diff --git a/oak-core/src/main/java/org/apache/jackrabbit/oak/plugins/document/rdb/RDBDocumentStoreJDBC.java b/oak-core/src/main/java/org/apache/jackrabbit/oak/plugins/document/rdb/RDBDocumentStoreJDBC.java
index e78af4c..fd85ce3 100644
--- a/oak-core/src/main/java/org/apache/jackrabbit/oak/plugins/document/rdb/RDBDocumentStoreJDBC.java
+++ b/oak-core/src/main/java/org/apache/jackrabbit/oak/plugins/document/rdb/RDBDocumentStoreJDBC.java
@@ -16,6 +16,8 @@
  */
 package org.apache.jackrabbit.oak.plugins.document.rdb;
 
+import static com.google.common.collect.Iterables.transform;
+import static com.google.common.collect.Sets.newHashSet;
 import static org.apache.jackrabbit.oak.plugins.document.rdb.RDBDocumentStore.CHAR2OCTETRATIO;
 import static org.apache.jackrabbit.oak.plugins.document.rdb.RDBDocumentStore.asBytes;
 import static org.apache.jackrabbit.oak.plugins.document.rdb.RDBJDBCTools.closeResultSet;
@@ -31,6 +33,7 @@ import java.sql.Types;
 import java.util.ArrayList;
 import java.util.Collection;
 import java.util.Collections;
+import java.util.Comparator;
 import java.util.HashMap;
 import java.util.HashSet;
 import java.util.Iterator;
@@ -266,8 +269,9 @@ public class RDBDocumentStoreJDBC {
                 "insert into " + tmd.getName() + "(ID, MODIFIED, HASBINARY, DELETEDONCE, MODCOUNT, CMODCOUNT, DSIZE, DATA, BDATA) "
                         + "values (?, ?, ?, ?, ?, ?, ?, ?, ?)");
 
+        List<T> sortedDocs = sortDocuments(documents);
         try {
-            for (T document : documents) {
+            for (T document : sortedDocs) {
                 String data = this.ser.asString(document);
                 String id = document.getId();
                 Number hasBinary = (Number) document.get(NodeDocument.HAS_BINARY_FLAG);
@@ -296,12 +300,12 @@ public class RDBDocumentStoreJDBC {
             int[] results = stmt.executeBatch();
 
             Set<String> succesfullyInserted = new HashSet<String>();
-            for (int i = 0; i < documents.size(); i++) {
+            for (int i = 0; i < sortedDocs.size(); i++) {
                 int result = results[i];
                 if (result != 1 && result != Statement.SUCCESS_NO_INFO) {
-                    LOG.error("DB insert failed for {}: {}", tmd.getName(), documents.get(i).getId());
+                    LOG.error("DB insert failed for {}: {}", tmd.getName(), sortedDocs.get(i).getId());
                 } else {
-                    succesfullyInserted.add(documents.get(i).getId());
+                    succesfullyInserted.add(sortedDocs.get(i).getId());
                 }
             }
             return succesfullyInserted;
@@ -318,6 +322,9 @@ public class RDBDocumentStoreJDBC {
      * <p>
      * If the {@code upsert} parameter is set to true, the method will also try to insert new documents, those
      * which modcount equals to 1.
+     * <p>
+     * The order of applying updates will be different than order of the passed list, so there shouldn't be two
+     * updates related to the same document. An {@link IllegalArgumentException} will be thrown if there are.
      *
      * @param connection JDBC connection
      * @param tmd Table metadata
@@ -328,13 +335,15 @@ public class RDBDocumentStoreJDBC {
      */
     public <T extends Document> Set<String> update(Connection connection, RDBTableMetaData tmd, List<T> documents, boolean upsert)
             throws SQLException {
+        assertNoDuplicatedIds(documents);
+
         Set<String> successfulUpdates = new HashSet<String>();
 
         PreparedStatement stmt = connection.prepareStatement("update " + tmd.getName()
             + " set MODIFIED = ?, HASBINARY = ?, DELETEDONCE = ?, MODCOUNT = ?, CMODCOUNT = ?, DSIZE = ?, DATA = ?, BDATA = ? where ID = ? and MODCOUNT = ?");
         try {
             List<String> updatedKeys = new ArrayList<String>();
-            for (T document : documents) {
+            for (T document : sortDocuments(documents)) {
                 Long modcount = (Long) document.get(MODCOUNT);
                 if (modcount == 1) {
                     continue; // This is a new document. We'll deal with the inserts later.
@@ -430,6 +439,12 @@ public class RDBDocumentStoreJDBC {
         return successfulUpdates;
     }
 
+    private static <T extends Document> void assertNoDuplicatedIds(List<T> documents) {
+        if (newHashSet(transform(documents, idExtractor)).size() < documents.size()) {
+            throw new IllegalArgumentException("There are duplicated ids in the document list");
+        }
+    }
+
     private final static Map<String, String> INDEXED_PROP_MAPPING;
     static {
         Map<String, String> tmp = new HashMap<String, String>();
@@ -753,6 +768,17 @@ public class RDBDocumentStoreJDBC {
         }
     }
 
+    private static <T extends Document> List<T> sortDocuments(Collection<T> documents) {
+        List<T> result = new ArrayList<T>(documents);
+        Collections.sort(result, new Comparator<T>() {
+            @Override
+            public int compare(T o1, T o2) {
+                return o1.getId().compareTo(o2.getId());
+            }
+        });
+        return result;
+    }
+
     private static final Function<Document, String> idExtractor = new Function<Document, String>() {
         @Override
         public String apply(Document input) {