The Keep on top button you see in Windows Calculator or on a Clock timer is not a Windows-wide setting. It is a feature each app has to build in, using a picture-in-picture view called compact overlay, so most apps simply do not have it. To keep any other window above your work, you need a pinning tool: PinPoint from Automata Labs pins any app window with a hotkey, and its auto-pinning rules re-pin the apps you choose every time they launch.
Pin the windows that have no Keep on top button, and keep them pinned after every relaunch.
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What does the Keep on top button actually do?
When you select Keep on top in Calculator, the app switches into a special window mode that Microsoft calls compact overlay. Microsoft introduced it in the Windows 10 Creators Update and described it on its developer blog in a post titled CompactOverlay mode, aka Picture-in-Picture:
“When an app window enters compact overlay mode it’ll be shown above other windows so it won’t get blocked.”
The same post names the use cases it was designed for: “The canonical example of an app taking advantage of this feature is a media player or a video chat app.” It also lists what happens to a window when it switches into this mode:
- It “will most likely become smaller” than it was.
- It “will be moved to the top-right corner area of the screen.”
- When you click away from it, “the title bar will disappear.”
Microsoft’s API reference for ApplicationViewMode defines the mode in one line: “The app window is in a compact overlay (picture-in-picture) mode.” Newer apps built on the Windows App SDK get the same thing through a CompactOverlayPresenter, which “displays an app window using a CompactOverlay (picture-in-picture) configuration.”
So the button is a doorway into a small, app-designed mini view. It is not the same thing as making the full window stay on top.
Which built-in Windows apps have a Keep on top button?
Only a handful, and each one documents it in its own way.
| App | Where the button is | Shortcut | Notes |
|---|---|---|---|
| Calculator | Standard mode, Keep on top | Alt+Up arrow to turn on, Alt+Down arrow to turn off | Microsoft Support documents both shortcuts |
| Clock (Timer) | Keep on top on a running timer | None documented | A Microsoft Q&A answer says the size of this view cannot be changed |
| Web browsers | Picture-in-picture on a playing video | Varies by browser | A browser feature for video, not for whole pages |
Microsoft’s Calculator help page puts it simply: “You can pin Calculator so it stays visible while you use other apps.” The steps are to switch to Standard mode, then select Keep on top or press Alt+Up arrow, and to turn it off with Keep on top or Alt+Down arrow. Because the option belongs to Standard mode, it disappears when you switch to Scientific or Programmer mode. That is a common reason people think the feature has gone.
The Clock app’s timer has a similar Keep on top view. In a Microsoft Q&A thread from January 2025, a user complained that the view had grown much larger after an update, and an independent advisor replied: “There is no way to decrease or increase the size of the Keep On Top option.” That is the trade-off of compact overlay. The app decides what the mini view looks like, and you get what it gives you.
For video, browsers have their own picture-in-picture players. We compare that approach with pinning a whole window in PinPoint vs browser picture-in-picture.
Why can’t every app have a Keep on top button?
There are three reasons, and none of them is that the developer forgot.
It is opt-in. An app has to add a button, check whether the mode is available, and then ask Windows to switch. Microsoft’s blog post walks developers through exactly that: show the button only if IsViewModeSupported(ApplicationViewMode.CompactOverlay) returns true, then call TryEnterViewModeAsync. If the developer does not write that code, there is no button.
It is not available everywhere. The same post warns that compact overlay “is not necessarily supported across all Windows devices and interaction modes,” which is why apps are told to check first.
Store-style apps cannot simply set topmost. Classic desktop programs can mark their own window as topmost. Apps built on the Universal Windows Platform cannot. In a Microsoft Q&A answer, a Microsoft staff member wrote: “Unlike desktop applications, UWP currently cannot set TopMost for Pages,” and pointed to compact overlay as the alternative. That is why Store-style apps such as Calculator use a mini view instead.
Most of the apps you actually want on top, such as a PDF viewer, a browser window with documentation, Excel, a chat app or a terminal, are desktop programs that never added either option. For those, the decision has to come from outside the app.
Is compact overlay the same as always on top?
No. They solve similar problems in different ways.
| Compact overlay (Keep on top button) | Always on top (pinning tool) | |
|---|---|---|
| Who turns it on | The app, from its own button | You, from a hotkey or rule |
| Which apps | Only apps that built it in | Most normal desktop windows |
| Window size and layout | A mini view the app designs | The full window, at the size you choose |
| Position | Starts near the top-right corner | Stays where you put it |
| Works with Calculator Scientific mode | No, Standard mode only | The whole window stays on top |
| Survives closing the app | The app decides | Depends on the tool; rules can re-pin on launch |
Always on top uses a different Windows mechanism, the topmost window flag. If you want the details of how that flag behaves, and why two topmost windows can fight, see our guide to always on top not working on Windows 11.
How do I keep an app without a Keep on top button on top?
You have two good routes.
PowerToys Always On Top. Microsoft’s free PowerToys Always On Top pins the active window with Win+Ctrl+T by default: “the utility pins the active window above all other windows.” Microsoft is also clear about its limit: it “can’t guarantee that the window will be above other topmost windows.” It is a manual pin, so you press the shortcut again each time you need it.
PinPoint. If you pin the same apps every day, PinPoint turns the pin into a rule. According to its Microsoft Store listing, it offers:
- A customizable global hotkey to pin any application window always on top.
- Intelligent Auto-Pinning, where you select an app from your active process list and PinPoint locks it to the foreground when it launches.
- Workspace Pin Profiles, so you can save layouts for contexts such as “Trading,” “Research,” or “Development” and swap between them with a single click.
- Custom visual borders in the colors and thicknesses you choose, so you can see at a glance what is pinned.
- Application exclusion rules, so utility panels and system alerts do not interrupt your focus zones.
- Timed countdown release, which unpins windows when a task duration you set runs out.
- Audio feedback for pin and unpin, and multi-window support.
- A small, offline footprint, with no account, no telemetry and no cloud dependency.
Give every app the Keep on top button it never had, with rules instead of repeated shortcuts.
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What is the fastest way to set this up?
- Use the built-in button where it exists. For quick sums, Calculator in Standard mode with Alt+Up arrow is hard to beat.
- List the apps you pin every day. Common ones are a PDF of instructions, a chat window, a video call, a terminal and a notes app.
- Create a PinPoint auto-pin rule for each. Pick the app from the process list once, and it is pinned whenever it starts.
- Group them into a profile if your day has distinct modes, so one click changes the whole set.
- Pick a border color so pinned windows are obvious, especially across monitors.
- Add exclusions for small helper windows you never want to cover your work.
For more setups, see our always on top guide for Windows 11 and the PinPoint vs PowerToys comparison.
Frequently asked questions
Why did Keep on top disappear from Calculator?
Keep on top is only in Standard mode. Switch Calculator back to Standard and the button returns, along with the Alt+Up arrow shortcut.
Is there a Windows setting to make any app stay on top?
No. Windows has no system-wide setting for this. Apps either build in their own option, such as compact overlay, or you use a pinning tool.
Can I resize the Clock app’s Keep on top timer?
According to an answer on Microsoft Q&A, no. The app controls the size of its compact view.
Does compact overlay work for any window?
No. Only apps that were written to use it can switch into it, and Windows may not offer it on every device or interaction mode.
Does PinPoint need an internet connection?
No. Its Store listing says it runs offline on your PC with no account and no telemetry.
Try PinPoint
Get PinPoint from the Microsoft Store. It is a one-time purchase with no subscription, and the Store listing shows the current price.
Pin any window on top, automatically, every time it opens.
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Microsoft, Windows and PowerToys are trademarks of the Microsoft group of companies. PinPoint is not affiliated with or endorsed by Microsoft.
Last updated 21 October 2026. Published by Automata Labs, a software company in Canada.