diff --git a/modules/openapi-generator/src/main/resources/python/api_client.mustache b/modules/openapi-generator/src/main/resources/python/api_client.mustache
index 71392d82e126..f742cffb87c8 100644
--- a/modules/openapi-generator/src/main/resources/python/api_client.mustache
+++ b/modules/openapi-generator/src/main/resources/python/api_client.mustache
@@ -840,11 +840,8 @@ https://github.com/OpenAPITools/openapi-generator/blob/c84b949df1a9ec04ba75989cb
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
index 594ec0e5a703..237696870257 100644
--- a/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
+++ b/samples/client/echo_api/python-disallowAdditionalPropertiesIfNotPresent/openapi_client/api_client.py
@@ -683,11 +683,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/client/echo_api/python/openapi_client/api_client.py b/samples/client/echo_api/python/openapi_client/api_client.py
index 594ec0e5a703..237696870257 100644
--- a/samples/client/echo_api/python/openapi_client/api_client.py
+++ b/samples/client/echo_api/python/openapi_client/api_client.py
@@ -683,11 +683,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py b/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
index 37ab9efc5d92..97d4d8f203ef 100644
--- a/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
+++ b/samples/client/others/python-legacy-model-dictionaries/legacy_model_dict_client/api_client.py
@@ -791,11 +791,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
index f90151f6105b..f37d3564026a 100644
--- a/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-aiohttp/petstore_api/api_client.py
@@ -682,11 +682,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
index 5fb082d86bc9..a82e242f5afe 100644
--- a/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-httpx-sync/petstore_api/api_client.py
@@ -685,11 +685,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
index 5fb082d86bc9..a82e242f5afe 100644
--- a/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-httpx/petstore_api/api_client.py
@@ -685,11 +685,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py b/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
index a26ad3c644a2..21489d50fb24 100644
--- a/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python-lazyImports/petstore_api/api_client.py
@@ -682,11 +682,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':
diff --git a/samples/openapi3/client/petstore/python/petstore_api/api_client.py b/samples/openapi3/client/petstore/python/petstore_api/api_client.py
index 4a91fbc24248..03370346fde2 100755
--- a/samples/openapi3/client/petstore/python/petstore_api/api_client.py
+++ b/samples/openapi3/client/petstore/python/petstore_api/api_client.py
@@ -682,11 +682,8 @@ def _apply_auth_params(
                 headers['Cookie'] = ""
             else:
                 headers['Cookie'] += "; "
-            # Account for cookie value containing spaces and special characters
-            cookie_value = str(auth_setting['value'])
-            if not re.match("^\".*\"$", cookie_value):
-                cookie_value = cookie_value.replace("\"", "\\\"")
-                cookie_value = f"\"{cookie_value}\""
+            # Account for cookie value containing spaces and special characters, excluding base64 delimiters
+            cookie_value = quote(str(auth_setting['value']), safe="!#$%&'()*+-./:<=>?@[]^_`{|}~%+/=")
             headers['Cookie'] += f"{auth_setting['key']}={cookie_value}"
         elif auth_setting['in'] == 'header':
             if auth_setting['type'] != 'http-signature':