diff --git a/doc/build/changelog/changelog_10.rst b/doc/build/changelog/changelog_10.rst
index c800647a69..40a251a222 100644
--- a/doc/build/changelog/changelog_10.rst
+++ b/doc/build/changelog/changelog_10.rst
@@ -18,6 +18,21 @@
 .. changelog::
     :version: 1.0.10
 
+    .. change::
+        :tags: bug, orm
+        :versions: 1.1.0b1
+        :tickets: 2696
+
+        A rare case which occurs when a :meth:`.Session.rollback` fails in the
+        scope of a :meth:`.Session.flush` operation that's raising an
+        exception, as has been observed in some MySQL SAVEPOINT cases, prevents
+        the original  database exception from being observed when it was
+        emitted during  flush, but only on Py2K because Py2K does not support
+        exception  chaining; on Py3K the originating exception is chained.  As
+        a workaround, a warning is emitted in this specific case showing at
+        least the string message of the original database error before we
+        proceed to raise  the rollback-originating exception.
+
     .. change::
         :tags: bug, postgresql
         :versions: 1.1.0b1
diff --git a/lib/sqlalchemy/orm/session.py b/lib/sqlalchemy/orm/session.py
index 6c3f392bac..17808e66ba 100644
--- a/lib/sqlalchemy/orm/session.py
+++ b/lib/sqlalchemy/orm/session.py
@@ -412,11 +412,23 @@ class SessionTransaction(object):
             for subtransaction in stx._iterate_parents(upto=self):
                 subtransaction.close()
 
+        if _capture_exception:
+            captured_exception = sys.exc_info()[1]
+
         boundary = self
         if self._state in (ACTIVE, PREPARED):
             for transaction in self._iterate_parents():
                 if transaction._parent is None or transaction.nested:
-                    transaction._rollback_impl()
+                    try:
+                        transaction._rollback_impl()
+                    except Exception:
+                        if _capture_exception:
+                            util.warn(
+                                "An exception raised during a Session "
+                                "persistence operation cannot be raised "
+                                "due to an additional ROLLBACK exception; "
+                                "the exception is: %s" % captured_exception)
+                        raise
                     transaction._state = DEACTIVE
                     boundary = transaction
                     break
@@ -438,7 +450,7 @@ class SessionTransaction(object):
 
         self.close()
         if self._parent and _capture_exception:
-            self._parent._rollback_exception = sys.exc_info()[1]
+            self._parent._rollback_exception = captured_exception
 
         sess.dispatch.after_soft_rollback(sess, self)
 
diff --git a/lib/sqlalchemy/testing/assertions.py b/lib/sqlalchemy/testing/assertions.py
index 21dc3e71ac..63667654d4 100644
--- a/lib/sqlalchemy/testing/assertions.py
+++ b/lib/sqlalchemy/testing/assertions.py
@@ -121,7 +121,7 @@ def uses_deprecated(*messages):
 def _expect_warnings(exc_cls, messages, regex=True, assert_=True):
 
     if regex:
-        filters = [re.compile(msg, re.I) for msg in messages]
+        filters = [re.compile(msg, re.I | re.S) for msg in messages]
     else:
         filters = messages
 
diff --git a/test/orm/test_transaction.py b/test/orm/test_transaction.py
index 91846a67e6..6918996a02 100644
--- a/test/orm/test_transaction.py
+++ b/test/orm/test_transaction.py
@@ -657,6 +657,31 @@ class SessionTransactionTest(FixtureTest):
         assert session.transaction is not None, \
             'autocommit=False should start a new transaction'
 
+    @testing.requires.savepoints
+    def test_report_primary_error_when_rollback_fails(self):
+        User, users = self.classes.User, self.tables.users
+
+        mapper(User, users)
+
+        session = Session(testing.db)
+
+        with expect_warnings(".*due to an additional ROLLBACK.*INSERT INTO"):
+            session.begin_nested()
+            savepoint = session.\
+                connection()._Connection__transaction._savepoint
+
+            # force the savepoint to disappear
+            session.execute("RELEASE SAVEPOINT %s" % savepoint)
+
+            # now do a broken flush
+            session.add_all([User(id=1), User(id=1)])
+
+            assert_raises_message(
+                sa_exc.DBAPIError,
+                "ROLLBACK TO SAVEPOINT ",
+                session.flush
+            )
+
 
 class _LocalFixture(FixtureTest):
     run_setup_mappers = 'once'