I have tried many things (disabled firewall, restarted several times, disabled internet sharing etc.) yet still when I run sudo ./PlexConnect.py I get the following:
I have tried many things (disabled firewall, restarted several times, disabled internet sharing etc.) yet still when I run sudo ./PlexConnect.py I get the following:
What happens if you change the ip_pms back to the default
Yeah do not change the entries in settings.cfg UNLESS you understand what you are doing 
I have the exact same problem.
Yesterday everything ran perfectly. Today, after a reboot, I get that same error message.
After a fresh install of plexconnect, I still get the same error message. Didn't mess with any config files, nothing.
Headscratching...
EDIT: problem solved by disconnecting my VPN connetion (privateinternetaccess).
NOW I get "Trailer unavailable" without any error message in the terminal.
MacBook-Air:~ sfx$ sudo /Applications/PlexConnect-master/PlexConnect.py
Password:
17:20:01 PlexConnect: ***
17:20:01 PlexConnect: PlexConnect
17:20:01 PlexConnect: Press CTRL-C to shut down.
17:20:01 PlexConnect: ***
17:20:01 PlexConnect: started: 17:20:01
17:20:01 PlexConnect: IP_self: 10.131.1.6
17:20:01 DNSServer: started: 17:20:01
17:20:01 DNSServer: ***
17:20:01 DNSServer: DNSServer: Serving DNS on port 53.
17:20:01 DNSServer: intercept: ['trailers.apple.com', 'atv.plexconnect'] => 10.131.1.6
17:20:01 DNSServer: restrain: ['mesu.apple.com', 'appldnld.apple.com', 'appldnld.apple.com.edgesuite.net'] => 127.0.0.1
17:20:01 DNSServer: forward other to higher level DNS: 8.8.8.8
17:20:01 DNSServer: ***
17:20:01 WebServer: started: 17:20:01
17:20:01 WebServer: ***
17:20:01 WebServer: WebServer: Serving HTTP on 0.0.0.0 port 80.
17:20:01 WebServer: WebServer: Serving HTTPS on 0.0.0.0 port 443.
17:20:01 WebServer: ***
17:20:01 PlexGDM: ***
17:20:01 PlexGDM: looking up Plex Media Server
17:20:01 PlexGDM: ***
Process Process-2:
Traceback (most recent call last):
File "/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/multiprocessing/process.py", line 258, in _bootstrap
self.run()
File "/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/multiprocessing/process.py", line 114, in run
self._target(*self._args, **self._kwargs)
File "/Applications/PlexConnect-master/WebServer.py", line 221, in Run
XMLConverter.discoverPMS()
File "/Applications/PlexConnect-master/XMLConverter.py", line 221, in discoverPMS
PMS_list = PlexGDM.Run()
File "/Applications/PlexConnect-master/PlexGDM.py", line 61, in Run
GDM.sendto(Msg_PlexGDM, (IP_PlexGDM, Port_PlexGDM))
error: [Errno 49] Can't assign requested address
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