diff --git a/crates/ty_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md b/crates/ty_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
index 678d1c1a11..83579a0e06 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
@@ -13,7 +13,7 @@ materializations of `B`, and all materializations of `B` are also materializatio
 ### Fully static
 
 ```py
-from typing_extensions import Literal, LiteralString, Never
+from typing_extensions import Literal, LiteralString, Protocol, Never
 from ty_extensions import Unknown, is_equivalent_to, static_assert, TypeOf, AlwaysTruthy, AlwaysFalsy
 from enum import Enum
 
@@ -43,6 +43,16 @@ static_assert(is_equivalent_to(Literal[Single.VALUE], Single))
 static_assert(is_equivalent_to(Single, Literal[Single.VALUE]))
 static_assert(is_equivalent_to(Literal[Single.VALUE], Literal[Single.VALUE]))
 
+static_assert(is_equivalent_to(tuple[Single] | int | str, str | int | tuple[Literal[Single.VALUE]]))
+
+class Protocol1(Protocol):
+    a: Single
+
+class Protocol2(Protocol):
+    a: Literal[Single.VALUE]
+
+static_assert(is_equivalent_to(Protocol1, Protocol2))
+
 static_assert(is_equivalent_to(Never, Never))
 static_assert(is_equivalent_to(AlwaysTruthy, AlwaysTruthy))
 static_assert(is_equivalent_to(AlwaysFalsy, AlwaysFalsy))
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index 8a01a5440b..9a0d9c86f8 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -1062,6 +1062,12 @@ impl<'db> Type<'db> {
                 type_is.with_type(db, type_is.return_type(db).normalized_impl(db, v))
             }),
             Type::Dynamic(dynamic) => Type::Dynamic(dynamic.normalized()),
+            Type::EnumLiteral(enum_literal)
+                if is_single_member_enum(db, enum_literal.enum_class(db)) =>
+            {
+                // Always normalize single-member enums to their class instance (`Literal[Single.VALUE]` => `Single`)
+                enum_literal.enum_class_instance(db)
+            }
             Type::LiteralString
             | Type::AlwaysFalsy
             | Type::AlwaysTruthy
diff --git a/crates/ty_python_semantic/src/types/property_tests/type_generation.rs b/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
index d0d7097af3..59c9a449b7 100644
--- a/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
+++ b/crates/ty_python_semantic/src/types/property_tests/type_generation.rs
@@ -1,5 +1,6 @@
 use crate::db::tests::TestDb;
 use crate::place::{builtins_symbol, known_module_symbol};
+use crate::types::enums::is_single_member_enum;
 use crate::types::tuple::TupleType;
 use crate::types::{
     BoundMethodType, CallableType, EnumLiteralType, IntersectionBuilder, KnownClass, Parameter,
@@ -27,6 +28,8 @@ pub(crate) enum Ty {
     BytesLiteral(&'static str),
     // An enum literal variant, using `uuid.SafeUUID` as base
     EnumLiteral(&'static str),
+    // A single-member enum literal, using `dataclasses.MISSING`
+    SingleMemberEnumLiteral,
     // BuiltinInstance("str") corresponds to an instance of the builtin `str` class
     BuiltinInstance(&'static str),
     /// Members of the `abc` stdlib module
@@ -145,6 +148,15 @@ impl Ty {
                     .expect_class_literal(),
                 Name::new(name),
             )),
+            Ty::SingleMemberEnumLiteral => {
+                let ty = known_module_symbol(db, KnownModule::Dataclasses, "MISSING")
+                    .place
+                    .expect_type();
+                debug_assert!(
+                    matches!(ty, Type::NominalInstance(instance) if is_single_member_enum(db, instance.class.class_literal(db).0))
+                );
+                ty
+            }
             Ty::BuiltinInstance(s) => builtins_symbol(db, s)
                 .place
                 .expect_type()
@@ -265,6 +277,7 @@ fn arbitrary_core_type(g: &mut Gen, fully_static: bool) -> Ty {
         Ty::EnumLiteral("safe"),
         Ty::EnumLiteral("unsafe"),
         Ty::EnumLiteral("unknown"),
+        Ty::SingleMemberEnumLiteral,
         Ty::KnownClassInstance(KnownClass::Object),
         Ty::KnownClassInstance(KnownClass::Str),
         Ty::KnownClassInstance(KnownClass::Int),