diff --git a/changelog.md b/changelog.md
index c14c6a6d..afa09ec5 100644
--- a/changelog.md
+++ b/changelog.md
@@ -6,6 +6,7 @@ Saves from 2.3 are not compatible with 2.4.
 
 * **[Flight Planner]** Air-to-air and SEAD escorts will no longer be automatically planned for packages that are not in range of threats.
 * **[Flight Planner]** Non-custom flight plans will now navigate around threat areas en route to the target area when practical.
+* **[Flight Planner]** Flight plans along front lines now ensure that the race track start is closer to the departure airfield than the race track end.
 * **[Campaign AI]** Auto-purchase now prefers airfields that are not within range of the enemy.
 * **[Campaign AI]** Auto-purchase now prefers the best aircraft for the task, but will attempt to maintain some variety.
 * **[Campaign AI]** Opfor now sells off odd aircraft since they're unlikely to be used.
diff --git a/gen/flights/flightplan.py b/gen/flights/flightplan.py
index 75ab8c42..4d5f563e 100644
--- a/gen/flights/flightplan.py
+++ b/gen/flights/flightplan.py
@@ -1078,7 +1078,7 @@ class FlightPlanBuilder:
         start = end.point_from_heading(heading - 180, diameter)
         return start, end
 
-    def racetrack_for_frontline(self,
+    def racetrack_for_frontline(self, origin: Point,
                                 front_line: FrontLine) -> Tuple[Point, Point]:
         ally_cp, enemy_cp = front_line.control_points
 
@@ -1099,10 +1099,12 @@ class FlightPlanBuilder:
             combat_width = 35000
 
         radius = combat_width * 1.25
-        orbit0p = orbit_center.point_from_heading(heading, radius)
-        orbit1p = orbit_center.point_from_heading(heading + 180, radius)
+        start = orbit_center.point_from_heading(heading, radius)
+        end = orbit_center.point_from_heading(heading + 180, radius)
 
-        return orbit0p, orbit1p
+        if end.distance_to_point(origin) < start.distance_to_point(origin):
+            start, end = end, start
+        return start, end
 
     def generate_tarcap(self, flight: Flight) -> TarCapFlightPlan:
         """Generate a CAP flight plan for the given front line.
@@ -1120,7 +1122,8 @@ class FlightPlanBuilder:
         builder = WaypointBuilder(flight, self.game, self.is_player)
 
         if isinstance(location, FrontLine):
-            orbit0p, orbit1p = self.racetrack_for_frontline(location)
+            orbit0p, orbit1p = self.racetrack_for_frontline(
+                flight.departure.position, location)
         else:
             orbit0p, orbit1p = self.racetrack_for_objective(location)
 
@@ -1279,6 +1282,11 @@ class FlightPlanBuilder:
         center = ingress.point_from_heading(heading, distance / 2)
         egress = ingress.point_from_heading(heading, distance)
 
+        ingress_distance = ingress.distance_to_point(flight.departure.position)
+        egress_distance = egress.distance_to_point(flight.departure.position)
+        if egress_distance < ingress_distance:
+            ingress, egress = egress, ingress
+
         builder = WaypointBuilder(flight, self.game, self.is_player)
 
         return CasFlightPlan(