diff --git a/modules/openapi-generator/src/main/resources/python-pydantic-v1/requirements.mustache b/modules/openapi-generator/src/main/resources/python-pydantic-v1/requirements.mustache
index f204cda05c52..8add30ffd46a 100644
--- a/modules/openapi-generator/src/main/resources/python-pydantic-v1/requirements.mustache
+++ b/modules/openapi-generator/src/main/resources/python-pydantic-v1/requirements.mustache
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
 {{#asyncio}}
diff --git a/modules/openapi-generator/src/main/resources/python-pydantic-v1/setup.mustache b/modules/openapi-generator/src/main/resources/python-pydantic-v1/setup.mustache
index 538a8dff90fb..74ca2c17e8df 100644
--- a/modules/openapi-generator/src/main/resources/python-pydantic-v1/setup.mustache
+++ b/modules/openapi-generator/src/main/resources/python-pydantic-v1/setup.mustache
@@ -17,7 +17,7 @@ PYTHON_REQUIRES = ">=3.7"
 {{#apis}}
 {{#-last}}
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
 {{#asyncio}}
     "aiohttp >= 3.0.0",
diff --git a/modules/openapi-generator/src/main/resources/python/requirements.mustache b/modules/openapi-generator/src/main/resources/python/requirements.mustache
index 5412515b5f4a..3c028ee44d60 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, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 2
 typing-extensions >= 4.7.1
 {{#asyncio}}
diff --git a/modules/openapi-generator/src/main/resources/python/setup.mustache b/modules/openapi-generator/src/main/resources/python/setup.mustache
index cb372a5e02e5..66b4aab86709 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, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
 {{#asyncio}}
     "aiohttp >= 3.0.0",
diff --git a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/requirements.txt b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/requirements.txt
index cc85509ec516..7d45544dedb0 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/requirements.txt
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/requirements.txt
@@ -1,5 +1,5 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 2
 typing-extensions >= 4.7.1
diff --git a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py
index 82528555eef1..d562c5359b38 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py
@@ -25,7 +25,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "pydantic >= 2",
     "typing-extensions >= 4.7.1",
diff --git a/samples/client/echo_api/python-pydantic-v1/requirements.txt b/samples/client/echo_api/python-pydantic-v1/requirements.txt
index 258c179c10b2..0a8bf96cadf2 100644
--- a/samples/client/echo_api/python-pydantic-v1/requirements.txt
+++ b/samples/client/echo_api/python-pydantic-v1/requirements.txt
@@ -1,5 +1,5 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
diff --git a/samples/client/echo_api/python-pydantic-v1/setup.py b/samples/client/echo_api/python-pydantic-v1/setup.py
index 192f8f2b0402..d91b9d9f069e 100644
--- a/samples/client/echo_api/python-pydantic-v1/setup.py
+++ b/samples/client/echo_api/python-pydantic-v1/setup.py
@@ -25,7 +25,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "pydantic >= 1.10.5, < 2",
     "aenum"
diff --git a/samples/client/echo_api/python/requirements.txt b/samples/client/echo_api/python/requirements.txt
index cc85509ec516..7d45544dedb0 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, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 2
 typing-extensions >= 4.7.1
diff --git a/samples/client/echo_api/python/setup.py b/samples/client/echo_api/python/setup.py
index 82528555eef1..d562c5359b38 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, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "pydantic >= 2",
     "typing-extensions >= 4.7.1",
diff --git a/samples/openapi3/client/petstore/python-aiohttp/requirements.txt b/samples/openapi3/client/petstore/python-aiohttp/requirements.txt
index 3564e66b316e..0039fe22568b 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, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 2
 typing-extensions >= 4.7.1
 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 a51834b09ae1..e3da12f1e660 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, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "aiohttp >= 3.0.0",
     "aiohttp-retry >= 2.8.3",
diff --git a/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/requirements.txt b/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/requirements.txt
index bd242be2a0f4..c8ee56b4876d 100644
--- a/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/requirements.txt
+++ b/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/requirements.txt
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
 aiohttp >= 3.0.0
diff --git a/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/setup.py b/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/setup.py
index e5b090da62b1..6c3c289d34cc 100644
--- a/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/setup.py
+++ b/samples/openapi3/client/petstore/python-pydantic-v1-aiohttp/setup.py
@@ -24,7 +24,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "aiohttp >= 3.0.0",
     "pem>=19.3.0",
diff --git a/samples/openapi3/client/petstore/python-pydantic-v1/requirements.txt b/samples/openapi3/client/petstore/python-pydantic-v1/requirements.txt
index e807d94fe0a2..2a3de4f163ef 100644
--- a/samples/openapi3/client/petstore/python-pydantic-v1/requirements.txt
+++ b/samples/openapi3/client/petstore/python-pydantic-v1/requirements.txt
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 1.10.5, < 2
 aenum >= 3.1.11
 pycryptodome >= 3.9.0
diff --git a/samples/openapi3/client/petstore/python-pydantic-v1/setup.py b/samples/openapi3/client/petstore/python-pydantic-v1/setup.py
index 283e0441c000..6af2c4f9a0be 100644
--- a/samples/openapi3/client/petstore/python-pydantic-v1/setup.py
+++ b/samples/openapi3/client/petstore/python-pydantic-v1/setup.py
@@ -24,7 +24,7 @@
 VERSION = "1.0.0"
 PYTHON_REQUIRES = ">=3.7"
 REQUIRES = [
-    "urllib3 >= 1.25.3, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "pem>=19.3.0",
     "pycryptodome>=3.9.0",
diff --git a/samples/openapi3/client/petstore/python/requirements.txt b/samples/openapi3/client/petstore/python/requirements.txt
index f74f344f853e..dcec5ea61eb5 100755
--- a/samples/openapi3/client/petstore/python/requirements.txt
+++ b/samples/openapi3/client/petstore/python/requirements.txt
@@ -1,6 +1,6 @@
 python_dateutil >= 2.5.3
 setuptools >= 21.0.0
-urllib3 >= 1.25.3, < 2.1.0
+urllib3 >= 1.25.3, < 3.0.0
 pydantic >= 2
 typing-extensions >= 4.7.1
 pycryptodome >= 3.9.0
diff --git a/samples/openapi3/client/petstore/python/setup.py b/samples/openapi3/client/petstore/python/setup.py
index ae616afcb1b9..2906e3928fd3 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, < 2.1.0",
+    "urllib3 >= 1.25.3, < 3.0.0",
     "python-dateutil",
     "pem>=19.3.0",
     "pycryptodome>=3.9.0",