Outlook (O365) not remembering default application to open .jpg files

[alex8654]

Windows 10 1809
Imageglass 6.0.12.29

To Reproduce

1. Open Outlook (O365 verison is equivalent to Oultlook 2019)
2. open email with .jpg file attached
3. it will ask which application you want to use, then I tick the always use this application for this filetype
4. try to open another .jpg file from the same email, I get asked again for the same thing as above

Actual behavior:

file associations are not working inside Outlook

Expected behavior:

File association follows the regular Windows association, which works in Windows Explorer

[jgodfrey]

On the surface, this sounds like an Outlook-related issue. What happens if you try to associate a different image viewer (not ImageGlass) to images inside of Outlook? Is that viewer also not remembered? If that's the case, I'm not sure what ImageGlass can do about it.

[d2phap]

Hi @alexbleicker

Probably it's Outlook-related issue in your machine.
However, you can try changing default photo viewer app to MS Photos, then open ImageGlass, go to Settings > File Associations, click on Set as Default photo viewer button to register the supported extensions again. After that, change default photo viewer back to ImageGlass.

[alex8654]

it was windows related issue in the end, I followed this guide and deleted the registry key associated with .jpg, restart and then did the file association procedure again, it worked fine.

https://www.thewindowsclub.com/outlook-keeps-asking-how-do-you-want-to-open-this-file