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jellyfin with subtitles on Chromecast
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i don't know too much about jellyfin compatibility, but your issue is probably ASS/SSA format subtitles, which are a complex graphical overlay subtitle, rather than simple text so device support is less guaranteed.
You could try pre-burning the subtitles in before hand by re-encoding the video, or find content with SRT subtitles which have wider support.
ASS on android clients is mostly a solved issue these days so as the other commenter suggests, the google TV chromecast with a native jellyfin app would be a more reliable solution for you.