How to Fix: Windows 10 Keeps Asking: 'How do you want to open this file?'

Dennis Faas's picture

Infopackets Reader Leonard C. writes:

" Dear Dennis,

I just upgraded to Windows 10 recently. Every time I click on a link in my emails, Windows 10 keeps asking me 'How do you want to open this file?'. It gives me three choices: 'Internet Explorer', 'Microsoft Edge', and 'Look for an app in the store'. How can I get rid of this annoying window? I am currently using Microsoft Outlook 10 as my email program and I use Internet Explorer to browse the web. "

My response:

If you are running Windows 10 and if you ever come across the window which says: "How do you want to open this file?", it is because a file association is not set for a specific file type. For example, a common file sent through email is a Portable Document File (.PDF). The default .PDF file reader for Windows 10 is Microsoft Edge. In this case, the PDF file is the "file type", and its "file association" is Microsoft Edge.

How to Fix: Windows 10 Keeps Asking: 'How do you want to open this file?'

To avoid seeing the message "How do you want to open this file?", you will need to specify the program you want to use as the default, then make Windows 10 remember that file association permanently so it doesn't keep asking you "How do you want to open this file?".

To do so:

  1. Open a file which invokes the "How do you want to open this file?" window.
  2. Scroll through the list of programs in the list available to you. If you don't see the correct program, scroll all the way down the list until you see a link which reads: "Look for another app on this PC". You will then need to manually scroll through your "c:\program files" or "c:\program files (x86)" directory(s) to choose the appropriate program. Once that has been done, you will be taken back to the "How do you want to open this file?" window.

    NOTE: if you scrolled through the "How do you want to open this file?" file list AND the "c:\program files" AND "c:\program files (x86)" directories AND you still don't see the proper program you want associated with your file: you may need to launch your web browser, then download and reinstall the appropriate program. For example: if I am trying to open a .PDF file and I want to use Foxit Reader as the default program, but Foxit Reader does not appear to be installed, then I would have to go online and search for Foxit Reader, download it, then reinstall it. Usually reinstalling a program will automatically reinstate its file association(s).
  3. One you have selected your default program, scroll all the way down the "How do you want to open this file?" window, and (!important!) check mark the box that says: "Always use this app to open [filename extension] files" (pic). Doing this last step will prevent Windows 10 from repeatedly asking you: "How do you want to open this file?"

Other Ways to Set File Associations in Windows 10

There are two other ways you can set file associations in Windows 10.

  1. Click Start, then type in "default programs" (no quotes), then scroll through the list and set the program. The only problem with this method is that you won't get the option to "Look for another app on this PC" if you don't see the program you're looking for. As such you might want to try option #2 below.
  2. Another way to set a file association is to browse the file using Windows Explorer, then right click the file, then select "Open With" option (pic) and then either select from the list of available choices, or select the option "Choose another app." In the latter option, you will then need to manually locate the program manually using Windows Explorer. If you still can't find the correct program to be associated with tie file, then you may need to launch your web browser, download the program and reinstall it.

I hope that helps.

Additional 1-on-1 Support: From Dennis

If all of this is over your head, or if you have a file that isn't opening up with program properly and you need additional support, you are welcome to contact me for remote desktop assistance. Simply send me a brief message describing your problem and I will get back to you as soon as possible.

Got a Computer Question or Problem? Ask Dennis!

I need more computer questions. If you have a computer question - or even a computer problem that needs fixing - please email me with your question so that I can write more articles like this one. I can't promise I'll respond to all the messages I receive (depending on the volume), but I'll do my best.

About the author: Dennis Faas is the owner and operator of With over 30 years of computing experience, Dennis' areas of expertise are a broad range and include PC hardware, Microsoft Windows, Linux, network administration, and virtualization. Dennis holds a Bachelors degree in Computer Science (1999) and has authored 6 books on the topics of MS Windows and PC Security. If you like the advice you received on this page, please up-vote / Like this page and share it with friends. For technical support inquiries, Dennis can be reached via Live chat online this site using the Zopim Chat service (currently located at the bottom left of the screen); optionally, you can contact Dennis through the website contact form.

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TG2's picture

Dennis, contrary to belief sometimes microsoft just doesn't do what it should.

Case in point .. I click on an AVI file ... and even though I already have .avi associated with VLC Media Player ... it continues to prompt me.

Part of this issue can be Microsoft trying to offer you "new" apps that can play the content (eg. you have a new app installed .. prompt) And its possible that microsoft is tweaking this function to not show you the words "New App Installed" but even in the screen when its "broken" that it clearly sees (my case) VLC is installed and is associated, but prompting me anyway.

The ambiguous window adds to the confusion on what triggered the "extension" and in business situations is often *not* wanted. Your admin's installed X .. that's what they want you to use.. regardless of the latest swiss knife of microsoft apps.