diff --git a/crates/ty_python_semantic/resources/mdtest/attributes.md b/crates/ty_python_semantic/resources/mdtest/attributes.md
index 488b82886b..f4b2d8c14b 100644
--- a/crates/ty_python_semantic/resources/mdtest/attributes.md
+++ b/crates/ty_python_semantic/resources/mdtest/attributes.md
@@ -2355,12 +2355,13 @@ import enum
 
 reveal_type(enum.Enum.__members__)  # revealed: MappingProxyType[str, Unknown]
 
-class Foo(enum.Enum):
-    BAR = 1
+class Answer(enum.Enum):
+    NO = 0
+    YES = 1
 
-reveal_type(Foo.BAR)  # revealed: Literal[Foo.BAR]
-reveal_type(Foo.BAR.value)  # revealed: Any
-reveal_type(Foo.__members__)  # revealed: MappingProxyType[str, Unknown]
+reveal_type(Answer.NO)  # revealed: Literal[Answer.NO]
+reveal_type(Answer.NO.value)  # revealed: Any
+reveal_type(Answer.__members__)  # revealed: MappingProxyType[str, Unknown]
 ```
 
 ## References
diff --git a/crates/ty_python_semantic/resources/mdtest/call/overloads.md b/crates/ty_python_semantic/resources/mdtest/call/overloads.md
index 1f41f34087..5ab5fb3360 100644
--- a/crates/ty_python_semantic/resources/mdtest/call/overloads.md
+++ b/crates/ty_python_semantic/resources/mdtest/call/overloads.md
@@ -369,6 +369,8 @@ def _(x: type[A | B]):
 
 ### Expanding enums
 
+#### Basic
+
 `overloaded.pyi`:
 
 ```pyi
@@ -394,15 +396,106 @@ def f(x: Literal[SomeEnum.C]) -> C: ...
 ```
 
 ```py
+from typing import Literal
 from overloaded import SomeEnum, A, B, C, f
 
-def _(x: SomeEnum):
+def _(x: SomeEnum, y: Literal[SomeEnum.A, SomeEnum.C]):
     reveal_type(f(SomeEnum.A))  # revealed: A
     reveal_type(f(SomeEnum.B))  # revealed: B
     reveal_type(f(SomeEnum.C))  # revealed: C
-    # TODO: This should not be an error. The return type should be `A | B | C` once enums are expanded
-    # error: [no-matching-overload]
-    reveal_type(f(x))  # revealed: Unknown
+    reveal_type(f(x))  # revealed: A | B | C
+    reveal_type(f(y))  # revealed: A | C
+```
+
+#### Enum with single member
+
+This pattern appears in typeshed. Here, it is used to represent two optional, mutually exclusive
+keyword parameters:
+
+`overloaded.pyi`:
+
+```pyi
+from enum import Enum, auto
+from typing import overload, Literal
+
+class Missing(Enum):
+    Value = auto()
+
+class OnlyASpecified: ...
+class OnlyBSpecified: ...
+class BothMissing: ...
+
+@overload
+def f(*, a: int, b: Literal[Missing.Value] = ...) -> OnlyASpecified: ...
+@overload
+def f(*, a: Literal[Missing.Value] = ..., b: int) -> OnlyBSpecified: ...
+@overload
+def f(*, a: Literal[Missing.Value] = ..., b: Literal[Missing.Value] = ...) -> BothMissing: ...
+```
+
+```py
+from typing import Literal
+from overloaded import f, Missing
+
+reveal_type(f())  # revealed: BothMissing
+reveal_type(f(a=0))  # revealed: OnlyASpecified
+reveal_type(f(b=0))  # revealed: OnlyBSpecified
+
+f(a=0, b=0)  # error: [no-matching-overload]
+
+def _(missing: Literal[Missing.Value], missing_or_present: Literal[Missing.Value] | int):
+    reveal_type(f(a=missing, b=missing))  # revealed: BothMissing
+    reveal_type(f(a=missing))  # revealed: BothMissing
+    reveal_type(f(b=missing))  # revealed: BothMissing
+    reveal_type(f(a=0, b=missing))  # revealed: OnlyASpecified
+    reveal_type(f(a=missing, b=0))  # revealed: OnlyBSpecified
+
+    reveal_type(f(a=missing_or_present))  # revealed: BothMissing | OnlyASpecified
+    reveal_type(f(b=missing_or_present))  # revealed: BothMissing | OnlyBSpecified
+
+    # Here, both could be present, so this should be an error
+    f(a=missing_or_present, b=missing_or_present)  # error: [no-matching-overload]
+```
+
+#### Enum subclass without members
+
+An `Enum` subclass without members should *not* be expanded:
+
+`overloaded.pyi`:
+
+```pyi
+from enum import Enum
+from typing import overload, Literal
+
+class MyEnumSubclass(Enum):
+    pass
+
+class ActualEnum(MyEnumSubclass):
+    A = 1
+    B = 2
+
+class OnlyA: ...
+class OnlyB: ...
+class Both: ...
+
+@overload
+def f(x: Literal[ActualEnum.A]) -> OnlyA: ...
+@overload
+def f(x: Literal[ActualEnum.B]) -> OnlyB: ...
+@overload
+def f(x: ActualEnum) -> Both: ...
+@overload
+def f(x: MyEnumSubclass) -> MyEnumSubclass: ...
+```
+
+```py
+from overloaded import MyEnumSubclass, ActualEnum, f
+
+def _(actual_enum: ActualEnum, my_enum_instance: MyEnumSubclass):
+    reveal_type(f(actual_enum))  # revealed: Both
+    reveal_type(f(ActualEnum.A))  # revealed: OnlyA
+    reveal_type(f(ActualEnum.B))  # revealed: OnlyB
+    reveal_type(f(my_enum_instance))  # revealed: MyEnumSubclass
 ```
 
 ### No matching overloads
diff --git a/crates/ty_python_semantic/resources/mdtest/enums.md b/crates/ty_python_semantic/resources/mdtest/enums.md
index e6fbf723d5..482fdd4960 100644
--- a/crates/ty_python_semantic/resources/mdtest/enums.md
+++ b/crates/ty_python_semantic/resources/mdtest/enums.md
@@ -570,7 +570,111 @@ To do: <https://typing.python.org/en/latest/spec/enums.html#enum-definition>
 
 ## Exhaustiveness checking
 
-To do
+## `if` statements
+
+```py
+from enum import Enum
+from typing_extensions import assert_never
+
+class Color(Enum):
+    RED = 1
+    GREEN = 2
+    BLUE = 3
+
+def color_name(color: Color) -> str:
+    if color is Color.RED:
+        return "Red"
+    elif color is Color.GREEN:
+        return "Green"
+    elif color is Color.BLUE:
+        return "Blue"
+    else:
+        assert_never(color)
+
+# No `invalid-return-type` error here because the implicit `else` branch is detected as unreachable:
+def color_name_without_assertion(color: Color) -> str:
+    if color is Color.RED:
+        return "Red"
+    elif color is Color.GREEN:
+        return "Green"
+    elif color is Color.BLUE:
+        return "Blue"
+
+def color_name_misses_one_variant(color: Color) -> str:
+    if color is Color.RED:
+        return "Red"
+    elif color is Color.GREEN:
+        return "Green"
+    else:
+        assert_never(color)  # error: [type-assertion-failure] "Argument does not have asserted type `Never`"
+
+class Singleton(Enum):
+    VALUE = 1
+
+def singleton_check(value: Singleton) -> str:
+    if value is Singleton.VALUE:
+        return "Singleton value"
+    else:
+        assert_never(value)
+```
+
+## `match` statements
+
+```toml
+[environment]
+python-version = "3.10"
+```
+
+```py
+from enum import Enum
+from typing_extensions import assert_never
+
+class Color(Enum):
+    RED = 1
+    GREEN = 2
+    BLUE = 3
+
+def color_name(color: Color) -> str:
+    match color:
+        case Color.RED:
+            return "Red"
+        case Color.GREEN:
+            return "Green"
+        case Color.BLUE:
+            return "Blue"
+        case _:
+            assert_never(color)
+
+# TODO: this should not be an error, see https://github.com/astral-sh/ty/issues/99#issuecomment-2983054488
+# error: [invalid-return-type] "Function can implicitly return `None`, which is not assignable to return type `str`"
+def color_name_without_assertion(color: Color) -> str:
+    match color:
+        case Color.RED:
+            return "Red"
+        case Color.GREEN:
+            return "Green"
+        case Color.BLUE:
+            return "Blue"
+
+def color_name_misses_one_variant(color: Color) -> str:
+    match color:
+        case Color.RED:
+            return "Red"
+        case Color.GREEN:
+            return "Green"
+        case _:
+            assert_never(color)  # error: [type-assertion-failure] "Argument does not have asserted type `Never`"
+
+class Singleton(Enum):
+    VALUE = 1
+
+def singleton_check(value: Singleton) -> str:
+    match value:
+        case Singleton.VALUE:
+            return "Singleton value"
+        case _:
+            assert_never(value)
+```
 
 ## References
 
diff --git a/crates/ty_python_semantic/resources/mdtest/intersection_types.md b/crates/ty_python_semantic/resources/mdtest/intersection_types.md
index 66f350bfe9..0f5b37eb88 100644
--- a/crates/ty_python_semantic/resources/mdtest/intersection_types.md
+++ b/crates/ty_python_semantic/resources/mdtest/intersection_types.md
@@ -763,6 +763,65 @@ def f(
     reveal_type(j)  # revealed: Unknown & Literal[""]
 ```
 
+## Simplifications involving enums and enum literals
+
+```toml
+[environment]
+python-version = "3.12"
+```
+
+```py
+from ty_extensions import Intersection, Not
+from typing import Literal
+from enum import Enum
+
+class Color(Enum):
+    RED = "red"
+    GREEN = "green"
+    BLUE = "blue"
+
+type Red = Literal[Color.RED]
+type Green = Literal[Color.GREEN]
+type Blue = Literal[Color.BLUE]
+
+def f(
+    a: Intersection[Color, Red],
+    b: Intersection[Color, Not[Red]],
+    c: Intersection[Color, Not[Red | Green]],
+    d: Intersection[Color, Not[Red | Green | Blue]],
+    e: Intersection[Red, Not[Color]],
+    f: Intersection[Red | Green, Not[Color]],
+    g: Intersection[Not[Red], Color],
+    h: Intersection[Red, Green],
+    i: Intersection[Red | Green, Green | Blue],
+):
+    reveal_type(a)  # revealed: Literal[Color.RED]
+    reveal_type(b)  # revealed: Literal[Color.GREEN, Color.BLUE]
+    reveal_type(c)  # revealed: Literal[Color.BLUE]
+    reveal_type(d)  # revealed: Never
+    reveal_type(e)  # revealed: Never
+    reveal_type(f)  # revealed: Never
+    reveal_type(g)  # revealed: Literal[Color.GREEN, Color.BLUE]
+    reveal_type(h)  # revealed: Never
+    reveal_type(i)  # revealed: Literal[Color.GREEN]
+
+class Single(Enum):
+    VALUE = 0
+
+def g(
+    a: Intersection[Single, Literal[Single.VALUE]],
+    b: Intersection[Single, Not[Literal[Single.VALUE]]],
+    c: Intersection[Not[Literal[Single.VALUE]], Single],
+    d: Intersection[Single, Not[Single]],
+    e: Intersection[Single | int, Not[Single]],
+):
+    reveal_type(a)  # revealed: Single
+    reveal_type(b)  # revealed: Never
+    reveal_type(c)  # revealed: Never
+    reveal_type(d)  # revealed: Never
+    reveal_type(e)  # revealed: int
+```
+
 ## Addition of a type to an intersection with many non-disjoint types
 
 This slightly strange-looking test is a regression test for a mistake that was nearly made in a PR:
diff --git a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md
index fb1943c0fe..6456b7764b 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md
@@ -1,4 +1,4 @@
-# Narrowing for `!=` conditionals
+# Narrowing for `!=` and `==` conditionals
 
 ## `x != None`
 
@@ -22,6 +22,12 @@ def _(x: bool):
         reveal_type(x)  # revealed: Literal[True]
     else:
         reveal_type(x)  # revealed: Literal[False]
+
+def _(x: bool):
+    if x == False:
+        reveal_type(x)  # revealed: Literal[False]
+    else:
+        reveal_type(x)  # revealed: Literal[True]
 ```
 
 ### Enums
@@ -35,11 +41,31 @@ class Answer(Enum):
 
 def _(answer: Answer):
     if answer != Answer.NO:
-        # TODO: This should be simplified to `Literal[Answer.YES]`
-        reveal_type(answer)  # revealed: Answer & ~Literal[Answer.NO]
+        reveal_type(answer)  # revealed: Literal[Answer.YES]
     else:
-        # TODO: This should be `Literal[Answer.NO]`
-        reveal_type(answer)  # revealed: Answer
+        reveal_type(answer)  # revealed: Literal[Answer.NO]
+
+def _(answer: Answer):
+    if answer == Answer.NO:
+        reveal_type(answer)  # revealed: Literal[Answer.NO]
+    else:
+        reveal_type(answer)  # revealed: Literal[Answer.YES]
+
+class Single(Enum):
+    VALUE = 1
+
+def _(x: Single | int):
+    if x != Single.VALUE:
+        reveal_type(x)  # revealed: int
+    else:
+        # `int` is not eliminated here because there could be subclasses of `int` with custom `__eq__`/`__ne__` methods
+        reveal_type(x)  # revealed: Single | int
+
+def _(x: Single | int):
+    if x == Single.VALUE:
+        reveal_type(x)  # revealed: Single | int
+    else:
+        reveal_type(x)  # revealed: int
 ```
 
 This narrowing behavior is only safe if the enum has no custom `__eq__`/`__ne__` method:
diff --git a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is.md b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is.md
index 8736ee40fd..e3c40104f1 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is.md
@@ -78,8 +78,16 @@ def _(answer: Answer):
     if answer is Answer.NO:
         reveal_type(answer)  # revealed: Literal[Answer.NO]
     else:
-        # TODO: This should be `Literal[Answer.YES]`
-        reveal_type(answer)  # revealed: Answer & ~Literal[Answer.NO]
+        reveal_type(answer)  # revealed: Literal[Answer.YES]
+
+class Single(Enum):
+    VALUE = 1
+
+def _(x: Single | int):
+    if x is Single.VALUE:
+        reveal_type(x)  # revealed: Single
+    else:
+        reveal_type(x)  # revealed: int
 ```
 
 ## `is` for `EllipsisType` (Python 3.10+)
diff --git a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is_not.md b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is_not.md
index fba62e9213..0c4e87c36c 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is_not.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/is_not.md
@@ -18,6 +18,8 @@ def _(flag: bool):
 
 ## `is not` for other singleton types
 
+Boolean literals:
+
 ```py
 def _(flag: bool):
     x = True if flag else False
@@ -29,6 +31,33 @@ def _(flag: bool):
         reveal_type(x)  # revealed: Literal[False]
 ```
 
+Enum literals:
+
+```py
+from enum import Enum
+
+class Answer(Enum):
+    NO = 0
+    YES = 1
+
+def _(answer: Answer):
+    if answer is not Answer.NO:
+        reveal_type(answer)  # revealed: Literal[Answer.YES]
+    else:
+        reveal_type(answer)  # revealed: Literal[Answer.NO]
+
+    reveal_type(answer)  # revealed: Answer
+
+class Single(Enum):
+    VALUE = 1
+
+def _(x: Single | int):
+    if x is not Single.VALUE:
+        reveal_type(x)  # revealed: int
+    else:
+        reveal_type(x)  # revealed: Single
+```
+
 ## `is not` for non-singleton types
 
 Non-singleton types should *not* narrow the type: two instances of a non-singleton class may occupy
diff --git a/crates/ty_python_semantic/resources/mdtest/type_properties/is_assignable_to.md b/crates/ty_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
index c499773536..028a411c51 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
@@ -138,11 +138,15 @@ class Answer(Enum):
 static_assert(is_assignable_to(Literal[Answer.YES], Literal[Answer.YES]))
 static_assert(is_assignable_to(Literal[Answer.YES], Answer))
 static_assert(is_assignable_to(Literal[Answer.YES, Answer.NO], Answer))
-# TODO: this should not be an error
-# error: [static-assert-error]
 static_assert(is_assignable_to(Answer, Literal[Answer.YES, Answer.NO]))
 
 static_assert(not is_assignable_to(Literal[Answer.YES], Literal[Answer.NO]))
+
+class Single(Enum):
+    VALUE = 1
+
+static_assert(is_assignable_to(Literal[Single.VALUE], Single))
+static_assert(is_assignable_to(Single, Literal[Single.VALUE]))
 ```
 
 ### Slice literals
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 d2815b3cdb..678d1c1a11 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
@@ -21,6 +21,9 @@ class Answer(Enum):
     NO = 0
     YES = 1
 
+class Single(Enum):
+    VALUE = 1
+
 static_assert(is_equivalent_to(Literal[1, 2], Literal[1, 2]))
 static_assert(is_equivalent_to(type[object], type))
 static_assert(is_equivalent_to(type, type[object]))
@@ -31,12 +34,15 @@ static_assert(not is_equivalent_to(Literal[1, 2], Literal[1, 2, 3]))
 static_assert(not is_equivalent_to(Literal[1, 2, 3], Literal[1, 2]))
 
 static_assert(is_equivalent_to(Literal[Answer.YES], Literal[Answer.YES]))
-# TODO: these should be equivalent
-# error: [static-assert-error]
+static_assert(is_equivalent_to(Literal[Answer.NO, Answer.YES], Answer))
 static_assert(is_equivalent_to(Literal[Answer.YES, Answer.NO], Answer))
 static_assert(not is_equivalent_to(Literal[Answer.YES], Literal[Answer.NO]))
 static_assert(not is_equivalent_to(Literal[Answer.YES], Answer))
 
+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(Never, Never))
 static_assert(is_equivalent_to(AlwaysTruthy, AlwaysTruthy))
 static_assert(is_equivalent_to(AlwaysFalsy, AlwaysFalsy))
@@ -69,8 +75,9 @@ static_assert(not is_equivalent_to(type[object], type[Any]))
 ## Unions and intersections
 
 ```py
-from typing import Any
+from typing import Any, Literal
 from ty_extensions import Intersection, Not, Unknown, is_equivalent_to, static_assert
+from enum import Enum
 
 static_assert(is_equivalent_to(str | int, str | int))
 static_assert(is_equivalent_to(str | int | Any, str | int | Unknown))
@@ -111,6 +118,11 @@ static_assert(is_equivalent_to(Intersection[P, Q], Intersection[Q, P]))
 static_assert(is_equivalent_to(Intersection[Q, Not[P]], Intersection[Not[P], Q]))
 static_assert(is_equivalent_to(Intersection[Q, R, Not[P]], Intersection[Not[P], R, Q]))
 static_assert(is_equivalent_to(Intersection[Q | R, Not[P | S]], Intersection[Not[S | P], R | Q]))
+
+class Single(Enum):
+    VALUE = 1
+
+static_assert(is_equivalent_to(P | Q | Single, Literal[Single.VALUE] | Q | P))
 ```
 
 ## Tuples
diff --git a/crates/ty_python_semantic/resources/mdtest/type_properties/is_single_valued.md b/crates/ty_python_semantic/resources/mdtest/type_properties/is_single_valued.md
index 5c97c2524c..ae070df864 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_properties/is_single_valued.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_properties/is_single_valued.md
@@ -47,6 +47,9 @@ class NormalEnum(Enum):
     NO = 0
     YES = 1
 
+class SingleValuedEnum(Enum):
+    VALUE = 1
+
 class ComparesEqualEnum(Enum):
     NO = 0
     YES = 1
@@ -70,13 +73,20 @@ class CustomNeEnum(Enum):
 
 static_assert(is_single_valued(Literal[NormalEnum.NO]))
 static_assert(is_single_valued(Literal[NormalEnum.YES]))
+static_assert(not is_single_valued(NormalEnum))
+
+static_assert(is_single_valued(Literal[SingleValuedEnum.VALUE]))
+static_assert(is_single_valued(SingleValuedEnum))
 
 static_assert(is_single_valued(Literal[ComparesEqualEnum.NO]))
 static_assert(is_single_valued(Literal[ComparesEqualEnum.YES]))
+static_assert(not is_single_valued(ComparesEqualEnum))
 
 static_assert(not is_single_valued(Literal[CustomEqEnum.NO]))
 static_assert(not is_single_valued(Literal[CustomEqEnum.YES]))
+static_assert(not is_single_valued(CustomEqEnum))
 
 static_assert(not is_single_valued(Literal[CustomNeEnum.NO]))
 static_assert(not is_single_valued(Literal[CustomNeEnum.YES]))
+static_assert(not is_single_valued(CustomNeEnum))
 ```
diff --git a/crates/ty_python_semantic/resources/mdtest/type_properties/is_singleton.md b/crates/ty_python_semantic/resources/mdtest/type_properties/is_singleton.md
index c50a968169..a6b87194c9 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_properties/is_singleton.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_properties/is_singleton.md
@@ -13,11 +13,16 @@ class Answer(Enum):
     NO = 0
     YES = 1
 
+class Single(Enum):
+    VALUE = 1
+
 static_assert(is_singleton(None))
 static_assert(is_singleton(Literal[True]))
 static_assert(is_singleton(Literal[False]))
 static_assert(is_singleton(Literal[Answer.YES]))
 static_assert(is_singleton(Literal[Answer.NO]))
+static_assert(is_singleton(Literal[Single.VALUE]))
+static_assert(is_singleton(Single))
 
 static_assert(is_singleton(type[bool]))
 
diff --git a/crates/ty_python_semantic/resources/mdtest/type_properties/is_subtype_of.md b/crates/ty_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
index 3d46d11a47..b3201da5e2 100644
--- a/crates/ty_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
+++ b/crates/ty_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
@@ -96,6 +96,9 @@ class Answer(Enum):
     NO = 0
     YES = 1
 
+class Single(Enum):
+    VALUE = 1
+
 # Boolean literals
 static_assert(is_subtype_of(Literal[True], bool))
 static_assert(is_subtype_of(Literal[True], int))
@@ -125,11 +128,12 @@ static_assert(is_subtype_of(Literal[b"foo"], object))
 static_assert(is_subtype_of(Literal[Answer.YES], Literal[Answer.YES]))
 static_assert(is_subtype_of(Literal[Answer.YES], Answer))
 static_assert(is_subtype_of(Literal[Answer.YES, Answer.NO], Answer))
-# TODO: this should not be an error
-# error: [static-assert-error]
 static_assert(is_subtype_of(Answer, Literal[Answer.YES, Answer.NO]))
 
 static_assert(not is_subtype_of(Literal[Answer.YES], Literal[Answer.NO]))
+
+static_assert(is_subtype_of(Literal[Single.VALUE], Single))
+static_assert(is_subtype_of(Single, Literal[Single.VALUE]))
 ```
 
 ## Heterogeneous tuple types
diff --git a/crates/ty_python_semantic/resources/mdtest/union_types.md b/crates/ty_python_semantic/resources/mdtest/union_types.md
index 919fd4921b..52a77028c7 100644
--- a/crates/ty_python_semantic/resources/mdtest/union_types.md
+++ b/crates/ty_python_semantic/resources/mdtest/union_types.md
@@ -114,6 +114,33 @@ def _(
     reveal_type(u5)  # revealed: bool | Literal[17]
 ```
 
+## Enum literals
+
+```py
+from enum import Enum
+from typing import Literal
+
+class Color(Enum):
+    RED = "red"
+    GREEN = "green"
+    BLUE = "blue"
+
+def _(
+    u1: Literal[Color.RED, Color.GREEN],
+    u2: Color | Literal[Color.RED],
+    u3: Literal[Color.RED] | Color,
+    u4: Literal[Color.RED] | Literal[Color.RED, Color.GREEN],
+    u5: Literal[Color.RED, Color.GREEN, Color.BLUE],
+    u6: Literal[Color.RED] | Literal[Color.GREEN] | Literal[Color.BLUE],
+) -> None:
+    reveal_type(u1)  # revealed: Literal[Color.RED, Color.GREEN]
+    reveal_type(u2)  # revealed: Color
+    reveal_type(u3)  # revealed: Color
+    reveal_type(u4)  # revealed: Literal[Color.RED, Color.GREEN]
+    reveal_type(u5)  # revealed: Color
+    reveal_type(u6)  # revealed: Color
+```
+
 ## Do not erase `Unknown`
 
 ```py
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index badb8d7b40..19be47b8ce 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -39,7 +39,7 @@ use crate::types::call::{Binding, Bindings, CallArguments, CallableBinding};
 pub(crate) use crate::types::class_base::ClassBase;
 use crate::types::context::{LintDiagnosticGuard, LintDiagnosticGuardBuilder};
 use crate::types::diagnostic::{INVALID_TYPE_FORM, UNSUPPORTED_BOOL_CONVERSION};
-use crate::types::enums::enum_metadata;
+use crate::types::enums::{enum_metadata, is_single_member_enum};
 use crate::types::function::{
     DataclassTransformerParams, FunctionSpans, FunctionType, KnownFunction,
 };
@@ -789,6 +789,19 @@ impl<'db> Type<'db> {
         matches!(self, Type::ClassLiteral(..))
     }
 
+    pub fn into_enum_literal(self) -> Option<EnumLiteralType<'db>> {
+        match self {
+            Type::EnumLiteral(enum_literal) => Some(enum_literal),
+            _ => None,
+        }
+    }
+
+    #[track_caller]
+    pub fn expect_enum_literal(self) -> EnumLiteralType<'db> {
+        self.into_enum_literal()
+            .expect("Expected a Type::EnumLiteral variant")
+    }
+
     pub(crate) const fn into_tuple(self) -> Option<TupleType<'db>> {
         match self {
             Type::Tuple(tuple_type) => Some(tuple_type),
@@ -1420,6 +1433,16 @@ impl<'db> Type<'db> {
             // All `StringLiteral` types are a subtype of `LiteralString`.
             (Type::StringLiteral(_), Type::LiteralString) => true,
 
+            // An instance is a subtype of an enum literal, if it is an instance of the enum class
+            // and the enum has only one member.
+            (Type::NominalInstance(_), Type::EnumLiteral(target_enum_literal)) => {
+                if target_enum_literal.enum_class_instance(db) != self {
+                    return false;
+                }
+
+                is_single_member_enum(db, target_enum_literal.enum_class(db))
+            }
+
             // Except for the special `LiteralString` case above,
             // most `Literal` types delegate to their instance fallbacks
             // unless `self` is exactly equivalent to `target` (handled above)
@@ -1656,6 +1679,17 @@ impl<'db> Type<'db> {
             | (nominal @ Type::NominalInstance(n), Type::ProtocolInstance(protocol)) => {
                 n.class.is_object(db) && protocol.normalized(db) == nominal
             }
+            // An instance of an enum class is equivalent to an enum literal of that class,
+            // if that enum has only has one member.
+            (Type::NominalInstance(instance), Type::EnumLiteral(literal))
+            | (Type::EnumLiteral(literal), Type::NominalInstance(instance)) => {
+                if literal.enum_class_instance(db) != Type::NominalInstance(instance) {
+                    return false;
+                }
+
+                let class_literal = instance.class.class_literal(db).0;
+                is_single_member_enum(db, class_literal)
+            }
             _ => false,
         }
     }
@@ -8409,6 +8443,7 @@ pub struct EnumLiteralType<'db> {
     /// A reference to the enum class this literal belongs to
     enum_class: ClassLiteral<'db>,
     /// The name of the enum member
+    #[returns(ref)]
     name: Name,
 }
 
diff --git a/crates/ty_python_semantic/src/types/builder.rs b/crates/ty_python_semantic/src/types/builder.rs
index 7087677322..a3f16c6178 100644
--- a/crates/ty_python_semantic/src/types/builder.rs
+++ b/crates/ty_python_semantic/src/types/builder.rs
@@ -37,6 +37,7 @@
 //! are subtypes of each other (unless exactly the same literal type), we can avoid many
 //! unnecessary `is_subtype_of` checks.
 
+use crate::types::enums::{enum_member_literals, enum_metadata};
 use crate::types::{
     BytesLiteralType, IntersectionType, KnownClass, StringLiteralType, Type,
     TypeVarBoundOrConstraints, UnionType,
@@ -87,6 +88,13 @@ enum UnionElement<'db> {
 }
 
 impl<'db> UnionElement<'db> {
+    const fn to_type_element(&self) -> Option<Type<'db>> {
+        match self {
+            UnionElement::Type(ty) => Some(*ty),
+            _ => None,
+        }
+    }
+
     /// Try reducing this `UnionElement` given the presence in the same union of `other_type`.
     fn try_reduce(&mut self, db: &'db dyn Db, other_type: Type<'db>) -> ReduceResult<'db> {
         match self {
@@ -374,6 +382,38 @@ impl<'db> UnionBuilder<'db> {
                     self.elements.swap_remove(index);
                 }
             }
+            Type::EnumLiteral(enum_member_to_add) => {
+                let enum_class = enum_member_to_add.enum_class(self.db);
+                let metadata =
+                    enum_metadata(self.db, enum_class).expect("Class of enum literal is an enum");
+
+                let enum_members_in_union = self
+                    .elements
+                    .iter()
+                    .filter_map(UnionElement::to_type_element)
+                    .filter_map(Type::into_enum_literal)
+                    .map(|literal| literal.name(self.db).clone())
+                    .chain(std::iter::once(enum_member_to_add.name(self.db).clone()))
+                    .collect::<FxOrderSet<_>>();
+
+                let all_members_are_in_union = metadata
+                    .members
+                    .difference(&enum_members_in_union)
+                    .next()
+                    .is_none();
+
+                if all_members_are_in_union {
+                    self.add_in_place(enum_member_to_add.enum_class_instance(self.db));
+                } else if !self
+                    .elements
+                    .iter()
+                    .filter_map(UnionElement::to_type_element)
+                    .any(|ty| Type::EnumLiteral(enum_member_to_add).is_subtype_of(self.db, ty))
+                {
+                    self.elements
+                        .push(UnionElement::Type(Type::EnumLiteral(enum_member_to_add)));
+                }
+            }
             // Adding `object` to a union results in `object`.
             ty if ty.is_object(self.db) => {
                 self.collapse_to_object();
@@ -501,72 +541,147 @@ impl<'db> IntersectionBuilder<'db> {
     }
 
     pub(crate) fn add_positive(mut self, ty: Type<'db>) -> Self {
-        if let Type::Union(union) = ty {
-            // Distribute ourself over this union: for each union element, clone ourself and
-            // intersect with that union element, then create a new union-of-intersections with all
-            // of those sub-intersections in it. E.g. if `self` is a simple intersection `T1 & T2`
-            // and we add `T3 | T4` to the intersection, we don't get `T1 & T2 & (T3 | T4)` (that's
-            // not in DNF), we distribute the union and get `(T1 & T3) | (T2 & T3) | (T1 & T4) |
-            // (T2 & T4)`. If `self` is already a union-of-intersections `(T1 & T2) | (T3 & T4)`
-            // and we add `T5 | T6` to it, that flattens all the way out to `(T1 & T2 & T5) | (T1 &
-            // T2 & T6) | (T3 & T4 & T5) ...` -- you get the idea.
-            union
-                .elements(self.db)
-                .iter()
-                .map(|elem| self.clone().add_positive(*elem))
-                .fold(IntersectionBuilder::empty(self.db), |mut builder, sub| {
-                    builder.intersections.extend(sub.intersections);
-                    builder
-                })
-        } else {
-            // If we are already a union-of-intersections, distribute the new intersected element
-            // across all of those intersections.
-            for inner in &mut self.intersections {
-                inner.add_positive(self.db, ty);
+        match ty {
+            Type::Union(union) => {
+                // Distribute ourself over this union: for each union element, clone ourself and
+                // intersect with that union element, then create a new union-of-intersections with all
+                // of those sub-intersections in it. E.g. if `self` is a simple intersection `T1 & T2`
+                // and we add `T3 | T4` to the intersection, we don't get `T1 & T2 & (T3 | T4)` (that's
+                // not in DNF), we distribute the union and get `(T1 & T3) | (T2 & T3) | (T1 & T4) |
+                // (T2 & T4)`. If `self` is already a union-of-intersections `(T1 & T2) | (T3 & T4)`
+                // and we add `T5 | T6` to it, that flattens all the way out to `(T1 & T2 & T5) | (T1 &
+                // T2 & T6) | (T3 & T4 & T5) ...` -- you get the idea.
+                union
+                    .elements(self.db)
+                    .iter()
+                    .map(|elem| self.clone().add_positive(*elem))
+                    .fold(IntersectionBuilder::empty(self.db), |mut builder, sub| {
+                        builder.intersections.extend(sub.intersections);
+                        builder
+                    })
+            }
+            // `(A & B & ~C) & (D & E & ~F)` -> `A & B & D & E & ~C & ~F`
+            Type::Intersection(other) => {
+                let db = self.db;
+                for pos in other.positive(db) {
+                    self = self.add_positive(*pos);
+                }
+                for neg in other.negative(db) {
+                    self = self.add_negative(*neg);
+                }
+                self
+            }
+            Type::NominalInstance(instance)
+                if enum_metadata(self.db, instance.class.class_literal(self.db).0).is_some() =>
+            {
+                let mut contains_enum_literal_as_negative_element = false;
+                for intersection in &self.intersections {
+                    if intersection.negative.iter().any(|negative| {
+                        negative
+                            .into_enum_literal()
+                            .is_some_and(|lit| lit.enum_class_instance(self.db) == ty)
+                    }) {
+                        contains_enum_literal_as_negative_element = true;
+                        break;
+                    }
+                }
+
+                if contains_enum_literal_as_negative_element {
+                    // If we have an enum literal of this enum already in the negative side of
+                    // the intersection, expand the instance into the union of enum members, and
+                    // add that union to the intersection.
+                    // Note: we manually construct a `UnionType` here instead of going through
+                    // `UnionBuilder` because we would simplify the union to just the enum instance
+                    // and end up in this branch again.
+                    let db = self.db;
+                    self.add_positive(Type::Union(UnionType::new(
+                        db,
+                        enum_member_literals(db, instance.class.class_literal(db).0, None)
+                            .expect("Calling `enum_member_literals` on an enum class")
+                            .collect::<Box<[_]>>(),
+                    )))
+                } else {
+                    for inner in &mut self.intersections {
+                        inner.add_positive(self.db, ty);
+                    }
+                    self
+                }
+            }
+            _ => {
+                // If we are already a union-of-intersections, distribute the new intersected element
+                // across all of those intersections.
+                for inner in &mut self.intersections {
+                    inner.add_positive(self.db, ty);
+                }
+                self
             }
-            self
         }
     }
 
     pub(crate) fn add_negative(mut self, ty: Type<'db>) -> Self {
+        let contains_enum = |enum_instance| {
+            self.intersections
+                .iter()
+                .flat_map(|intersection| &intersection.positive)
+                .any(|ty| *ty == enum_instance)
+        };
+
         // See comments above in `add_positive`; this is just the negated version.
-        if let Type::Union(union) = ty {
-            for elem in union.elements(self.db) {
-                self = self.add_negative(*elem);
+        match ty {
+            Type::Union(union) => {
+                for elem in union.elements(self.db) {
+                    self = self.add_negative(*elem);
+                }
+                self
             }
-            self
-        } else if let Type::Intersection(intersection) = ty {
-            // (A | B) & ~(C & ~D)
-            // -> (A | B) & (~C | D)
-            // -> ((A | B) & ~C) | ((A | B) & D)
-            // i.e. if we have an intersection of positive constraints C
-            // and negative constraints D, then our new intersection
-            // is (existing & ~C) | (existing & D)
+            Type::Intersection(intersection) => {
+                // (A | B) & ~(C & ~D)
+                // -> (A | B) & (~C | D)
+                // -> ((A | B) & ~C) | ((A | B) & D)
+                // i.e. if we have an intersection of positive constraints C
+                // and negative constraints D, then our new intersection
+                // is (existing & ~C) | (existing & D)
 
-            let positive_side = intersection
-                .positive(self.db)
-                .iter()
-                // we negate all the positive constraints while distributing
-                .map(|elem| self.clone().add_negative(*elem));
+                let positive_side = intersection
+                    .positive(self.db)
+                    .iter()
+                    // we negate all the positive constraints while distributing
+                    .map(|elem| self.clone().add_negative(*elem));
 
-            let negative_side = intersection
-                .negative(self.db)
-                .iter()
-                // all negative constraints end up becoming positive constraints
-                .map(|elem| self.clone().add_positive(*elem));
+                let negative_side = intersection
+                    .negative(self.db)
+                    .iter()
+                    // all negative constraints end up becoming positive constraints
+                    .map(|elem| self.clone().add_positive(*elem));
 
-            positive_side.chain(negative_side).fold(
-                IntersectionBuilder::empty(self.db),
-                |mut builder, sub| {
-                    builder.intersections.extend(sub.intersections);
-                    builder
-                },
-            )
-        } else {
-            for inner in &mut self.intersections {
-                inner.add_negative(self.db, ty);
+                positive_side.chain(negative_side).fold(
+                    IntersectionBuilder::empty(self.db),
+                    |mut builder, sub| {
+                        builder.intersections.extend(sub.intersections);
+                        builder
+                    },
+                )
+            }
+            Type::EnumLiteral(enum_literal)
+                if contains_enum(enum_literal.enum_class_instance(self.db)) =>
+            {
+                let db = self.db;
+                self.add_positive(UnionType::from_elements(
+                    db,
+                    enum_member_literals(
+                        db,
+                        enum_literal.enum_class(db),
+                        Some(enum_literal.name(db)),
+                    )
+                    .expect("Calling `enum_member_literals` on an enum class"),
+                ))
+            }
+            _ => {
+                for inner in &mut self.intersections {
+                    inner.add_negative(self.db, ty);
+                }
+                self
             }
-            self
         }
     }
 
@@ -643,15 +758,7 @@ impl<'db> InnerIntersectionBuilder<'db> {
                 self.add_positive(db, Type::LiteralString);
                 self.add_negative(db, Type::string_literal(db, ""));
             }
-            // `(A & B & ~C) & (D & E & ~F)` -> `A & B & D & E & ~C & ~F`
-            Type::Intersection(other) => {
-                for pos in other.positive(db) {
-                    self.add_positive(db, *pos);
-                }
-                for neg in other.negative(db) {
-                    self.add_negative(db, *neg);
-                }
-            }
+
             _ => {
                 let known_instance = new_positive
                     .into_nominal_instance()
@@ -961,7 +1068,10 @@ impl<'db> InnerIntersectionBuilder<'db> {
 mod tests {
     use super::{IntersectionBuilder, Type, UnionBuilder, UnionType};
 
+    use crate::KnownModule;
     use crate::db::tests::setup_db;
+    use crate::place::known_module_symbol;
+    use crate::types::enums::enum_member_literals;
     use crate::types::{KnownClass, Truthiness};
 
     use test_case::test_case;
@@ -1044,4 +1154,77 @@ mod tests {
             .build();
         assert_eq!(ty, Type::BooleanLiteral(!bool_value));
     }
+
+    #[test]
+    fn build_intersection_enums() {
+        let db = setup_db();
+
+        let safe_uuid_class = known_module_symbol(&db, KnownModule::Uuid, "SafeUUID")
+            .place
+            .ignore_possibly_unbound()
+            .unwrap();
+
+        let literals = enum_member_literals(&db, safe_uuid_class.expect_class_literal(), None)
+            .unwrap()
+            .collect::<Vec<_>>();
+        assert_eq!(literals.len(), 3);
+
+        // SafeUUID.safe
+        let l_safe = literals[0];
+        assert_eq!(l_safe.expect_enum_literal().name(&db), "safe");
+        // SafeUUID.unsafe
+        let l_unsafe = literals[1];
+        assert_eq!(l_unsafe.expect_enum_literal().name(&db), "unsafe");
+        // SafeUUID.unknown
+        let l_unknown = literals[2];
+        assert_eq!(l_unknown.expect_enum_literal().name(&db), "unknown");
+
+        // The enum itself: SafeUUID
+        let safe_uuid = l_safe.expect_enum_literal().enum_class_instance(&db);
+
+        {
+            let actual = IntersectionBuilder::new(&db)
+                .add_positive(safe_uuid)
+                .add_negative(l_safe)
+                .build();
+
+            assert_eq!(
+                actual.display(&db).to_string(),
+                "Literal[SafeUUID.unsafe, SafeUUID.unknown]"
+            );
+        }
+        {
+            // Same as above, but with the order reversed
+            let actual = IntersectionBuilder::new(&db)
+                .add_negative(l_safe)
+                .add_positive(safe_uuid)
+                .build();
+
+            assert_eq!(
+                actual.display(&db).to_string(),
+                "Literal[SafeUUID.unsafe, SafeUUID.unknown]"
+            );
+        }
+        {
+            // Also the same, but now with a nested intersection
+            let actual = IntersectionBuilder::new(&db)
+                .add_positive(safe_uuid)
+                .add_positive(IntersectionBuilder::new(&db).add_negative(l_safe).build())
+                .build();
+
+            assert_eq!(
+                actual.display(&db).to_string(),
+                "Literal[SafeUUID.unsafe, SafeUUID.unknown]"
+            );
+        }
+        {
+            let actual = IntersectionBuilder::new(&db)
+                .add_negative(l_safe)
+                .add_positive(safe_uuid)
+                .add_negative(l_unsafe)
+                .build();
+
+            assert_eq!(actual.display(&db).to_string(), "Literal[SafeUUID.unknown]");
+        }
+    }
 }
diff --git a/crates/ty_python_semantic/src/types/call/arguments.rs b/crates/ty_python_semantic/src/types/call/arguments.rs
index 89c3cf0112..c463d0a982 100644
--- a/crates/ty_python_semantic/src/types/call/arguments.rs
+++ b/crates/ty_python_semantic/src/types/call/arguments.rs
@@ -5,6 +5,7 @@ use ruff_python_ast as ast;
 
 use crate::Db;
 use crate::types::KnownClass;
+use crate::types::enums::enum_member_literals;
 use crate::types::tuple::{TupleSpec, TupleType};
 
 use super::Type;
@@ -199,13 +200,22 @@ impl<'a, 'db> FromIterator<(Argument<'a>, Option<Type<'db>>)> for CallArguments<
 ///
 /// Returns [`None`] if the type cannot be expanded.
 fn expand_type<'db>(db: &'db dyn Db, ty: Type<'db>) -> Option<Vec<Type<'db>>> {
-    // TODO: Expand enums to their variants
     match ty {
-        Type::NominalInstance(instance) if instance.class.is_known(db, KnownClass::Bool) => {
-            Some(vec![
-                Type::BooleanLiteral(true),
-                Type::BooleanLiteral(false),
-            ])
+        Type::NominalInstance(instance) => {
+            if instance.class.is_known(db, KnownClass::Bool) {
+                return Some(vec![
+                    Type::BooleanLiteral(true),
+                    Type::BooleanLiteral(false),
+                ]);
+            }
+
+            let class_literal = instance.class.class_literal(db).0;
+
+            if let Some(enum_members) = enum_member_literals(db, class_literal, None) {
+                return Some(enum_members.collect());
+            }
+
+            None
         }
         Type::Tuple(tuple_type) => {
             // Note: This should only account for tuples of known length, i.e., `tuple[bool, ...]`
diff --git a/crates/ty_python_semantic/src/types/enums.rs b/crates/ty_python_semantic/src/types/enums.rs
index 85b3c56094..59c814c147 100644
--- a/crates/ty_python_semantic/src/types/enums.rs
+++ b/crates/ty_python_semantic/src/types/enums.rs
@@ -2,22 +2,27 @@ use ruff_python_ast::name::Name;
 use rustc_hash::FxHashMap;
 
 use crate::{
-    Db,
+    Db, FxOrderSet,
     place::{Place, PlaceAndQualifiers, place_from_bindings, place_from_declarations},
     semantic_index::{place_table, use_def_map},
-    types::{ClassLiteral, DynamicType, KnownClass, MemberLookupPolicy, Type, TypeQualifiers},
+    types::{
+        ClassLiteral, DynamicType, EnumLiteralType, KnownClass, MemberLookupPolicy, Type,
+        TypeQualifiers,
+    },
 };
 
-#[derive(Debug, PartialEq, Eq, get_size2::GetSize)]
+#[derive(Debug, PartialEq, Eq)]
 pub(crate) struct EnumMetadata {
-    pub(crate) members: Box<[Name]>,
+    pub(crate) members: FxOrderSet<Name>,
     pub(crate) aliases: FxHashMap<Name, Name>,
 }
 
+impl get_size2::GetSize for EnumMetadata {}
+
 impl EnumMetadata {
     fn empty() -> Self {
         EnumMetadata {
-            members: Box::new([]),
+            members: FxOrderSet::default(),
             aliases: FxHashMap::default(),
         }
     }
@@ -48,7 +53,7 @@ fn enum_metadata_cycle_initial(_db: &dyn Db, _class: ClassLiteral<'_>) -> Option
 
 /// List all members of an enum.
 #[allow(clippy::ref_option, clippy::unnecessary_wraps)]
-#[salsa::tracked(returns(ref), cycle_fn=enum_metadata_cycle_recover, cycle_initial=enum_metadata_cycle_initial, heap_size=get_size2::GetSize::get_heap_size)]
+#[salsa::tracked(returns(as_ref), cycle_fn=enum_metadata_cycle_recover, cycle_initial=enum_metadata_cycle_initial, heap_size=get_size2::GetSize::get_heap_size)]
 pub(crate) fn enum_metadata<'db>(
     db: &'db dyn Db,
     class: ClassLiteral<'db>,
@@ -208,7 +213,7 @@ pub(crate) fn enum_metadata<'db>(
             Some(name)
         })
         .cloned()
-        .collect::<Box<_>>();
+        .collect::<FxOrderSet<_>>();
 
     if members.is_empty() {
         // Enum subclasses without members are not considered enums.
@@ -217,3 +222,21 @@ pub(crate) fn enum_metadata<'db>(
 
     Some(EnumMetadata { members, aliases })
 }
+
+pub(crate) fn enum_member_literals<'a, 'db: 'a>(
+    db: &'db dyn Db,
+    class: ClassLiteral<'db>,
+    exclude_member: Option<&'a Name>,
+) -> Option<impl Iterator<Item = Type<'a>> + 'a> {
+    enum_metadata(db, class).map(|metadata| {
+        metadata
+            .members
+            .iter()
+            .filter(move |name| Some(*name) != exclude_member)
+            .map(move |name| Type::EnumLiteral(EnumLiteralType::new(db, class, name.clone())))
+    })
+}
+
+pub(crate) fn is_single_member_enum<'db>(db: &'db dyn Db, class: ClassLiteral<'db>) -> bool {
+    enum_metadata(db, class).is_some_and(|metadata| metadata.members.len() == 1)
+}
diff --git a/crates/ty_python_semantic/src/types/instance.rs b/crates/ty_python_semantic/src/types/instance.rs
index c92885adeb..3959b041e1 100644
--- a/crates/ty_python_semantic/src/types/instance.rs
+++ b/crates/ty_python_semantic/src/types/instance.rs
@@ -6,6 +6,7 @@ use super::protocol_class::ProtocolInterface;
 use super::{ClassType, KnownClass, SubclassOfType, Type, TypeVarVariance};
 use crate::place::PlaceAndQualifiers;
 use crate::types::cyclic::PairVisitor;
+use crate::types::enums::is_single_member_enum;
 use crate::types::protocol_class::walk_protocol_interface;
 use crate::types::tuple::TupleType;
 use crate::types::{DynamicType, TypeMapping, TypeRelation, TypeTransformer, TypeVarInstance};
@@ -125,12 +126,14 @@ impl<'db> NominalInstanceType<'db> {
 
     pub(super) fn is_singleton(self, db: &'db dyn Db) -> bool {
         self.class.known(db).is_some_and(KnownClass::is_singleton)
+            || is_single_member_enum(db, self.class.class_literal(db).0)
     }
 
     pub(super) fn is_single_valued(self, db: &'db dyn Db) -> bool {
         self.class
             .known(db)
             .is_some_and(KnownClass::is_single_valued)
+            || is_single_member_enum(db, self.class.class_literal(db).0)
     }
 
     pub(super) fn to_meta_type(self, db: &'db dyn Db) -> Type<'db> {
diff --git a/crates/ty_python_semantic/src/types/narrow.rs b/crates/ty_python_semantic/src/types/narrow.rs
index 1838255223..d1c0f9cef7 100644
--- a/crates/ty_python_semantic/src/types/narrow.rs
+++ b/crates/ty_python_semantic/src/types/narrow.rs
@@ -5,6 +5,7 @@ use crate::semantic_index::place_table;
 use crate::semantic_index::predicate::{
     CallableAndCallExpr, PatternPredicate, PatternPredicateKind, Predicate, PredicateNode,
 };
+use crate::types::enums::{enum_member_literals, enum_metadata};
 use crate::types::function::KnownFunction;
 use crate::types::infer::infer_same_file_expression_type;
 use crate::types::{
@@ -559,6 +560,17 @@ impl<'db, 'ast> NarrowingConstraintsBuilder<'db, 'ast> {
                                 .map(|ty| filter_to_cannot_be_equal(db, ty, rhs_ty)),
                         )
                     }
+                    // Treat enums as a union of their members.
+                    Type::NominalInstance(instance)
+                        if enum_metadata(db, instance.class.class_literal(db).0).is_some() =>
+                    {
+                        UnionType::from_elements(
+                            db,
+                            enum_member_literals(db, instance.class.class_literal(db).0, None)
+                                .expect("Calling `enum_member_literals` on an enum class")
+                                .map(|ty| filter_to_cannot_be_equal(db, ty, rhs_ty)),
+                        )
+                    }
                     _ => {
                         if ty.is_single_valued(db) && !could_compare_equal(db, ty, rhs_ty) {
                             ty