It uses the sort order of the criteria specified. It is unable to do a counterclockwise (or clockwise) numbering ... AC does not have any kind of geometry 'auto detection' filter to figure out that kind of thing. (In years past, there were numerous threads here from people doing commercial work who needed their ID's numbered in that way.)
Cheers,
Karl
One of the forum moderators
AC 28 USA and earlier • macOS Sonoma 14.7.1, MacBook Pro M2 Max 12CPU/30GPU cores, 32GB