diff --git a/Source/Tests/TrackableEntities.Client.Tests/ChangeTrackingCollectionTests.cs b/Source/Tests/TrackableEntities.Client.Tests/ChangeTrackingCollectionTests.cs
index 1ce56dca..7f18f24a 100644
--- a/Source/Tests/TrackableEntities.Client.Tests/ChangeTrackingCollectionTests.cs
+++ b/Source/Tests/TrackableEntities.Client.Tests/ChangeTrackingCollectionTests.cs
@@ -152,6 +152,24 @@ public void Added_Employee_After_Tracking_Enabled_Should_Not_Mark_Manually_Added
             Assert.Equal(TrackingState.Added, employee.TrackingState);
             Assert.True(employee.Territories.All(t => t.TrackingState == TrackingState.Added));
         }
+        
+        [Fact]
+        public void Adding_And_Removing_The_Same_Territory_Should_Not_Keep_Added_Territory_In_Territory_Collection()
+        {
+            // Arrange
+            var database = new MockNorthwind();
+            var employee = database.Employees[0];
+            var changeTracker = new ChangeTrackingCollection<Employee>(employee);
+
+            // Act
+            employee.Territories.Add(database.Territories[4]);
+            employee.Territories.Remove(database.Territories[4]);
+
+            // Assert
+            var changes = changeTracker.GetChanges();
+            Assert.Equal(0, changes.Count);
+            Assert.Equal(3, employee.Territories.Count);
+        }
 
         #endregion
 
diff --git a/Source/TrackableEntities.Client/ChangeTrackingCollection.cs b/Source/TrackableEntities.Client/ChangeTrackingCollection.cs
index 076ba024..c427f9b3 100644
--- a/Source/TrackableEntities.Client/ChangeTrackingCollection.cs
+++ b/Source/TrackableEntities.Client/ChangeTrackingCollection.cs
@@ -235,6 +235,7 @@ protected override void RemoveItem(int index)
                 item.SetTracking(false, visitationHelper.Clone(), true);
 
                 // Mark item and trackable collection properties
+                bool manyToManyAdded = Parent != null && item.TrackingState == TrackingState.Added;
                 item.SetState(TrackingState.Deleted, visitationHelper.Clone());
 
                 // Fire EntityChanged event
@@ -242,6 +243,7 @@ protected override void RemoveItem(int index)
 
                 // Cache deleted item if not added or already cached
                 if (item.TrackingState != TrackingState.Added
+                    && !manyToManyAdded
                     && !_deletedEntities.Contains(item))
                     _deletedEntities.Add(item);
             }