diff --git a/apps/edr-freight-api/src/modules/first-mile/first-mile.service.ts b/apps/edr-freight-api/src/modules/first-mile/first-mile.service.ts
index 43f02442a..20048c94d 100644
--- a/apps/edr-freight-api/src/modules/first-mile/first-mile.service.ts
+++ b/apps/edr-freight-api/src/modules/first-mile/first-mile.service.ts
@@ -550,6 +550,34 @@ export class FirstMileService {
       previousVehicleIds.filter((id) => !vehicleIds.has(id)),
     );
 
+    // History: one event per vehicle actually added or removed by this
+    // multi-car (re)allocation, so reassignments show on every timeline.
+    const prevSet = new Set(previousVehicleIds);
+    const bookingRef = await this.resolveBookingRef(firstMile);
+    for (const vehicleId of vehicleIds) {
+      if (prevSet.has(vehicleId)) continue;
+      const info = await this.vehicleInfo(vehicleId);
+      await this.history.record({
+        eventType: FleetEventType.MILE_VEHICLE_ASSIGNED,
+        vehicleId,
+        firstMileId,
+        driverId: info.driverId,
+        label: firstMile.status,
+        metadata: { mile: 'FIRST', bookingRef, vehiclePlate: info.plate, driverName: info.driverName },
+      });
+    }
+    for (const vehicleId of previousVehicleIds) {
+      if (vehicleIds.has(vehicleId)) continue;
+      const info = await this.vehicleInfo(vehicleId);
+      await this.history.record({
+        eventType: FleetEventType.MILE_VEHICLE_RELEASED,
+        vehicleId,
+        firstMileId,
+        driverId: info.driverId,
+        metadata: { mile: 'FIRST', bookingRef, vehiclePlate: info.plate, driverName: info.driverName },
+      });
+    }
+
     return {
       success: true,
       allocated: allocations.length,
diff --git a/apps/edr-freight-api/src/modules/last-mile/last-mile.service.ts b/apps/edr-freight-api/src/modules/last-mile/last-mile.service.ts
index 1e952b1ce..811ddd36b 100644
--- a/apps/edr-freight-api/src/modules/last-mile/last-mile.service.ts
+++ b/apps/edr-freight-api/src/modules/last-mile/last-mile.service.ts
@@ -1,5 +1,5 @@
 import { Injectable, Logger, NotFoundException } from '@nestjs/common';
-import { DataSource, FindOptionsWhere } from 'typeorm';
+import { DataSource, FindOptionsWhere, In } from 'typeorm';
 
 import { BookingsRepository } from '../bookings/bookings.repository';
 import { DriversService } from '../drivers/drivers.service';
@@ -348,6 +348,21 @@ export class LastMileService {
       throw new NotFoundException(`Last-mile record ${lastMileId} not found`);
     }
 
+    // Capture the vehicles currently on these containers so a reallocation can
+    // be diffed into assigned/released history events below.
+    const previousAllocations = await this.dataSource.manager.find(
+      LastMileContainerAllocation,
+      {
+        where: {
+          lastMileId,
+          containerId: In(allocations.map((a) => a.containerId)),
+        },
+      },
+    );
+    const previousVehicleIds = previousAllocations
+      .map((a) => a.vehicleId)
+      .filter((id): id is string => Boolean(id));
+
     await this.dataSource.transaction(async (manager) => {
       for (const allocation of allocations) {
         await manager.delete(LastMileContainerAllocation, {
@@ -364,6 +379,35 @@ export class LastMileService {
       }
     });
 
+    // History: one event per vehicle actually added or removed by this
+    // multi-car (re)allocation, so reassignments show on every timeline.
+    const vehicleIds = new Set(allocations.map((a) => a.vehicleId));
+    const prevSet = new Set(previousVehicleIds);
+    const bookingRef = await this.resolveBookingRef(lastMile);
+    for (const vehicleId of vehicleIds) {
+      if (prevSet.has(vehicleId)) continue;
+      const info = await this.vehicleInfo(vehicleId);
+      await this.history.record({
+        eventType: FleetEventType.MILE_VEHICLE_ASSIGNED,
+        vehicleId,
+        lastMileId,
+        driverId: info.driverId,
+        label: lastMile.status,
+        metadata: { mile: 'LAST', bookingRef, vehiclePlate: info.plate, driverName: info.driverName },
+      });
+    }
+    for (const vehicleId of previousVehicleIds) {
+      if (vehicleIds.has(vehicleId)) continue;
+      const info = await this.vehicleInfo(vehicleId);
+      await this.history.record({
+        eventType: FleetEventType.MILE_VEHICLE_RELEASED,
+        vehicleId,
+        lastMileId,
+        driverId: info.driverId,
+        metadata: { mile: 'LAST', bookingRef, vehiclePlate: info.plate, driverName: info.driverName },
+      });
+    }
+
     return {
       success: true,
       allocated: allocations.length,