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The Image Annotator is a full-screen modal for drawing on top of images you’re about to attach to a prompt. Circle the bug, point an arrow at the misaligned button, scribble a quick note - then save back into the message and send. It works on every image surface in Maestro: staged attachments in the input area, attachments inside Group Chat, the lightbox preview, inline images in Auto Run documents, image files open in the File Preview pane, and the image currently on your system clipboard.

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Opening the Annotator

A pencil button appears on every image thumbnail Maestro renders:
  • Input area - Hover any staged image thumbnail and click the pencil overlay in the corner. Saving replaces the staged image in place; the next send will use the annotated version.
  • Group Chat input - Same hover-overlay pattern on staged thumbnails.
  • Lightbox - Open any image in the lightbox (Cmd+Y / Ctrl+Y carousel, or click an attachment) and press the Annotate button in the top-right, or use Cmd+E / Ctrl+E.
  • Auto Run attachments - Hover an inline image in an Auto Run document and click the pencil overlay. Saving rewrites the file on disk so subsequent runs pick up the annotations.
  • File Preview - Open an image file from the Files pane and click the Edit image (wand) button in the preview toolbar. Saving prompts you to overwrite the file or write a new one (see Saving and copying).
  • Clipboard - Press Opt+Cmd+E / Alt+Ctrl+E (or run Edit Image from Clipboard from the Command Palette) to open the annotator on whatever image is currently on your system clipboard. Saving (or pressing the copy icon) writes the edited image back to the clipboard, ready to paste anywhere. If the clipboard has no image, a flash tells you so. This turns the annotator into a standalone image editor: copy a screenshot, mark it up, and paste it into Slack, a GitHub issue, or any other app without ever attaching it to a prompt.

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Tools

The vertical toolbar lives on the right edge of the modal. Click an icon to switch tools, or press the tool’s hotkey. Hotkeys work whenever the annotator is open and you’re not typing in a text label. Shapes are first-class objects after they’re committed:
  • Click a shape to select it. Resize handles appear at the corners (rect / ellipse) or at each end (arrow).
  • Drag the body to reposition.
  • Drag a handle to resize.
  • For rect / ellipse, a small fill toggle appears next to the selected shape - click to flip between outlined and filled.
  • Press Delete or Backspace while a shape or text label is selected to remove it.
Pen strokes are immutable once committed - they can be erased or undone, but not edited. This keeps freehand input fast and predictable.

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Pen settings

Click the sliders icon in the toolbar to slide out the Drawing settings drawer.
  • Color - Eight preset swatches plus a custom hex picker. The active swatch persists across sessions.
  • Size - Pen width in pixels (1-64).
  • Thinning - How much pointer pressure affects stroke width (0-1).
  • Smoothing - Curve smoothing applied to the raw input (0-1).
  • Streamline - Pointer-jitter dampening; higher values produce steadier lines for shaky hands or trackpad use (0-1).
  • Taper Start / Taper End - Pixel distance over which strokes fade in / out at each end. Useful for arrow-tip aesthetics.
The drawer also has Text settings - color, size (10-120px), and font - that drive new text labels. As with strokes and shapes, each label captures the style in effect when it was created. Settings apply immediately and are remembered across the app - including a Reset to defaults button at the bottom of the drawer. Each stroke and shape captures the style in effect at the time it was drawn, so changing settings later only affects new content.

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Saving and copying

Two ways to leave the annotator with your work intact:
  • Save (green check icon, Cmd+S / Ctrl+S) - Composites the annotations onto the underlying image and returns the result to whatever opened the annotator. For staged images, this updates the thumbnail; for the lightbox, it writes back to the originating message; for Auto Run attachments, it rewrites the file on disk.
  • Copy (clipboard icon) - Composites and copies the annotated PNG to your system clipboard without closing the modal. A “Copied annotated image to clipboard” flash confirms success. Handy when you want to drop the annotated screenshot into a different message, a Slack thread, or a GitHub issue.
Cancel (Esc or the X button) discards all changes. When you open the annotator from the File Preview pane, saving opens a destination picker first: Overwrite the existing file, or Save to a new file (named alongside the original). The annotator always exports PNG, so if the original isn’t a PNG (for example a .jpg), overwrite can’t reproduce the original format and instead writes a sibling .png next to it.

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Keyboard shortcuts

The annotator’s shortcuts are bound at the modal layer with capture-phase priority, so they always win over the rest of the app’s keymap while the modal is open.

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Tips

  • The annotator works directly on the image’s native pixels - no resampling - so saved annotations are pixel-perfect even on retina captures.
  • Pair with the Image Carousel (Cmd+Y / Ctrl+Y) to flip through staged images and annotate each in turn.
  • For long-form markup (mockups, design feedback), draw with Streamline turned up to ~0.7 - it gives surprisingly clean lines from a regular trackpad.
  • Hold Shift while drawing with the Pen to snap the stroke to a straight line - handy for underlines, crop guides, or connecting two points cleanly.
  • The clipboard copy flow is the fastest way to share an annotated screenshot outside Maestro: open the lightbox on any past attachment, press Cmd+E, mark it up, then click the copy icon and paste anywhere.
  • To mark up a screenshot you just captured (without attaching it to a prompt first), copy it to the clipboard and press Opt+Cmd+E / Alt+Ctrl+E. Edit, save, and the result lands right back on the clipboard to paste wherever you need it.