I discovered this problem after updating to Windows 10 version 19045.4355 on three separate PCs. I've also found it affects at least three Windows app packages: Snip & Sketch, Calculator and Sticky Notes. A right-click and a click on any entry in the 'Tasks' list such as "New snip", "Date calculation" or "Show all notes" respectively, throws up the "How do you want to open this file?" window.
In the case of Snip & Sketch, apparently it wants to know how to open the file type ".Microsoft.ScreenSketch_8wekyb3d8bbwe!App". I guessed I might solve this as I have in the past with more normal file extensions such as .log by navigating to an appropriate .exe file somewhere in C:\Program Files (x86)\ or System32 or wherever. So (after finding the .exe via Task Manager, Details, 'Open file location'), I clicked "More apps" and tried to navigate directly to "C:\Program Files\WindowsApps\Microsoft.ScreenSketch_10.2008.3001.0_x64__8wekyb3d8bbwe\ScreenSketch.exe" but hit permissions problems and I didn't want to mess with the ownerships.
Looking in the Microsoft store results in "No results found There is no result for this extension".
I tried checking default apps and protocols, app Reset, uninstall with PowerShell and reinstalling, running sfc and dism checks, rebooting trying different user logins all to no avail. And I didn't really want to try a complete repair/install of Windows from an ISO.
It's astounding that Microsoft seem to be oblivious to this annoying bug.
At one stage I had Adobe Acrobat selected by mistake and clicked OK and after a right-click and "Take a new snip", ended up with the full Adobe Reader window popping up, displaying its own error message "error opening file" or similar. So now I had to close the error message and main Adobe window before proceeding with the screenshot which was very annoying.
After about three weeks pondering and fruitless searches for solutions (this is the first place I've found that talks about it) and lots of thinking about file types, protocols and registry entries, more by luck than judgement, I stumbled upon a fix by modifying the registry with a reg file as follows:
Windows Registry Editor Version 5.00
[HKEY_CURRENT_USER\SOFTWARE\Classes\ScreenSketch_8wekyb3d8bbwe!App_auto_file]
[HKEY_CURRENT_USER\SOFTWARE\Classes\ScreenSketch_8wekyb3d8bbwe!App_auto_file\shell]
[HKEY_CURRENT_USER\SOFTWARE\Classes\ScreenSketch_8wekyb3d8bbwe!App_auto_file\shell\open]
[HKEY_CURRENT_USER\SOFTWARE\Classes\ScreenSketch_8wekyb3d8bbwe!App_auto_file\shell\open\command]
@=""C:\Program Files\WindowsApps\Microsoft.ScreenSketch_10.2008.3001.0_x64__8wekyb3d8bbwe\ScreenSketch.exe" "%1""
(Very strangely on an earlier version of Windows (19045.4291) where none of these problems exist, the above registry key doesn't exist!).
I also fixed the Adobe problem with changing "Computer\HKEY_CURRENT_USER\SOFTWARE\Microsoft\Windows\CurrentVersion\Explorer\FileExts.ScreenSketch_8wekyb3d8bbwe!App\OpenWithList" where Acrobat.exe was showing as well as ScreenSketch.exe ('a' and 'b' entries) . It should look like this:
And, Progids shows:
A right-click on Snip & Sketch (either in the taskbar or the App list) followed by 'Take a new snip' or the two 'delay' options does not now elicit the "How do you want to open this file?" nonsense.
This works for the currently logged in Windows user only. There may be a more general fix that could be applied by going into HKLM or elsewhere in the registry but I haven't experimented.
I profess no real expertise delving down into this level of detail in Windows and feel a little resentful about having to do so when it should be a simple fix for Microsoft. The calculator oddly seems to be behaving now (I'm not sure if I've done something there or not) but Sticky Notes still exhibits the same problem. Since I never actually use it I'm in no hurry to try to fix it although I might. But it's interesting that there seems to be a pattern related to "Tasks" lists and right-clicking some Windows Store apps.
This Snip & Sketch fix works for me (tested on three PCs) but I don't know if it's a 'proper' fix or a work around sticking plaster solution that I've stumbled across.
The problem persists in the latest build 19045.4412 by the way.
At the very least I hope this helps some people and perhaps alerts Microsoft to the problem.
Shaun.