diff --git a/changelog.md b/changelog.md
index 5051dbfd..f89e9bfe 100644
--- a/changelog.md
+++ b/changelog.md
@@ -4,6 +4,7 @@ Saves from 8.x are not compatible with 9.0.0.
 
 ## Features/Improvements
 
+* **[Flight Planning]** Improved IP selection for targets that are near the center of a threat zone.
 * **[Modding]** Factions can now specify the ship type to be used for cargo shipping. The Handy Wind will be used by default, but WW2 factions can pick something more appropriate.
 
 ## Fixes
diff --git a/client/src/api/_liberationApi.ts b/client/src/api/_liberationApi.ts
index a1c35b43..abcf3d50 100644
--- a/client/src/api/_liberationApi.ts
+++ b/client/src/api/_liberationApi.ts
@@ -384,6 +384,8 @@ export type IpZones = {
   ipBubble: LatLng[][];
   permissibleZone: LatLng[][];
   safeZones: LatLng[][][];
+  preferredThreatenedZones: LatLng[][][];
+  tolerableThreatenedLines: LatLng[][];
 };
 export type JoinZones = {
   homeBubble: LatLng[][];
diff --git a/client/src/components/waypointdebugzones/IpZones.tsx b/client/src/components/waypointdebugzones/IpZones.tsx
index 39beef27..fe93e1b5 100644
--- a/client/src/components/waypointdebugzones/IpZones.tsx
+++ b/client/src/components/waypointdebugzones/IpZones.tsx
@@ -1,5 +1,5 @@
 import { useGetDebugIpZonesQuery } from "../../api/liberationApi";
-import { LayerGroup, Polygon } from "react-leaflet";
+import { LayerGroup, Polygon, Polyline } from "react-leaflet";
 
 interface IpZonesProps {
   flightId: string;
@@ -56,6 +56,29 @@ function IpZones(props: IpZonesProps) {
           />
         );
       })}
+
+      {data.preferredThreatenedZones.map((zone, idx) => {
+        return (
+          <Polygon
+            key={idx}
+            positions={zone}
+            color="#fe7d0a"
+            fillOpacity={0.1}
+            interactive={false}
+          />
+        );
+      })}
+
+      {data.tolerableThreatenedLines.map((line, idx) => {
+        return (
+          <Polyline
+            key={idx}
+            positions={line}
+            color="#80BA80"
+            interactive={false}
+          />
+        );
+      })}
     </>
   );
 }
diff --git a/game/flightplan/ipzonegeometry.py b/game/flightplan/ipzonegeometry.py
index 70b5a072..3d8ea923 100644
--- a/game/flightplan/ipzonegeometry.py
+++ b/game/flightplan/ipzonegeometry.py
@@ -4,7 +4,7 @@ from typing import TYPE_CHECKING
 
 import shapely.ops
 from dcs import Point
-from shapely.geometry import MultiPolygon, Point as ShapelyPoint
+from shapely.geometry import MultiPolygon, Point as ShapelyPoint, MultiLineString
 
 from game.utils import meters, nautical_miles
 
@@ -90,6 +90,32 @@ class IpZoneGeometry:
             safe_zones = MultiPolygon([safe_zones])
         self.safe_zones = safe_zones
 
+        # See explanation where this is used in _unsafe_ip.
+        # https://github.com/dcs-liberation/dcs_liberation/issues/2754
+        preferred_threatened_zone_wiggle_room = nautical_miles(5)
+        threat_buffer_distance = self.permissible_zone.distance(
+            self.threat_zone.boundary
+        )
+        preferred_threatened_zone_mask = self.threat_zone.buffer(
+            -threat_buffer_distance - preferred_threatened_zone_wiggle_room.meters
+        )
+        preferred_threatened_zones = self.threat_zone.difference(
+            preferred_threatened_zone_mask
+        )
+
+        if not isinstance(preferred_threatened_zones, MultiPolygon):
+            preferred_threatened_zones = MultiPolygon([preferred_threatened_zones])
+        self.preferred_threatened_zones = preferred_threatened_zones
+
+        tolerable_threatened_lines = self.preferred_threatened_zones.intersection(
+            self.permissible_zone.boundary
+        )
+        if tolerable_threatened_lines.is_empty:
+            tolerable_threatened_lines = MultiLineString([])
+        elif not isinstance(tolerable_threatened_lines, MultiLineString):
+            tolerable_threatened_lines = MultiLineString([tolerable_threatened_lines])
+        self.tolerable_threatened_lines = tolerable_threatened_lines
+
     def _unsafe_ip(self) -> ShapelyPoint:
         unthreatened_home_zone = self.home_bubble.difference(self.threat_zone)
         if unthreatened_home_zone.is_empty:
@@ -100,8 +126,28 @@ class IpZoneGeometry:
                 self.permissible_zone, self.threat_zone.boundary
             )[0]
 
-        # No safe point in the IP zone, but the home zone is safe. Pick the max-
-        # distance IP that's closest to the untreatened home zone.
+        # No safe point in the IP zone, but the home zone is safe. Pick an IP within
+        # both the permissible zone and preferred threatened zone that's as close to the
+        # unthreatened home zone as possible. This should get us a max-range IP that
+        # is roughly as safe as possible without unjustifiably long routes.
+        #
+        # If we do the obvious thing and pick the IP that minimizes threatened travel
+        # time (the IP closest to the threat boundary) and the objective is near the
+        # center of the threat zone (common when there is an airbase covered only by air
+        # defenses with shorter range than the BARCAP zone, and the target is a TGO near
+        # the CP), the IP could be placed such that the flight would fly all the way
+        # around the threat zone just to avoid a few more threatened miles of travel. To
+        # avoid that, we generate a set of preferred threatened areas that offer a
+        # trade-off between travel time and safety.
+        #
+        # https://github.com/dcs-liberation/dcs_liberation/issues/2754
+        if not self.tolerable_threatened_lines.is_empty:
+            return shapely.ops.nearest_points(
+                self.tolerable_threatened_lines, self.home
+            )[0]
+
+        # But if no part of the permissible zone is tolerably threatened, fall back to
+        # the old safety maximizing approach.
         return shapely.ops.nearest_points(
             self.permissible_zone, unthreatened_home_zone
         )[0]
diff --git a/game/server/debuggeometries/models.py b/game/server/debuggeometries/models.py
index 8dd271cf..93ecd166 100644
--- a/game/server/debuggeometries/models.py
+++ b/game/server/debuggeometries/models.py
@@ -64,14 +64,16 @@ class IpZonesJs(BaseModel):
     ipBubble: LeafletPoly = Field(alias="ipBubble")
     permissibleZone: LeafletPoly = Field(alias="permissibleZone")
     safeZones: list[LeafletPoly] = Field(alias="safeZones")
+    preferred_threatened_zones: list[LeafletPoly] = Field(
+        alias="preferredThreatenedZones"
+    )
+    tolerable_threatened_lines: list[LeafletLine] = Field(
+        alias="tolerableThreatenedLines"
+    )
 
     class Config:
         title = "IpZones"
 
-    @classmethod
-    def empty(cls) -> IpZonesJs:
-        return IpZonesJs(homeBubble=[], ipBubble=[], permissibleZone=[], safeZones=[])
-
     @classmethod
     def for_flight(cls, flight: Flight, game: Game) -> IpZonesJs:
         target = flight.package.target
@@ -84,6 +86,12 @@ class IpZonesJs(BaseModel):
                 geometry.permissible_zone, game.theater
             ),
             safeZones=ShapelyUtil.polys_to_leaflet(geometry.safe_zones, game.theater),
+            preferredThreatenedZones=ShapelyUtil.polys_to_leaflet(
+                geometry.preferred_threatened_zones, game.theater
+            ),
+            tolerableThreatenedLines=ShapelyUtil.lines_to_leaflet(
+                geometry.tolerable_threatened_lines, game.theater
+            ),
         )