# Reliable image uploads in chat: no overwrites or file cap

> Same-named photo uploads no longer collide, the 20-file attachment cap is gone, images are resized for AI models, and oversized requests compact.

Sep 30, 2026. Topics: Agents. https://www.generalinput.com/changelog/2026-09-30-image-heavy-chats

Image-heavy conversations could go wrong four separate ways. Pasted phone photos could replace or corrupt each other, a large folder hit a fixed attachment cap, a request with many big images was rejected outright, and a request over a size limit ended the run. Between September 26 and 30 we fixed each one where it happened.

### How it works

- **Every upload gets its own path.** Phone photos are all called image.png, and paths came from the filename alone, so small uploads replaced each other and two large ones could write into the same file, leaving the agent with an image that was black below its top fifth. Your preview was always right; only the agent's copy was damaged. Each upload now lands in its own folder derived from its storage key.
- **No 20-file cap.** Attachments are planned against separate budgets for disk and for what's held inline, so a large folder works without flooding storage.
- **Images resized before sending.** Anthropic rejects a whole request when it carries more than 20 images and any is over 2,000 pixels on a side, so every outbound image is scaled to at most 2,000 pixels. For Claude this costs no quality.
- **Too big means compact, not fail.** A request over a size limit, such as 18 screenshots in one turn, now condenses the conversation and retries.

### Also shipped

- Condensed conversations keep your latest message word for word.