diff --git a/py/bin/sanitize_schema_typing.py b/py/bin/sanitize_schema_typing.py
index 6138127e9f..48c6baf919 100644
--- a/py/bin/sanitize_schema_typing.py
+++ b/py/bin/sanitize_schema_typing.py
@@ -45,7 +45,7 @@
 from _ast import AST
 from datetime import datetime
 from pathlib import Path
-from typing import Type, cast
+from typing import Any, Type, cast
 
 
 class ClassTransformer(ast.NodeTransformer):
@@ -118,7 +118,18 @@ def has_model_config(self, node: ast.ClassDef) -> ast.Assign | None:
                         return item
         return None
 
-    def visit_ClassDef(self, _node: ast.ClassDef) -> ast.ClassDef:  # noqa: N802
+    def visit_AnnAssign(self, node: ast.AnnAssign) -> ast.AnnAssign:
+        """Visit and transform annotated assignment."""
+        if isinstance(node.annotation, ast.Name) and node.annotation.id == 'Role':
+            node.annotation = ast.BinOp(
+                left=ast.Name(id='Role', ctx=ast.Load()),
+                op=ast.BitOr(),
+                right=ast.Name(id='str', ctx=ast.Load()),
+            )
+            self.modified = True
+        return node
+
+    def visit_ClassDef(self, node: ast.ClassDef) -> Any:
         """Visit and transform a class definition node.
 
         Args:
@@ -128,11 +139,16 @@ def visit_ClassDef(self, _node: ast.ClassDef) -> ast.ClassDef:  # noqa: N802
             The transformed ClassDef node.
         """
         # First apply base class transformations recursively
-        node = super().generic_visit(_node)
+        node = cast(ast.ClassDef, super().generic_visit(node))
         new_body: list[ast.stmt | ast.Constant | ast.Assign] = []
 
         # Handle Docstrings
-        if not node.body or not isinstance(node.body[0], ast.Expr) or not isinstance(node.body[0].value, ast.Constant):
+        if (
+            not node.body
+            or not isinstance(node.body[0], ast.Expr)
+            or not isinstance(node.body[0].value, ast.Constant)
+            or not isinstance(node.body[0].value.value, str)
+        ):
             # Generate a more descriptive docstring based on class type
             if self.is_rootmodel_class(node):
                 docstring = f'Root model for {node.name.lower().replace("_", " ")}.'
@@ -151,13 +167,21 @@ def visit_ClassDef(self, _node: ast.ClassDef) -> ast.ClassDef:  # noqa: N802
 
         # Handle model_config for BaseModel and RootModel
         existing_model_config_assign = self.has_model_config(node)
+
         existing_model_config_call = None
         if existing_model_config_assign and isinstance(existing_model_config_assign.value, ast.Call):
             existing_model_config_call = existing_model_config_assign.value
 
         # Determine start index for iterating original body (skip docstring)
         body_start_index = (
-            1 if (node.body and isinstance(node.body[0], ast.Expr) and isinstance(node.body[0].value, ast.Str)) else 0
+            1
+            if (
+                node.body
+                and isinstance(node.body[0], ast.Expr)
+                and isinstance(node.body[0].value, ast.Constant)
+                and isinstance(node.body[0].value.value, str)
+            )
+            else 0
         )
 
         if self.is_rootmodel_class(node):
diff --git a/py/packages/genkit/src/genkit/core/typing.py b/py/packages/genkit/src/genkit/core/typing.py
index dce5a4f7f1..68fd541101 100644
--- a/py/packages/genkit/src/genkit/core/typing.py
+++ b/py/packages/genkit/src/genkit/core/typing.py
@@ -913,7 +913,7 @@ class Message(BaseModel):
     """Model for message data."""
 
     model_config = ConfigDict(extra='forbid', populate_by_name=True)
-    role: Role
+    role: Role | str
     content: list[Part]
     metadata: dict[str, Any] | None = None
 
diff --git a/py/pyproject.toml b/py/pyproject.toml
index 5fadf9d6ba..5ee43b379b 100644
--- a/py/pyproject.toml
+++ b/py/pyproject.toml
@@ -199,9 +199,9 @@ convention = "google"
 docstring-code-format      = true
 docstring-code-line-length = 120
 indent-style               = "space"
+line-ending                = "lf"
 quote-style                = "single"
 skip-magic-trailing-comma  = false
-line-ending                = "lf"
 
 [tool.datamodel-codegen]
 #collapse-root-models = true # Don't use; produces Any as types.
diff --git a/py/samples/evaluator-demo/pyproject.toml b/py/samples/evaluator-demo/pyproject.toml
index eb049714a7..771c966747 100644
--- a/py/samples/evaluator-demo/pyproject.toml
+++ b/py/samples/evaluator-demo/pyproject.toml
@@ -15,7 +15,7 @@
 # SPDX-License-Identifier: Apache-2.0
 
 [project]
-authors = [{ name = "Google" }]
+authors         = [{ name = "Google" }]
 dependencies    = ["genkit", "pydantic>=2.0.0", "structlog>=24.0.0", "pypdf"]
 description     = "Genkit Python Evaluation Demo"
 name            = "eval-demo"
diff --git a/py/samples/multi-server/pyproject.toml b/py/samples/multi-server/pyproject.toml
index 364e053b2e..7163fd5d6d 100644
--- a/py/samples/multi-server/pyproject.toml
+++ b/py/samples/multi-server/pyproject.toml
@@ -16,7 +16,6 @@
 
 [project]
 authors = [{ name = "Google" }]
-license = "Apache-2.0"
 classifiers = [
   "Development Status :: 3 - Alpha",
   "Environment :: Console",
@@ -43,6 +42,7 @@ dependencies = [
   "uvicorn>=0.34.0",
 ]
 description = "Sample implementation to exercise the Genkit multi server manager."
+license = "Apache-2.0"
 name = "multi-server"
 readme = "README.md"
 requires-python = ">=3.10"