diff --git a/openstack_requirements/cmds/generate.py b/openstack_requirements/cmds/generate.py
index 9bd50f7092..4c6d21ec3b 100644
--- a/openstack_requirements/cmds/generate.py
+++ b/openstack_requirements/cmds/generate.py
@@ -139,12 +139,12 @@ def _clone_versions(freezes, options):
     for freeze_data in freezes:
         versions = [v for v, d in freezes]
         version, freeze = freeze_data
-        if (version in options.version_map and
-                options.version_map[version] not in versions):
-            print("Duplicating %s freeze to %s" %
-                  (version, options.version_map[version]),
-                  file=sys.stderr)
-            freezes.append((options.version_map[version], copy.copy(freeze)))
+        if version in options.version_map:
+            for dst_version in sorted(options.version_map[version]):
+                if dst_version not in versions:
+                    print("Duplicating %s freeze to %s" %
+                          (version, dst_version), file=sys.stderr)
+                    freezes.append((dst_version, copy.copy(freeze)))
 
 
 # -- untested UI glue from here down.
@@ -177,7 +177,8 @@ def _validate_options(options):
                 "Invalid version-map entry %(map_entry)s"
                 % dict(map_entry=map_entry))
         src, dst = map_entry.split(':')
-        version_map[src] = dst
+        version_map.setdefault(src, set())
+        version_map[src].add(dst)
     options.version_map = version_map
 
 
diff --git a/openstack_requirements/tests/test_generate.py b/openstack_requirements/tests/test_generate.py
index 9a33124336..ebc0332ef0 100644
--- a/openstack_requirements/tests/test_generate.py
+++ b/openstack_requirements/tests/test_generate.py
@@ -110,7 +110,8 @@ class TestClone(testtools.TestCase):
     def test_py34_clone_py35(self):
         # Simulate an environment where we have python 3.4 data and need to
         # clone that to python 3.5
-        options = Namespace(version_map={'3.4': '3.5', '3.5': '3.4'})
+        options = Namespace(version_map={'3.4': set(['3.5']),
+                                         '3.5': set(['3.4'])})
         freeze_27 = ('2.7', [('dnspython', '1.15.0')])
         freeze_34 = ('3.4', [('dnspython3', '1.12.0')])
         freeze_35 = ('3.5', [('dnspython3', '1.12.0')])
@@ -125,7 +126,8 @@ class TestClone(testtools.TestCase):
     def test_py34_noclone_py35(self):
         # Simulate an environment where we have python 3.4 and python 3.5 data
         # so there is no need to clone.
-        options = Namespace(version_map={'3.4': '3.5', '3.5': '3.4'})
+        options = Namespace(version_map={'3.4': set(['3.5']),
+                                         '3.5': set(['3.4'])})
         freeze_27 = ('2.7', [('dnspython', '1.15.0')])
         freeze_34 = ('3.4', [('dnspython3', '1.12.0')])
         freeze_35 = ('3.5', [('other-pkg', '1.0.0')])
@@ -140,7 +142,8 @@ class TestClone(testtools.TestCase):
     def test_py35_clone_py34(self):
         # Simulate an environment where we have python 3.5 data and need to
         # clone that to python 3.4
-        options = Namespace(version_map={'3.4': '3.5', '3.5': '3.4'})
+        options = Namespace(version_map={'3.4': set(['3.5']),
+                                         '3.5': set(['3.4'])})
         freeze_27 = ('2.7', [('dnspython', '1.15.0')])
         freeze_34 = ('3.4', [('dnspython3', '1.12.0')])
         freeze_35 = ('3.5', [('dnspython3', '1.12.0')])
@@ -151,3 +154,19 @@ class TestClone(testtools.TestCase):
         generate._clone_versions(freezes, options)
 
         self.assertEqual(expected_freezes, freezes)
+
+    def test_py35_clone_py34_py36(self):
+        # Simulate an environment where we have python 3.5 data and need to
+        # clone that to python 3.4
+        options = Namespace(version_map={'3.5': set(['3.4', '3.6'])})
+        freeze_27 = ('2.7', [('dnspython', '1.15.0')])
+        freeze_34 = ('3.4', [('dnspython3', '1.12.0')])
+        freeze_35 = ('3.5', [('dnspython3', '1.12.0')])
+        freeze_36 = ('3.6', [('dnspython3', '1.12.0')])
+
+        freezes = [freeze_27, freeze_35]
+        expected_freezes = [freeze_27, freeze_35, freeze_34, freeze_36]
+
+        generate._clone_versions(freezes, options)
+
+        self.assertEqual(expected_freezes, freezes)