diff --git a/.azure-pipelines/jobs/test-windows.yml b/.azure-pipelines/jobs/test-windows.yml
index f0ab8f812..1a933a693 100644
--- a/.azure-pipelines/jobs/test-windows.yml
+++ b/.azure-pipelines/jobs/test-windows.yml
@@ -26,7 +26,10 @@ jobs:
       Python37-x64:
         python.version: '3.7'
         python.architecture: x64
-    maxParallel: 5
+      Python38-x64:
+        python.version: '3.8'
+        python.architecture: x64
+    maxParallel: 6
 
   steps:
   - template: ../steps/run-tests-windows.yml
@@ -54,7 +57,10 @@ jobs:
       Python37-x86:
         python.version: '3.7'
         python.architecture: x86
-    maxParallel: 5
+      Python38-x86:
+        python.version: '3.8'
+        python.architecture: x86
+    maxParallel: 6
 
   steps:
   - template: ../steps/run-tests-windows.yml
diff --git a/.azure-pipelines/steps/run-tests-windows.yml b/.azure-pipelines/steps/run-tests-windows.yml
index 30b0021cb..4908c0ec7 100644
--- a/.azure-pipelines/steps/run-tests-windows.yml
+++ b/.azure-pipelines/steps/run-tests-windows.yml
@@ -25,7 +25,7 @@ steps:
     Set-Acl "R:\Temp" $acl
   displayName: Set RAMDisk Permissions
 
-- bash: pip install --upgrade setuptools tox
+- bash: pip install --upgrade setuptools tox virtualenv
   displayName: Install Tox
 
 - script: tox -e py -- -m unit -n auto --junit-xml=junit/unit-test.xml
diff --git a/docs/html/development/ci.rst b/docs/html/development/ci.rst
index e758705b2..e68b2b4e6 100644
--- a/docs/html/development/ci.rst
+++ b/docs/html/development/ci.rst
@@ -99,7 +99,7 @@ Actual testing
 |           |          +-------+---------------+-----------------+
 |           |   x86    | CP3.7 |   Azure       |                 |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.8 |               |                 |
+|           |          | CP3.8 |   Azure       |                 |
 |           |          +-------+---------------+-----------------+
 |           |          | PyPy  |               |                 |
 |           |          +-------+---------------+-----------------+
@@ -113,7 +113,7 @@ Actual testing
 |           |          +-------+---------------+-----------------+
 |           |   x64    | CP3.7 |   Azure       |   Azure         |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.8 |               |                 |
+|           |          | CP3.8 |   Azure       |   Azure         |
 |           |          +-------+---------------+-----------------+
 |           |          | PyPy  |               |                 |
 |           |          +-------+---------------+-----------------+
diff --git a/tests/unit/test_compat.py b/tests/unit/test_compat.py
index 634aacc40..1f31bc5ce 100644
--- a/tests/unit/test_compat.py
+++ b/tests/unit/test_compat.py
@@ -136,4 +136,5 @@ def test_console_to_str_warning(monkeypatch):
 ])
 def test_expanduser(home, path, expanded, monkeypatch):
     monkeypatch.setenv("HOME", home)
+    monkeypatch.setenv("USERPROFILE", home)
     assert expanduser(path) == expanded