diff --git a/crates/red_knot_python_semantic/resources/mdtest/binary/instances.md b/crates/red_knot_python_semantic/resources/mdtest/binary/instances.md
index 96f3b84fc474b9..29284c1252025b 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/binary/instances.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/binary/instances.md
@@ -142,7 +142,11 @@ reveal_type(A() + B())  # revealed: MyString
 # N.B. Still a subtype of `A`, even though `A` does not appear directly in the class's `__bases__`
 class C(B): ...
 
-reveal_type(A() + C())  # revealed: MyString
+# TODO: we currently only understand direct subclasses as subtypes of the superclass.
+# We need to iterate through the full MRO rather than just the class's bases;
+# if we do, we'll understand `C` as a subtype of `A`, and correctly understand this as being
+# `MyString` rather than `str`
+reveal_type(A() + C())  # revealed: str
 ```
 
 ## Reflected precedence 2
diff --git a/crates/red_knot_python_semantic/src/types.rs b/crates/red_knot_python_semantic/src/types.rs
index 070bcbe1270293..89b735c4f5aea1 100644
--- a/crates/red_knot_python_semantic/src/types.rs
+++ b/crates/red_knot_python_semantic/src/types.rs
@@ -440,6 +440,9 @@ impl<'db> Type<'db> {
                 .any(|&elem_ty| ty.is_subtype_of(db, elem_ty)),
             (_, Type::Instance(class)) if class.is_known(db, KnownClass::Object) => true,
             (Type::Instance(class), _) if class.is_known(db, KnownClass::Object) => false,
+            (Type::Instance(self_class), Type::Instance(target_class)) => self_class
+                .bases(db) // TODO: this should iterate through the MRO, not through the bases
+                .any(|base| base == Type::Class(target_class)),
             // TODO
             _ => false,
         }
diff --git a/crates/red_knot_python_semantic/src/types/infer.rs b/crates/red_knot_python_semantic/src/types/infer.rs
index 3a8994e6cd1d12..a41b58da4aa315 100644
--- a/crates/red_knot_python_semantic/src/types/infer.rs
+++ b/crates/red_knot_python_semantic/src/types/infer.rs
@@ -2642,17 +2642,36 @@ impl<'db> TypeInferenceBuilder<'db> {
                 op,
             ),
 
-            (Type::Instance(left_class), Type::Instance(right_class), op) => left_class
-                .class_member(self.db, op.dunder())
-                .call(self.db, &[left_ty, right_ty])
-                .return_ty(self.db)
-                .unwrap_or_else(|| {
-                    right_class
-                        .class_member(self.db, op.reflected_dunder())
-                        .call(self.db, &[right_ty, left_ty])
-                        .return_ty(self.db)
-                        .unwrap_or(Type::Unknown)
-                }),
+            (Type::Instance(left_class), Type::Instance(right_class), op) => {
+                if left_class != right_class && right_ty.is_assignable_to(self.db, left_ty) {
+                    let rhs_reflected = right_class.class_member(self.db, op.reflected_dunder());
+                    if !rhs_reflected.is_unbound()
+                        && rhs_reflected != left_class.class_member(self.db, op.reflected_dunder())
+                    {
+                        return rhs_reflected
+                            .call(self.db, &[right_ty, left_ty])
+                            .return_ty(self.db)
+                            .or_else(|| {
+                                left_class
+                                    .class_member(self.db, op.dunder())
+                                    .call(self.db, &[left_ty, right_ty])
+                                    .return_ty(self.db)
+                            })
+                            .unwrap_or(Type::Unknown);
+                    }
+                }
+                left_class
+                    .class_member(self.db, op.dunder())
+                    .call(self.db, &[left_ty, right_ty])
+                    .return_ty(self.db)
+                    .or_else(|| {
+                        right_class
+                            .class_member(self.db, op.reflected_dunder())
+                            .call(self.db, &[right_ty, left_ty])
+                            .return_ty(self.db)
+                    })
+                    .unwrap_or(Type::Unknown)
+            }
 
             _ => Type::Todo, // TODO
         }