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.

Update 20171105: yet another scenario is somewhat similar to above, except that you don't know which program is causing the "How do you want to open this file?" request, and these popups seemingly appear at random. In this case, I will explain another approach further down (solution #2).

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

Solution #1: You know the program causing the popups

If you know the program responsible for the "How do you want to open this file?" popup notifications, then you can easily and permanently set the file association using Windows 10.

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.

Solution #2: You don't know the program causing the popups

In a situation where you are receiving a barrage of popups asking "How do you want to open this file?" it's because (a) a file association for a particular program has not been set (as discussed in Solution #1), and (b) you don't know which program is causing this to happen in the first place.

In this case, you will need to do little bit of detective work. When you receive the popup question "How do you want to open the file?" look at the bottom of the requestor window - it will say "Always use this app to open [SOME FILE EXTENSION]". See this image as an example which is asking for a file association for .FLV files.

Once you know the extension, go to Google and type in "flv file extension" (for example) and it should tell you what programs are associated with that extension. After that, you can click Start -> Control Panel, then to Programs and Features, then look for a program related to the .FLV extension (example: a media player, or flash player, etc) and try uninstalling it. If the popups go away, you've solved the riddle.

Yet another possibility! is that you are infected with a virus, which is attempting to open a randomly generated file which then causes the system to keep asking you "How do you want to open this file?" - yet there is no known file extension because the extension is random. Solving this can be tricky at best - I suggest you do a virus scan and if that doesn't fix it, you can always send me an email and I can look at it using my remote desktop support service.

Additional 1-on-1 Support: From Dennis

If all of this is over your head, or if you are still having issues with "How do you want to open this file?", 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.

Rate this article: 
Average: 2.8 (20 votes)


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.


tirespider_10352's picture

I had this problem which is how I came to find this page. In my case it was an .html file created at the time of last Win10 reinstall. It is understandable that between then and the point Chrome was reinstalled that Windows would ask which app to use to open it. But the file claimed to be 'Type: Chrome HTML Document' in the popup box. So if it's Win10 telling me this, why doesn't Win10 know this? I guessed that it wasn't Win10 at all telling me this, but something else. So I looked at installed apps and, surprise, it showed Skype had been installed yesterday. By removing Skype the problem appears to have gone away. However, it makes me think that future messages like this should be thought of to contain more information than one knows. I've saved a screenshot of the message as a note to myself with the comment, "MS could be telling you something; check apps list for new clutter."

drewplanner_11119's picture

Every time I try to open a PDF from Microsoft Outlook (windows 10), the popup appears and asks how to open the program. Even if I check the "always use this program" box, it still pops up every single time.

It says:

Keep using this app: Adobe Acrobat

Features in Windows 10: Microsoft Edge

Other Options: lists some random programs

Always use this app to open PDF files.

Every single time. I have tried numerous things such as turning off Microsoft edge in default programs and apps settings, turning it off in other settings. Making sure Adobe is still the default program for PDF's etc. Nothing seems to work.

ITKevinFromIrvine's picture

Hello Drew,

Have you tried re-installing/ repairing outlook?