diff --git a/python/python/lancedb/pydantic.py b/python/python/lancedb/pydantic.py
index 6838ccf3..855503f2 100644
--- a/python/python/lancedb/pydantic.py
+++ b/python/python/lancedb/pydantic.py
@@ -199,18 +199,29 @@ else:
         ]
 
 
+def _pydantic_type_to_arrow_type(tp: Any, field: FieldInfo) -> pa.DataType:
+    if inspect.isclass(tp):
+        if issubclass(tp, pydantic.BaseModel):
+            # Struct
+            fields = _pydantic_model_to_fields(tp)
+            return pa.struct(fields)
+        if issubclass(tp, FixedSizeListMixin):
+            return pa.list_(tp.value_arrow_type(), tp.dim())
+    return _py_type_to_arrow_type(tp, field)
+
+
 def _pydantic_to_arrow_type(field: FieldInfo) -> pa.DataType:
     """Convert a Pydantic FieldInfo to Arrow DataType"""
-
     if isinstance(field.annotation, (_GenericAlias, GenericAlias)):
         origin = field.annotation.__origin__
         args = field.annotation.__args__
+
         if origin is list:
             child = args[0]
             return pa.list_(_py_type_to_arrow_type(child, field))
         elif origin == Union:
             if len(args) == 2 and args[1] is type(None):
-                return _py_type_to_arrow_type(args[0], field)
+                return _pydantic_type_to_arrow_type(args[0], field)
     elif sys.version_info >= (3, 10) and isinstance(field.annotation, types.UnionType):
         args = field.annotation.__args__
         if len(args) == 2:
@@ -218,14 +229,7 @@ def _pydantic_to_arrow_type(field: FieldInfo) -> pa.DataType:
                 if typ is type(None):
                     continue
                 return _py_type_to_arrow_type(typ, field)
-    elif inspect.isclass(field.annotation):
-        if issubclass(field.annotation, pydantic.BaseModel):
-            # Struct
-            fields = _pydantic_model_to_fields(field.annotation)
-            return pa.struct(fields)
-        elif issubclass(field.annotation, FixedSizeListMixin):
-            return pa.list_(field.annotation.value_arrow_type(), field.annotation.dim())
-    return _py_type_to_arrow_type(field.annotation, field)
+    return _pydantic_type_to_arrow_type(field.annotation, field)
 
 
 def is_nullable(field: FieldInfo) -> bool:
diff --git a/python/python/tests/test_pydantic.py b/python/python/tests/test_pydantic.py
index 0e76c3ad..1648a518 100644
--- a/python/python/tests/test_pydantic.py
+++ b/python/python/tests/test_pydantic.py
@@ -10,6 +10,7 @@ import pyarrow as pa
 import pydantic
 import pytest
 from lancedb.pydantic import PYDANTIC_VERSION, LanceModel, Vector, pydantic_to_schema
+from pydantic import BaseModel
 from pydantic import Field
 
 
@@ -252,3 +253,104 @@ def test_lance_model():
 
     t = TestModel()
     assert t == TestModel(vec=[0.0] * 16, li=[1, 2, 3])
+
+
+def test_optional_nested_model():
+    class WAMedia(BaseModel):
+        url: str
+        mimetype: str
+        filename: Optional[str]
+        error: Optional[str]
+        data: bytes
+
+    class WALocation(BaseModel):
+        description: Optional[str]
+        latitude: str
+        longitude: str
+
+    class ReplyToMessage(BaseModel):
+        id: str
+        participant: str
+        body: str
+
+    class Message(BaseModel):
+        id: str
+        timestamp: int
+        from_: str
+        fromMe: bool
+        to: str
+        body: str
+        hasMedia: Optional[bool]
+        media: WAMedia
+        mediaUrl: Optional[str]
+        ack: Optional[int]
+        ackName: Optional[str]
+        author: Optional[str]
+        location: Optional[WALocation]
+        vCards: Optional[List[str]]
+        replyTo: Optional[ReplyToMessage]
+
+    class AnyEvent(LanceModel):
+        id: str
+        session: str
+        metadata: Optional[str] = None
+        engine: str
+        event: str
+
+    class MessageEvent(AnyEvent):
+        payload: Message
+
+    schema = pydantic_to_schema(MessageEvent)
+
+    payload = schema.field("payload")
+    assert payload.type == pa.struct(
+        [
+            pa.field("id", pa.utf8(), False),
+            pa.field("timestamp", pa.int64(), False),
+            pa.field("from_", pa.utf8(), False),
+            pa.field("fromMe", pa.bool_(), False),
+            pa.field("to", pa.utf8(), False),
+            pa.field("body", pa.utf8(), False),
+            pa.field("hasMedia", pa.bool_(), True),
+            pa.field(
+                "media",
+                pa.struct(
+                    [
+                        pa.field("url", pa.utf8(), False),
+                        pa.field("mimetype", pa.utf8(), False),
+                        pa.field("filename", pa.utf8(), True),
+                        pa.field("error", pa.utf8(), True),
+                        pa.field("data", pa.binary(), False),
+                    ]
+                ),
+                False,
+            ),
+            pa.field("mediaUrl", pa.utf8(), True),
+            pa.field("ack", pa.int64(), True),
+            pa.field("ackName", pa.utf8(), True),
+            pa.field("author", pa.utf8(), True),
+            pa.field(
+                "location",
+                pa.struct(
+                    [
+                        pa.field("description", pa.utf8(), True),
+                        pa.field("latitude", pa.utf8(), False),
+                        pa.field("longitude", pa.utf8(), False),
+                    ]
+                ),
+                True,  # Optional
+            ),
+            pa.field("vCards", pa.list_(pa.utf8()), True),
+            pa.field(
+                "replyTo",
+                pa.struct(
+                    [
+                        pa.field("id", pa.utf8(), False),
+                        pa.field("participant", pa.utf8(), False),
+                        pa.field("body", pa.utf8(), False),
+                    ]
+                ),
+                True,
+            ),
+        ]
+    )