Forum Discussion
To be charitable, Windows Media Server is "lacking" in their capabilities. I never bothered using it, mostly because it doesn't transcode a lot of media, and Roku devices only support a small handful of codecs and containers. There are other DLNA servers available for Windows (most free), and there's also some dedicated servers that have Roku channels, such as Emby and Plex. However, Plex doesn't support playlist files (it does have internal playlists, but can't use PLS files), and I don't believe Emby does either.
I have used Serviio for over ten years now. Disclaimer: I am the author of the Roku profiles that are included with Serviio, and I am a forum moderator there. Serviio works great with playlist files in the PLS and M3U format. For home use, the free version is all you need. But there is a paid version that provides access remotely via a web based player.
If you want to give Serviio a try, remember you have to manually select the Roku profile for your player. I never could get them to auto assign correctly. For any current 4K Roku player, you should use the "Roku 4K Media Player w/MPEG2" profile.