Annotate pasted images (arrows, circles, numbered comments) before sending

[arthureffting]

Problem

When I paste a screenshot into the chat input, the only thing I can do with the thumbnail is look at it or remove it. Most screenshots I send are about one specific spot ("this button is misaligned", "this error here"), and I end up describing positions in words, or annotating in another tool first and pasting the result.

Proposal

Clicking an attached image thumbnail opens a lightweight annotation editor:

• Tools: line, arrow, circle, and numbered marker.
• Comments: each numbered marker can carry a short comment. Undo and delete for every mark.
• Done returns to the composer with the annotated image attached.

What the agent receives

• The image with the marks flattened into it, so any vision model sees where they are.
• A numbered list appended as text, for example:
  1. This button is misaligned.
  2. This error appears after saving.

Comments travel as text rather than drawn pixels, because small rendered text is read unreliably by models, and the numbers on the image tie each comment to its spot. The original image should stay recoverable (re-open the thumbnail to edit marks again).

Out of scope for a first version

Freehand drawing, rectangles, text boxes and cropping. They can follow if the basics prove useful.

Why

It turns "the third button in the second row, the one next to the dropdown" into a circle and a number, and it makes UI feedback loops with the agent much faster and less ambiguous.

[Felippen]

Adding the ChatGPT desktop UX details and screenshots from #19885, which was closed as a duplicate of this discussion.

I agree with this feature request , the workflow would be:

1. Open an attached or displayed image and choose Comment from a toolbar.
2. Click a point or select an area, then write a comment. Show numbered markers for each comment.
3. Collect the comments alongside the image in the composer, with options to edit or remove them before sending.
4. Send the image and comments to the agent, preserving the link between each comment and its location.

For example, I could point to a button and say "Move this below the heading" without having to describe its location. Location-based comments alone would be useful to me, independently of drawing or cropping tools and browser-preview annotations.

Reference screenshots

The image toolbar and Comment action

A numbered comment placed on the image

The comment collected beside the image in the composer