diff --git a/changelog/62968.fixed b/changelog/62968.fixed
new file mode 100644
index 00000000000..891c319c423
--- /dev/null
+++ b/changelog/62968.fixed
@@ -0,0 +1 @@
+Issue #62968: Fix issue where cloud deployments were putting the keys in the wrong location on Windows hosts
diff --git a/changelog/63024.fixed b/changelog/63024.fixed
new file mode 100644
index 00000000000..e3544b9bc14
--- /dev/null
+++ b/changelog/63024.fixed
@@ -0,0 +1 @@
+Issue #63024: Fix issue where grains and config data were being place in the wrong location on Windows hosts
diff --git a/tests/pytests/unit/utils/test_cloud.py b/tests/pytests/unit/utils/test_cloud.py
index 12b76786d31..3ed38031dd2 100644
--- a/tests/pytests/unit/utils/test_cloud.py
+++ b/tests/pytests/unit/utils/test_cloud.py
@@ -206,6 +206,225 @@ def test_deploy_windows_custom_port():
         mock.assert_called_once_with("test", "Administrator", None, 1234)
 
 
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            cloud.deploy_windows(host="test", win_installer="")
+            expected = "ProgramData/Salt Project/Salt/conf/pki/minion"
+            mock_smb.mkdirs.assert_called_with(expected, conn=mock_conn)
+
+
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata_minion_pub():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.put_str.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            cloud.deploy_windows(host="test", minion_pub="pub", win_installer="")
+            expected = (
+                "ProgramData\\Salt Project\\Salt\\conf\\pki\\minion\\minion.pub"
+            )
+            mock_smb.put_str.assert_called_with("pub", expected, conn=mock_conn)
+
+
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata_minion_pem():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.put_str.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            cloud.deploy_windows(host="test", minion_pem="pem", win_installer="")
+            expected = (
+                "ProgramData\\Salt Project\\Salt\\conf\\pki\\minion\\minion.pem"
+            )
+            mock_smb.put_str.assert_called_with("pem", expected, conn=mock_conn)
+
+
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata_master_sign_pub_file():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.put_str.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            cloud.deploy_windows(
+                host="test", master_sign_pub_file="test.txt", win_installer=""
+            )
+            expected = (
+                "ProgramData\\Salt Project\\Salt\\conf\\pki\\minion\\master_sign.pub"
+            )
+            called = False
+            for call in mock_smb.put_file.mock_calls:
+                if expected in call[1]:
+                    called = True
+            assert called
+
+
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata_minion_conf_grains():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.put_str.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            minion_conf = {"grains": {"spongebob": "squarepants"}}
+            cloud.deploy_windows(
+                host="test", minion_conf=minion_conf, win_installer=""
+            )
+            expected = "ProgramData\\Salt Project\\Salt\\conf\\grains"
+            called = False
+            for call in mock_smb.put_str.mock_calls:
+                if expected in call[1]:
+                    called = True
+            assert called
+
+
+@pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
+def test_deploy_windows_programdata_minion_conf():
+    """
+    Test deploy_windows with a custom port
+    """
+    mock_true = MagicMock(return_value=True)
+    mock_tuple = MagicMock(return_value=(0, 0, 0))
+    mock_conn = MagicMock()
+
+    with patch("salt.utils.smb", MagicMock()) as mock_smb:
+        mock_smb.get_conn.return_value = mock_conn
+        mock_smb.mkdirs.return_value = None
+        mock_smb.put_file.return_value = None
+        mock_smb.put_str.return_value = None
+        mock_smb.delete_file.return_value = None
+        mock_smb.delete_directory.return_value = None
+        with patch(
+            "time.sleep", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_port", mock_true
+        ), patch.object(
+            cloud, "fire_event", MagicMock()
+        ), patch.object(
+            cloud, "wait_for_psexecsvc", mock_true
+        ), patch.object(
+            cloud, "run_psexec_command", mock_tuple
+        ):
+            minion_conf = {"master": "test-master"}
+            cloud.deploy_windows(
+                host="test", minion_conf=minion_conf, win_installer=""
+            )
+            config = (
+                "ipc_mode: tcp\r\n"
+                "master: test-master\r\n"
+                "multiprocessing: true\r\n"
+                "pki_dir: /conf/pki/minion\r\n"
+            )
+            expected = "ProgramData\\Salt Project\\Salt\\conf\\minion"
+            mock_smb.put_str.assert_called_with(config, expected, conn=mock_conn)
+
+
 @pytest.mark.skip_unless_on_windows(reason="Only applicable for Windows.")
 def test_winrm_pinnned_version():
     """