diff --git a/pydantic/_internal/_generate_schema.py b/pydantic/_internal/_generate_schema.py
index 18fc920b10..a710e740de 100644
--- a/pydantic/_internal/_generate_schema.py
+++ b/pydantic/_internal/_generate_schema.py
@@ -33,7 +33,7 @@
 )
 from warnings import warn
 
-from pydantic_core import CoreSchema, PydanticUndefined, core_schema
+from pydantic_core import CoreSchema, PydanticUndefined, core_schema, to_jsonable_python
 from typing_extensions import Annotated, Final, Literal, TypeAliasType, TypedDict, get_args, get_origin, is_typeddict
 
 from ..annotated_handlers import GetCoreSchemaHandler, GetJsonSchemaHandler
@@ -945,7 +945,7 @@ def set_discriminator(schema: CoreSchema) -> CoreSchema:
         json_schema_updates = {
             'title': field_info.title,
             'description': field_info.description,
-            'examples': field_info.examples,
+            'examples': to_jsonable_python(field_info.examples),
         }
         json_schema_updates = {k: v for k, v in json_schema_updates.items() if v is not None}
 
@@ -954,7 +954,7 @@ def set_discriminator(schema: CoreSchema) -> CoreSchema:
         def json_schema_update_func(schema: CoreSchemaOrField, handler: GetJsonSchemaHandler) -> JsonSchemaValue:
             json_schema = {**handler(schema), **json_schema_updates}
             if isinstance(json_schema_extra, dict):
-                json_schema.update(json_schema_extra)
+                json_schema.update(to_jsonable_python(json_schema_extra))
             elif callable(json_schema_extra):
                 json_schema_extra(json_schema)
             return json_schema
@@ -1647,7 +1647,7 @@ def _apply_single_annotation_json_schema(
             if metadata.description:
                 json_schema_update['description'] = metadata.description
             if metadata.examples:
-                json_schema_update['examples'] = metadata.examples
+                json_schema_update['examples'] = to_jsonable_python(metadata.examples)
 
             json_schema_extra = metadata.json_schema_extra
             if json_schema_update or json_schema_extra:
@@ -1658,7 +1658,7 @@ def json_schema_update_func(
                     json_schema = handler(core_schema)
                     json_schema.update(json_schema_update)
                     if isinstance(json_schema_extra, dict):
-                        json_schema.update(json_schema_extra)
+                        json_schema.update(to_jsonable_python(json_schema_extra))
                     elif callable(json_schema_extra):
                         json_schema_extra(json_schema)
                     return json_schema
diff --git a/tests/test_json_schema.py b/tests/test_json_schema.py
index 6b4ee9b199..dbb3fac17e 100644
--- a/tests/test_json_schema.py
+++ b/tests/test_json_schema.py
@@ -4701,6 +4701,20 @@ class Outer(BaseModel):
     }
 
 
+def test_extras_and_examples_are_json_encoded():
+    class Toy(BaseModel):
+        name: Annotated[str, Field(examples=['mouse', 'ball'])]
+
+    class Cat(BaseModel):
+        toys: Annotated[
+            List[Toy],
+            Field(examples=[[Toy(name='mouse'), Toy(name='ball')]], json_schema_extra={'special': Toy(name='bird')}),
+        ]
+
+    assert Cat.model_json_schema()['properties']['toys']['examples'] == [[{'name': 'mouse'}, {'name': 'ball'}]]
+    assert Cat.model_json_schema()['properties']['toys']['special'] == {'name': 'bird'}
+
+
 def test_computed_field():
     class Model(BaseModel):
         x: int