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Currently the CLI only sends images from the most recent image- containing message. This prevents doing things like sending one message with an image and then a follow message with a second image and asking for comparision based on additional information not present in any text that was output. It's possible that some models have a problem with this but the CLI is not the right place to do this since any adjustments are model-specific and should affect all clients. Both llava:34b and minicpm-v do reasonable things with multiple images in the history.