Great info! As you alluded to, this isn’t something I generally need to do on a frequent basis or to multiple file types at once, so approaching it via the properties of a specific file would be a lot cleaner than trying to navigate that monstrous list. I didn’t realize you could access that setting from file properties. Thank you very much, Brian. 

It still might be worth at least keeping in the back of our minds to come up with an accessible solution for navigating the file extensions list from Windows settings, in case people encounter use cases where that approach makes more sense. The navigation there is currently quite poor, as I outlined previously. This is no fault of NVDA nor any other screen reader, just a poorly thought out design in that area of the settings app. It could be easily mitigated if Microsoft added a search box at the top as is found in most other areas of settings, but such a relatively low traffic part of the OS isn’t likely to get that much attention from them, so perhaps a clever user could come up with some kind of NVDA plug-in to help bridge the gap. There are some other sections and windows with a similarly poor interface, where you are forced to tab between large lists of buttons, so the usefulness of such a plug-in could extend beyond that one screen. Thanks again.