So this started working for me maybe a week ago. I wasn’t testing it though as I got in the habit of launching my downloaded playlist before I left WiFi. I had made it a habit so I had to do it consciously 
So why is it working? I combed the release notes: Plex Media Server - #328 by ahiyahiya
I’m currently on Plex Media Server for Windows V1.18.9.2578. Tested with Android Plex V7.30.1.16475
I came across these two fixes that may have fixed it:
-
1.18.6.2348 (beta Feb 3 / general Feb 10)
(Performance) Speed up connectivity tests and library discovery (#10930) -
Version 1.18.8.2461 (beta Feb 26, skipped to release 1.18.8.2527 March 11)
(DLNA) Don’t start DLNA server after leaving Plex Home (#11061)
Based on shibereit’s post, I’m thinking it might be the DNLA issue. Can everyone please test and report back?
