Neither macOS nor Windows has a built-in way to pin a screenshot so it floats above your other windows. On a Mac, the thumbnail that appears after ⌘⇧4 slides away after a few seconds, and Preview has no “float on top” option. On Windows, Microsoft’s free PowerToys adds Always On Top (Win+Ctrl+T), which pins whatever window is active, so you can open the screenshot in Photos and pin that window. To pin the image itself, frameless and resizable, use a screenshot app with a pin feature: in hypershot, open the capture in the editor and click the pin button in the export pane.

The built-in way

Mac

There isn’t one for images. macOS has no always-on-top switch for ordinary windows, and none of the screenshot pieces stay put:

  • The floating thumbnail after a screenshot is a few-second preview. Hovering keeps it on screen only while your pointer stays on it.
  • Preview windows go behind whatever you click next, like any other window.

The workarounds are layout, not pinning: put the screenshot in Preview on a second display, or tile Preview next to your working app with the green window button. Both work. Both cost you a chunk of screen for a window that’s mostly title bar and toolbar around a small image.

Windows

  1. Install Microsoft PowerToys and make sure Always On Top is enabled in its settings.
  2. Open the screenshot in Photos (or any image viewer).
  3. Click the viewer’s window and press Win+Ctrl+T. A colored border shows it’s pinned.
  4. Press Win+Ctrl+T again on that window to unpin it, or close the window.

This is a good, general tool, and it does exactly what it says: it pins a window. The image comes with the viewer’s title bar, toolbar and minimum window size, and you’re resizing an app window rather than the picture. Microsoft also notes some topmost windows, like Remote Desktop or VMware, can still cover it.

With hypershot

hypershot pins the capture itself, as a borderless image that stays above everything else (pin to screen).

  1. Take the capture, for example a region with ⌘⇧2 on macOS or Ctrl+Shift+3 on Windows, and open it in the editor (click Edit on its card in the preview folder).
  2. Mark it up if you want. Arrows, highlights and redactions come along.
  3. Click the pin button: the last button in the export pane, the bar on the editor’s left edge, below a divider.

The pin appears in the middle of your main screen at its actual on-screen size, 1:1 with your display, shrunk to fit if it would cover more than 80% of the screen. From there:

  • Move it: drag anywhere on the image.
  • Resize it: on macOS, drag any edge or corner, and it keeps its aspect ratio. On Windows, click the scale pill at the bottom and pick 10%, 25%, 50%, 100% or 200%.
  • Lock it: hover, click Lock, and it stops moving or resizing, so you can click right next to it without nudging it.
  • Use it: the hover bar has Copy (to the clipboard) and Drag (into another app). Close is in the top-right corner.

Until you hover over it, the pin shows nothing but the image; then the controls appear. On very small pins the side bar and scale pill hide so they don’t cover what you’re looking at.

What people pin

  • Numbers to retype: a confirmation code, an invoice total, an IBAN you need in a form in another app.
  • A design reference while you build the thing it shows.
  • An error message while you search for it or dig through the code.
  • Before, while you work on after.
  • Instructions from someone else’s screen while you follow them in your own.

Good to know

  • One pin at a time. Pinning another capture replaces the current one.
  • It outlives the editor. Close the editor and the pin stays.
  • It doesn’t survive a restart. Pins last until you close them or quit hypershot. The capture itself is already saved as a .hypercapture in your save folder, so you can reopen it and pin it again.
  • Scale settings don’t apply. A pin is always the whole artboard at 100%, whatever the export pane is set to.

Questions people ask

Can I pin a screenshot without opening the editor?

No, pinning starts from the editor’s export pane. If you pin often, set Settings → Captures → After capture to Edit so every capture opens straight in the editor and the pin button is one click away.

Can I pin more than one?

One at a time. If you need two references side by side, copy one and paste it into the other in the editor (it lands as an image you can move and resize; widen the artboard with B if it needs the room), then pin the result. Or pin the one you look at most and keep the other in the preview folder.