diff --git a/modules/openapi-generator/src/main/resources/python/pyproject.mustache b/modules/openapi-generator/src/main/resources/python/pyproject.mustache
index a3813662150..8dab7dec7c4 100644
--- a/modules/openapi-generator/src/main/resources/python/pyproject.mustache
+++ b/modules/openapi-generator/src/main/resources/python/pyproject.mustache
@@ -12,14 +12,14 @@ include = ["{{packageName}}/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3 < 3.0.0"
+urllib3 = ">= 1.25.3, < 3.0.0"
 python-dateutil = ">= 2.8.2"
 {{#asyncio}}
 aiohttp = ">= 3.8.4"
 aiohttp-retry = ">= 2.8.3"
 {{/asyncio}}
 {{#tornado}}
-tornado = ">=4.2 <5"
+tornado = ">=4.2, <5"
 {{/tornado}}
 {{#hasHttpSignatureMethods}}
 pem = ">= 19.3.0"
diff --git a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/pyproject.toml b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/pyproject.toml
index 0d2e8a39c93..89df0faa8de 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/pyproject.toml
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/pyproject.toml
@@ -12,7 +12,7 @@ include = ["openapi_client/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3 < 3.0.0"
+urllib3 = ">= 1.25.3, < 3.0.0"
 python-dateutil = ">= 2.8.2"
 pydantic = ">= 2"
 typing-extensions = ">= 4.7.1"
diff --git a/samples/client/echo_api/python/pyproject.toml b/samples/client/echo_api/python/pyproject.toml
index 0d2e8a39c93..89df0faa8de 100644
--- a/samples/client/echo_api/python/pyproject.toml
+++ b/samples/client/echo_api/python/pyproject.toml
@@ -12,7 +12,7 @@ include = ["openapi_client/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3 < 3.0.0"
+urllib3 = ">= 1.25.3, < 3.0.0"
 python-dateutil = ">= 2.8.2"
 pydantic = ">= 2"
 typing-extensions = ">= 4.7.1"
diff --git a/samples/openapi3/client/petstore/python-aiohttp/pyproject.toml b/samples/openapi3/client/petstore/python-aiohttp/pyproject.toml
index d6d15ec1469..58157165aee 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/pyproject.toml
+++ b/samples/openapi3/client/petstore/python-aiohttp/pyproject.toml
@@ -12,7 +12,7 @@ include = ["petstore_api/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3 < 3.0.0"
+urllib3 = ">= 1.25.3, < 3.0.0"
 python-dateutil = ">= 2.8.2"
 aiohttp = ">= 3.8.4"
 aiohttp-retry = ">= 2.8.3"
diff --git a/samples/openapi3/client/petstore/python/pyproject.toml b/samples/openapi3/client/petstore/python/pyproject.toml
index 1204de255ba..28d95fc5ec3 100644
--- a/samples/openapi3/client/petstore/python/pyproject.toml
+++ b/samples/openapi3/client/petstore/python/pyproject.toml
@@ -12,7 +12,7 @@ include = ["petstore_api/py.typed"]
 [tool.poetry.dependencies]
 python = "^3.8"
 
-urllib3 = ">= 1.25.3 < 3.0.0"
+urllib3 = ">= 1.25.3, < 3.0.0"
 python-dateutil = ">= 2.8.2"
 pem = ">= 19.3.0"
 pycryptodome = ">= 3.9.0"