diff --git a/crates/ty_python_semantic/src/types/constraints.rs b/crates/ty_python_semantic/src/types/constraints.rs
index 515a264401..d876e99857 100644
--- a/crates/ty_python_semantic/src/types/constraints.rs
+++ b/crates/ty_python_semantic/src/types/constraints.rs
@@ -2715,17 +2715,36 @@ impl<'db> SequentMap<'db> {
                 let left_upper = left_constraint.upper(db);
                 let right_lower = right_constraint.lower(db);
                 let right_upper = right_constraint.upper(db);
+                let new_constraint = |bound_typevar: BoundTypeVarInstance<'db>,
+                                      right_lower: Type<'db>,
+                                      right_upper: Type<'db>| {
+                    let right_lower = if let Type::TypeVar(other_bound_typevar) = right_lower
+                        && bound_typevar.is_same_typevar_as(db, other_bound_typevar)
+                    {
+                        Type::Never
+                    } else {
+                        right_lower
+                    };
+                    let right_upper = if let Type::TypeVar(other_bound_typevar) = right_upper
+                        && bound_typevar.is_same_typevar_as(db, other_bound_typevar)
+                    {
+                        Type::object()
+                    } else {
+                        right_upper
+                    };
+                    ConstrainedTypeVar::new(db, bound_typevar, right_lower, right_upper)
+                };
                 let post_constraint = match (left_lower, left_upper) {
                     (Type::TypeVar(bound_typevar), Type::TypeVar(other_bound_typevar))
                         if bound_typevar.is_same_typevar_as(db, other_bound_typevar) =>
                     {
-                        ConstrainedTypeVar::new(db, bound_typevar, right_lower, right_upper)
+                        new_constraint(bound_typevar, right_lower, right_upper)
                     }
                     (Type::TypeVar(bound_typevar), _) => {
-                        ConstrainedTypeVar::new(db, bound_typevar, Type::Never, right_upper)
+                        new_constraint(bound_typevar, Type::Never, right_upper)
                     }
                     (_, Type::TypeVar(bound_typevar)) => {
-                        ConstrainedTypeVar::new(db, bound_typevar, right_lower, Type::object())
+                        new_constraint(bound_typevar, right_lower, Type::object())
                     }
                     _ => return,
                 };