I was delighted to recently discover this:

Moneydance 2021.2 build 3089 (Wed, 04 Aug 2021 17:00:00 +0000)

[...]

• If a category is supplied in a downloaded QIF file, don't ignore it

I imagined finally being able to implement and use the highly capableMD Confirmation process in a meaningful fashion.

So I tried it out and at first glance I was over-the-moon. Unfortunately, a closer look reveals that actually, it's not the whole story.

More accurately, it should read

• If a category is supplied in a downloaded QIF file, don't ignore it BUT STRIP THE TAG INFO FROM THE END!!!

Sean, thanks for listening on the inclusion of the category, I really do appreciate it, but I'm totally baffled to imagine any rationale that would suggest if my QIFs are carefully manipulated or exported to contain a Category (which in QIFs may include an appended tag as you know, and that structure is handled perfectly by MD elsewhere) why destroy or ignore THAT tag information?

Please consider this an Enhancement Request when next modifying the Import process.

I've carefully automated (or exported) my QIFs (I'm in Australia - no direct connect) because all of my several banks auto-assign categories that are useless when combined. (For instance, one uses Alcohol, one uses Liquor and one uses Tobacco & Alcohol.
MD creates these categories, and I haven't find a suitable way to combine them form within MD so I scrub them through an Excel lookup process that modifies them to my consistent category (Alcohol) and appends a tag depending on factors I'm able to define in Excel.
The "file was downloaded" checkbox might be better renamed "File contains Category (& Tag!!?? ;-) ) Information.

(As a 25 year user extensively of tags elsewhere and someone who includes a tag in almost every transaction, my biggest frustration on a daily basis with MD is that it doesn't really treasure tags. i.e. no ability to enter them in the mobile app, requiring re-editing of all mobile entries (Batch Change helps but doesn't remove a frustration), tags not preserved when "splotting" an Auto-filled Transaction (this would possibly need to be implemented with a system wide flag so as to allow optional implementation and default preservation of existing behaviour) and almost no Tag subtotalling in Reports.)