I started everything fresh updated both plex connect and pms and made a new cert.
16:36:44 PlexConnect: started: 16:36:44
16:36:44 PlexConnect: IP_self: 192.168.2.27
16:36:45 DNSServer: started: 16:36:45
16:36:45 DNSServer: ***
16:36:45 DNSServer: DNSServer: Serving DNS on 192.168.2.27 port 53.
16:36:45 DNSServer: ***
16:36:45 WebServer: started: 16:36:45
16:36:45 WebServer: ***
16:36:45 WebServer: WebServer: Serving HTTP on 192.168.2.27 port 80.
16:36:45 WebServer: ***
16:36:45 WebServer: started: 16:36:45
16:36:45 WebServer: ***
16:36:45 WebServer: WebServer: Serving HTTPS on 192.168.2.27 port 443.
16:36:45 WebServer: ***
16:37:41 PlexConnect: Shutting down.
16:37:42 WebServer: Shutting down.
16:37:42 WebServer: Shutting down.
16:37:43 DNSServer: Shutting down.
16:37:43 PlexConnect: shutdown
[PlexConnect]
port_pms = 32400
port_webserver = 80
ip_plexconnect = 0.0.0.0
certfile = ./assets/certificates/trailers.pem
ip_dnsmaster = 8.8.8.8
loglevel = high
enable_dnsserver = True
logpath = .
ip_pms = 192.168.178.10
enable_plexgdm = True
hosttointercept = trailers.apple.com
port_ssl = 443
enable_webserver_ssl = True
prevent_atv_update = True
port_dnsserver = 53
enable_plexconnect_autodetect = True
still getting the same msg.