diff --git a/ddtrace/contrib/pymongo/client.py b/ddtrace/contrib/pymongo/client.py
index ab1916b582b..429826df811 100644
--- a/ddtrace/contrib/pymongo/client.py
+++ b/ddtrace/contrib/pymongo/client.py
@@ -68,6 +68,7 @@ def __init__(self, client=None, *args, **kwargs):
                 client = _MongoClient(client, *args, **kwargs)
 
         super(TracedMongoClient, self).__init__(client)
+        client._datadog_proxy = self
         # NOTE[matt] the TracedMongoClient attempts to trace all of the network
         # calls in the trace library. This is good because it measures the
         # actual network time. It's bad because it uses a private API which
@@ -85,6 +86,25 @@ def __getddpin__(self):
         return ddtrace.Pin.get_from(self._topology)
 
 
+@contextlib.contextmanager
+def wrapped_validate_session(wrapped, instance, args, kwargs):
+    # We do this to handle a validation `A is B` in pymongo that
+    # relies on IDs being equal. Since we are proxying objects, we need
+    # to ensure we're compare proxy with proxy or wrapped with wrapped
+    # or this validation will fail
+    client = args[0]
+    session = args[1]
+    session_client = session._client
+    if isinstance(session_client, TracedMongoClient):
+        if isinstance(client, _MongoClient):
+            client = getattr(client, "_datadog_proxy", client)
+    elif isinstance(session_client, _MongoClient):
+        if isinstance(client, TracedMongoClient):
+            client = client.__wrapped__
+
+    yield wrapped(client, session)
+
+
 class TracedTopology(ObjectProxy):
     def __init__(self, topology):
         super(TracedTopology, self).__init__(topology)
diff --git a/ddtrace/contrib/pymongo/patch.py b/ddtrace/contrib/pymongo/patch.py
index 13ee461689e..aa838a8c9ee 100644
--- a/ddtrace/contrib/pymongo/patch.py
+++ b/ddtrace/contrib/pymongo/patch.py
@@ -17,6 +17,7 @@
 from ..trace_utils import unwrap as _u
 from .client import TracedMongoClient
 from .client import set_address_tags
+from .client import wrapped_validate_session
 
 
 config._add(
@@ -35,6 +36,7 @@ def get_version():
 
 _VERSION = pymongo.version_tuple
 _CHECKOUT_FN_NAME = "get_socket" if _VERSION < (4, 5) else "checkout"
+_VERIFY_VERSION_CLASS = pymongo.pool.SocketInfo if _VERSION < (4, 5) else pymongo.pool.Connection
 
 
 def patch():
@@ -59,6 +61,7 @@ def patch_pymongo_module():
     # - Creates a new socket & performs a TCP handshake
     # - Grabs a socket already initialized before
     _w("pymongo.server", "Server.%s" % _CHECKOUT_FN_NAME, traced_get_socket)
+    _w("pymongo.pool", f"{_VERIFY_VERSION_CLASS.__name__}.validate_session", wrapped_validate_session)
 
 
 def unpatch_pymongo_module():
@@ -67,6 +70,7 @@ def unpatch_pymongo_module():
     pymongo._datadog_patch = False
 
     _u(pymongo.server.Server, _CHECKOUT_FN_NAME)
+    _u(_VERIFY_VERSION_CLASS, "validate_session")
 
 
 @contextlib.contextmanager
diff --git a/releasenotes/notes/pymongo-fix-session-validation-error-1a05f8ad45bbbc35.yaml b/releasenotes/notes/pymongo-fix-session-validation-error-1a05f8ad45bbbc35.yaml
new file mode 100644
index 00000000000..92f081038cb
--- /dev/null
+++ b/releasenotes/notes/pymongo-fix-session-validation-error-1a05f8ad45bbbc35.yaml
@@ -0,0 +1,3 @@
+fixes:
+  - |
+    pymongo: this resolves an issue where the library raised an error in ``pymongo.pool.validate_session``
\ No newline at end of file
diff --git a/tests/contrib/pymongo/test.py b/tests/contrib/pymongo/test.py
index aa3d77387d6..2ef8e10af7f 100644
--- a/tests/contrib/pymongo/test.py
+++ b/tests/contrib/pymongo/test.py
@@ -768,6 +768,17 @@ def test_single_op(self):
         self.check_socket_metadata(spans[0])
         assert spans[1].name == "pymongo.cmd"
 
+    def test_validate_session_equivalence(self):
+        """
+        This tests validate_session from:
+        https://github.com/mongodb/mongo-python-driver/blob/v3.13/pymongo/pool.py#L884-L898
+        which fails under some circumstances unless we patch correctly
+        """
+        # Trigger a command which calls validate_session internal to PyMongo
+        db_conn = pymongo.database.Database(self.client, "foo")
+        collection = db_conn["mycollection"]
+        collection.insert_one({"Foo": "Bar"})
+
     def test_service_name_override(self):
         with TracerTestCase.override_config("pymongo", dict(service_name="testdb")):
             self.client["some_db"].drop_collection("some_collection")