Earlier quoted context omitted.
>Depending on the decision, either lists of decimal numbers or lists of version numbers will be sorted wrong. Yes. I don’t see why this is a big deal. I didn’t suggest adjusting the logic based on the number of decimal points.
Ah ok. I understand that you found your perfect trade-off for sorting based on longer considerations. But it will be difficult to communicate such a concept to a user. Applying partial rules to improve sorting in one direction is not a lossless activity, it makes the UX actually worse in other scenarios as the user is first guided to assume a certain behavior, but then learns that his expectation is broken in adjacen…
This isn't a prerequisite, since the existing naive character sort approach is not communicated either. In fact, it's almost universally unexpected by any user who hasn't written a naive string sort. Apple doesn't do this, and I very much did not need it communicated to me why 10 was coming after 2, because that's what everyone, who's not a programmer, expects.
As a litmus test, go ask some people, who are not programmers, without loading the question beyond "here are some files, how would you expect for them to be displayed in a list?". Show the lists side by side. It should not surprise you.