App.plex.tv is unable to connect to "Plex Server" securely

Running Plex: 1.28.0.5999 on TrueNas Core 12.0

TrueNas is running fine with no issues reported, and according to dashboard nothing is out of the ordinary.

Plex stops working on any player, or in any browser after a few minutes of uptime. It still states that it is up and running (in the TrueNas interface) but there is no way to connect with it on any player or browser, LAN or WAN.

The error i get is the following:
app.plex.tv is unable to connect to “Plex Server” securely

System has been running more or less without any problems for 2 years now, with the only upgrade being FreeNas to TrueNas Core, along with scheduled updates to both TrueNas & Plex

The only change made to the local network was adding a managed PoE switch to the network. Now my local network consists of a 2 switches directly connected to a router and the TrueNas fileserver also connected directly to the router. All cables are either CAT 5e or CAT 6. Various devices are connected to the switches (2 Access points, 2PC’s, Open Media Vault Fileserver, Apple TV and a couple of TV’s)

From what i have read most of the secure connection problems arise from local network settings. But which settings? I have not changed any of them. I have tried to mess with the settings in the Plex Server forth and back, but to no avail.

Any ideas?

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