Pennywise Open Websites in Floating Window?

Pennywise does not open websites in a floating window. It is a screen annotation tool for Windows that lets you draw, highlight, and write over any application, but it does not have a built-in browser or a feature to embed web pages in an always-on-top overlay. If you need a floating browser window, you should use a different tool, and this article explains the options.

What Pennywise Actually Does

Pennywise is a free, open-source utility that places a transparent overlay on top of your screen. You can then draw lines, rectangles, arrows, and text with a stylus or mouse, which is useful for presentations, video tutorials, or online teaching. The overlay stays on top of all other windows until you close it, but it does not load any web content. The project is hosted on GitHub, and its official description focuses on screen annotation, not on browsing.

Because the overlay is purely graphical, it cannot render HTML, JavaScript, or any interactive content. If you try to “open a website” in Pennywise, you would only be drawing over the screen, not actually navigating a page. The confusion often comes from the name, which sounds like it could be a browser, but it is unrelated to web browsing.

Why People Want a Floating Browser Window

A floating browser window is a small, always-on-top web view that stays visible while you work in other applications. Common uses include:

Watching a video or live stream while taking notes in a word processor.
Keeping a reference page (like a dictionary or API docs) open next to a code editor.
Monitoring a dashboard or chat while working in a spreadsheet.
Following a tutorial while practicing in another app.

Pennywise is sometimes suggested in forum threads about this, but it is the wrong tool. The overlay does not have a URL bar, a back button, or any way to load a page. You would need to draw a rectangle and then switch to your actual browser, which defeats the purpose.

How to Get a Floating Browser on Windows

If you want a genuine always-on-top browser window, you have several practical options. None of them are built into Pennywise, but they are easy to set up.

Use your existing browser with an always-on-top extension. Chrome and Edge have extensions like “Always on Top” or “Popout” that let you set a specific tab or window to stay above other windows. You simply click the extension icon, and the browser window becomes pinned.
Use the Picture-in-Picture feature for videos. If your need is specifically video, most browsers support a native picture-in-picture mode. Right-click on a video twice (or use the dedicated button) and select “Picture in Picture” to get a small floating player that works even when the browser is minimized.
Use a dedicated floating browser app. There are small, open-source tools like “Floating Browser” or “Mini Browser” that are designed for this exact purpose. They are lightweight, always-on-top, and often have a transparent background option.
Use a desktop widget or gadget. Some Windows widgets (like those from the Windows 11 widgets panel) can display web content, though they are limited to approved providers.

If you prefer not to install anything, you can also manually resize your browser window and use Windows’ snap features to place it side-by-side, but that is not truly “floating” above other windows.

Common Problems and Misconceptions

The most common problem is that people install Pennywise expecting a browser and then cannot find how to enter a URL. There is no such field. Another misconception is that the overlay can interact with the underlying page, but it cannot. It is just a drawing layer, so clicks pass through to the application below, which means you cannot scroll a website inside the overlay.

If you have already installed Pennywise and want to use it for its actual purpose, remember that you can adjust the overlay’s opacity and color in the settings. To close it, you usually press the hotkey (often Ctrl+Alt+D or similar) or click the tray icon. The overlay does not save your drawings unless you take a screenshot, which is a separate feature.

Another issue is that Pennywise may not work on all Windows versions or with certain graphics drivers. If the overlay does not appear, check that you have the latest version and that your graphics drivers are up to date. This is a common troubleshooting step for any screen annotation tool.

Alternatives to Pennywise for Floating Web Content

If you are open to other tools, here is a quick comparison of what each one does:

Pennywise – Screen annotation only, no web browsing.
Always-on-top browser extensions – Pin any tab or window above others; works with your existing browser.
Picture-in-Picture – Built into browsers, only for video, not full web pages.
Dedicated floating browser apps – Purpose-built, often with adjustable transparency and size.
Windows PowerToys – A Microsoft utility that includes an “Always on Top” feature for any window, including your browser. You press a shortcut (default Win+Ctrl+T) to pin the active window.

PowerToys is particularly useful because it works with any application, not just browsers. You can pin your browser window, then switch to another app, and the browser stays visible. This is the closest to a native solution without installing a separate browser.

Safety and Privacy Considerations

When using any floating browser, be aware of what you display. If you are screen-sharing or recording, a floating window can accidentally show sensitive information like email or banking pages. Always check what is visible before presenting.

Also, be cautious with third-party floating browser apps. Some may be ad-supported or request unnecessary permissions. Stick to well-known open-source projects or official browser extensions. For Pennywise itself, it is open-source, so you can inspect the code if you are concerned, but it does not handle any web content, so there is no risk of it tracking your browsing.

Finally, if you are using a floating browser for work, make sure your employer allows it. Some corporate environments restrict always-on-top tools because they can interfere with screen capture or remote desktop sessions.

Frequently Asked Questions

Can I use Pennywise to browse the internet?

No. Pennywise is a screen annotation tool. It does not have a browser engine, so it cannot load or display websites. You can only draw over your screen.

How do I make my browser always on top without a separate app?

Use your browser’s built-in picture-in-picture for videos, or install an extension like “Always on Top” for Chrome or Edge. For any window, you can also use Microsoft PowerToys’ Always on Top feature (Win+Ctrl+T).

Is there a floating browser that is free and safe?

Yes. Microsoft PowerToys is free and open-source. Also, browser extensions from official stores are generally safe. For a dedicated floating browser, look for open-source options on GitHub with a good number of stars and recent updates.

Why does Pennywise not have a URL bar?

Because it is not a browser. Its purpose is to let you draw on the screen, not to navigate the web. The absence of a URL bar is by design, not a bug.

Can I click links inside a Pennywise overlay?

No. The overlay is transparent to mouse clicks, so clicks pass through to the application below. You cannot interact with any web content because there is none.

What is the best way to watch a video while working?

Use the picture-in-picture mode in your browser. It is built-in, free, and works with most video sites. You can resize the floating video and move it anywhere on your screen.

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