Automatic retrieval of subtitles not working

I simply can not get the subtitles to automatically appear no matter what I try.
Using a mac as a server and activated agents, logged in to opensubtitles.org etc. Did refresh libraries, files individually to see if they would download but cant get anywhere with my knowledge. Only manually downloading the srt gets me the subtitle.
Is there a guide stating all the steps and settings - perhaps I am missing one step?

Check out the bottom of https://support.plex.tv/articles/200471113-configuring-subtitle-support/.

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