Customizing the “Open With” Menu on Windows 10 and 11
Ever right-click a file and see the “Open with” menu? Yeah, it’s pretty handy — until you realize your favorite app isn’t showing up there, or maybe you want to add a program manually. That’s where things get a little confusing. Honestly, it’s not super straightforward, and sometimes Windows makes it harder than it needs to be.
I got stuck trying to add my regular editors and tools, especially on the newer Windows 11 build — stuff just wasn’t appearing without a bit of tinkering. It’s not always obvious where to find settings or how to make Windows recognize new programs, especially with how many different menus, updates, or OEM restrictions come into play. And forget about it if your options are grayed out or missing entirely; sometimes the right settings are buried deep or require registry edits.
First things first: find the file type you want to customize
This sounds simple — just know the extension, like .xyz or .abc. But truthfully, Windows uses those extensions to distinguish file types, so if the file extension isn’t clear or is buried behind some obscure setting, you might be stuck. Check the file’s extension carefully — sometimes, a typo or rare extension throws things off. Once you’ve got that, you can start linking your program to it or just tell Windows to recognize that extension as one it can open.
If your app isn’t already associated with that extension, you might need to register it manually via the command line or tweak the registry. For most users, the easiest way to start is through “Open with,” but beware — the process isn’t universal and can be inconsistent depending on Windows version or OEM customizations.
How to add a program manually via “Open with”
Now, right-click any file matching that extension. The menu appears, and you go to “Open with”. Here’s where I ran into confusion — sometimes, only a handful of apps are shown. To add a new one, you need to click “Choose another app”. On Windows 11, I noticed you might have to click “More apps” or scroll to find the link “Look for another app on this PC”. It’s usually at the bottom, and honestly, it gets hidden pretty well sometimes, especially in newer builds.
Click that, and a file browser window pops up. Now, you have to find the executable (.exe) for your app. Typical locations are C:\Program Files\MyApp\myapp.exe, but depending on how you installed it, it might be in Program Files (x86) or somewhere else. If you’re lazy like me, right-click the shortcut of your program and select “Open file location”. That’ll jump straight to the folder where the executable lives, saving some navigating.
Once you select the correct executable, make sure to check the box “Always use this app to open .xyz files”. This step is important because it tells Windows to remember your choice for future files of the same extension. Otherwise, every time you open a file, Windows might revert to its default, which can be frustrating.
Finish up and see your new program in the list
Click “OK”. Windows should now remember this association and, more importantly, add your app to the “Open with” list for this file type. When you right-click that kind of file later, your program should show up right there, ready to go. Sometimes, the menu doesn’t refresh immediately. In my experience, restarting Windows Explorer (via taskkill /f /im explorer.exe then start explorer.exe) helps refresh the context menu nicely, but that’s not always necessary.
I’ve done this for multiple file types now, and it seriously saves a bunch of time — especially if you switch between editors like Notepad++, VS Code, or specific image viewers. Once set, it feels much more seamless, and you don’t have to dig through the default apps constantly.
Repeat for other extensions if needed
If you want your app to handle multiple file types, just repeat the process for each extension. Keep in mind, some extensions are registered differently or tied to default handlers managed by Windows. So, if things don’t seem to stick, you might need to tweak default app settings in Settings > Apps > Default apps. Or, if you’re comfortable with registry hacking, editing the keys under HKEY_CLASSES_ROOT can give more control.
But honestly, I’ve only needed to do that when things get really stubborn. For most, manually adding via “Open with” and then setting as default works pretty reliably — once you get the hang of it.
Tips based on my experience
Windows occasionally resets these associations after big updates or reinstalls. I’ve lost some custom links that way and had to redo everything. So, if your favorite apps disappear from the menu, don’t be surprised — it’s normal, but annoying. To avoid that, double-check the default app settings regularly or keep a backup of your preferred associations.
Another thing: navigating to find the right app can be a pain. Always verify you’re selecting the correct executable — I’ve accidentally linked to the wrong file or a suspicious-looking shortcut before, which can be risky. It’s easy to click “Open” too fast without double-checking, so take your time.
And if manual adding still fails, registry edits or third-party tools like Default Programs Editor can be helpful, but I try to avoid those unless absolutely necessary. Usually, the “Open with” method suffices if you’re patient.
Summary — what to double-check
- File extension matches the type you want to change.
- You’ve navigated to the correct app executable.
- Checked “Always use this app” to set the default.
- Refreshed Explorer if changes don’t appear immediately (with
taskkill /f /im explorer.exe). - Remember system updates might reset associations — revisit setup if things break after updates.
Hope this dragged-out explanation helps — it honestly took me way too long to figure this stuff out. But once it clicks, customizing the “Open with” menu can make life a lot easier. Good luck, and may your file associations stay put!