Server Version#:1.32.4.7195
Player Version#:4.108.0 (on web browsers)
I set it to use my custom .pfx certificate. Chrome still shows it as insecure, because the plex.direct certificate doesn’t match my custom domain name. Logs say this:
ERROR - [CERT] PKCS12_parse failed: error:0308010C:digital envelope routines::unsupported
ERROR - [CERT] Found a user-provided certificate, but couldn’t install it.
update:
fixed it. MacOS has outdated version of openssl. That’s why Plex couldn’t install the cert. I installed the most recent version of openssl with Homebrew. Generated new .pfx file with Homebrew version of openssl. Restarted Plex and now the cert works!