diff --git a/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md b/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
index 777b6c3ec2..6e3434aaae 100644
--- a/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
+++ b/crates/ty_python_semantic/resources/mdtest/generics/pep695/functions.md
@@ -624,8 +624,7 @@ class ClassWithNewAndInit:
 
     def __init__(self, x: int) -> None: ...
 
-# TODO: revealed: ClassWithNewAndInit
-# revealed: Unknown
+# revealed: ClassWithNewAndInit
 reveal_type(accepts_callable(ClassWithNewAndInit)())
 
 class Meta(type):
@@ -660,10 +659,10 @@ class ClassWithOverloadedInit[T]:
     def __init__(self, x: int | str) -> None: ...
 
 # TODO: revealed: ClassWithOverloadedInit[int]
-# revealed: Unknown
+# revealed: Top[ClassWithOverloadedInit[Unknown]]
 reveal_type(accepts_callable(ClassWithOverloadedInit)(0))
 # TODO: revealed: ClassWithOverloadedInit[str]
-# revealed: Unknown
+# revealed: Top[ClassWithOverloadedInit[Unknown]]
 reveal_type(accepts_callable(ClassWithOverloadedInit)(""))
 
 class GenericClass[T]:
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index 210e6a2e4f..8e86c0d51f 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -11966,6 +11966,10 @@ impl<'db> CallableTypes<'db> {
         }
     }
 
+    fn as_slice(&self) -> &SmallVec<[CallableType<'db>; 1]> {
+        &self.0
+    }
+
     fn into_inner(self) -> SmallVec<[CallableType<'db>; 1]> {
         self.0
     }
diff --git a/crates/ty_python_semantic/src/types/generics.rs b/crates/ty_python_semantic/src/types/generics.rs
index 8b5d472589..bf5893208f 100644
--- a/crates/ty_python_semantic/src/types/generics.rs
+++ b/crates/ty_python_semantic/src/types/generics.rs
@@ -17,12 +17,11 @@ use crate::types::signatures::Parameters;
 use crate::types::tuple::{TupleSpec, TupleType, walk_tuple_type};
 use crate::types::visitor::{TypeCollector, TypeVisitor, walk_type_with_recursion_guard};
 use crate::types::{
-    ApplyTypeMappingVisitor, BoundTypeVarIdentity, BoundTypeVarInstance, CallableTypes,
-    ClassLiteral, FindLegacyTypeVarsVisitor, HasRelationToVisitor, IsDisjointVisitor,
-    IsEquivalentVisitor, KnownClass, KnownInstanceType, MaterializationKind, NormalizedVisitor,
-    Type, TypeContext, TypeMapping, TypeRelation, TypeVarBoundOrConstraints, TypeVarIdentity,
-    TypeVarInstance, TypeVarKind, TypeVarVariance, UnionType, declaration_type,
-    walk_bound_type_var_type,
+    ApplyTypeMappingVisitor, BoundTypeVarIdentity, BoundTypeVarInstance, ClassLiteral,
+    FindLegacyTypeVarsVisitor, HasRelationToVisitor, IsDisjointVisitor, IsEquivalentVisitor,
+    KnownClass, KnownInstanceType, MaterializationKind, NormalizedVisitor, Type, TypeContext,
+    TypeMapping, TypeRelation, TypeVarBoundOrConstraints, TypeVarIdentity, TypeVarInstance,
+    TypeVarKind, TypeVarVariance, UnionType, declaration_type, walk_bound_type_var_type,
 };
 use crate::{Db, FxOrderMap, FxOrderSet};
 
@@ -1650,27 +1649,26 @@ impl<'db> SpecializationBuilder<'db> {
             }
 
             (Type::Callable(formal_callable), _) => {
-                let Some(actual_callable) = actual
-                    .try_upcast_to_callable(self.db)
-                    .and_then(CallableTypes::exactly_one)
-                else {
+                let Some(actual_callables) = actual.try_upcast_to_callable(self.db) else {
                     return Ok(());
                 };
 
-                let [formal_signature] = formal_callable.signatures(self.db).overloads.as_slice()
-                else {
-                    return Ok(());
-                };
-                let [actual_signature] = actual_callable.signatures(self.db).overloads.as_slice()
-                else {
-                    return Ok(());
-                };
+                let mut when = ConstraintSet::from(false);
+                for formal_signature in &formal_callable.signatures(self.db).overloads {
+                    for actual_callable in actual_callables.as_slice() {
+                        for actual_signature in &actual_callable.signatures(self.db).overloads {
+                            when.union(
+                                self.db,
+                                formal_signature.when_constraint_set_assignable_to(
+                                    self.db,
+                                    actual_signature,
+                                    self.inferable,
+                                ),
+                            );
+                        }
+                    }
+                }
 
-                let when = formal_signature.when_constraint_set_assignable_to(
-                    self.db,
-                    actual_signature,
-                    self.inferable,
-                );
                 when.for_each_path(self.db, |path| {
                     for constraint in path.positive_constraints() {
                         let typevar = constraint.typevar(self.db);