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Ok, turns out it was upgrade connection and websocket causing issues. However as those are needed for Trilium, I had the choice between having trilium work or the chat work, not both at the same time with the same nginx settings.
So while keeping the settings for nginx for general Trilium the same, I created a separate nginx location with some settings adjusted so only the LLM chat would use these nginx settings, not the entirity of Trilium.

Using the NGINX plugin in OPNSense btw.
In the nginx plugin UI you can duplicate the location you use for Trilium, set URL pattern to /api/llm-chat/stream, set match type to dont check regex on longest prefix and disable websockets. Then adjust the ht…

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Answer selected by eliandoran
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State: Triage Issues that need to be verified awaiting feedback llm
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Converted from issue

This discussion was converted from issue #11107 on August 21, 2026 08:48.