@Suty Thanks for the quick response!

When I view a KML file [attached] in Windy that crosses the antimeridian, the set of waypoints is drawn in a disjoint manner with long lines displayed across the entirety of the Earth. It appears as if the waypoints are being connected "long-ways" across the entirety of the Earth, rather than "short-ways" across the antimeridian.

Shown here is the expected shape of waypoints crossing the antimeridian (plotted in google earth as the same kml as windy), "short-ways"

Shown here is the close-up view of how the waypoints are displayed in windy "long-ways":

Shown here is the far-out view of how the waypoints are displayed in windy "long-ways":

I would expect the set of waypoints to be displayed in the same shape as on Google Earth, but am receiving the disjointed set of waypoints shown in the short and long images that I have attached.

I couldn't figure out how to attach a .KML file, so it is linked through pastebin here:
https://pastebin.com/Lff38pvV