Documents and images should be displayed (previewed) inline with the conversation and be referenced in the order they were uploaded. Right now all of the files are listed at the top of the chat and the chat is always reference the last first file uploaded. Just look at how ChatGPT UI handles this. It’s the reference standard 
This is not technically bug, just how the system works. So moving this to feature request for us to note as a possible improvement.
I would just like to second this feature request.
During testing of an image recognition bot we seem to be getting more users than not who don’t realize their image has been uploaded as it seems most users are waiting for a thumbnail image to display and completely overlook the image name banner at the top that indicates an image has been uploaded.
Obviously, once you know it’s easy to see but for whatever reason it’s not as intuitive as the actual thumbnail displaying in the chat box.
At this stage, even as a workaround, I would be happy to know if there was a way to have the bot print a generic ‘Thanks, your image has been uploaded’ type message just to let the user know that the image is uploaded and is now viewable by the bot.
Additionally, I have also noticed that once an image has been uploaded, every response there after will be in reference to the uploaded image even if it the question is no longer related to the image.
I would just like to say, outside of some quality of life features such as this, you guys have done an amazing job with Pickaxe. Very helpful platform that I would happily recommend even from our limited use so far. Great work!