diff --git a/Makefile b/Makefile
index 219a4dcd..91bea4bb 100644
--- a/Makefile
+++ b/Makefile
@@ -22,10 +22,10 @@ virtualenv:
 
 virtualenv-windows:
 	virtualenv --prompt '|> cement <| ' env-windows
-	env-windows\\Scripts\\pip.exe install -r requirements-dev.txt
-	env\\bin\\python.exe setup.py develop
+	env-windows\\Scripts\\pip.exe install -r requirements-dev-windows.txt
+	env-windows\\Scripts\\python.exe setup.py develop
 	@echo
-	@echo "VirtualENV Setup Complete. Now run: .\\env\\Scripts\\activate.ps1"
+	@echo "VirtualENV Setup Complete. Now run: .\env-windows\Scripts\activate.ps1"
 	@echo
 
 comply:
diff --git a/README.md b/README.md
index ba729b6d..f420b459 100644
--- a/README.md
+++ b/README.md
@@ -67,6 +67,18 @@ $ docker-compose up -d
 $ docker-compose exec cement /bin/ash
 ```
 
+### VirtualENV
+
+An traditional VirtualENV helper is available:
+
+```
+$ make virtualenv
+
+$ source env/bin/activate
+
+|> cement <| $
+```
+
 ### Vagrant
 
 An alternative option is included to run Vagrant for development.  This is partially supported, primarily for the purpose of developing/testing on Windows as well as testing specific issues on target operating systems.
@@ -88,11 +100,11 @@ vagrant@linux $ cd /vagrant
 
 vagrant@linux $ bash scripts/vagrant/bootstrap.sh
 
+vagrant@linux $ make virtualenv
+
 vagrant@linux $ source env/bin/activate
 
-|> cement >| $ pip install -r requirements-dev.txt
-
-|> cement >| $ python setup.py develop
+|> cement >| $
 ```
 
 #### Windows
@@ -114,13 +126,15 @@ C:\> cd C:\Vagrant
 
 C:\Vagrant> powershell.exe scripts\vagrant\bootstrap.ps1
 
+C:\Vagrant> make virtualenv-windows
+
 C:\Vagrant> .\env-windows\Scripts\activate.ps1
 
-C:\Vagrant> pip install -r requirements-dev.txt
-
-C:\Vagrant> python setup.py develop
+C:\Vagrant> make test-core
 ```
 
+*Note that only the core library is fully tested on Windows.*
+
 
 ### Running Tests and Compliance
 
diff --git a/cement/core/template.py b/cement/core/template.py
index fd37d81f..6edcbad3 100644
--- a/cement/core/template.py
+++ b/cement/core/template.py
@@ -5,6 +5,7 @@ import sys
 import pkgutil
 import re
 import shutil
+import platform
 from abc import abstractmethod
 from ..core import exc
 from ..core.interface import Interface
@@ -232,6 +233,11 @@ class TemplateHandler(TemplateInterface, Handler):
                     os.makedirs(sub_dir_dest)
 
             for _file in files:
+                # windows paths (if condition to avoid unknown breakage)
+                if platform.system().lower() in ['windows']:
+                    src = src.encode('unicode-escape')      # pragma: nocover
+                    src = str(src)                          # pragma: nocover
+
                 new_file = re.sub(src, '', self.render(_file, data))
                 _file = fs.abspath(os.path.join(cur_dir, _file))
                 _file_dest = fs.abspath(os.path.join(cur_dir_dest, new_file))
diff --git a/requirements-dev-windows.txt b/requirements-dev-windows.txt
new file mode 100644
index 00000000..db5c42db
--- /dev/null
+++ b/requirements-dev-windows.txt
@@ -0,0 +1,29 @@
+# The following are only required for Cement development
+pytest
+pytest-cov
+coverage
+sphinx
+sphinx_rtd_theme
+pep8
+autopep8
+# version cap due to bug: https://gitlab.com/pycqa/flake8/issues/406
+pycodestyle<2.4
+flake8
+guzzle_sphinx_theme
+sphinxcontrib-napoleon
+mock
+twine>=1.11.0
+setuptools>=38.6.0
+wheel>=0.31.0
+
+# Required for optional extensions
+pystache
+pyYaml
+redis
+colorlog
+tabulate
+jinja2
+watchdog
+
+# unknown/broken/untested
+# pylibmc
diff --git a/requirements-dev.txt b/requirements-dev.txt
index f15368aa..e9a8b8df 100644
--- a/requirements-dev.txt
+++ b/requirements-dev.txt
@@ -24,6 +24,4 @@ colorlog
 tabulate
 jinja2
 watchdog
-
-# These are known to fail on windows (put at end so it doesn't block)
 pylibmc
diff --git a/scripts/vagrant/bootstrap.ps1 b/scripts/vagrant/bootstrap.ps1
index de80f4c9..55d6a362 100644
--- a/scripts/vagrant/bootstrap.ps1
+++ b/scripts/vagrant/bootstrap.ps1
@@ -78,7 +78,6 @@ Function Do-Python {
     }
 
     C:\Python37\Scripts\pip.exe install virtualenv
-    C:\Python37\Scripts\virtualenv.exe env-windows
 }
 
 Function Do-Misc {
diff --git a/scripts/vagrant/bootstrap.sh b/scripts/vagrant/bootstrap.sh
index 3958a1a9..abd6bb1f 100755
--- a/scripts/vagrant/bootstrap.sh
+++ b/scripts/vagrant/bootstrap.sh
@@ -98,10 +98,6 @@ case "$DISTRO" in
 
 esac
 
-### should work on all distros we are trying to support
-
-virtualenv --prompt="|> cement <| " --python=$(which python3) /vagrant/env
-
 # for tests
 
 sudo systemctl restart memcached
diff --git a/tests/conftest.py b/tests/conftest.py
index d166a73d..aba3f11d 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -3,18 +3,12 @@ import os
 import shutil
 import pytest
 from cement.utils.misc import rando as _rando
-from tempfile import mkstemp, mkdtemp
+from cement.utils import fs
 
 
 @pytest.fixture(scope="function")
 def tmp(request):
-    class Tmp(object):
-        cleanup = True
-
-        def __init__(self):
-            self.dir = mkdtemp()
-            _, self.file = mkstemp(dir=self.dir)
-    t = Tmp()
+    t = fs.Tmp()
     yield t
 
     # cleanup
diff --git a/tests/core/test_foundation.py b/tests/core/test_foundation.py
index e8af6248..37439c96 100644
--- a/tests/core/test_foundation.py
+++ b/tests/core/test_foundation.py
@@ -5,6 +5,7 @@ import re
 import pytest
 import json
 import signal
+import platform
 from unittest.mock import Mock, MagicMock
 
 from cement import App, Controller, ex
@@ -101,22 +102,35 @@ def test_basic():
         app.run()
 
 
-def test_loaded():
-    ext_list = [
-                'alarm',
-                'colorlog',
-                'daemon',
-                'dummy',
-                'jinja2',
-                'json',
-                'memcached',
-                'mustache',
-                'redis',
-                'smtp',
-                'tabulate',
-                'watchdog',
-                'yaml',
-            ]
+def test_loaded_extensions():
+    if platform.system().lower() in ['windows']:
+        ext_list = [
+            'colorlog',
+            'dummy',
+            'jinja2',
+            'json',
+            'mustache',
+            'smtp',
+            'tabulate',
+            'watchdog',
+            'yaml',
+        ]
+    else:
+        ext_list = [
+            'alarm',
+            'colorlog',
+            'daemon',
+            'dummy',
+            'jinja2',
+            'json',
+            'memcached',
+            'mustache',
+            'redis',
+            'smtp',
+            'tabulate',
+            'watchdog',
+            'yaml',
+        ]
 
     class MyApp(TestApp):
         class Meta:
@@ -324,12 +338,20 @@ def test_config_files_is_none():
 
     with ThisApp('test-app', config_files=None) as app:
         user_home = fs.abspath(fs.HOME_DIR)
-        files = [
-            os.path.join('/', 'etc', app.label, '%s.conf' % app.label),
-            os.path.join(user_home, '.%s.conf' % app.label),
-            os.path.join(user_home, '.%s' % app.label, 'config',
-                         '%s.conf' % app.label),
-        ]
+        if platform.system().lower() in ['windows']:
+            files = [
+                os.path.join('C:\\', 'etc', app.label, '%s.conf' % app.label),
+                os.path.join(user_home, '.%s.conf' % app.label),
+                os.path.join(user_home, '.%s' % app.label, 'config',
+                             '%s.conf' % app.label),
+            ]
+        else:
+            files = [
+                os.path.join('/', 'etc', app.label, '%s.conf' % app.label),
+                os.path.join(user_home, '.%s.conf' % app.label),
+                os.path.join(user_home, '.%s' % app.label, 'config',
+                             '%s.conf' % app.label),
+            ]
         for f in files:
             assert f in app._meta.config_files
 
@@ -470,6 +492,9 @@ def test_reload():
 
 
 def test_run_forever():
+    if platform.system().lower() in ['windows']:
+        pytest.skip('Unable to test run_forever on Windows')
+
     class MyController(Controller):
         class Meta:
             label = 'base'