Following the answer posted by @greglingman, I was able to resolve my problem.
I have a pfsense router and I was able to work around the issue. I had to look at information on the client side (e.g. Plex on Android). You need to go to:
Hamburger menu on top left > Gear icon > Help & Support > Debugging
Check the “Network logging” box.
Note down the Wi-Fi IP address and port.
Attempt the media file download to reproduce the error, then using the browser, go to the location of the logs as specified in the Plex app (e.g. “http://WiFi IP address:port/logging”, scroll all the way down, then slowly back up and check for the error/exception about unresolved host message or something similar in the log. You want to locate an address that looks like this:
[PMS IP Address].[32 character string].plex.direct
Example:
192-168-0-2.2f970eb5e3ae4326a3ca18e35940ab82.plex.direct
It might be easier to search for “plex.direct”.
Note down the IP address and the 32 character string.
In your pfsense router GUI page, go to:
Service > DNS Resolver > General Settings > Host Overrides
Add a new entry with the following fields:
Host = The IP address where your Plex Media Server is hosted, with dashes instead of dots (e.g. 192-168-0-2)
Parent domain of host = 2f970eb5e3ae4326a3ca18e35940ab82.plex.direct
IP to return for host = The same address as in the Host, but with the dots (e.g. 192.168.0.2 )
Description = Workaround for Plex download bug.
After setting this and saving in pfsense, the downloads started working. While there is no progress bar, the “Waiting for downloads” keeps showing for a while but eventually downloads the media file (it’s a movie in my case).
I hope this helps!
Thanks to @greglingman!!
