diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index b2cb2d61f1..5dc0e4e9b0 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -1576,12 +1576,28 @@ impl<'db> Type<'db> {
             {
                 match bound_typevar.typevar(db).bound_or_constraints(db) {
                     None => unreachable!(),
+                    // Verify that the upper bound satisfies the relation. (If it does, than any
+                    // subtype of the upper bound will too.) Also add a safety constraint that
+                    // ensures that the typevar specializes to a subtype of the upper bound.
                     Some(TypeVarBoundOrConstraints::UpperBound(bound)) => {
-                        bound.has_relation_to_impl(db, target, relation, visitor)
+                        ConstraintSet::constrain_typevar(db, bound_typevar, Type::Never, bound)
+                            .implies(db, || {
+                                bound.has_relation_to_impl(db, target, relation, visitor)
+                            })
                     }
                     Some(TypeVarBoundOrConstraints::Constraints(constraints)) => {
                         constraints.elements(db).iter().when_all(db, |constraint| {
-                            constraint.has_relation_to_impl(db, target, relation, visitor)
+                            // Note that constrained typevars must specialize to _exactly_ one of the
+                            // constraints, not to a _subtype_ of one.
+                            ConstraintSet::constrain_typevar(
+                                db,
+                                bound_typevar,
+                                *constraint,
+                                *constraint,
+                            )
+                            .implies(db, || {
+                                constraint.has_relation_to_impl(db, target, relation, visitor)
+                            })
                         })
                     }
                 }
diff --git a/crates/ty_python_semantic/src/types/constraints.rs b/crates/ty_python_semantic/src/types/constraints.rs
index cb4e504196..7e62695426 100644
--- a/crates/ty_python_semantic/src/types/constraints.rs
+++ b/crates/ty_python_semantic/src/types/constraints.rs
@@ -171,6 +171,19 @@ impl<'db> ConstraintSet<'db> {
         }
     }
 
+    /// Returns a constraint set that constraints a typevar to a particular range of types.
+    pub(crate) fn constrain_typevar(
+        db: &'db dyn Db,
+        typevar: BoundTypeVarInstance<'db>,
+        lower: Type<'db>,
+        upper: Type<'db>,
+    ) -> Self {
+        let lower = lower.bottom_materialization(db);
+        let upper = upper.top_materialization(db);
+        let node = RangeConstraint::new_node(db, lower, typevar, upper);
+        Self { node }
+    }
+
     /// Returns whether this constraint set never holds
     pub(crate) fn is_never_satisfied(self) -> bool {
         self.node.is_never_satisfied()
@@ -220,6 +233,15 @@ impl<'db> ConstraintSet<'db> {
         self
     }
 
+    /// Returns a constraint set encoding that this constraint set implies another.
+    ///
+    /// In Boolean logic, `p → q` is usually translated into `¬p ∨ q`. However, we translate it
+    /// into the equivalent `¬p ∨ (p ∧ q)`. This ensures that the constraints under which `q` is
+    /// true are compatible with the assumptions introduced by `p`.
+    pub(crate) fn implies(self, db: &'db dyn Db, other: impl FnOnce() -> Self) -> Self {
+        self.clone().negate(db).or(db, || self.and(db, other))
+    }
+
     pub(crate) fn range(
         db: &'db dyn Db,
         lower: Type<'db>,