even when accessed via the custom url domain, for which the custom certificate has been issued.
I tried to isolate the problem, and finally confirmed that something broke between these two versions. Indeed, I ended up downgrading the new server, in-place, to version 1.21.3.4014 and, without changing anything to its configuration or to the certificates, my custom certificate started to be picked up.
Here are the relevant CERT logs from both versions
1.21.3.4014 (WORKING):
Feb 24, 2021 18:31:49.867 [0x7f17c2208100] DEBUG - [CERT] Loaded a user-provided certificate.
Feb 24, 2021 18:31:49.867 [0x7f17c2208100] DEBUG - [CERT/OCSP] no URL available
Feb 24, 2021 18:31:49.867 [0x7f17c2208100] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Feb 24, 2021 18:31:55.529 [0x7f17b9ffb700] DEBUG - CERT: Certificate did not exist, fetching a new one.
Feb 24, 2021 18:31:56.009 [0x7f17baffd700] DEBUG - [CERT] Installed certificate with fingerprint <redacted>.
Feb 24, 2021 18:31:56.009 [0x7f17baffd700] DEBUG - [CERT] Installed new private key.
Feb 24, 2021 18:31:56.010 [0x7f17baffd700] DEBUG - [CERT] Subject name is /CN=*.<redacted>.plex.direct
Feb 24, 2021 18:31:56.010 [0x7f17baffd700] DEBUG - [CERT/OCSP] Stapling requests will be made to 'http://r3.o.lencr.org/'.
Feb 24, 2021 18:31:56.010 [0x7f17baffd700] INFO - [CERT/OCSP] No relevant response in cache.
Feb 24, 2021 18:31:56.010 [0x7f17baffd700] INFO - [CERT/OCSP] Couldn't install the cached response; fetching from network.
Feb 24, 2021 18:31:56.010 [0x7f17baffd700] DEBUG - [CERT] Installed intermediate certificate.
Feb 24, 2021 18:31:56.011 [0x7f178ffff700] DEBUG - [CERT/OCSP] HTTP requesting GET http://r3.o.lencr.org/<redacted>
Feb 24, 2021 18:31:56.014 [0x7f17baffd700] DEBUG - [CERT] Loaded a user-provided certificate.
Feb 24, 2021 18:31:56.014 [0x7f17baffd700] DEBUG - [CERT/OCSP] no URL available
Feb 24, 2021 18:31:56.014 [0x7f17baffd700] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Feb 24, 2021 18:31:56.014 [0x7f17baffd700] DEBUG - [CERT] MyPlex: Updating device connections (from timer: 0)
Feb 24, 2021 18:31:56.015 [0x7f17baffd700] DEBUG - [CERT] HTTP requesting PUT https://plex.tv/devices/<redacted>?Connection[][uri]=http://[<redacted ip>:32400&Connection[][uri]=http://[[<redacted ip>]:32400&Connection[][uri]=http://[<redacted ip>]:32400&httpsEnabled=1&httpsRequired=0&dnsRebindingProtection=1&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
Feb 24, 2021 18:31:56.190 [0x7f17baffd700] DEBUG - [CERT] HTTP 200 response from PUT https://plex.tv/devices/<redacted>?Connection[][uri]=http://[<redacted ip>&Connection[][uri]=http://[[<redacted ip>]:32400&Connection[][uri]=http://[[<redacted ip>]:32400&httpsEnabled=1&httpsRequired=0&dnsRebindingProtection=1&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
Feb 24, 2021 18:31:56.382 [0x7f178ffff700] DEBUG - [CERT/OCSP] HTTP 200 response from GET http://r3.o.lencr.org/<redacted>
Feb 24, 2021 18:31:56.382 [0x7f178ffff700] INFO - [CERT/OCSP] Successfully retrieved response.
1.21.3.4046 (NOT WORKING)
Feb 24, 2021 18:22:24.615 [0x7ff2eb6ff100] DEBUG - [CERT] Installed certificate with fingerprint <redacted>.
Feb 24, 2021 18:22:24.615 [0x7ff2eb6ff100] DEBUG - [CERT] Installed new private key.
Feb 24, 2021 18:22:24.615 [0x7ff2eb6ff100] DEBUG - [CERT] Subject name is /CN=*.<redacted>.plex.direct
Feb 24, 2021 18:22:24.615 [0x7ff2eb6ff100] DEBUG - [CERT/OCSP] Stapling requests will be made to 'http://r3.o.lencr.org/'.
Feb 24, 2021 18:22:24.615 [0x7ff2eb6ff100] INFO - [CERT/OCSP] Successfully retrieved response from cache.
Feb 24, 2021 18:22:24.641 [0x7ff2eb6ff100] DEBUG - [CERT] Loaded a user-provided certificate.
Feb 24, 2021 18:22:24.641 [0x7ff2eb6ff100] DEBUG - [CERT/OCSP] no URL available
Feb 24, 2021 18:22:24.641 [0x7ff2eb6ff100] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Feb 24, 2021 18:22:30.193 [0x7ff2e1ffb700] DEBUG - CERT: Certificate will not expire soon; we'll check again in a week.
Feb 24, 2021 18:22:30.196 [0x7ff2e8c00700] DEBUG - [CERT] Installed certificate with fingerprint <redacted>.
Feb 24, 2021 18:22:30.196 [0x7ff2e8c00700] DEBUG - [CERT] Installed new private key.
Feb 24, 2021 18:22:30.196 [0x7ff2e8c00700] DEBUG - [CERT] Subject name is /CN=*.<redacted>.plex.direct
Feb 24, 2021 18:22:30.196 [0x7ff2e8c00700] DEBUG - [CERT/OCSP] Stapling requests will be made to 'http://r3.o.lencr.org/'.
Feb 24, 2021 18:22:30.197 [0x7ff2e8c00700] INFO - [CERT/OCSP] Successfully retrieved response from cache.
Feb 24, 2021 18:22:30.202 [0x7ff2e8c00700] DEBUG - [CERT] Loaded a user-provided certificate.
Feb 24, 2021 18:22:30.202 [0x7ff2e8c00700] DEBUG - [CERT/OCSP] no URL available
Feb 24, 2021 18:22:30.202 [0x7ff2e8c00700] WARN - [CERT/OCSP] getCertInfo failed; skipping stapling
Feb 24, 2021 18:22:30.202 [0x7ff2e8c00700] DEBUG - [CERT] MyPlex: Last published value didn't change, we're done.
Feb 24, 2021 18:23:50.288 [0x7ff2e9401700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown