diff --git a/releasenotes/notes/ansible-shell-type-d76d84b940d21eea.yaml b/releasenotes/notes/ansible-shell-type-d76d84b940d21eea.yaml
new file mode 100644
index 0000000000..95cc72f3d7
--- /dev/null
+++ b/releasenotes/notes/ansible-shell-type-d76d84b940d21eea.yaml
@@ -0,0 +1,10 @@
+---
+features:
+  - |
+    Zuul now honors the shell-type configuration from nodepool and
+    uses it to set ansible_shell_type, a setting that is required
+    when connecting to Windows workers over ssh.
+
+    For Linux workers, there is a long standing ansible issue with 
+    using non-default ansible_shell_type and become, so this feature
+    is primarily targeting Windows workers.
diff --git a/tests/base.py b/tests/base.py
index 1b0c6791e6..6afd36ddda 100644
--- a/tests/base.py
+++ b/tests/base.py
@@ -3369,6 +3369,7 @@ class FakeNodepool(object):
         self.attributes = None
         self.resources = None
         self.python_path = 'auto'
+        self.shell_type = None
 
     def stop(self):
         self._running = False
@@ -3466,6 +3467,7 @@ class FakeNodepool(object):
                     private_ipv4=None,
                     public_ipv6=None,
                     python_path=self.python_path,
+                    shell_type=self.shell_type,
                     allocated_to=request_id,
                     state='ready',
                     state_time=now,
diff --git a/tests/unit/test_executor.py b/tests/unit/test_executor.py
index 2652f7f4f5..baca6e053e 100644
--- a/tests/unit/test_executor.py
+++ b/tests/unit/test_executor.py
@@ -474,6 +474,30 @@ class TestAnsibleJob(ZuulTestCase):
             host['host_vars']['ansible_ssh_common_args'],
             '-o StrictHostKeyChecking=false')
 
+    def test_getHostList_shell_type(self):
+        # Test without shell type set
+        node = {'name': 'fake-host',
+                'host_keys': ['fake-host-key'],
+                'interface_ip': 'localhost'}
+        host = self.test_job.getHostList({'nodes': [node],
+                                          'host_vars': {},
+                                          'vars': {},
+                                          'groups': [],
+                                          })[0]
+        self.assertNotIn('ansible_shell_type', host['host_vars'])
+
+        # Test with custom shell type set.
+        node['shell_type'] = 'cmd'
+        host = self.test_job.getHostList({'nodes': [node],
+                                          'host_vars': {},
+                                          'vars': {},
+                                          'groups': [],
+                                          })[0]
+        self.assertIn('ansible_shell_type', host['host_vars'])
+        self.assertEqual(
+            host['host_vars']['ansible_shell_type'],
+            'cmd')
+
 
 class TestExecutorHostname(ZuulTestCase):
     config_file = 'zuul-executor-hostname.conf'
diff --git a/tests/unit/test_inventory.py b/tests/unit/test_inventory.py
index 024e438a44..3dbc078d05 100644
--- a/tests/unit/test_inventory.py
+++ b/tests/unit/test_inventory.py
@@ -27,10 +27,12 @@ class TestInventoryBase(ZuulTestCase):
     tenant_config_file = 'config/inventory/main.yaml'
     use_gerrit = True
 
-    def setUp(self, python_path=None):
+    def setUp(self, python_path=None, shell_type=None):
         super(TestInventoryBase, self).setUp()
         if python_path:
             self.fake_nodepool.python_path = python_path
+        if shell_type:
+            self.fake_nodepool.shell_type = shell_type
         self.executor_server.hold_jobs_in_build = True
         self.gearman_server.hold_jobs_in_queue = True
 
@@ -141,6 +143,36 @@ class TestInventoryPythonPath(TestInventoryBase):
         self.waitUntilSettled()
 
 
+class TestInventoryShellType(TestInventoryBase):
+
+    def setUp(self):
+        super(TestInventoryShellType, self).setUp(shell_type='cmd')
+
+    def test_single_inventory(self):
+        inventory = self._get_build_inventory('single-inventory')
+
+        all_nodes = ('ubuntu-xenial',)
+        self.assertIn('all', inventory)
+        self.assertIn('hosts', inventory['all'])
+        self.assertIn('vars', inventory['all'])
+        for node_name in all_nodes:
+            self.assertIn(node_name, inventory['all']['hosts'])
+            node_vars = inventory['all']['hosts'][node_name]
+            self.assertEqual(
+                'cmd', node_vars['ansible_shell_type'])
+
+        self.assertIn('zuul', inventory['all']['vars'])
+        z_vars = inventory['all']['vars']['zuul']
+        self.assertIn('executor', z_vars)
+        self.assertIn('src_root', z_vars['executor'])
+        self.assertIn('job', z_vars)
+        self.assertEqual(z_vars['job'], 'single-inventory')
+        self.assertEqual(z_vars['message'], 'QQ==')
+
+        self.executor_server.release()
+        self.waitUntilSettled()
+
+
 class TestInventoryAutoPython(TestInventoryBase):
 
     def test_auto_python_ansible28_inventory(self):
@@ -183,6 +215,8 @@ class TestInventory(TestInventoryBase):
             node_vars = inventory['all']['hosts'][node_name]
             self.assertEqual(
                 'auto', node_vars['ansible_python_interpreter'])
+            self.assertNotIn(
+                'ansible_shell_type', node_vars)
         self.assertIn('zuul', inventory['all']['vars'])
         self.assertIn('attempts', inventory['all']['vars']['zuul'])
         self.assertEqual(1, inventory['all']['vars']['zuul']['attempts'])
diff --git a/zuul/executor/server.py b/zuul/executor/server.py
index f59d1b48a0..7360878ba4 100644
--- a/zuul/executor/server.py
+++ b/zuul/executor/server.py
@@ -1590,6 +1590,10 @@ class AnsibleJob(object):
                         host_vars['ansible_kubectl_context'] = \
                             node.get('kubectl_context')
 
+                shell_type = node.get('shell_type')
+                if shell_type:
+                    host_vars['ansible_shell_type'] = shell_type
+
                 host_keys = []
                 for key in node.get('host_keys', []):
                     if port != 22: