diff --git a/news/2454.bugfix b/news/2454.bugfix
new file mode 100644
index 00000000..d60b047f
--- /dev/null
+++ b/news/2454.bugfix
@@ -0,0 +1 @@
+Pipenv will now always use ``pathlib2`` for ``Path`` based filesystem interactions by default on ``python<3.5``.
diff --git a/pipenv/_compat.py b/pipenv/_compat.py
index 68d8069d..07e75072 100644
--- a/pipenv/_compat.py
+++ b/pipenv/_compat.py
@@ -29,10 +29,13 @@ except ImportError:
                 _types.add(type(arg))
         return _types.pop()
 
-try:
-    from pathlib import Path
-except ImportError:
-    from pathlib2 import Path
+if sys.version_info[:2] >= (3, 5):
+    try:
+        from pathlib import Path
+    except ImportError:
+        from .vendor.pathlib2 import Path
+else:
+    from .vendor.pathlib2 import Path
 
 
 try:
diff --git a/pipenv/project.py b/pipenv/project.py
index d13f6491..9c8901e8 100644
--- a/pipenv/project.py
+++ b/pipenv/project.py
@@ -14,10 +14,7 @@ import six
 import toml
 import json as simplejson
 
-try:
-    from pathlib import Path
-except ImportError:
-    from pathlib2 import Path
+from ._compat import Path
 
 from .cmdparse import Script
 from .vendor.requirementslib import Requirement
diff --git a/pipenv/utils.py b/pipenv/utils.py
index a19f7ed0..12cd8283 100644
--- a/pipenv/utils.py
+++ b/pipenv/utils.py
@@ -36,13 +36,7 @@ try:
     from urllib.parse import urlparse
 except ImportError:
     from urlparse import urlparse
-try:
-    from pathlib import Path
-except ImportError:
-    try:
-        from .vendor.pathlib2 import Path
-    except ImportError:
-        pass
+
 from distutils.spawn import find_executable
 from contextlib import contextmanager
 from .pep508checker import lookup
@@ -231,7 +225,7 @@ def actually_resolve_deps(
     from pipenv.patched.piptools.scripts.compile import get_pip_command
     from pipenv.patched.piptools import logging as piptools_logging
     from pipenv.patched.piptools.exceptions import NoCandidateFound
-    from ._compat import TemporaryDirectory, NamedTemporaryFile
+    from ._compat import TemporaryDirectory, NamedTemporaryFile, Path
 
     class PipCommand(basecommand.Command):
         """Needed for pip-tools."""