No need to.
The "crossing" flag is an old and obsolete flag that used to be automatically added to all team-specific waypoints (i.e. the red T-important and the blue CT-important waypoints) and to all camp waypoints, if I remember correctly.
TBH, I don't even know if it still exists, although I'm fiddling around with the WP editor often enough, lol. Which proves that this "crossing" flag can be safely ignored.
