diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 9fb3e0d6e3..9c57d2efac 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -38,6 +38,11 @@ variables:
 - group: deploy-secrets
 
 jobs:
+- template: pip-install-packages.yml@templates
+    parameters:
+      packages:
+      - mock
+
 - template: build-pipeline.yml@templates
   parameters:
     # After the tests have run, run the integration tests.
diff --git a/python/tank/template.py b/python/tank/template.py
index 77c135fc57..eba299a006 100644
--- a/python/tank/template.py
+++ b/python/tank/template.py
@@ -557,6 +557,17 @@ def root_path(self):
         """
         return self._prefix
 
+    def _dirname(self):
+        """
+        Returns the directory part of the template.
+
+        :returns: String
+        """
+        dirname, basename = os.path.split(self._repr_def)
+        if "[" in basename and "]" not in basename:
+            return dirname.split("[")[0]
+        return dirname
+
     @property
     def parent(self):
         """
@@ -566,8 +577,8 @@ def parent(self):
 
         :returns: :class:`Template`
         """
-        parent_definition = os.path.dirname(self.definition)
-        if parent_definition:
+        parent_definition = self._dirname()
+        if parent_definition and parent_definition != "/":
             return TemplatePath(
                 parent_definition,
                 self.keys,
diff --git a/tests/core_tests/test_templatepath.py b/tests/core_tests/test_templatepath.py
index ef7625bb9e..d9ea70df77 100644
--- a/tests/core_tests/test_templatepath.py
+++ b/tests/core_tests/test_templatepath.py
@@ -1184,3 +1184,43 @@ def test_aliased_key(self):
         template = TemplatePath(definition, keys, root_path=self.project_root)
         result = template.parent
         self.assertEqual("{new_name}", result.definition)
+
+    def test_parent_with_optional(self):
+        definition = "shots/{Sequence}[-{seq_num}]/{Shot}/{Step}/work"
+        parent_expected_definitions = [
+            "shots/{Sequence}-{seq_num}/{Shot}/{Step}",
+            "shots/{Sequence}/{Shot}/{Step}",
+        ]
+        parent_expected__repr_def = os.path.dirname(definition)
+
+        template = TemplatePath(definition, self.keys, root_path=self.project_root)
+        parent = template.parent
+        self.assertEqual(parent_expected_definitions, parent._definitions)
+        self.assertEqual(parent_expected__repr_def, parent._repr_def)
+
+
+class TestDirname(TestTemplatePath):
+    def test_dirname_with_word(self):
+        definition = "shots/{Sequence}/{Shot}/{Step}/work"
+        template = TemplatePath(definition, self.keys, root_path=self.project_root)
+        self.assertEqual("shots/{Sequence}/{Shot}/{Step}", template.dirname)
+
+    def test_dirname_with_key(self):
+        definition = "shots/{Sequence}/{Shot}/{Step}"
+        template = TemplatePath(definition, self.keys, root_path=self.project_root)
+        self.assertEqual("shots/{Sequence}/{Shot}", template.dirname)
+
+    def test_dirname_with_optional(self):
+        definition = "shots/{Sequence}/{Shot}[/{Step}]"
+        template = TemplatePath(definition, {}, root_path=self.project_root)
+        self.assertEqual("shots/{Sequence}/{Shot}", template.dirname)
+
+    def test_dirname_with_optional_word_and_key(self):
+        definition = "shots/{Sequence}/{Shot}/[abc_{Step}]"
+        template = TemplatePath(definition, {}, root_path=self.project_root)
+        self.assertEqual("shots/{Sequence}/{Shot}", template.dirname)
+
+    def test_dirname_with_optional_key_and_key(self):
+        definition = "shots/{Sequence}/[{Shot}]-{Step}"
+        template = TemplatePath(definition, {}, root_path=self.project_root)
+        self.assertEqual("shots/{Sequence}", template.dirname)