diff --git a/lib/Doctrine/ORM/PersistentCollection.php b/lib/Doctrine/ORM/PersistentCollection.php
index bf7c6da..f578a22 100644
--- a/lib/Doctrine/ORM/PersistentCollection.php
+++ b/lib/Doctrine/ORM/PersistentCollection.php
@@ -487,6 +487,11 @@ final class PersistentCollection implements Collection
         $this->initialize();
         $this->coll->set($key, $value);
         $this->changed();
+
+        if ($this->association !== null && $this->association['type'] == ClassMetadata::ONE_TO_MANY &&
+                $this->association['orphanRemoval']) {
+            $this->em->getUnitOfWork()->unscheduleOrphanRemoval($value);
+        }
     }
 
     /**
@@ -496,6 +501,12 @@ final class PersistentCollection implements Collection
     {
         $this->coll->add($value);
         $this->changed();
+
+        if ($this->association !== null && $this->association['type'] == ClassMetadata::ONE_TO_MANY &&
+                $this->association['orphanRemoval']) {
+            $this->em->getUnitOfWork()->unscheduleOrphanRemoval($value);
+        }
+
         return true;
     }
 
diff --git a/lib/Doctrine/ORM/UnitOfWork.php b/lib/Doctrine/ORM/UnitOfWork.php
index 76ce521..7e8ac49 100644
--- a/lib/Doctrine/ORM/UnitOfWork.php
+++ b/lib/Doctrine/ORM/UnitOfWork.php
@@ -1797,6 +1797,20 @@ class UnitOfWork implements PropertyChangedListener
     {
         $this->orphanRemovals[spl_object_hash($entity)] = $entity;
     }
+
+    /**
+     * INTERNAL:
+     * Unschedules an orphaned entity from removal during flush().
+     *
+     * This can happen if an orphan entity is moved from one to another collection.
+     *
+     * @ignore
+     * @param object $entity
+     */
+    public function unscheduleOrphanRemoval($entity)
+    {
+        unset($this->orphanRemovals[spl_object_hash($entity)]);
+    }
     
     /**
      * INTERNAL:
diff --git a/tests/Doctrine/Tests/ORM/Functional/BasicFunctionalTest.php b/tests/Doctrine/Tests/ORM/Functional/BasicFunctionalTest.php
index 7a7da0c..35810ee 100644
--- a/tests/Doctrine/Tests/ORM/Functional/BasicFunctionalTest.php
+++ b/tests/Doctrine/Tests/ORM/Functional/BasicFunctionalTest.php
@@ -172,6 +172,37 @@ class BasicFunctionalTest extends \Doctrine\Tests\OrmFunctionalTestCase
         $this->assertEquals(0, $this->_em->getConnection()->fetchColumn("select count(*) from cms_phonenumbers"));
     }
 
+    /**
+     * @group DDC-166
+     */
+    public function testReuseOrphanUnschedulesRemoval()
+    {
+        $user1 = new CmsUser;
+        $user1->name = 'Roman';
+        $user1->username = 'romanb';
+        $user1->status = 'developer';
+
+        $phone = new CmsPhonenumber;
+        $phone->phonenumber = 100;
+        $user1->addPhonenumber($phone);
+
+        $user2 = new CmsUser;
+        $user2->name = 'Guilherme';
+        $user2->username = 'gblanco';
+        $user2->status = 'developer';
+        $this->_em->persist($user1);
+        $this->_em->persist($user2);
+        $this->_em->persist($phone);
+        $this->_em->flush();
+
+        $user1->getPhonenumbers()->remove(0); // here its scheduled for orphan removal
+        $user2->addPhonenumber($phone); // here its reused in another collection
+
+        $this->_em->flush();
+
+        $this->assertTrue($this->_em->contains($phone), "The Phonenumber should be contained in the UoW and associated with user2.");
+    }
+
     public function testBasicQuery()
     {
         $user = new CmsUser;