diff --git a/source/java/org/alfresco/repo/domain/contentdata/AbstractContentDataDAOImpl.java b/source/java/org/alfresco/repo/domain/contentdata/AbstractContentDataDAOImpl.java
index a18a0143ab..1dcdf5291f 100644
--- a/source/java/org/alfresco/repo/domain/contentdata/AbstractContentDataDAOImpl.java
+++ b/source/java/org/alfresco/repo/domain/contentdata/AbstractContentDataDAOImpl.java
@@ -614,9 +614,56 @@ public abstract class AbstractContentDataDAOImpl implements ContentDataDAO
      * @return              Returns the number of rows deleted
      */
     protected abstract int deleteContentDataEntity(Long id);
+
     protected abstract int deleteContentUrlEntity(long id);
     protected abstract int updateContentUrlEntity(ContentUrlEntity existing, ContentUrlEntity entity);
 
+    @Override
+    public boolean updateContentUrlKey(String contentUrl, ContentUrlKeyEntity contentUrlKey)
+    {
+        boolean success = true;
+
+        ContentUrlEntity existing = getContentUrl(contentUrl);
+        if(existing != null)
+        {
+            ContentUrlEntity entity = ContentUrlEntity.setContentUrlKey(existing, contentUrlKey);
+            updateContentUrl(entity);
+        }
+        else
+        {
+            if (logger.isDebugEnabled())
+            {
+                logger.debug("No content url, not updating symmetric key");
+            }
+            success = false;
+        }
+
+        return success;
+    }
+
+    @Override
+    public boolean updateContentUrlKey(long contentUrlId, ContentUrlKeyEntity contentUrlKey)
+    {
+        boolean success = true;
+
+        ContentUrlEntity existing = getContentUrl(contentUrlId);
+        if(existing != null)
+        {
+            ContentUrlEntity entity = ContentUrlEntity.setContentUrlKey(existing, contentUrlKey);
+            updateContentUrl(entity);
+        }
+        else
+        {
+            if (logger.isDebugEnabled())
+            {
+                logger.debug("No content url, not updating symmetric key");
+            }
+            success = false;
+        }
+
+        return success;
+    }
+
     /**
      * Transactional listener that deletes unreferenced <b>content_url</b> entities.
      * 
diff --git a/source/java/org/alfresco/repo/domain/contentdata/ContentDataDAO.java b/source/java/org/alfresco/repo/domain/contentdata/ContentDataDAO.java
index be01be0533..87f63a6b2f 100644
--- a/source/java/org/alfresco/repo/domain/contentdata/ContentDataDAO.java
+++ b/source/java/org/alfresco/repo/domain/contentdata/ContentDataDAO.java
@@ -147,6 +147,24 @@ public interface ContentDataDAO
      */
     void updateContentUrl(ContentUrlEntity contentUrlEntity);
 
+    /**
+     * Updates the content key for the given content url
+     * 
+     * @since 5.0
+     * @param contentUrl
+     * @param contentUrlKeyEntity
+     */
+    boolean updateContentUrlKey(String contentUrl, ContentUrlKeyEntity contentUrlKeyEntity);
+
+    /**
+     * Updates the content key for the given content url
+     * 
+     * @since 5.0
+     * @param contentUrlId
+     * @param contentUrlKeyEntity
+     */
+    boolean updateContentUrlKey(long contentUrlId, ContentUrlKeyEntity contentUrlKey);
+
     /**
      * Get symmetric keys entities for symmetric keys that have been encrypted using the given
      * master key, starting from 'fromId' and returning at most 'maxResults' entities.
diff --git a/source/java/org/alfresco/repo/domain/contentdata/ContentUrlEntity.java b/source/java/org/alfresco/repo/domain/contentdata/ContentUrlEntity.java
index fba9a7033b..6e829b737a 100644
--- a/source/java/org/alfresco/repo/domain/contentdata/ContentUrlEntity.java
+++ b/source/java/org/alfresco/repo/domain/contentdata/ContentUrlEntity.java
@@ -72,7 +72,8 @@ public class ContentUrlEntity implements Serializable
         else if (obj instanceof ContentUrlEntity)
         {
             ContentUrlEntity that = (ContentUrlEntity) obj;
-            return EqualsHelper.nullSafeEquals(this.contentUrl, that.contentUrl);
+            return EqualsHelper.nullSafeEquals(this.contentUrl, that.contentUrl)
+                    && EqualsHelper.nullSafeEquals(contentUrlKey, that.getContentUrlKey());
         }
         else
         {
diff --git a/source/java/org/alfresco/repo/domain/contentdata/ContentUrlKeyEntity.java b/source/java/org/alfresco/repo/domain/contentdata/ContentUrlKeyEntity.java
index 64421f0d57..d4063a4add 100644
--- a/source/java/org/alfresco/repo/domain/contentdata/ContentUrlKeyEntity.java
+++ b/source/java/org/alfresco/repo/domain/contentdata/ContentUrlKeyEntity.java
@@ -79,15 +79,34 @@ public class ContentUrlKeyEntity implements Serializable
         return encryptedKeyAsBytes;
     }
 
-    public void updateEncryptedKey(EncryptedKey encryptedKey)
+    public void setEncryptedKey(EncryptedKey encryptedKey)
     {
         byte[] encryptedKeyAsBytes = new byte[encryptedKey.getByteBuffer().remaining()];
         encryptedKey.getByteBuffer().get(encryptedKeyAsBytes);
+
         this.encryptedKeyAsBytes = encryptedKeyAsBytes;
-        setKeySize(encryptedKeyAsBytes.length*8);
-        setAlgorithm(encryptedKey.getAlgorithm());
-        setMasterKeyAlias(encryptedKey.getMasterKeyAlias());
-        setMasterKeystoreId(encryptedKey.getMasterKeystoreId());
+        this.keySize = encryptedKeyAsBytes.length*8;
+        this.algorithm = encryptedKey.getAlgorithm();
+        this.masterKeyAlias = encryptedKey.getMasterKeyAlias();
+        this.masterKeystoreId = encryptedKey.getMasterKeystoreId();
+    }
+
+    public static ContentUrlKeyEntity setEncryptedKey(ContentUrlKeyEntity existing, EncryptedKey encryptedKey)
+    {
+        ContentUrlKeyEntity newContentUrlKeyEntity = new ContentUrlKeyEntity();
+
+        byte[] encryptedKeyAsBytes = new byte[encryptedKey.getByteBuffer().remaining()];
+        encryptedKey.getByteBuffer().get(encryptedKeyAsBytes);
+        newContentUrlKeyEntity.setEncryptedKeyAsBytes(encryptedKeyAsBytes);
+        newContentUrlKeyEntity.setKeySize(encryptedKeyAsBytes.length*8);
+        newContentUrlKeyEntity.setAlgorithm(encryptedKey.getAlgorithm());
+        newContentUrlKeyEntity.setMasterKeyAlias(encryptedKey.getMasterKeyAlias());
+        newContentUrlKeyEntity.setMasterKeystoreId(encryptedKey.getMasterKeystoreId());
+        newContentUrlKeyEntity.setContentUrlId(existing.getContentUrlId());
+        newContentUrlKeyEntity.setUnencryptedFileSize(existing.getUnencryptedFileSize());
+        newContentUrlKeyEntity.setId(existing.getId());
+
+        return newContentUrlKeyEntity;
     }
 
     public Long getId()
@@ -157,6 +176,55 @@ public class ContentUrlKeyEntity implements Serializable
         this.masterKeyAlias = masterKeyAlias;
     }
 
+	@Override
+    public int hashCode()
+	{
+        final int prime = 31;
+        int result = 1;
+        result = prime * result
+                + ((algorithm == null) ? 0 : algorithm.hashCode());
+        result = prime * result + ((id == null) ? 0 : id.hashCode());
+        result = prime * result
+                + ((masterKeyAlias == null) ? 0 : masterKeyAlias.hashCode());
+        result = prime
+                * result
+                + ((masterKeystoreId == null) ? 0 : masterKeystoreId.hashCode());
+        return result;
+    }
+
+    @Override
+    public boolean equals(Object obj)
+    {
+        if (this == obj)
+            return true;
+        if (obj == null)
+            return false;
+        if (getClass() != obj.getClass())
+            return false;
+        ContentUrlKeyEntity other = (ContentUrlKeyEntity) obj;
+        if (algorithm == null) {
+            if (other.algorithm != null)
+                return false;
+        } else if (!algorithm.equals(other.algorithm))
+            return false;
+        if (id == null) {
+            if (other.id != null)
+                return false;
+        } else if (!id.equals(other.id))
+            return false;
+        if (masterKeyAlias == null) {
+            if (other.masterKeyAlias != null)
+                return false;
+        } else if (!masterKeyAlias.equals(other.masterKeyAlias))
+            return false;
+        if (masterKeystoreId == null) {
+            if (other.masterKeystoreId != null)
+                return false;
+        } else if (!masterKeystoreId.equals(other.masterKeystoreId))
+            return false;
+        return true;
+    }
+
     @Override
     public String toString()
     {