How to keep a screenshot on top of every window on Mac

macOS has no “always on top” for pictures: a screenshot opened in Preview goes behind the next window you click. To keep one in view while you work, pin it with a capture app. In SimpleShot you press Pin on the thumbnail and the screenshot floats above every window, where you can move it, resize it, make it see-through or let clicks pass through it.

Updated November 2, 2026

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What people pin a screenshot for

Copying numbers from one app into another: a bank detail, a code, an address.
Rebuilding a design or a layout next to the original.
Following steps from a guide while you click through the real app.
Comparing a before and an after.

Pin a screenshot with SimpleShot

Take a screenshot with ⇧⌘4 (or open one from the Library).
Point at the thumbnail in the corner and click Pin. In the All-in-One bar (⇧⌘5) Pin is a button too.
Drag the pinned image anywhere. Scroll or pinch to resize it; ⌘+, ⌘− and ⌘0 work too.
Right-click it for Opacity, Lock (clicks go through it to the window below), Actual Size, Copy, Save, Edit or Close. Esc closes it.

SimpleShot is a free capture app for Mac. Pinned images are listed in its menu bar menu, with Unlock All and Close All, so a locked one is never stuck on screen.

Without an app

The nearest built-in trick is Split View or a second display: open the screenshot in Preview on one side and your work on the other. It works, but takes half the screen, and the picture can’t sit over what you are working on.

Questions

Can a Mac keep a window always on top?

Not for any app: macOS has no “always on top” setting. Apps can offer it for their own windows, as SimpleShot does for pinned screenshots.

How do I make a pinned screenshot see-through?

Right-click it and choose Opacity. With Lock on as well, clicks pass through it to the window underneath, so you can trace or compare.

How do I get rid of a pinned screenshot?

Click it and press Esc, or right-click › Close. A locked one: open the SimpleShot menu in the menu bar and choose Unlock All or Close All.

Can I pin more than one?

Yes. Pin as many as you need; each moves and resizes on its own.

Keep it in sight
while you work.