User guide for macOS

Getting started

Draw On Clipboard lives in your menu bar. The whole loop is three steps:

1 — Capture. Press ⌃⇧⌘4 and drag over any area. That copies it to your clipboard. (Plain ⇧⌘4 saves a file instead — that works too, see "Getting an image in".)

2 — Open it. Click the Draw On Clipboard icon in the menu bar, or press ⌃⌥A. Your capture opens ready to draw.

3 — Send it back out. Mark it up, then hit Copy (⌘C) and paste it wherever you were going — Slack, Mail, a doc. Or Save, Share, or drag it out.

That's it. Everything else in this guide is optional depth.

Menu-bar menu: Right-click or ⌥-click the app icon. Its five commands, in order, are Annotate Clipboard, Blank Image…, Settings…, Manage Past Sessions…, Quit Draw On Clipboard. Manage Past Sessions is directly below Settings. A normal click still opens your clipboard image immediately. The same manager is also available in File and Settings.

Language and help: when Draw On Clipboard is the active app, use the globe menu after Help to choose a language or Follow System Language. Built-in Help changes with the app. Choose Help ▸ Send Feedback… to report a bug, suggest an improvement, or request a language. My Reports… is also in Help. More from HumansAreUseful… and About are in the Draw On Clipboard app menu.

Open at login: On first launch, choose Open at login to keep the app ready in your menu bar when you sign in, or Not now to leave it off. You can change this later in Settings. If macOS asks for approval, use Open System Settings to review the login item. A failed request does not enable it; retry or choose Not now.

Getting an image in

Use an image from the clipboard or a file, or start with a blank canvas. For a new screenshot, use the macOS keyboard shortcuts, then bring the image into Draw On Clipboard.

From the clipboard (the main way). Copy any image — ⌃⇧⌘4, "Copy Image" in a browser, a copied file in Finder — then click the menu bar icon or press ⌃⌥A.

Already have an empty window open? Return to it to check the current clipboard, then choose Load Clipboard Image. Returning never replaces an image you are editing.

Open File… (⌘O). PNG, JPEG, TIFF, HEIC, GIF, WebP, or the first page of a PDF. You can also open a saved .docsession to resume past work.

Drag and drop. Drop an image file onto an empty Draw On Clipboard window.

From Finder. Right-click an image ▸ Open With ▸ Draw On Clipboard.

Blank Image… No screenshot involved — start on a white page. Pick Small, Medium (landscape or portrait), or Large square. It's in the File menu, in the menu bar icon's menu, and on the empty window.

Multi-frame files (animated GIFs, multi-page PDFs/TIFFs) load the first frame and tell you so.

Drawing tools

Every tool has a one-key shortcut. The current tool is highlighted in the toolbar.

V — Select. Click an object to select it. Drag to move, drag a corner handle to resize, ⌘D to duplicate, ⌫ to delete, arrow keys to nudge. Changing the color or width while something is selected restyles it.

P — Pen. Freehand. A single click makes a dot.

H — Highlighter. Translucent, multiplies with what's underneath, like a real marker.

L — Line · A — Arrow · R — Rectangle · O — Ellipse. Drag to draw. Shapes are outline-only.

T — Text. Click to place a box and start typing. Return commits it; Esc cancels; ⌥Return makes a new line. Text automatically gets a subtle outline so it stays readable on any background.

N — Numbered badge. Click to drop 1, 2, 3… They renumber themselves automatically if you delete one.

X — Redact. See "Hiding sensitive things".

C — Crop. Drag a box, then Return to apply or Esc to cancel. A crop is just another step, so you can undo it later.

Hold ⇧ to constrain: lines and arrows snap to 45°, rectangles and ellipses become squares and circles.

Color and width are in the toolbar; the dot next to the slider previews your current stroke width. Both are remembered between sessions.

Zoom with ⌘+ / ⌘− / ⌘0, or pinch on a trackpad. Zoom only affects your view — exports are always full resolution.

Accessibility and non-pointer editing

Draw On Clipboard supports VoiceOver, Voice Control, Full Keyboard Access, Increase Contrast, Differentiate Without Color, and Reduce Motion.

Create without pointing. Choose any drawing tool, then choose Add [tool] at Center. The new annotation is selected automatically.

Edit without hit-testing pixels. Use Annotations to choose an object. The nearby native controls move it by 10 pixels, resize supported objects, edit text, duplicate, or delete. For crop, use Apply or Cancel.

Understand the canvas. VoiceOver reports the image size, annotation count, selected object, true color names, and export state. Selection is shown by shape and status as well as color.

Export without dragging. The export chip is a button: focus it and press Return or Space to open Save As. Copy, Save, Share, and every timeline frame are keyboard reachable.

If something still blocks you, send Feedback from Help. Accessibility defects are release-blocking for us.

Browse past work without pointing. Open Manage Past Sessions… from File, Settings, or the icon’s menu. Select a session in the left list with the arrow keys. Focus a history thumbnail, then use Left/Right to preview neighboring steps. VoiceOver announces the step name and the Left off here / Last copied markers. A checkmark and focus outline identify the selected step without relying on color. Copy and Save have their own buttons; Escape closes the manager.

Hiding sensitive things

The X tool covers an area. There are two styles, and the difference matters:

Solid (default). A flat opaque block. Nothing can be recovered from it. Use this for passwords, tokens, account numbers — anything that actually matters.

Pixelate. Chunky blocks that still hint at the underlying shape. It looks tidier, but for known text in a known font, pixelation can sometimes be reversed by an attacker. It's fine for faces or general clutter; it is not the right choice for secrets.

What's guaranteed in exports: every image you copy, save, share or drag out is a flattened render. The hidden pixels are genuinely gone from it — not layered underneath — and exports carry no embedded thumbnail, no leftover metadata, and no hidden trailing data. (That last part is the flaw that famously leaked "cropped" screenshots in other tools; it's excluded here by construction and covered by an automated test.)

One honest caveat: while the session is still open or saved, the original un-redacted image is kept in that session's autosave so you can undo. It lives only on your Mac, but it will also be in any backup (Time Machine) that copies it. If a capture is sensitive enough that this bothers you, use File ▸ Delete Session Now — that erases the session's saved data immediately and stops it being saved further.

History, undo, and forking

The strip under the toolbar is your history. Every change is one frame, oldest on the left, starting with "base" (the untouched image).

Undo / Redo. The two arrows in the toolbar, or ⌘Z / ⇧⌘Z.

Jump anywhere. Click any frame to rewind to that exact point. Hover over a frame for a moment to peek at it enlarged without committing.

Undo, then draw. Undo means the last change was a mistake, so drawing again replaces the undone steps automatically — no extra question.

Click a frame, then draw. Choosing an earlier timeline frame is deliberate version navigation, so Draw On Clipboard asks before anything is discarded:

• Fork to New Window — keeps both versions. The original window stays exactly as it is with all its steps, and your new direction continues in a fresh window. Nothing is lost.
• Replace Later Steps — discards the steps after the selected frame and continues here.

Frames after your current position appear dimmed, which is your cue that they're the ones at stake.

Whatever you're viewing is exactly what exports — if you rewind to step 3 and hit Copy, you get step 3.

The clipboard badge. After you Copy, a small orange clipboard mark appears in the corner of the frame you copied. Keep drawing and it stays put, so you can always see which version you last copied. Copy again and it moves to the new frame. (It marks what you copied from here — it can't know whether you've since copied something else in another app.) If you rewind and draw over the steps that were copied, that version no longer exists and the mark goes away.

Getting the result out

Four ways out, all producing the same full-resolution, faithful image (original scale, original colors — Retina captures stay sharp):

Copy (⌘C). Straight to the clipboard, ready to paste. This is the fast path.

Save… (⌘S). A file on disk. PNG by default, JPEG if you choose it. Defaults to your Desktop and then remembers wherever you last saved.

The first two are on the toolbar and also in the File menu, as Copy Image and Save Image….

Share. The standard macOS share sheet — AirDrop, Mail, Messages, Notes, and so on.

Drag out. Drag the small image chip at the right end of the toolbar straight into Finder, a chat window, or an email. Often the fastest route of all.

The status chip next to those buttons always tells you the truth about where things stand: "Not exported yet", "Copied ✓ 2:41 PM", or "Edited since export" if you've drawn something since. Hover it to see every export you've made in this session.

When a close warning appears, Copy & Close copies the result and closes the window in one click. You can resume the editable session later only if session backups are enabled (see “Past sessions”). Copies and saved images are separate from session backups.

Past sessions

When session backups are enabled, Draw On Clipboard saves while you work.

Browse visually: right-click the app’s menu-bar icon and choose Manage Past Sessions…, directly below Settings…. You can also open it from File or Settings. The left panel lists closed saved sessions, including interrupted work, newest first. Select a thumbnail; search by name or use All / Kept to narrow the list. Open editor sessions are not listed.

Inspect the result: use Fit to see the whole image or Actual Size for a closer view; scroll larger images. Dimensions, edit count, last-worked date, and retention status appear beside the preview. The history below has named steps: Left off here marks the saved viewing position, and Last copied marks the step last copied from this session—not necessarily what is on your clipboard now.

Choose a step: the preview starts where you left off. Select an earlier history thumbnail to inspect it. Browsing changes nothing. Open Selected Step resumes that step with later history intact; editing still asks before replacing later work. The manager closes only after Open succeeds. If that session is already open elsewhere, its editor comes to the front without changing the active work.

Retrieve an image: Copy Image and Save Image As… export the previewed step without opening an editor. Previews and these exports keep redactions hidden, even in earlier steps. The original remains inside the session so undo can work.

Name and keep: enter an optional name and choose Save Name. Use name search and All/Kept to find work. Keep protects a session from automatic cleanup while Keep is selected. Renaming, browsing, and Keep do not restart its age.

Automatic cleanup: unkept sessions expire 14 days after last work. Above 50 unkept closed sessions, fully exported ones may be removed sooner; unexported work is not removed early by that limit. Kept and open sessions are exempt. Removing Keep from an expired session requires confirmation.

Delete…: permanently removes the selected session’s original image and entire history after confirmation, including kept sessions. Exported files remain untouched. Clear All Data also includes kept sessions. Close leaves your work unchanged.

Everything stays local. For troubleshooting, use a session’s shortcut menu to show its actual location in Finder.

Your data and privacy

Your drawings, screenshots, clipboard contents, and sessions stay local. No accounts, sync, or analytics. My Reports and More Apps open from saved or bundled content without a network request. Choose Check for status or Check for new apps to request current information. Feedback sends your entered text and the compatibility facts shown for review, plus your email only if you choose contact by email. It never sends images, paths, files, logs, or clipboard contents. Checking available apps sends only compatibility facts. Managing a report’s contact information also requires an explicit network action.

What's stored on your Mac:

• Sessions — DrawOnClip/Sessions in the app’s Application Support directory. Use Settings ▸ Reveal in Finder to find the actual folder; the App Store build stores it inside its sandbox. Unkept sessions normally expire after 14 days; Keep protects them from automatic cleanup. Sessions contain the original image, including anything you have redacted, so undo can work.

• Preferences — your tool, color, hotkey, and window choices.

• Saved feedback — your submitted text and the private details the app needs for an explicit status check.

• Diagnostic logs — standard macOS logs, which age out on their own. They record that things happened, never your image contents or the text you type.

Files you export are yours. Draw On Clipboard never touches them again, and "Clear All Data" doesn't delete them.

To erase things:

• File ▸ Delete Session Now — wipes this session's saved data immediately (including the un-redacted original) and stops saving it. The window stays open so you can finish and export.

• My Reports ▸ Delete contact information — deletes a verified optional email address for that report.

• Settings ▸ Clear All Data — removes every saved session and resets preferences. It tells you exactly what will go before you confirm.

To remove the app entirely: drag it to the Trash, then delete the Sessions folder above and the app's preferences file.

Keyboard shortcuts

Getting started

⌃⇧⌘4 — capture an area to the clipboard (macOS)

⌃⌥A — open the clipboard image in Draw On Clipboard

⌘N — annotate clipboard · ⌘O — open a file · ⌘W — close window · ⌘, — settings · ⌘/ — this help

Tools

V select · P pen · H highlighter · L line · A arrow

R rectangle · O ellipse · T text · N numbered badge · X redact · C crop

⇧ (held) — constrain to 45° / squares / circles

Editing

⌘Z undo · ⇧⌘Z redo · ⌘D duplicate selection · ⌫ delete selection · arrow keys nudge

Return — apply crop / commit text · Esc — cancel crop, text, or selection · ⌥Return — new line in text

View

⌘+ zoom in · ⌘− zoom out · ⌘0 fit to window · pinch to zoom

Sending it out

⌘C copy · ⌘S save… · drag the toolbar chip, or focus it and press Return or Space to open Save As

Troubleshooting

How do I take a screenshot?

Use the macOS shortcut ⌃⇧⌘4, select an area, then click the Draw On Clipboard menu-bar icon to open the clipboard image. ⇧⌘4 saves a file instead; open it with Open File… or drag it into an empty editor. Draw On Clipboard does not capture the screen itself.

Nothing happens when I click the icon.

It opens whatever image is on your clipboard. If there isn't one, you'll get a window explaining how to capture. If an empty Draw On Clipboard window is already open, it comes to the front.

I can't find the menu.

A normal click on the icon annotates immediately. Right-click (or ⌥-click) the icon for the menu. If the icon is hidden behind the notch on a smaller MacBook, use ⌃⌥A instead.

A banner says autosaving is failing.

Usually a full disk. Copy your work out (the banner offers a button) and free some space.

Where did my work go?

Right-click the menu-bar icon and choose Manage Past Sessions…, below Settings; File and Settings offer the same command. Clear the name search, choose All, then Refresh. Check any editor windows that are still open: those sessions are not listed in the manager.

Session backups are off.

In Settings, enable Keep sessions on this Mac to save work for later. Turning backups off does not erase existing sessions, but new unsaved work cannot appear in the manager. Automatic cleanup still follows the rules in Past sessions; use Keep for work you want to protect.

A saved session will not open.

Choose Refresh to reload its current state. A newer session format may require a compatible app version. Missing or unreadable files are not automatically deleted just because loading fails. For troubleshooting only, use Settings ▸ Reveal in Finder or a session’s shortcut menu to locate the actual folder. If it still fails, report the problem from Help; do not attach private images or session files.