[BUG]: Files uploaded to thread aren't recognised as files by the LLM

[scottybo]

How are you running AnythingLLM?

Docker (local)

What happened?

If a user uploads a file to the thread (not the workspace), then talks about "the file", the LLM will respond saying it doesn't have a file.

See example conversation below:

Are there known steps to reproduce?

No response

[angelplusultra]

If possible, can you provide the file you are using so we can reproduce the bug? Also, what model and provider are you using?

[timothycarambat]

Is this reproduction incorrect? Made a new thread, dropped in a file and ran a chat, even cleared and re-ran the prompt. It knew there was a file?

Screen.Recording.2025-11-20.at.5.32.19.PM.mp4

[scottybo]

@timothycarambat the issue happens if the file isn't uploaded in the initial message.

So if you start a chat "Hey, I'd like your help with a putting together a report", and then the AI responds, and then you reply with "Here's the file" it responds saying it doesn't know about the file.

In the screenshot below, I didn't include any files in my first message, but did in the second.

[timothycarambat]

The way I was able to reproduce this was to ask a qualifying question, then upload the document as seen above.

• Specifically, I was using Gemini for this
• Additionally, the context is 100% injected into the system prompt - so it is present and available
• When I force the context into the user prompt it acts as if the file was "attached"

Seems the context in the system prompt is seemingly ignored by Gemini in this instance. I was able to reproduce this with OpenAI models as well

[priyanksperidian]

I have the same issue. I have faced it multiple times now. I am using Azure openai model.