diff --git a/.github/workflows/pytest.yaml b/.github/workflows/pytest.yaml
index 8f6ff79e009a1..028aec017afa6 100644
--- a/.github/workflows/pytest.yaml
+++ b/.github/workflows/pytest.yaml
@@ -17,8 +17,7 @@ jobs:
   python-test:
     strategy:
       matrix:
-        # TODO(b/281098312): pytest fails on windows-latest
-        os: [ubuntu-latest]
+        os: [ubuntu-latest, windows-latest]
         python-version: ['3.7', '3.11']
       fail-fast: false
     runs-on: ${{ matrix.os }}
@@ -32,6 +31,7 @@ jobs:
         uses: actions/setup-python@v4
         with:
           python-version: ${{ matrix.python-version }}
+          cache: 'pip'
       - name: Install Pip Packages
         run: pip install --require-hashes --no-deps -r ${{ github.workspace }}/docker/pytest/requirements.txt
       - name: Run Tests
diff --git a/cobalt/build/get_build_id_test.py b/cobalt/build/get_build_id_test.py
index 0579a72940caa..f9ea8c3c3033c 100644
--- a/cobalt/build/get_build_id_test.py
+++ b/cobalt/build/get_build_id_test.py
@@ -26,6 +26,8 @@
 _TEST_BUILD_NUMBER = 1234 + get_build_id.COMMIT_COUNT_BUILD_NUMBER_OFFSET
 
 
+# TODO(b/282040638): fix and re-enabled this
+@unittest.skipIf(os.name == 'nt', 'Broken on Windows')
 class GetBuildIdTest(unittest.TestCase):
 
   def setUp(self):
diff --git a/docker/pytest/requirements.in b/docker/pytest/requirements.in
index a15dd49dfe2b4..fffb347035535 100644
--- a/docker/pytest/requirements.in
+++ b/docker/pytest/requirements.in
@@ -5,3 +5,4 @@ jsonschema<5
 junitparser==2.8.0
 pexpect==4.8.0
 six==1.12.0
+atomicwrites==1.4.1
diff --git a/docker/pytest/requirements.txt b/docker/pytest/requirements.txt
index be346fdc5f10e..3dcbe0f1819e5 100644
--- a/docker/pytest/requirements.txt
+++ b/docker/pytest/requirements.txt
@@ -4,6 +4,9 @@
 #
 #    pip-compile --generate-hashes requirements.in
 #
+atomicwrites==1.4.1 \
+    --hash=sha256:81b2c9071a49367a7f770170e5eec8cb66567cfbbc8c73d20ce5ca4a8d71cf11
+    # via -r docker/pytest/requirements.in
 attrs==21.4.0 \
     --hash=sha256:2d27e3784d7a565d36ab851fe94887c5eccd6a463168875832a1be79c82828b4 \
     --hash=sha256:626ba8234211db98e869df76230a137c4c40a12d72445c45d5f5b716f076e2fd
diff --git a/starboard/raspi/shared/launcher_test.py b/starboard/raspi/shared/launcher_test.py
index 5fe6794046187..58712cbaad31c 100644
--- a/starboard/raspi/shared/launcher_test.py
+++ b/starboard/raspi/shared/launcher_test.py
@@ -28,6 +28,7 @@
 # pylint: disable=missing-class-docstring
 
 
+@unittest.skipIf(os.name == 'nt', 'Pexpect does not work on Windows')
 class LauncherTest(unittest.TestCase):
 
   def setUp(self):
diff --git a/starboard/sabi/generate_sabi_id_test.py b/starboard/sabi/generate_sabi_id_test.py
index 8b9477d75512f..ec230f67b9288 100755
--- a/starboard/sabi/generate_sabi_id_test.py
+++ b/starboard/sabi/generate_sabi_id_test.py
@@ -45,6 +45,9 @@ def testRainyDayNonexistentFile(self):
     with self.assertRaises(IOError):
       generate_sabi_id.DoMain(['-f', 'invalid_filename'])
 
+  # TODO(b/281098312): fix and re-enable this
+  @unittest.skipIf(os.name == 'nt',
+                   'Broken on Windows due to temp path handling')
   def testRainyDayBadFile(self):
     bad_sabi_json = tempfile.NamedTemporaryFile(mode='w')  # pylint: disable=consider-using-with
     bad_sabi_json.write('{}')