diff --git a/modules/openapi-generator/src/main/resources/python/requirements.mustache b/modules/openapi-generator/src/main/resources/python/requirements.mustache
index e18a97e55fd8..bd4fe39d883b 100644
--- a/modules/openapi-generator/src/main/resources/python/requirements.mustache
+++ b/modules/openapi-generator/src/main/resources/python/requirements.mustache
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3
+urllib3 >= 1.25.3, < 2.1.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
 {{#asyncio}}
diff --git a/modules/openapi-generator/src/main/resources/python/setup.mustache b/modules/openapi-generator/src/main/resources/python/setup.mustache
index 49c26ba563ce..3edd643dcb00 100644
--- a/modules/openapi-generator/src/main/resources/python/setup.mustache
+++ b/modules/openapi-generator/src/main/resources/python/setup.mustache
@@ -17,7 +17,7 @@ PYTHON_REQUIRES = ">=3.7"
 {{#apis}}
 {{#-last}}
 REQUIRES = [
-    "urllib3 >= 1.25.3",
+    "urllib3 >= 1.25.3, < 2.1.0",
     "python-dateutil",
 {{#asyncio}}
     "aiohttp >= 3.0.0",
diff --git a/samples/client/echo_api/python/requirements.txt b/samples/client/echo_api/python/requirements.txt
index 74ede174a0a0..258c179c10b2 100644
--- a/samples/client/echo_api/python/requirements.txt
+++ b/samples/client/echo_api/python/requirements.txt
@@ -1,5 +1,5 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3
+urllib3 >= 1.25.3, < 2.1.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
diff --git a/samples/client/echo_api/python/setup.py b/samples/client/echo_api/python/setup.py
index d5f807e3d7b1..e24ae77ecedf 100644
--- a/samples/client/echo_api/python/setup.py
+++ b/samples/client/echo_api/python/setup.py
@@ -25,7 +25,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3",
+    "urllib3 >= 1.25.3, < 2.1.0",
     "python-dateutil",
     "pydantic >= 1.10.5, < 2",
     "aenum"
diff --git a/samples/openapi3/client/petstore/python-aiohttp/requirements.txt b/samples/openapi3/client/petstore/python-aiohttp/requirements.txt
index 8bb00c2c243a..6833ad6202a4 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/requirements.txt
+++ b/samples/openapi3/client/petstore/python-aiohttp/requirements.txt
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3
+urllib3 >= 1.25.3, < 2.1.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
 aiohttp >= 3.0.0
diff --git a/samples/openapi3/client/petstore/python-aiohttp/setup.py b/samples/openapi3/client/petstore/python-aiohttp/setup.py
index e72baa799849..b617cede0bb0 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/setup.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/setup.py
@@ -24,7 +24,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3",
+    "urllib3 >= 1.25.3, < 2.1.0",
     "python-dateutil",
     "aiohttp >= 3.0.0",
     "pem>=19.3.0",
diff --git a/samples/openapi3/client/petstore/python/requirements.txt b/samples/openapi3/client/petstore/python/requirements.txt
index 74ede174a0a0..258c179c10b2 100755
--- a/samples/openapi3/client/petstore/python/requirements.txt
+++ b/samples/openapi3/client/petstore/python/requirements.txt
@@ -1,5 +1,5 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3
+urllib3 >= 1.25.3, < 2.1.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
diff --git a/samples/openapi3/client/petstore/python/setup.py b/samples/openapi3/client/petstore/python/setup.py
index b1160e7ee866..79f290bff815 100755
--- a/samples/openapi3/client/petstore/python/setup.py
+++ b/samples/openapi3/client/petstore/python/setup.py
@@ -24,7 +24,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3",
+    "urllib3 >= 1.25.3, < 2.1.0",
     "python-dateutil",
     "pem>=19.3.0",
     "pycryptodome>=3.9.0",