diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index bd0ac738..f79929bc 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -14,6 +14,7 @@ jobs:
           - { os: 'ubuntu-latest', python-version: "3.10" }
           - { os: 'ubuntu-latest', python-version: "3.11" }
           - { os: 'macos-latest', python-version: "3.11" }
+          - { os: 'windows-latest', python-version: "3.11" }
           
     name: test (os=${{ matrix.entry.os }}, python=${{ matrix.entry.python-version }})
     continue-on-error: ${{ matrix.entry.experimental || false }}
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5bd0ff04..c1c2286b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@ Inspired from [Keep a Changelog](https://keepachangelog.com/en/1.0.0/)
 - Added a utf-8 header to all .py files ([#557](https://github.com/opensearch-project/opensearch-py/pull/557))
 - Added `samples`, `benchmarks` and `docs` to `nox -rs format` ([#556](https://github.com/opensearch-project/opensearch-py/pull/556))
 - Added guide on the document lifecycle API(s) ([#559](https://github.com/opensearch-project/opensearch-py/pull/559))
+- Added Windows CI ([#569](https://github.com/opensearch-project/opensearch-py/pull/569))
 ### Changed
 - Generate `tasks` client from API specs ([#508](https://github.com/opensearch-project/opensearch-py/pull/508))
 - Generate `ingest` client from API specs ([#513](https://github.com/opensearch-project/opensearch-py/pull/513))
diff --git a/opensearchpy/_async/http_aiohttp.py b/opensearchpy/_async/http_aiohttp.py
index 3c7010ed..f36080e7 100644
--- a/opensearchpy/_async/http_aiohttp.py
+++ b/opensearchpy/_async/http_aiohttp.py
@@ -183,7 +183,9 @@ def __init__(
                 ssl_context.check_hostname = False
                 ssl_context.verify_mode = ssl.CERT_NONE
 
-            ca_certs = self.default_ca_certs() if ca_certs is None else ca_certs
+            if ca_certs is None:
+                ca_certs = self.default_ca_certs()
+
             if verify_certs:
                 if not ca_certs:
                     raise ImproperlyConfigured(
diff --git a/opensearchpy/connection/base.py b/opensearchpy/connection/base.py
index 59418bfa..54308c72 100644
--- a/opensearchpy/connection/base.py
+++ b/opensearchpy/connection/base.py
@@ -138,6 +138,11 @@ def __eq__(self, other: object) -> bool:
             raise TypeError("Unsupported equality check for %s and %s" % (self, other))
         return self.__hash__() == other.__hash__()
 
+    def __lt__(self, other: object) -> bool:
+        if not isinstance(other, Connection):
+            raise TypeError("Unsupported lt check for %s and %s" % (self, other))
+        return self.__hash__() < other.__hash__()
+
     def __hash__(self) -> int:
         return id(self)
 
diff --git a/test_opensearchpy/test_async/test_connection.py b/test_opensearchpy/test_async/test_connection.py
index 9413d0e8..7969e987 100644
--- a/test_opensearchpy/test_async/test_connection.py
+++ b/test_opensearchpy/test_async/test_connection.py
@@ -37,7 +37,7 @@
 import aiohttp
 import pytest
 from _pytest.mark.structures import MarkDecorator
-from mock import patch
+from mock import MagicMock, patch
 from multidict import CIMultiDict
 from pytest import raises
 
@@ -254,26 +254,29 @@ async def test_warns_if_using_non_default_ssl_kwargs_with_ssl_context(self) -> N
                     == str(w[0].message)
                 )
 
-    @patch("ssl.SSLContext.load_verify_locations")
-    async def test_uses_given_ca_certs(
-        self, load_verify_locations: Any, tmp_path: Any
-    ) -> None:
+    @patch("ssl.SSLContext", return_value=MagicMock())
+    async def test_uses_given_ca_certs(self, ssl_context: Any, tmp_path: Any) -> None:
         path = tmp_path / "ca_certs.pem"
         path.touch()
+        ssl_context.return_value.load_verify_locations.return_value = None
         AIOHttpConnection(use_ssl=True, ca_certs=str(path))
-        load_verify_locations.assert_called_once_with(cafile=str(path))
+        ssl_context.return_value.load_verify_locations.assert_called_once_with(
+            cafile=str(path)
+        )
 
-    @patch("ssl.SSLContext.load_verify_locations")
-    async def test_uses_default_ca_certs(self, load_verify_locations: Any) -> None:
+    @patch("ssl.SSLContext", return_value=MagicMock())
+    async def test_uses_default_ca_certs(self, ssl_context: Any) -> None:
+        ssl_context.return_value.load_verify_locations.return_value = None
         AIOHttpConnection(use_ssl=True)
-        load_verify_locations.assert_called_once_with(
+        ssl_context.return_value.load_verify_locations.assert_called_once_with(
             cafile=Connection.default_ca_certs()
         )
 
-    @patch("ssl.SSLContext.load_verify_locations")
-    async def test_uses_no_ca_certs(self, load_verify_locations: Any) -> None:
+    @patch("ssl.SSLContext", return_value=MagicMock())
+    async def test_uses_no_ca_certs(self, ssl_context: Any) -> None:
+        ssl_context.return_value.load_verify_locations.return_value = None
         AIOHttpConnection(use_ssl=True, verify_certs=False)
-        load_verify_locations.assert_not_called()
+        ssl_context.return_value.load_verify_locations.assert_not_called()
 
     async def test_trust_env(self) -> None:
         con: Any = AIOHttpConnection(trust_env=True)
diff --git a/test_opensearchpy/test_async/test_transport.py b/test_opensearchpy/test_async/test_transport.py
index 4ef80707..b494f83f 100644
--- a/test_opensearchpy/test_async/test_transport.py
+++ b/test_opensearchpy/test_async/test_transport.py
@@ -272,7 +272,7 @@ async def test_add_connection(self) -> None:
 
     async def test_request_will_fail_after_X_retries(self) -> None:
         t: Any = AsyncTransport(
-            [{"exception": ConnectionError("abandon ship")}],
+            [{"exception": ConnectionError(None, "abandon ship", Exception())}],
             connection_class=DummyConnection,
         )
 
@@ -287,7 +287,7 @@ async def test_request_will_fail_after_X_retries(self) -> None:
 
     async def test_failed_connection_will_be_marked_as_dead(self) -> None:
         t: Any = AsyncTransport(
-            [{"exception": ConnectionError("abandon ship")}] * 2,
+            [{"exception": ConnectionError(None, "abandon ship", Exception())}] * 2,
             connection_class=DummyConnection,
         )
 
@@ -381,7 +381,10 @@ async def test_sniff_reuses_connection_instances_if_possible(self) -> None:
 
     async def test_sniff_on_fail_triggers_sniffing_on_fail(self) -> None:
         t: Any = AsyncTransport(
-            [{"exception": ConnectionError("abandon ship")}, {"data": CLUSTER_NODES}],
+            [
+                {"exception": ConnectionError(None, "abandon ship", Exception())},
+                {"data": CLUSTER_NODES},
+            ],
             connection_class=DummyConnection,
             sniff_on_connection_fail=True,
             max_retries=0,
@@ -407,7 +410,10 @@ async def test_sniff_on_fail_failing_does_not_prevent_retires(
     ) -> None:
         sniff_hosts.side_effect = [TransportError("sniff failed")]
         t: Any = AsyncTransport(
-            [{"exception": ConnectionError("abandon ship")}, {"data": CLUSTER_NODES}],
+            [
+                {"exception": ConnectionError(None, "abandon ship", Exception())},
+                {"data": CLUSTER_NODES},
+            ],
             connection_class=DummyConnection,
             sniff_on_connection_fail=True,
             max_retries=3,
diff --git a/test_opensearchpy/test_transport.py b/test_opensearchpy/test_transport.py
index dc1a8f9e..4b37e3ac 100644
--- a/test_opensearchpy/test_transport.py
+++ b/test_opensearchpy/test_transport.py
@@ -266,7 +266,7 @@ def test_add_connection(self) -> None:
 
     def test_request_will_fail_after_X_retries(self) -> None:
         t: Any = Transport(
-            [{"exception": ConnectionError("abandon ship")}],
+            [{"exception": ConnectionError(None, "abandon ship", Exception())}],
             connection_class=DummyConnection,
         )
 
@@ -275,7 +275,7 @@ def test_request_will_fail_after_X_retries(self) -> None:
 
     def test_failed_connection_will_be_marked_as_dead(self) -> None:
         t: Any = Transport(
-            [{"exception": ConnectionError("abandon ship")}] * 2,
+            [{"exception": ConnectionError(None, "abandon ship", Exception())}] * 2,
             connection_class=DummyConnection,
         )
 
@@ -349,7 +349,10 @@ def test_sniff_reuses_connection_instances_if_possible(self) -> None:
 
     def test_sniff_on_fail_triggers_sniffing_on_fail(self) -> None:
         t: Any = Transport(
-            [{"exception": ConnectionError("abandon ship")}, {"data": CLUSTER_NODES}],
+            [
+                {"exception": ConnectionError(None, "abandon ship", Exception())},
+                {"data": CLUSTER_NODES},
+            ],
             connection_class=DummyConnection,
             sniff_on_connection_fail=True,
             max_retries=0,
@@ -366,7 +369,10 @@ def test_sniff_on_fail_failing_does_not_prevent_retires(
     ) -> None:
         sniff_hosts.side_effect = [TransportError("sniff failed")]
         t: Any = Transport(
-            [{"exception": ConnectionError("abandon ship")}, {"data": CLUSTER_NODES}],
+            [
+                {"exception": ConnectionError(None, "abandon ship", Exception())},
+                {"data": CLUSTER_NODES},
+            ],
             connection_class=DummyConnection,
             sniff_on_connection_fail=True,
             max_retries=3,