So the NAS has it’s primary DNS server pointing to one of my virtual machines (192.168.1.4)… I do that because my NAS is Active Directory joined and my two virtual servers host AD and DNS.
The NAS must point to the modem/router’s IP.
If the NAS points to its own VM, how does it learn? By definition, it can’t as you’ve created a circular reference.
Your LAN -> Modem/Gateway Device -> Internet.
If you run Windows Active Directory, it must be a DNS slave of either the NAS or the Modem/Router, not the other way around.
Your AD must rely on the DNS provided by the NAS which is itself downstream from the modem/router.
DNS resolution flows inbound:
Internet -> Modem/router -> NAS -> VM -> LAN (If you wish).
I’m not sure I know what you mean by “learn”. DNS is DNS regardless of OS. The NAS points to a Virtual Windows DNS server who in turn points to my ISP’s resolvers. The NAS resolves internal and external names perfectly. All of my installed packages like CloudSync, ActiveBackup, etc, etc all work just fine. 'm not sure what you mean and why only Plex has the sporadic resolution issue.
What you have for DNS configuration is 100% non-standard
As a result of whatever configuration you actually have (a Synology container-VM) it’s blocking Plex from resolving and finding plex.tv when it runs on the native host.
I liken this to putting a pfSense box in the computer which is trying to use the pfSense as the gateway / fireway. While that may work on Windows, It will NOT work here. DSM is too fickle
Hmmm… OK, is there any way we can use (test) a hosts file on the unit itself to possibly do some testing? I hate to change DNS on the NAS itself only because I use NTFS group permissions on file shares and i’m afraid of breaking all of that.
Long story short, I had a dedicated physical HP ProLiant server running AD when I bought the Syno… After adding the Syno to my network/domain, I wanted to get rid of the power thirsty proliant so I created two virtual servers on the Syno and moved AD to them and walla! Bob is your Uncle.
Since EVERYTHING works like a charm (like GPOS, folder redirection, and all my Syno packages) except TrueHD transcoding, I’m going to just leave things as-is at this point. I appreciate all of your support.