diff --git a/crates/red_knot_python_semantic/resources/mdtest/exception/control_flow.md b/crates/red_knot_python_semantic/resources/mdtest/exception/control_flow.md
index 284b0f24d5620..a6e703dff5b6e 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/exception/control_flow.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/exception/control_flow.md
@@ -455,9 +455,9 @@ else:
     reveal_type(x)  # revealed: slice
 finally:
     # TODO: should be `Literal[1] | str | bytes | bool | memoryview | float | range | slice`
-    reveal_type(x)  # revealed: bool | float | slice
+    reveal_type(x)  # revealed: bool | slice | float
 
-reveal_type(x)  # revealed: bool | float | slice
+reveal_type(x)  # revealed: bool | slice | float
 ```
 
 ## Nested `try`/`except` blocks
@@ -534,7 +534,7 @@ try:
         reveal_type(x)  # revealed: slice
     finally:
         # TODO: should be `Literal[1] | str | bytes | bool | memoryview | float | range | slice`
-        reveal_type(x)  # revealed: bool | float | slice
+        reveal_type(x)  # revealed: bool | slice | float
         x = 2
         reveal_type(x)  # revealed: Literal[2]
     reveal_type(x)  # revealed: Literal[2]
diff --git a/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md b/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md
index b3975c1a813b7..203ffe9827aa4 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md
@@ -11,37 +11,37 @@ x = foo()
 if x:
     reveal_type(x)  # revealed: Literal[-1, True, "foo", b"bar"]
 else:
-    reveal_type(x)  # revealed: Literal[0, False, "", b""] | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, False, "", b""] | tuple[()] | None
 
 if not x:
-    reveal_type(x)  # revealed: Literal[0, False, "", b""] | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, False, "", b""] | tuple[()] | None
 else:
     reveal_type(x)  # revealed: Literal[-1, True, "foo", b"bar"]
 
 if x and not x:
     reveal_type(x)  # revealed: Never
 else:
-    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, b"bar", "", "foo", b""] | bool | tuple[()] | None
 
 if not (x and not x):
-    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, b"bar", "", "foo", b""] | bool | tuple[()] | None
 else:
     reveal_type(x)  # revealed: Never
 
 if x or not x:
-    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, b"bar", "", "foo", b""] | bool | tuple[()] | None
 else:
     reveal_type(x)  # revealed: Never
 
 if not (x or not x):
     reveal_type(x)  # revealed: Never
 else:
-    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, b"bar", "", "foo", b""] | bool | tuple[()] | None
 
 if (isinstance(x, int) or isinstance(x, str)) and x:
     reveal_type(x)  # revealed: Literal[-1, True, "foo"]
 else:
-    reveal_type(x)  # revealed: Literal[b"", b"bar", 0, False, ""] | None | tuple[()]
+    reveal_type(x)  # revealed: tuple[()] | None | Literal[b"", b"bar", 0, False, ""]
 ```
 
 ## Function Literals
diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_assignable_to.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
index 06ee56aaf0d5f..318af242476d4 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_assignable_to.md
@@ -346,4 +346,24 @@ static_assert(is_assignable_to(Never, type[str]))
 static_assert(is_assignable_to(Never, type[Any]))
 ```
 
+### `bool` is assignable to unions that include `bool`
+
+Since we decompose `bool` to `Literal[True, False]` in unions, it would be surprisingly easy to get
+this wrong if we forgot to normalize `bool` to `Literal[True, False]` when it appeared on the
+left-hand side in `Type::is_assignable_to()`.
+
+```py
+from knot_extensions import is_assignable_to, static_assert
+
+static_assert(is_assignable_to(bool, str | bool))
+```
+
+### `bool` is assignable to `AlwaysTruthy | AlwaysFalsy`
+
+```py
+from knot_extensions import static_assert, is_assignable_to, AlwaysTruthy, AlwaysFalsy
+
+static_assert(is_assignable_to(bool, AlwaysTruthy | AlwaysFalsy))
+```
+
 [typing documentation]: https://typing.readthedocs.io/en/latest/spec/concepts.html#the-assignable-to-or-consistent-subtyping-relation
diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
index 047a45fc2fd0b..b607b05f1b663 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_equivalent_to.md
@@ -118,4 +118,48 @@ class R: ...
 static_assert(is_equivalent_to(Intersection[tuple[P | Q], R], Intersection[tuple[Q | P], R]))
 ```
 
+## Unions containing tuples containing `bool`
+
+```py
+from knot_extensions import is_equivalent_to, static_assert
+from typing_extensions import Literal
+
+class P: ...
+
+static_assert(is_equivalent_to(tuple[Literal[True, False]] | P, tuple[bool] | P))
+static_assert(is_equivalent_to(P | tuple[bool], P | tuple[Literal[True, False]]))
+```
+
+## Unions and intersections involving `AlwaysTruthy`, `bool` and `AlwaysFalsy`
+
+```py
+from knot_extensions import AlwaysTruthy, AlwaysFalsy, static_assert, is_equivalent_to, Not
+from typing_extensions import Literal
+
+static_assert(is_equivalent_to(AlwaysTruthy | bool, Literal[False] | AlwaysTruthy))
+static_assert(is_equivalent_to(AlwaysFalsy | bool, Literal[True] | AlwaysFalsy))
+static_assert(is_equivalent_to(Not[AlwaysTruthy] | bool, Not[AlwaysTruthy] | Literal[True]))
+static_assert(is_equivalent_to(Not[AlwaysFalsy] | bool, Literal[False] | Not[AlwaysFalsy]))
+```
+
+## Unions and intersections involving `AlwaysTruthy`, `LiteralString` and `AlwaysFalsy`
+
+```py
+from knot_extensions import AlwaysTruthy, AlwaysFalsy, static_assert, is_equivalent_to, Not, Intersection
+from typing_extensions import Literal, LiteralString
+
+# TODO: these should all pass!
+
+# error: [static-assert-error]
+static_assert(is_equivalent_to(AlwaysTruthy | LiteralString, Literal[""] | AlwaysTruthy))
+# error: [static-assert-error]
+static_assert(is_equivalent_to(AlwaysFalsy | LiteralString, Intersection[LiteralString, Not[Literal[""]]] | AlwaysFalsy))
+# error: [static-assert-error]
+static_assert(is_equivalent_to(Not[AlwaysFalsy] | LiteralString, Literal[""] | Not[AlwaysFalsy]))
+# error: [static-assert-error]
+static_assert(
+    is_equivalent_to(Not[AlwaysTruthy] | LiteralString, Not[AlwaysTruthy] | Intersection[LiteralString, Not[Literal[""]]])
+)
+```
+
 [the equivalence relation]: https://typing.readthedocs.io/en/latest/spec/glossary.html#term-equivalent
diff --git a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
index 4e081338d38bc..c120023f819a3 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/type_properties/is_subtype_of.md
@@ -449,5 +449,31 @@ static_assert(not is_subtype_of(Intersection[Unknown, int], int))
 static_assert(not is_subtype_of(tuple[int, int], tuple[int, Unknown]))
 ```
 
+## `bool` is a subtype of `AlwaysTruthy | AlwaysFalsy`
+
+`bool` is equivalent to `Literal[True] | Literal[False]`. `Literal[True]` is a subtype of
+`AlwaysTruthy` and `Literal[False]` is a subtype of `AlwaysFalsy`; it therefore stands to reason
+that `bool` is a subtype of `AlwaysTruthy | AlwaysFalsy`.
+
+```py
+from knot_extensions import AlwaysTruthy, AlwaysFalsy, is_subtype_of, static_assert, Not, is_disjoint_from
+from typing_extensions import Literal
+
+static_assert(is_subtype_of(bool, AlwaysTruthy | AlwaysFalsy))
+
+# the inverse also applies -- TODO: this should pass!
+# See the TODO comments in the `Type::Intersection` branch of `Type::is_disjoint_from()`.
+static_assert(is_disjoint_from(bool, Not[AlwaysTruthy | AlwaysFalsy]))  # error: [static-assert-error]
+
+# `Type::is_subtype_of` delegates many questions of `bool` subtyping to `int`,
+# but set-theoretic types like intersections and unions are still handled differently to `int`
+static_assert(is_subtype_of(Literal[True], Not[Literal[2]]))
+static_assert(is_subtype_of(bool, Not[Literal[2]]))
+static_assert(is_subtype_of(Literal[True], bool | None))
+static_assert(is_subtype_of(bool, bool | None))
+
+static_assert(not is_subtype_of(int, Not[Literal[2]]))
+```
+
 [special case for float and complex]: https://typing.readthedocs.io/en/latest/spec/special-types.html#special-cases-for-float-and-complex
 [typing documentation]: https://typing.readthedocs.io/en/latest/spec/concepts.html#subtype-supertype-and-type-equivalence
diff --git a/crates/red_knot_python_semantic/src/types.rs b/crates/red_knot_python_semantic/src/types.rs
index a056c176c7cd0..e6e2f9eea7699 100644
--- a/crates/red_knot_python_semantic/src/types.rs
+++ b/crates/red_knot_python_semantic/src/types.rs
@@ -881,6 +881,15 @@ impl<'db> Type<'db> {
             (Type::Never, _) => true,
             (_, Type::Never) => false,
 
+            (Type::Instance(InstanceType { class }), _) if class.is_known(db, KnownClass::Bool) => {
+                Type::BooleanLiteral(true).is_subtype_of(db, target)
+                    && Type::BooleanLiteral(false).is_subtype_of(db, target)
+            }
+            (_, Type::Instance(InstanceType { class })) if class.is_known(db, KnownClass::Bool) => {
+                self.is_subtype_of(db, Type::BooleanLiteral(true))
+                    || self.is_subtype_of(db, Type::BooleanLiteral(false))
+            }
+
             (Type::Union(union), _) => union
                 .elements(db)
                 .iter()
@@ -961,7 +970,7 @@ impl<'db> Type<'db> {
                 KnownClass::Str.to_instance(db).is_subtype_of(db, target)
             }
             (Type::BooleanLiteral(_), _) => {
-                KnownClass::Bool.to_instance(db).is_subtype_of(db, target)
+                KnownClass::Int.to_instance(db).is_subtype_of(db, target)
             }
             (Type::IntLiteral(_), _) => KnownClass::Int.to_instance(db).is_subtype_of(db, target),
             (Type::BytesLiteral(_), _) => {
@@ -1077,6 +1086,7 @@ impl<'db> Type<'db> {
         if self.is_gradual_equivalent_to(db, target) {
             return true;
         }
+
         match (self, target) {
             // Never can be assigned to any type.
             (Type::Never, _) => true,
@@ -1093,6 +1103,15 @@ impl<'db> Type<'db> {
                 true
             }
 
+            (Type::Instance(InstanceType { class }), _) if class.is_known(db, KnownClass::Bool) => {
+                Type::BooleanLiteral(true).is_assignable_to(db, target)
+                    && Type::BooleanLiteral(false).is_assignable_to(db, target)
+            }
+            (_, Type::Instance(InstanceType { class })) if class.is_known(db, KnownClass::Bool) => {
+                self.is_assignable_to(db, Type::BooleanLiteral(false))
+                    || self.is_assignable_to(db, Type::BooleanLiteral(true))
+            }
+
             // A union is assignable to a type T iff every element of the union is assignable to T.
             (Type::Union(union), ty) => union
                 .elements(db)
diff --git a/crates/red_knot_python_semantic/src/types/builder.rs b/crates/red_knot_python_semantic/src/types/builder.rs
index c19a4f06cefa4..a9430f37a1fa7 100644
--- a/crates/red_knot_python_semantic/src/types/builder.rs
+++ b/crates/red_knot_python_semantic/src/types/builder.rs
@@ -33,6 +33,7 @@ use smallvec::SmallVec;
 pub(crate) struct UnionBuilder<'db> {
     elements: Vec<Type<'db>>,
     db: &'db dyn Db,
+    bool_literals_present: BoolLiteralsPresent,
 }
 
 impl<'db> UnionBuilder<'db> {
@@ -40,6 +41,7 @@ impl<'db> UnionBuilder<'db> {
         Self {
             db,
             elements: vec![],
+            bool_literals_present: BoolLiteralsPresent::Zero,
         }
     }
 
@@ -54,28 +56,16 @@ impl<'db> UnionBuilder<'db> {
                 }
             }
             Type::Never => {}
+            Type::Instance(InstanceType { class }) if class.is_known(self.db, KnownClass::Bool) => {
+                self = self
+                    .add(Type::BooleanLiteral(false))
+                    .add(Type::BooleanLiteral(true));
+            }
             _ => {
-                let bool_pair = if let Type::BooleanLiteral(b) = ty {
-                    Some(Type::BooleanLiteral(!b))
-                } else {
-                    None
-                };
-
-                let mut to_add = ty;
                 let mut to_remove = SmallVec::<[usize; 2]>::new();
                 let ty_negated = ty.negate(self.db);
 
                 for (index, element) in self.elements.iter().enumerate() {
-                    if Some(*element) == bool_pair {
-                        to_add = KnownClass::Bool.to_instance(self.db);
-                        to_remove.push(index);
-                        // The type we are adding is a BooleanLiteral, which doesn't have any
-                        // subtypes. And we just found that the union already contained our
-                        // mirror-image BooleanLiteral, so it can't also contain bool or any
-                        // supertype of bool. Therefore, we are done.
-                        break;
-                    }
-
                     if ty.is_same_gradual_form(*element) || ty.is_subtype_of(self.db, *element) {
                         return self;
                     } else if element.is_subtype_of(self.db, ty) {
@@ -93,9 +83,14 @@ impl<'db> UnionBuilder<'db> {
                         return self;
                     }
                 }
+
+                if ty.is_boolean_literal() {
+                    self.bool_literals_present.increment();
+                }
+
                 match to_remove[..] {
-                    [] => self.elements.push(to_add),
-                    [index] => self.elements[index] = to_add,
+                    [] => self.elements.push(ty),
+                    [index] => self.elements[index] = ty,
                     _ => {
                         let mut current_index = 0;
                         let mut to_remove = to_remove.into_iter();
@@ -110,7 +105,7 @@ impl<'db> UnionBuilder<'db> {
                             current_index += 1;
                             retain
                         });
-                        self.elements.push(to_add);
+                        self.elements.push(ty);
                     }
                 }
             }
@@ -119,14 +114,56 @@ impl<'db> UnionBuilder<'db> {
     }
 
     pub(crate) fn build(self) -> Type<'db> {
-        match self.elements.len() {
+        let UnionBuilder {
+            mut elements,
+            db,
+            bool_literals_present,
+        } = self;
+
+        match elements.len() {
             0 => Type::Never,
-            1 => self.elements[0],
-            _ => Type::Union(UnionType::new(self.db, self.elements.into_boxed_slice())),
+            1 => elements[0],
+            _ => {
+                if bool_literals_present.is_two() {
+                    let mut element_iter = elements.iter();
+                    if let Some(first_pos) = element_iter.position(Type::is_boolean_literal) {
+                        if let Some(second_pos) = element_iter.position(Type::is_boolean_literal) {
+                            let bool_instance = KnownClass::Bool.to_instance(db);
+                            if elements.len() == 2 {
+                                return bool_instance;
+                            }
+                            elements.swap_remove(first_pos + second_pos + 1);
+                            elements[first_pos] = bool_instance;
+                        }
+                    }
+                }
+                Type::Union(UnionType::new(db, elements.into_boxed_slice()))
+            }
         }
     }
 }
 
+#[derive(Debug, Copy, Clone, PartialEq, Eq)]
+enum BoolLiteralsPresent {
+    Zero,
+    One,
+    Two,
+}
+
+impl BoolLiteralsPresent {
+    fn increment(&mut self) {
+        *self = match self {
+            BoolLiteralsPresent::Zero => BoolLiteralsPresent::One,
+            BoolLiteralsPresent::One => BoolLiteralsPresent::Two,
+            BoolLiteralsPresent::Two => BoolLiteralsPresent::Two,
+        };
+    }
+
+    const fn is_two(self) -> bool {
+        matches!(self, BoolLiteralsPresent::Two)
+    }
+}
+
 #[derive(Clone)]
 pub(crate) struct IntersectionBuilder<'db> {
     // Really this builds a union-of-intersections, because we always keep our set-theoretic types
@@ -154,7 +191,18 @@ impl<'db> IntersectionBuilder<'db> {
     }
 
     pub(crate) fn add_positive(mut self, ty: Type<'db>) -> Self {
-        if let Type::Union(union) = ty {
+        const BOOL_LITERALS: &[Type] = &[Type::BooleanLiteral(false), Type::BooleanLiteral(true)];
+
+        // Treat `bool` as `Literal[True] | Literal[False]`
+        let union_elements = match ty {
+            Type::Union(union) => Some(union.elements(self.db)),
+            Type::Instance(InstanceType { class }) if class.is_known(self.db, KnownClass::Bool) => {
+                Some(BOOL_LITERALS)
+            }
+            _ => None,
+        };
+
+        if let Some(elements) = union_elements {
             // 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`
@@ -163,8 +211,7 @@ impl<'db> IntersectionBuilder<'db> {
             // (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)
+            elements
                 .iter()
                 .map(|elem| self.clone().add_positive(*elem))
                 .fold(IntersectionBuilder::empty(self.db), |mut builder, sub| {
@@ -183,43 +230,52 @@ impl<'db> IntersectionBuilder<'db> {
 
     pub(crate) fn add_negative(mut self, ty: Type<'db>) -> Self {
         // 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);
-            }
-            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)
-
-            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));
-
-            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);
+        match ty {
+            Type::Union(union) => {
+                for elem in union.elements(self.db) {
+                    self = self.add_negative(*elem);
+                }
+                self
+            }
+            Type::Instance(InstanceType { class }) if class.is_known(self.db, KnownClass::Bool) => {
+                self.add_negative(Type::BooleanLiteral(false))
+                    .add_negative(Type::BooleanLiteral(true))
+            }
+            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 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
+                    },
+                )
+            }
+            _ => {
+                for inner in &mut self.intersections {
+                    inner.add_negative(self.db, ty);
+                }
+                self
             }
-            self
         }
     }
 
@@ -246,7 +302,7 @@ struct InnerIntersectionBuilder<'db> {
 
 impl<'db> InnerIntersectionBuilder<'db> {
     /// Adds a positive type to this intersection.
-    fn add_positive(&mut self, db: &'db dyn Db, mut new_positive: Type<'db>) {
+    fn add_positive(&mut self, db: &'db dyn Db, new_positive: Type<'db>) {
         match new_positive {
             // `LiteralString & AlwaysTruthy` -> `LiteralString & ~Literal[""]`
             Type::AlwaysTruthy if self.positive.contains(&Type::LiteralString) => {
@@ -293,62 +349,6 @@ impl<'db> InnerIntersectionBuilder<'db> {
                     return;
                 }
 
-                let addition_is_bool_instance = known_instance == Some(KnownClass::Bool);
-
-                for (index, existing_positive) in self.positive.iter().enumerate() {
-                    match existing_positive {
-                        // `AlwaysTruthy & bool` -> `Literal[True]`
-                        Type::AlwaysTruthy if addition_is_bool_instance => {
-                            new_positive = Type::BooleanLiteral(true);
-                        }
-                        // `AlwaysFalsy & bool` -> `Literal[False]`
-                        Type::AlwaysFalsy if addition_is_bool_instance => {
-                            new_positive = Type::BooleanLiteral(false);
-                        }
-                        Type::Instance(InstanceType { class })
-                            if class.is_known(db, KnownClass::Bool) =>
-                        {
-                            match new_positive {
-                                // `bool & AlwaysTruthy` -> `Literal[True]`
-                                Type::AlwaysTruthy => {
-                                    new_positive = Type::BooleanLiteral(true);
-                                }
-                                // `bool & AlwaysFalsy` -> `Literal[False]`
-                                Type::AlwaysFalsy => {
-                                    new_positive = Type::BooleanLiteral(false);
-                                }
-                                _ => continue,
-                            }
-                        }
-                        _ => continue,
-                    }
-                    self.positive.swap_remove_index(index);
-                    break;
-                }
-
-                if addition_is_bool_instance {
-                    for (index, existing_negative) in self.negative.iter().enumerate() {
-                        match existing_negative {
-                            // `bool & ~Literal[False]` -> `Literal[True]`
-                            // `bool & ~Literal[True]` -> `Literal[False]`
-                            Type::BooleanLiteral(bool_value) => {
-                                new_positive = Type::BooleanLiteral(!bool_value);
-                            }
-                            // `bool & ~AlwaysTruthy` -> `Literal[False]`
-                            Type::AlwaysTruthy => {
-                                new_positive = Type::BooleanLiteral(false);
-                            }
-                            // `bool & ~AlwaysFalsy` -> `Literal[True]`
-                            Type::AlwaysFalsy => {
-                                new_positive = Type::BooleanLiteral(true);
-                            }
-                            _ => continue,
-                        }
-                        self.negative.swap_remove_index(index);
-                        break;
-                    }
-                }
-
                 let mut to_remove = SmallVec::<[usize; 1]>::new();
                 for (index, existing_positive) in self.positive.iter().enumerate() {
                     // S & T = S    if S <: T
@@ -396,14 +396,6 @@ impl<'db> InnerIntersectionBuilder<'db> {
 
     /// Adds a negative type to this intersection.
     fn add_negative(&mut self, db: &'db dyn Db, new_negative: Type<'db>) {
-        let contains_bool = || {
-            self.positive
-                .iter()
-                .filter_map(|ty| ty.into_instance())
-                .filter_map(|instance| instance.class.known(db))
-                .any(KnownClass::is_bool)
-        };
-
         match new_negative {
             Type::Intersection(inter) => {
                 for pos in inter.positive(db) {
@@ -427,20 +419,10 @@ impl<'db> InnerIntersectionBuilder<'db> {
                 // simplify the representation.
                 self.add_positive(db, ty);
             }
-            // `bool & ~AlwaysTruthy` -> `bool & Literal[False]`
-            // `bool & ~Literal[True]` -> `bool & Literal[False]`
-            Type::AlwaysTruthy | Type::BooleanLiteral(true) if contains_bool() => {
-                self.add_positive(db, Type::BooleanLiteral(false));
-            }
             // `LiteralString & ~AlwaysTruthy` -> `LiteralString & Literal[""]`
             Type::AlwaysTruthy if self.positive.contains(&Type::LiteralString) => {
                 self.add_positive(db, Type::string_literal(db, ""));
             }
-            // `bool & ~AlwaysFalsy` -> `bool & Literal[True]`
-            // `bool & ~Literal[False]` -> `bool & Literal[True]`
-            Type::AlwaysFalsy | Type::BooleanLiteral(false) if contains_bool() => {
-                self.add_positive(db, Type::BooleanLiteral(true));
-            }
             // `LiteralString & ~AlwaysFalsy` -> `LiteralString & ~Literal[""]`
             Type::AlwaysFalsy if self.positive.contains(&Type::LiteralString) => {
                 self.add_negative(db, Type::string_literal(db, ""));
diff --git a/crates/red_knot_python_semantic/src/types/property_tests.rs b/crates/red_knot_python_semantic/src/types/property_tests.rs
index 5f6e8edf06ce3..f4471826cc4d4 100644
--- a/crates/red_knot_python_semantic/src/types/property_tests.rs
+++ b/crates/red_knot_python_semantic/src/types/property_tests.rs
@@ -328,8 +328,9 @@ fn union<'db>(db: &'db TestDb, tys: impl IntoIterator<Item = Type<'db>>) -> Type
 }
 
 mod stable {
-    use super::union;
+    use super::{intersection, union};
     use crate::types::{KnownClass, Type};
+    use itertools::Itertools;
 
     // Reflexivity: `T` is equivalent to itself.
     type_property_test!(
@@ -474,6 +475,32 @@ mod stable {
         all_type_pairs_are_assignable_to_their_union, db,
         forall types s, t. s.is_assignable_to(db, union(db, [s, t])) && t.is_assignable_to(db, union(db, [s, t]))
     );
+
+    // Equal element sets of intersections implies equivalence
+    type_property_test!(
+        intersection_equivalence_not_order_dependent, db,
+        forall types s, t, u.
+            s.is_fully_static(db) && t.is_fully_static(db) && u.is_fully_static(db)
+            => [s, t, u]
+                .into_iter()
+                .permutations(3)
+                .map(|trio_of_types| intersection(db, trio_of_types))
+                .permutations(2)
+                .all(|vec_of_intersections| vec_of_intersections[0].is_equivalent_to(db, vec_of_intersections[1]))
+    );
+
+    // Equal element sets of unions implies equivalence
+    type_property_test!(
+        union_equivalence_not_order_dependent, db,
+        forall types s, t, u.
+            s.is_fully_static(db) && t.is_fully_static(db) && u.is_fully_static(db)
+            => [s, t, u]
+                .into_iter()
+                .permutations(3)
+                .map(|trio_of_types| union(db, trio_of_types))
+                .permutations(2)
+                .all(|vec_of_unions| vec_of_unions[0].is_equivalent_to(db, vec_of_unions[1]))
+    );
 }
 
 /// This module contains property tests that currently lead to many false positives.
@@ -484,8 +511,6 @@ mod stable {
 /// tests to the `stable` section. In the meantime, it can still be useful to run these
 /// tests (using [`types::property_tests::flaky`]), to see if there are any new obvious bugs.
 mod flaky {
-    use itertools::Itertools;
-
     use super::{intersection, union};
 
     // Negating `T` twice is equivalent to `T`.
@@ -522,34 +547,6 @@ mod flaky {
         forall types s, t. intersection(db, [s, t]).is_assignable_to(db, s) && intersection(db, [s, t]).is_assignable_to(db, t)
     );
 
-    // Equal element sets of intersections implies equivalence
-    // flaky at least in part because of https://github.com/astral-sh/ruff/issues/15513
-    type_property_test!(
-        intersection_equivalence_not_order_dependent, db,
-        forall types s, t, u.
-            s.is_fully_static(db) && t.is_fully_static(db) && u.is_fully_static(db)
-            => [s, t, u]
-                .into_iter()
-                .permutations(3)
-                .map(|trio_of_types| intersection(db, trio_of_types))
-                .permutations(2)
-                .all(|vec_of_intersections| vec_of_intersections[0].is_equivalent_to(db, vec_of_intersections[1]))
-    );
-
-    // Equal element sets of unions implies equivalence
-    // flaky at laest in part because of https://github.com/astral-sh/ruff/issues/15513
-    type_property_test!(
-        union_equivalence_not_order_dependent, db,
-        forall types s, t, u.
-            s.is_fully_static(db) && t.is_fully_static(db) && u.is_fully_static(db)
-            => [s, t, u]
-                .into_iter()
-                .permutations(3)
-                .map(|trio_of_types| union(db, trio_of_types))
-                .permutations(2)
-                .all(|vec_of_unions| vec_of_unions[0].is_equivalent_to(db, vec_of_unions[1]))
-    );
-
     // `S | T` is always a supertype of `S`.
     // Thus, `S` is never disjoint from `S | T`.
     type_property_test!(