diff --git a/data/MANIFEST.txt b/data/MANIFEST.txt
index 8f0ac6e142..0c4b749446 100644
--- a/data/MANIFEST.txt
+++ b/data/MANIFEST.txt
@@ -221,9 +221,9 @@ dcf786ec9ad3284e6f70179e19795720  data/system/scenarios/downtown/weekday.bin
 370928cacb5d28ce7adb845982dd58b3  data/system/scenarios/huge_seattle/weekday.bin
 7292bd648e628e38b381e27dec613893  data/system/scenarios/caphill/weekday.bin
 c92d3580f01b37aad20dfede7270039d  data/system/scenarios/montlake/weekday.bin
-38dfab26d52367c16ab429ec710546c3  data/system/prebaked_results/23rd/weekday.bin
+1a7506556b01f99e7cc9336727111459  data/system/prebaked_results/23rd/weekday.bin
 ad5d2c7a2c73ef5bf4a09ff11845c166  data/system/prebaked_results/signal_single/tutorial lvl1.bin
 81081122aa46e8651d8f07bb606bc77a  data/system/prebaked_results/signal_single/tutorial lvl2.bin
 e15dd2d01fccadb1f16c4ed9f732b377  data/system/prebaked_results/montlake/car vs bike contention.bin
-b375f2ef55cefc0bad90fe630adb0061  data/system/prebaked_results/montlake/weekday.bin
+2e7e97dc4a513c087e1e73ed9df65b56  data/system/prebaked_results/montlake/weekday.bin
 ba713f7f6ad0c0201f1447d77957ce75  data/system/prebaked_results/montlake/car vs bus contention.bin
diff --git a/sim/src/mechanics/parking.rs b/sim/src/mechanics/parking.rs
index 1bde8ebce4..1506346181 100644
--- a/sim/src/mechanics/parking.rs
+++ b/sim/src/mechanics/parking.rs
@@ -134,15 +134,25 @@ impl ParkingSimState {
         self.parked_cars.insert(p.vehicle.id, p);
     }
 
-    pub fn dynamically_reserve_car(&mut self, b: BuildingID) -> Option<ParkedCar> {
+    pub fn dynamically_reserve_car(
+        &mut self,
+        b: BuildingID,
+        closest_to: Pt2D,
+        map: &Map,
+    ) -> Option<ParkedCar> {
+        let mut candidates = Vec::new();
         for c in self.owned_cars_per_building.get(b) {
-            if self.dynamically_reserved_cars.contains(c) {
-                continue;
+            if !self.dynamically_reserved_cars.contains(c) {
+                let pt = match self.parked_cars[c].spot {
+                    ParkingSpot::Onstreet(l, _) => map.get_l(l).lane_center_pts.middle(),
+                    ParkingSpot::Offstreet(b, _) => map.get_b(b).label_center,
+                };
+                candidates.push((*c, pt.dist_to(closest_to)));
             }
-            self.dynamically_reserved_cars.insert(*c);
-            return Some(self.parked_cars[c].clone());
         }
-        None
+        let (c, _) = candidates.into_iter().min_by_key(|(_, dist)| *dist)?;
+        self.dynamically_reserved_cars.insert(c);
+        Some(self.parked_cars[&c].clone())
     }
 
     pub fn dynamically_return_car(&mut self, p: ParkedCar) {
diff --git a/sim/src/sim.rs b/sim/src/sim.rs
index 6bc7e18924..2f43ad8784 100644
--- a/sim/src/sim.rs
+++ b/sim/src/sim.rs
@@ -461,7 +461,11 @@ impl Sim {
                 let ok = if let SidewalkPOI::DeferredParkingSpot(b, driving_goal) =
                     create_ped.goal.connection.clone()
                 {
-                    if let Some(parked_car) = self.parking.dynamically_reserve_car(b) {
+                    if let Some(parked_car) = self.parking.dynamically_reserve_car(
+                        b,
+                        create_ped.start.sidewalk_pos.pt(map),
+                        map,
+                    ) {
                         create_ped.goal =
                             SidewalkSpot::parking_spot(parked_car.spot, map, &self.parking);
                         create_ped.req = PathRequest {