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 pencil 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.

A note on the menu bar icon: a normal click opens your clipboard image immediately — that's the fast path. To reach the menu (Past Sessions, Settings, Help), right-click the icon or hold ⌥ while clicking.

Getting an image in

There are several ways to get something to draw on, and none of them require special permissions except the last one.

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.

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.

New Screenshot. Takes the shot from inside the app (menu bar ▸ New Screenshot). This is the only path that needs Screen Recording permission — see Troubleshooting if it asks and won't proceed.

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.

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.

If you close a window with unexported changes, you'll be asked first — and "Copy & Close" does both in one click. Sessions are kept afterwards anyway (see "Past sessions").

Past sessions

Draw On Clipboard saves continuously while you work — you never have to. If the app quits, crashes, or you close a window by accident, the work is still there.

To get back to it: right-click the menu bar icon ▸ Past Sessions ▸. That lists your most recent sessions newest-first, each with its size, when you last touched it, and how many steps it has. Ones that were interrupted rather than closed cleanly are tagged "· recovered". Pick one and it reopens exactly where you left off — full timeline, even the step you were viewing.

If something crashed, you'll also be offered the recovered sessions the next time you open a window.

How long they last: 14 days. Work you never exported is never removed early to save space — only sessions whose exact contents you already exported can be trimmed, and only past 50 of them.

Where they live: ~/Library/Application Support/Draw On Clipboard/Sessions. Each is a .docsession bundle you can double-click in Finder to reopen, or move somewhere safe if you want to keep it beyond 14 days.

Your data and privacy

Your drawings, screenshots, clipboard contents, and sessions stay local. No accounts, sync, or analytics. Network access occurs only when you explicitly submit feedback, open My Reports, or open More Apps. Feedback sends only the text you enter plus compatibility facts shown for review; it never sends images, paths, files, logs, or clipboard contents. More Apps sends only those compatibility facts and runs only when opened.

What's stored on your Mac:

• Sessions — ~/Library/Application Support/Draw On Clipboard/Sessions (kept 14 days). These contain the original image, including anything you've redacted, so undo can work.

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

• Private feedback receipts — opaque report capabilities used only when you open My Reports.

• 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 to export by dragging

Troubleshooting

"New Screenshot" says it needs Screen Recording permission.

Taking a screenshot from inside an app requires that permission from macOS. Turn on Draw On Clipboard in System Settings ▸ Privacy & Security ▸ Screen Recording, then quit and reopen Draw On Clipboard. If it already looks enabled, switch it off and on again — a stale grant can linger after an update. You can skip all of this by capturing with ⌃⇧⌘4 and clicking the menu bar icon instead; that needs no permission.

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. Check the top of the menu — it always says what's currently on your clipboard.

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?

Nowhere — see "Past sessions". Right-click the menu bar icon ▸ Past Sessions.