Having similar issues as the OP. Used all the suggestions mentioned above. Using the plexconnectip/trailers.cer instead of the http://trailers.apple.com/trailers.cerwhile adding the profile on ATV 3. The latter gives :Unable to add profile" type of error message. The log is attached below. ANy help would be highly appreciated.
14:55:17 PlexConnect: started: 14:55:17
14:55:17 PlexConnect: Version: 0.5-dev
14:55:17 PlexConnect: Python: 2.7.9 (default, Dec 10 2014, 12:28:03) [MSC v.1500 64 bit (AMD64)]
14:55:17 PlexConnect: Host OS: win32
14:55:17 PlexConnect: PILBackgrounds: Is PIL installed? False
14:55:17 Settings: getsetting enable_plexconnect_autodetect=True
14:55:17 PlexConnect: IP_self: 192.168.1.6
14:55:17 Settings: getsetting hosttointercept=trailers.apple.com
14:55:17 Settings: getsetting enable_dnsserver=True
14:55:17 DNSServer: started: 14:55:17
14:55:17 Settings: getsetting port_dnsserver=53
14:55:17 Settings: getsetting ip_dnsmaster=192.168.1.1
14:55:17 Settings: getsetting prevent_atv_update=True
14:55:17 DNSServer: ***
14:55:17 DNSServer: DNSServer: Serving DNS on 192.168.1.6 port 53.
14:55:17 DNSServer: intercept: ['trailers.apple.com'] => 192.168.1.6
14:55:17 DNSServer: restrain: ['mesu.apple.com', 'appldnld.apple.com', 'appldnld.apple.com.edgesuite.net'] => 127.0.0.1
14:55:17 DNSServer: forward other to higher level DNS: 192.168.1.1
14:55:17 DNSServer: ***
14:55:17 WebServer: started: 14:55:17
14:55:17 Settings: getsetting port_webserver=80
14:55:17 Settings: getsetting enable_webserver_ssl=True
14:55:17 WebServer: ***
14:55:17 WebServer: WebServer: Serving HTTP on 192.168.1.6 port 80.
14:55:17 WebServer: ***
14:55:17 WebServer: started: 14:55:17
14:55:17 Settings: getsetting port_ssl=443
14:55:17 Settings: getsetting certfile=./assets/certificates/trailers.pem
14:55:17 Settings: getsetting certfile=./assets/certificates/trailers.pem
14:55:18 WebServer: Failed to connect to HTTPS on 192.168.1.6 port 443: [SSL] PEM lib (_ssl.c:2525)