diff --git a/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md b/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
index 9745fdca21..2bbe85b5ec 100644
--- a/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
+++ b/crates/ty_python_semantic/resources/mdtest/generics/legacy/functions.md
@@ -545,3 +545,28 @@ def f(x: T, y: Not[T]) -> T:
     y = x  # error: [invalid-assignment]
     return x
 ```
+
+## Prefer exact matches for constrained typevars
+
+```py
+from typing import TypeVar
+
+class Base: ...
+class Sub(Base): ...
+
+# We solve to `Sub`, regardless of the order of constraints.
+T = TypeVar("T", Base, Sub)
+T2 = TypeVar("T2", Sub, Base)
+
+def f(x: T) -> list[T]:
+    return [x]
+
+def f2(x: T2) -> list[T2]:
+    return [x]
+
+x: list[Sub] = f(Sub())
+reveal_type(x)  # revealed: list[Sub]
+
+y: list[Sub] = f2(Sub())
+reveal_type(y)  # revealed: list[Sub]
+```
diff --git a/crates/ty_python_semantic/src/types/generics.rs b/crates/ty_python_semantic/src/types/generics.rs
index 59216ca607..8485931ff2 100644
--- a/crates/ty_python_semantic/src/types/generics.rs
+++ b/crates/ty_python_semantic/src/types/generics.rs
@@ -1483,6 +1483,14 @@ impl<'db> SpecializationBuilder<'db> {
                         self.add_type_mapping(bound_typevar, ty);
                     }
                     Some(TypeVarBoundOrConstraints::Constraints(constraints)) => {
+                        // Prefer an exact match first.
+                        for constraint in constraints.elements(self.db) {
+                            if ty == *constraint {
+                                self.add_type_mapping(bound_typevar, ty);
+                                return Ok(());
+                            }
+                        }
+
                         for constraint in constraints.elements(self.db) {
                             if ty
                                 .when_assignable_to(self.db, *constraint, self.inferable)