If Outlook keeps asking you How do you want to open this file for JPG, PDF, PNG, etc file types, even when you have made your choice clear, then see this fix.

If the How do you want to open this file keeps popping up in Windows 11/10, select the default app. If this does not work, use these fixes.

There are instances where users reports getting an error “File is open in COM surrogate” when trying to access or rename and edit a file on Windows Properties.

If you can't open a file on your computer, don't give up right away. These tricks will give you a fighting chance of accessing or recovering its contents.

Disabling File-Type Warnings Close the program you are using to open the file that gives you the "Always ask before opening this type of file" message, if it's currently running.

When a file extension is not associated with a program, however, you are prompted by a "How do you want to open this type of file" or "Windows can't open this file" dialog when you try to open it.