I've been having a strange networking problem lately that I suspect is due to my network setup rather than a problem with Plex, but I'd appreciate any help in troubleshooting since I'm at my wits' end. My Plex Media Server seems to be working just fine remotely, but when I'm on the LAN at home, it will sometimes be recognized as a Remote server, sometimes Indirect, and sometimes actually Nearby as one would expect. Refreshing a client on the LAN or stopping/starting the server will result in one of those 3 statuses seemingly at random.
The network/server is a little complex, so I'll give a quick rundown of the topology:
The LAN is 10.12.34.0/24. The router (ip 10.12.34.1) is virtualized pfSense on an ESXi 6.0 hypervisor, and the "machine" (ip 10.12.34.35) running the current plexmediaserver-plexpass package (1.2.2.2857) is actually a FreeBSD 10.3-STABLE jail running on FreeNAS 9.10.1 (d989edd), which is also a virtual machine on the same hardware as pfSense and a couple other VMs. FreeNAS and the LAN side of pfSense have virtual NICs on a virtual switch which interfaces with the rest of my LAN via a single hardware Intel NIC (I had difficulties setting up a dual NIC "team" - that's the subject of some separate troubleshooting). WiFi is provided by a Unifi AP, and is on the same subnet as everything else. NAT is configured on pfSense; port 32400 is the manually-specified port in the Plex server's remote settings, and remote clients seem to be working as expected.
The clients I've tested include an Android phone (WiFi and 4G), ChromeOS desktop (hardwired via PowerLine), and a ChromeOS laptop (WiFi). Client software has included the web app at "10.12.34.35:32400/web"; the web app at "[public_ip]:32400/web" (from the phone on 4G, to verify that NAT was correctly configured) and that "Remote" was working fine; launching the web app via plex.tv; using the Chrome app (which I believe is just a wrapper for the plex.tv-launched web app, but I'm not positive); and the Android app (v4.32.3.676), which performs as expected (Remote) on 4G and experiences the intermittent Indirect/Remote on the home WiFi. I've been troubleshooting this problem for a while now, and it has persisted across a couple of different server versions.
With a setup this complex, and with me still learning the ins and outs of virtualization and advanced network setup, I really doubt that Plex is the problem. However, any insight into how Plex network discovery works and how it determines when it's Nearby vs Remote vs Indirect would be very helpful as I try to figure out what's going on. I've run a successful Plex server before in a FreeNAS jail on an older version of FreeNAS/FreeBSD, but that was with FreeNAS running on bare metal and with a more conventional router.
My Preferences.xml:
<?xml version="1.0" encoding="utf-8"?>
<Preferences MachineIdentifier="[removed]" ProcessedMachineIdentifier="[removed]" AcceptedEULA="1" FriendlyName="Nateflix" PlexOnlineMail="[removed]" PlexOnlineToken="[removed]" PlexOnlineUsername="[removed]" PublishServerOnPlexOnlineKey="1" ManualPortMappingMode="1" allowedNetworks="127.0.0.1/255.255.255.255" FSEventLibraryPartialScanEnabled="1" FSEventLibraryUpdatesEnabled="1" ScheduledLibraryUpdateInterval="1800" ScheduledLibraryUpdatesEnabled="1" autoEmptyTrash="0" ApertureSharingEnabled="0" iPhotoSharingEnabled="0" iTunesSharingEnabled="0" DlnaClientPreferences="IP=10.12.34.164,DirectPlay=true,DirectStream=true,LocalResolution=1920x1080,RemoteResolution=1280x720,OnlineResolution=1280x720,LocalVideoQuality=74,RemoteVideoQuality=49,OnlineVideoQuality=49,SubtitleSize=100,AudioBoost=100,MusicBitrate=64" AnonymousMachineIdentifier="[removed]" PlexOnlineHome="1" DlnaEnabled="0" CertificateVersion="2" MetricsEpoch="1" CinemaTrailersFromBluRay="1" CinemaTrailersFromTheater="1" CinemaTrailersType="0" LanguageInCloud="1" PubSubServerPing="54" PubSubServer="45.79.210.23" OldestPreviousVersion="legacy" agentAutoEnabled.com.plexapp.agents.lastfm.Artists.com.plexapp.agents.vevo="1" agentAutoEnabled.com.plexapp.agents.lastfm.Albums.com.plexapp.agents.lyricfind="1" agentAutoEnabled.com.plexapp.agents.plexmusic.Albums.com.plexapp.agents.lyricfind="1" CloudSyncNeedsUpdate="0" ButlerUpdateChannel="8"/>