diff --git a/.chronus/changes/do-not-pad-for-enum-2024-5-14-16-6-32.md b/.chronus/changes/do-not-pad-for-enum-2024-5-14-16-6-32.md
new file mode 100644
index 00000000000..0f628053141
--- /dev/null
+++ b/.chronus/changes/do-not-pad-for-enum-2024-5-14-16-6-32.md
@@ -0,0 +1,7 @@
+---
+changeKind: fix
+packages:
+  - "@autorest/python"
+---
+
+Do not pad name for enum when generate SDK from Typespec
\ No newline at end of file
diff --git a/packages/autorest.python/autorest/preprocess/__init__.py b/packages/autorest.python/autorest/preprocess/__init__.py
index e212aa2eecc..a38719ac4d7 100644
--- a/packages/autorest.python/autorest/preprocess/__init__.py
+++ b/packages/autorest.python/autorest/preprocess/__init__.py
@@ -17,7 +17,7 @@
 from .python_mappings import CADL_RESERVED_WORDS, RESERVED_WORDS, PadType
 
 from .. import YamlUpdatePlugin, YamlUpdatePluginAutorest
-from .._utils import parse_args, get_body_type_for_description, JSON_REGEXP, KNOWN_TYPES
+from .._utils import parse_args, get_body_type_for_description, JSON_REGEXP, KNOWN_TYPES, update_enum_value
 
 
 def update_overload_section(
@@ -241,11 +241,24 @@ def update_types(self, yaml_data: List[Dict[str, Any]]) -> None:
                 type["snakeCaseName"] = to_snake_case(type["name"])
             if type.get("values"):
                 # we're enums
+                values_to_add = []
                 for value in type["values"]:
                     padded_name = self.pad_reserved_words(value["name"].lower(), PadType.ENUM).upper()
-                    if padded_name[0] in "0123456789":
-                        padded_name = "ENUM_" + padded_name
-                    value["name"] = padded_name
+                    if self.version_tolerant:
+                        if padded_name[0] in "0123456789":
+                            padded_name = "ENUM_" + padded_name
+                            value["name"] = padded_name
+                    else:
+                        if value["name"] != padded_name:
+                            values_to_add.append(
+                                update_enum_value(
+                                    name=padded_name,
+                                    value=value["value"],
+                                    description=value["description"],
+                                    enum_type=value["enumType"],
+                                )
+                            )
+                type["values"].extend(values_to_add)
 
         # add type for reference
         for v in HEADERS_CONVERT_IN_METHOD.values():
diff --git a/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/asynctests/test_reserved_words.py b/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/asynctests/test_reserved_words.py
index 9c70f27c289..8c362e6323f 100644
--- a/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/asynctests/test_reserved_words.py
+++ b/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/asynctests/test_reserved_words.py
@@ -65,4 +65,5 @@ async def test_operation_with_url(client):
 
 @pytest.mark.asyncio
 async def test_operation_with_enum(client):
+    await client.reserved_enum(models.MyEnum.IMPORT)
     await client.reserved_enum(models.MyEnum.IMPORT_ENUM)
diff --git a/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/test_reserved_words.py b/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/test_reserved_words.py
index 3774520f8a6..fbfceb2fe25 100644
--- a/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/test_reserved_words.py
+++ b/packages/autorest.python/test/vanilla/legacy/AcceptanceTests/test_reserved_words.py
@@ -58,4 +58,5 @@ def test_operation_with_url(client):
 
 
 def test_operation_with_enum(client):
+    client.reserved_enum(models.MyEnum.IMPORT)
     client.reserved_enum(models.MyEnum.IMPORT_ENUM)
diff --git a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/aio/operations/_reserved_words_client_operations.py b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/aio/operations/_reserved_words_client_operations.py
index df0449c8e3e..bd1f75e3517 100644
--- a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/aio/operations/_reserved_words_client_operations.py
+++ b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/aio/operations/_reserved_words_client_operations.py
@@ -329,8 +329,8 @@ async def operation_with_url(
     async def reserved_enum(self, enum_parameter: Union[str, _models.MyEnum], **kwargs: Any) -> JSON:
         """Operation that accepts a reserved enum value.
 
-        :param enum_parameter: Pass in MyEnum.IMPORT to pass. Known values are: "import" and "other".
-         Required.
+        :param enum_parameter: Pass in MyEnum.IMPORT to pass. Known values are: "import", "other", and
+         "import". Required.
         :type enum_parameter: str or ~reservedwords.models.MyEnum
         :return: JSON or the result of cls(response)
         :rtype: JSON
diff --git a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/models/_reserved_words_client_enums.py b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/models/_reserved_words_client_enums.py
index 67513eae646..4dbf78eda21 100644
--- a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/models/_reserved_words_client_enums.py
+++ b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/models/_reserved_words_client_enums.py
@@ -13,5 +13,6 @@
 class MyEnum(str, Enum, metaclass=CaseInsensitiveEnumMeta):
     """MyEnum."""
 
-    IMPORT_ENUM = "import"
+    IMPORT = "import"
     OTHER = "other"
+    IMPORT_ENUM = "import"
diff --git a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/operations/_reserved_words_client_operations.py b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/operations/_reserved_words_client_operations.py
index d4a7137b4ae..e396c7f7b9c 100644
--- a/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/operations/_reserved_words_client_operations.py
+++ b/packages/autorest.python/test/vanilla/legacy/Expected/AcceptanceTests/ReservedWords/reservedwords/operations/_reserved_words_client_operations.py
@@ -435,8 +435,8 @@ def operation_with_url(
     def reserved_enum(self, enum_parameter: Union[str, _models.MyEnum], **kwargs: Any) -> JSON:
         """Operation that accepts a reserved enum value.
 
-        :param enum_parameter: Pass in MyEnum.IMPORT to pass. Known values are: "import" and "other".
-         Required.
+        :param enum_parameter: Pass in MyEnum.IMPORT to pass. Known values are: "import", "other", and
+         "import". Required.
         :type enum_parameter: str or ~reservedwords.models.MyEnum
         :return: JSON or the result of cls(response)
         :rtype: JSON