diff --git a/strawberry/relay/fields.py b/strawberry/relay/fields.py
index 5af00700f8..a65a2ed279 100644
--- a/strawberry/relay/fields.py
+++ b/strawberry/relay/fields.py
@@ -23,6 +23,7 @@
     Tuple,
     Type,
     Union,
+    UnionType,
     cast,
     overload,
 )
@@ -233,7 +234,21 @@ def apply(self, field: StrawberryField) -> None:
             f_type = f_type.resolve_type()
             field.type = f_type
 
+        # Handle Optional[Connection[T]] and Union[Connection[T], None] cases
         type_origin = get_origin(f_type) if is_generic_alias(f_type) else f_type
+
+        # If it's Optional or Union, extract the inner type
+        if type_origin in (Union, UnionType):
+            types = getattr(f_type, "__args__", ())
+            # Find the non-None type in the Union
+            inner_type = next((t for t in types if t is not type(None)), None)
+            if inner_type is not None:
+                type_origin = (
+                    get_origin(inner_type)
+                    if is_generic_alias(inner_type)
+                    else inner_type
+                )
+
         if not isinstance(type_origin, type) or not issubclass(type_origin, Connection):
             raise RelayWrongAnnotationError(field.name, cast(type, field.origin))
 
diff --git a/tests/relay/test_connection.py b/tests/relay/test_connection.py
new file mode 100644
index 0000000000..40a8203eda
--- /dev/null
+++ b/tests/relay/test_connection.py
@@ -0,0 +1,122 @@
+from typing import Optional, Union
+
+import strawberry
+from strawberry.permission import BasePermission
+from strawberry.relay import Connection, Node, connection
+
+
+@strawberry.type
+class User(Node):
+    name: str = "John"
+
+    @classmethod
+    def resolve_nodes(cls, *, info, node_ids, required):
+        return [cls() for _ in node_ids]
+
+
+class TestPermission(BasePermission):
+    message = "Not allowed"
+
+    def has_permission(self, source, info, **kwargs):
+        return False
+
+
+def test_nullable_connection_with_optional():
+    @strawberry.type
+    class Query:
+        @connection
+        def users(self) -> Optional[Connection[User]]:
+            return None
+
+    schema = strawberry.Schema(query=Query)
+    query = """
+        query {
+            users {
+                edges {
+                    node {
+                        name
+                    }
+                }
+            }
+        }
+    """
+
+    result = schema.execute_sync(query)
+    assert result.data == {"users": None}
+    assert not result.errors
+
+
+def test_nullable_connection_with_union():
+    @strawberry.type
+    class Query:
+        @connection
+        def users(self) -> Union[Connection[User], None]:
+            return None
+
+    schema = strawberry.Schema(query=Query)
+    query = """
+        query {
+            users {
+                edges {
+                    node {
+                        name
+                    }
+                }
+            }
+        }
+    """
+
+    result = schema.execute_sync(query)
+    assert result.data == {"users": None}
+    assert not result.errors
+
+
+def test_nullable_connection_with_permission():
+    @strawberry.type
+    class Query:
+        @strawberry.permission_classes([TestPermission])
+        @connection
+        def users(self) -> Optional[Connection[User]]:
+            return Connection[User](edges=[], page_info=None)
+
+    schema = strawberry.Schema(query=Query)
+    query = """
+        query {
+            users {
+                edges {
+                    node {
+                        name
+                    }
+                }
+            }
+        }
+    """
+
+    result = schema.execute_sync(query)
+    assert result.data == {"users": None}
+    assert not result.errors
+
+
+def test_non_nullable_connection():
+    @strawberry.type
+    class Query:
+        @connection
+        def users(self) -> Connection[User]:
+            return Connection[User](edges=[], page_info=None)
+
+    schema = strawberry.Schema(query=Query)
+    query = """
+        query {
+            users {
+                edges {
+                    node {
+                        name
+                    }
+                }
+            }
+        }
+    """
+
+    result = schema.execute_sync(query)
+    assert result.data == {"users": {"edges": []}}
+    assert not result.errors