diff --git a/game/ato/flight.py b/game/ato/flight.py
index 048738c8..278283f5 100644
--- a/game/ato/flight.py
+++ b/game/ato/flight.py
@@ -272,5 +272,5 @@ class Flight(SidcDescribable):
             if pilot is not None:
                 results.kill_pilot(self, pilot)
 
-    def recreate_flight_plan(self) -> None:
-        self._flight_plan_builder.regenerate()
+    def recreate_flight_plan(self, dump_debug_info: bool = False) -> None:
+        self._flight_plan_builder.regenerate(dump_debug_info)
diff --git a/game/ato/flightplans/ibuilder.py b/game/ato/flightplans/ibuilder.py
index a1b6c905..b85589e4 100644
--- a/game/ato/flightplans/ibuilder.py
+++ b/game/ato/flightplans/ibuilder.py
@@ -32,9 +32,9 @@ class IBuilder(ABC, Generic[FlightPlanT, LayoutT]):
             assert self._flight_plan is not None
         return self._flight_plan
 
-    def regenerate(self) -> None:
+    def regenerate(self, dump_debug_info: bool = False) -> None:
         try:
-            self._generate_package_waypoints_if_needed()
+            self._generate_package_waypoints_if_needed(dump_debug_info)
             self._flight_plan = self.build()
         except NavMeshError as ex:
             color = "blue" if self.flight.squadron.player else "red"
@@ -43,14 +43,15 @@ class IBuilder(ABC, Generic[FlightPlanT, LayoutT]):
                 f"{self.flight.departure} to {self.package.target}"
             ) from ex
 
-    def _generate_package_waypoints_if_needed(self) -> None:
+    def _generate_package_waypoints_if_needed(self, dump_debug_info: bool) -> None:
         # Package waypoints are only valid for offensive missions. Skip this if the
         # target is friendly.
-        if self.package.waypoints is None and not self.package.target.is_friendly(
-            self.is_player
-        ):
+        if self.package.target.is_friendly(self.is_player):
+            return
+
+        if self.package.waypoints is None or dump_debug_info:
             self.package.waypoints = PackageWaypoints.create(
-                self.package, self.coalition
+                self.package, self.coalition, dump_debug_info
             )
 
     @property
diff --git a/game/ato/packagewaypoints.py b/game/ato/packagewaypoints.py
index e0092ad0..d53bc558 100644
--- a/game/ato/packagewaypoints.py
+++ b/game/ato/packagewaypoints.py
@@ -9,6 +9,7 @@ from game.ato.flightplans.waypointbuilder import WaypointBuilder
 from game.flightplan import JoinZoneGeometry
 from game.flightplan.ipsolver import IpSolver
 from game.flightplan.refuelzonegeometry import RefuelZoneGeometry
+from game.persistence.paths import liberation_user_dir
 from game.utils import dcs_to_shapely_point
 
 if TYPE_CHECKING:
@@ -24,16 +25,27 @@ class PackageWaypoints:
     refuel: Point
 
     @staticmethod
-    def create(package: Package, coalition: Coalition) -> PackageWaypoints:
+    def create(
+        package: Package, coalition: Coalition, dump_debug_info: bool
+    ) -> PackageWaypoints:
         origin = package.departure_closest_to_target()
 
+        waypoint_debug_directory = liberation_user_dir() / "Debug/Waypoints"
+
         # Start by picking the best IP for the attack.
-        ingress_point_shapely = IpSolver(
+        ip_solver = IpSolver(
             dcs_to_shapely_point(origin.position),
             dcs_to_shapely_point(package.target.position),
             coalition.doctrine,
             coalition.opponent.threat_zone.all,
-        ).solve()
+        )
+        ip_solver.set_debug_properties(
+            waypoint_debug_directory / "IP", coalition.game.theater.terrain
+        )
+        ingress_point_shapely = ip_solver.solve()
+        if dump_debug_info:
+            ip_solver.dump_debug_info()
+
         ingress_point = origin.position.new_in_same_map(
             ingress_point_shapely.x, ingress_point_shapely.y
         )
diff --git a/qt_ui/windows/mission/flight/waypoints/QFlightWaypointTab.py b/qt_ui/windows/mission/flight/waypoints/QFlightWaypointTab.py
index 416e5d23..29c5e545 100644
--- a/qt_ui/windows/mission/flight/waypoints/QFlightWaypointTab.py
+++ b/qt_ui/windows/mission/flight/waypoints/QFlightWaypointTab.py
@@ -167,7 +167,7 @@ class QFlightWaypointTab(QFrame):
         if result == QMessageBox.Yes:
             self.flight.set_flight_type(task)
             try:
-                self.flight.recreate_flight_plan()
+                self.flight.recreate_flight_plan(dump_debug_info=True)
             except PlanningError as ex:
                 self.flight.set_flight_type(original_task)
                 logging.exception("Could not recreate flight")