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..2068a227 100644
--- a/pipenv/utils.py
+++ b/pipenv/utils.py
@@ -14,7 +14,6 @@ import warnings
 
 from click import echo as click_echo
 from first import first
-
 try:
     from weakref import finalize
 except ImportError:
@@ -36,13 +35,7 @@ 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
@@ -609,6 +602,7 @@ def is_installable_file(path):
     from .patched.notpip._internal.utils.misc import is_installable_dir
     from .patched.notpip._internal.utils.packaging import specifiers
     from .patched.notpip._internal.download import is_archive_file
+    from ._compat import Path
 
     if hasattr(path, 'keys') and any(
         key for key in path.keys() if key in ['file', 'path']
@@ -853,6 +847,7 @@ def find_windows_executable(bin_path, exe_name):
 
 
 def path_to_url(path):
+    from ._compat import Path
     return Path(normalize_drive(os.path.abspath(path))).as_uri()
 
 
@@ -1158,7 +1153,7 @@ def get_vcs_deps(
     pypi_mirror=None,
 ):
     from .patched.notpip._internal.vcs import VcsSupport
-    from ._compat import TemporaryDirectory
+    from ._compat import TemporaryDirectory, Path
 
     section = "vcs_dev_packages" if dev else "vcs_packages"
     reqs = []
diff --git a/tests/integration/conftest.py b/tests/integration/conftest.py
index 6141eeac..d71f0f89 100644
--- a/tests/integration/conftest.py
+++ b/tests/integration/conftest.py
@@ -4,18 +4,12 @@ import warnings
 
 import pytest
 
-from pipenv._compat import TemporaryDirectory
+from pipenv._compat import TemporaryDirectory, Path
 from pipenv.vendor import delegator
 from pipenv.vendor import requests
 from pipenv.vendor import six
 from pipenv.vendor import toml
 
-try:
-    from pathlib import Path
-except ImportError:
-    from pipenv.vendor.pathlib2 import Path
-
-
 if six.PY2:
     class ResourceWarning(Warning):
         pass
diff --git a/tests/integration/test_install_basic.py b/tests/integration/test_install_basic.py
index 71e3ed5d..d4e967d4 100644
--- a/tests/integration/test_install_basic.py
+++ b/tests/integration/test_install_basic.py
@@ -2,13 +2,9 @@ import contextlib
 import os
 
 from pipenv.utils import temp_environ
-from pipenv._compat import TemporaryDirectory
+from pipenv._compat import TemporaryDirectory, Path
 from pipenv.vendor import delegator
 from pipenv.project import Project
-try:
-    from pathlib import Path
-except ImportError:
-    from pipenv.vendor.pathlib2 import Path
 
 import pytest
 
diff --git a/tests/integration/test_install_twists.py b/tests/integration/test_install_twists.py
index 8750d463..95d67daf 100644
--- a/tests/integration/test_install_twists.py
+++ b/tests/integration/test_install_twists.py
@@ -1,10 +1,7 @@
 import os
 import shutil
 from pipenv.project import Project
-try:
-    import pathlib
-except ImportError:
-    import pathlib2 as pathlib
+from pipenv._compat import Path
 
 from pipenv.utils import mkdir_p, temp_environ
 
@@ -223,7 +220,7 @@ def test_relative_paths(PipenvInstance, pypi, testsroot):
         dep = p.pipfile['packages'][key]
 
         assert 'path' in dep
-        assert pathlib.Path('.', artifact_dir, file_name) == pathlib.Path(dep['path'])
+        assert Path('.', artifact_dir, file_name) == Path(dep['path'])
         assert c.return_code == 0
 
 
diff --git a/tests/integration/test_install_uri.py b/tests/integration/test_install_uri.py
index 709ba8eb..df2d44d8 100644
--- a/tests/integration/test_install_uri.py
+++ b/tests/integration/test_install_uri.py
@@ -2,10 +2,7 @@ import pytest
 import os
 from flaky import flaky
 import delegator
-try:
-    from pathlib import Path
-except ImportError:
-    from pathlib2 import Path
+from pipenv._compat import Path
 
 
 @pytest.mark.vcs
diff --git a/tests/integration/test_pipenv.py b/tests/integration/test_pipenv.py
index 7077d6e7..89ee793e 100644
--- a/tests/integration/test_pipenv.py
+++ b/tests/integration/test_pipenv.py
@@ -11,11 +11,7 @@ import pytest
 from pipenv.core import activate_virtualenv
 from pipenv.project import Project
 from pipenv.vendor import delegator
-
-try:
-    from pathlib import Path
-except ImportError:
-    from pipenv.vendor.pathlib2 import Path
+from pipenv._compat import Path
 
 
 @pytest.mark.code
@@ -123,4 +119,4 @@ def test_directory_with_leading_dash(PipenvInstance):
             assert os.path.isdir(venv_path)
             # Manually clean up environment, since PipenvInstance assumes that
             # the virutalenv is in the project directory.
-            p.pipenv('--rm')
\ No newline at end of file
+            p.pipenv('--rm')
diff --git a/tests/integration/test_windows.py b/tests/integration/test_windows.py
index 91b4f995..bd6eaf19 100644
--- a/tests/integration/test_windows.py
+++ b/tests/integration/test_windows.py
@@ -1,7 +1,7 @@
 import os
 
 from pipenv.project import Project
-from pipenv.vendor import pathlib2 as pathlib
+from pipenv._compat import Path
 
 import pytest
 
@@ -33,7 +33,7 @@ def test_case_changes_windows(PipenvInstance, pypi):
 @pytest.mark.files
 def test_local_path_windows(PipenvInstance, pypi):
     whl = (
-        pathlib.Path(__file__).parent.parent
+        Path(__file__).parent.parent
         .joinpath('pypi', 'six', 'six-1.11.0-py2.py3-none-any.whl')
     )
     try:
@@ -48,7 +48,7 @@ def test_local_path_windows(PipenvInstance, pypi):
 @pytest.mark.files
 def test_local_path_windows_forward_slash(PipenvInstance, pypi):
     whl = (
-        pathlib.Path(__file__).parent.parent
+        Path(__file__).parent.parent
         .joinpath('pypi', 'six', 'six-1.11.0-py2.py3-none-any.whl')
     )
     try: