A friend of mine was trying to open a hyperlink email he received in Microsoft Outlook, when he clicked on "always use this app" it would still prompt him again then next time.
I reset all internet explorer options and rebooted but this did not help, the only thing I could do was open it in Microsoft edge every time.
Fix
Download outlook-ie-opennew.zip
Unpack or unzip the zip file, open the outlook-ie-opennew folder, then right click on outlook-ie-opennew.reg, then click Merge.
https://www.winhelponline.com/blog/wp-content/uploads/q1-16/outlook-ie-opennew.zip
Worked a treat.
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