diff --git a/src/python/pants/backend/project_info/tasks/export.py b/src/python/pants/backend/project_info/tasks/export.py
index 00270bdee4d..a9c8425b0d7 100644
--- a/src/python/pants/backend/project_info/tasks/export.py
+++ b/src/python/pants/backend/project_info/tasks/export.py
@@ -336,8 +336,8 @@ def iter_transitive_jars(jar_lib):
       # across all the python targets in-play.
       #
       # For now, make our arbitrary historical choice of a default interpreter explicit and use the
-      # lowest version.
-      default_interpreter = min(python_interpreter_targets_mapping.keys())
+      # highest version.
+      default_interpreter = max(python_interpreter_targets_mapping.keys())
 
       interpreters_info = {}
       for interpreter, targets in six.iteritems(python_interpreter_targets_mapping):
diff --git a/src/python/pants/backend/python/interpreter_cache.py b/src/python/pants/backend/python/interpreter_cache.py
index e0126f74e13..8350d9d0169 100644
--- a/src/python/pants/backend/python/interpreter_cache.py
+++ b/src/python/pants/backend/python/interpreter_cache.py
@@ -112,8 +112,8 @@ def select_interpreter_for_targets(self, targets):
         'Unable to detect a suitable interpreter for compatibilities: {} '
         '(Conflicting targets: {})'.format(' && '.join(sorted(unique_compatibilities_strs)),
                                            ', '.join(tgts_by_compatibilities_strs)))
-    # Return the lowest compatible interpreter.
-    return min(allowed_interpreters)
+    # Return the highest compatible interpreter.
+    return max(allowed_interpreters)
 
   def _interpreter_from_path(self, path, filters=()):
     try:
diff --git a/tests/python/pants_test/backend/python/interpreter_selection_utils.py b/tests/python/pants_test/backend/python/interpreter_selection_utils.py
index 90d3ccc69f3..101a8ef5e6d 100644
--- a/tests/python/pants_test/backend/python/interpreter_selection_utils.py
+++ b/tests/python/pants_test/backend/python/interpreter_selection_utils.py
@@ -36,7 +36,7 @@ def python_interpreter_path(version):
     command = ['python{}'.format(version), '-c', 'import sys; print(sys.executable)']
     py_path = subprocess.check_output(command).decode('utf-8').strip()
     return os.path.realpath(py_path)
-  except subprocess.CalledProcessError:
+  except (subprocess.CalledProcessError, OSError):
     return None
 
 
diff --git a/tests/python/pants_test/backend/python/tasks/test_select_interpreter.py b/tests/python/pants_test/backend/python/tasks/test_select_interpreter.py
index 07fcfb626fa..7f3efaa68db 100644
--- a/tests/python/pants_test/backend/python/tasks/test_select_interpreter.py
+++ b/tests/python/pants_test/backend/python/tasks/test_select_interpreter.py
@@ -105,14 +105,14 @@ def _select_interpreter_and_get_version(self, target_roots, should_invalidate=No
 
   def test_interpreter_selection(self):
     self.assertIsNone(self._select_interpreter([]))
-    self.assertEqual('IronPython-2.77.777', self._select_interpreter_and_get_version([self.reqtgt]))
-    self.assertEqual('IronPython-2.77.777', self._select_interpreter_and_get_version([self.tgt1]))
-    self.assertEqual('IronPython-2.88.888', self._select_interpreter_and_get_version([self.tgt2]))
+    self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.reqtgt]))
+    self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt1]))
+    self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt2]))
     self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt3]))
-    self.assertEqual('IronPython-2.77.777', self._select_interpreter_and_get_version([self.tgt4]))
-    self.assertEqual('IronPython-2.88.888', self._select_interpreter_and_get_version([self.tgt20]))
+    self.assertEqual('IronPython-2.88.888', self._select_interpreter_and_get_version([self.tgt4]))
+    self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt20]))
     self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt30]))
-    self.assertEqual('IronPython-2.77.777', self._select_interpreter_and_get_version([self.tgt40]))
+    self.assertEqual('IronPython-2.88.888', self._select_interpreter_and_get_version([self.tgt40]))
     self.assertEqual('IronPython-2.99.999', self._select_interpreter_and_get_version([self.tgt2, self.tgt3]))
     self.assertEqual('IronPython-2.88.888', self._select_interpreter_and_get_version([self.tgt2, self.tgt4]))