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 f204cda05c5..8add30ffd46 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 538a8dff90f..74ca2c17e8d 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 5412515b5f4..3c028ee44d6 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 cb372a5e02e..66b4aab8670 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 cc85509ec51..7d45544dedb 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 82528555eef..d562c5359b3 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/setup.py
@@ -25,7 +25,7 @@ NAME = "openapi-client"
 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 258c179c10b..0a8bf96cadf 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 192f8f2b040..d91b9d9f069 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 @@ NAME = "openapi-client"
 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 cc85509ec51..7d45544dedb 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 82528555eef..d562c5359b3 100644
--- a/samples/client/echo_api/python/setup.py
+++ b/samples/client/echo_api/python/setup.py
@@ -25,7 +25,7 @@ NAME = "openapi-client"
 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 3564e66b316..0039fe22568 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 a51834b09ae..e3da12f1e66 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/setup.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/setup.py
@@ -24,7 +24,7 @@ NAME = "petstore-api"
 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 bd242be2a0f..c8ee56b4876 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 e5b090da62b..6c3c289d34c 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 @@ NAME = "petstore-api"
 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 e807d94fe0a..2a3de4f163e 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 283e0441c00..6af2c4f9a0b 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 @@ NAME = "petstore-api"
 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 f74f344f853..dcec5ea61eb 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 ae616afcb1b..2906e3928fd 100755
--- a/samples/openapi3/client/petstore/python/setup.py
+++ b/samples/openapi3/client/petstore/python/setup.py
@@ -24,7 +24,7 @@ NAME = "petstore-api"
 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",