I really don't know how is working or rather say how is not working. For me only one time VO2max was calculated 3 months ago. I run 3 times peer week, and usually with hr strap. I do not remember when was calculated I had hr strap with me or no. But I can clearly tell is not depending how intense your run. Because for me was calculated when I run in very slow pace (40 min run after Xmas diner).
So according apple description from health app it should working always outdoor walk/run more than 20 min with pulse data....! doesn't mater if you using hr strap or AW hand reading... yee apple of course...