diff --git a/sqlmodel/main.py b/sqlmodel/main.py
index 38c85915aa..66d9cf6823 100644
--- a/sqlmodel/main.py
+++ b/sqlmodel/main.py
@@ -52,7 +52,13 @@
 from sqlalchemy.orm.instrumentation import is_instrumented
 from sqlalchemy.sql.schema import MetaData
 from sqlalchemy.sql.sqltypes import LargeBinary, Time, Uuid
-from typing_extensions import Literal, TypeAlias, deprecated, get_origin
+from typing_extensions import (
+    Literal,
+    TypeAlias,
+    _AnnotatedAlias,
+    deprecated,
+    get_origin,
+)
 
 from ._compat import (  # type: ignore[attr-defined]
     IS_PYDANTIC_V2,
@@ -653,13 +659,24 @@ def get_sqlalchemy_type(field: Any) -> Any:
         return sa_type
 
     type_ = get_sa_type_from_field(field)
-    metadata = get_field_metadata(field)
+    if isinstance(type_, _AnnotatedAlias):
+        class_to_compare = type_.__origin__
+        if len(type_.__metadata__) == 1:
+            metadata = get_field_metadata(type_.__metadata__[0])
+        else:
+            # not sure if this is the right behavior
+            raise ValueError(
+                f"AnnotatedAlias with multiple metadata is not supported: {type_}"
+            )
+    else:
+        class_to_compare = type_
+        metadata = get_field_metadata(field)
 
     # Check enums first as an enum can also be a str, needed by Pydantic/FastAPI
-    if issubclass(type_, Enum):
+    if issubclass(class_to_compare, Enum):
         return sa_Enum(type_)
     if issubclass(
-        type_,
+        class_to_compare,
         (
             str,
             ipaddress.IPv4Address,
@@ -674,28 +691,28 @@ def get_sqlalchemy_type(field: Any) -> Any:
         if max_length:
             return AutoString(length=max_length)
         return AutoString
-    if issubclass(type_, float):
+    if issubclass(class_to_compare, float):
         return Float
-    if issubclass(type_, bool):
+    if issubclass(class_to_compare, bool):
         return Boolean
-    if issubclass(type_, int):
+    if issubclass(class_to_compare, int):
         return Integer
-    if issubclass(type_, datetime):
+    if issubclass(class_to_compare, datetime):
         return DateTime
-    if issubclass(type_, date):
+    if issubclass(class_to_compare, date):
         return Date
-    if issubclass(type_, timedelta):
+    if issubclass(class_to_compare, timedelta):
         return Interval
-    if issubclass(type_, time):
+    if issubclass(class_to_compare, time):
         return Time
-    if issubclass(type_, bytes):
+    if issubclass(class_to_compare, bytes):
         return LargeBinary
-    if issubclass(type_, Decimal):
+    if issubclass(class_to_compare, Decimal):
         return Numeric(
             precision=getattr(metadata, "max_digits", None),
             scale=getattr(metadata, "decimal_places", None),
         )
-    if issubclass(type_, uuid.UUID):
+    if issubclass(class_to_compare, uuid.UUID):
         return Uuid
     raise ValueError(f"{type_} has no matching SQLAlchemy type")
 
diff --git a/tests/test_main.py b/tests/test_main.py
index 60d5c40ebb..3b99833c9c 100644
--- a/tests/test_main.py
+++ b/tests/test_main.py
@@ -1,4 +1,5 @@
-from typing import List, Optional
+from decimal import Decimal
+from typing import Annotated, List, Optional
 
 import pytest
 from sqlalchemy.exc import IntegrityError
@@ -125,3 +126,25 @@ class Hero(SQLModel, table=True):
         # The next statement should not raise an AttributeError
         assert hero_rusty_man.team
         assert hero_rusty_man.team.name == "Preventers"
+
+
+def test_optional_annotated_decimal():
+    class Model(SQLModel, table=True):
+        id: Optional[int] = Field(default=None, primary_key=True)
+        dec: Annotated[Decimal, Field(max_digits=4, decimal_places=2)] | None = None
+
+    engine = create_engine("sqlite://")
+
+    SQLModel.metadata.create_all(engine)
+
+    with Session(engine) as session:
+        session.add(model := Model(dec=Decimal("3.14")))
+        session.commit()
+        session.refresh(model)
+        assert model.dec == Decimal("3.14")
+
+    with Session(engine) as session:
+        session.add(model := Model(dec=Decimal("3.142")))
+        session.commit()
+        session.refresh(model)
+        assert model.dec == Decimal("3.14")