diff --git a/crates/red_knot_python_semantic/resources/mdtest/intersection_types.md b/crates/red_knot_python_semantic/resources/mdtest/intersection_types.md
index 8a85ebc000..676878fb4f 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/intersection_types.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/intersection_types.md
@@ -313,22 +313,24 @@ def _(
 
 ### Union of a type and its negation
 
-Similarly, if we have both `P` and `~P` in a _union_, we could simplify that to `object`. However,
-this is a rather costly operation which would require us to build the negation of each type that we
-add to a union, so this is not implemented at the moment.
+Similarly, if we have both `P` and `~P` in a _union_, we can simplify that to `object`.
 
 ```py
 from knot_extensions import Intersection, Not
 
 class P: ...
+class Q: ...
 
 def _(
     i1: P | Not[P],
     i2: Not[P] | P,
+    i3: P | Q | Not[P],
+    i4: Not[P] | Q | P,
 ) -> None:
-    # These could be simplified to `object`
-    reveal_type(i1)  # revealed: P | ~P
-    reveal_type(i2)  # revealed: ~P | P
+    reveal_type(i1)  # revealed: object
+    reveal_type(i2)  # revealed: object
+    reveal_type(i3)  # revealed: object
+    reveal_type(i4)  # revealed: object
 ```
 
 ### Negation is an involution
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 5cf287329a..54c3f167ca 100644
--- a/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md
+++ b/crates/red_knot_python_semantic/resources/mdtest/narrow/truthiness.md
@@ -21,22 +21,22 @@ else:
 if x and not x:
     reveal_type(x)  # revealed: Never
 else:
-    reveal_type(x)  # revealed: Literal[0, "", b"", -1, "foo", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
 
 if not (x and not x):
-    reveal_type(x)  # revealed: Literal[0, "", b"", -1, "foo", b"bar"] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
 else:
     reveal_type(x)  # revealed: Never
 
 if x or not x:
-    reveal_type(x)  # revealed: Literal[-1, "foo", b"bar", 0, "", b""] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
 else:
     reveal_type(x)  # revealed: Never
 
 if not (x or not x):
     reveal_type(x)  # revealed: Never
 else:
-    reveal_type(x)  # revealed: Literal[-1, "foo", b"bar", 0, "", b""] | bool | None | tuple[()]
+    reveal_type(x)  # revealed: Literal[0, -1, "", "foo", b"", b"bar"] | bool | None | tuple[()]
 
 if (isinstance(x, int) or isinstance(x, str)) and x:
     reveal_type(x)  # revealed: Literal[-1, True, "foo"]
@@ -87,10 +87,10 @@ def f(x: A | B):
     if x and not x:
         reveal_type(x)  # revealed: A & ~AlwaysFalsy & ~AlwaysTruthy | B & ~AlwaysFalsy & ~AlwaysTruthy
     else:
-        reveal_type(x)  # revealed: A & ~AlwaysTruthy | B & ~AlwaysTruthy | A & ~AlwaysFalsy | B & ~AlwaysFalsy
+        reveal_type(x)  # revealed: A | B
 
     if x or not x:
-        reveal_type(x)  # revealed: A & ~AlwaysFalsy | B & ~AlwaysFalsy | A & ~AlwaysTruthy | B & ~AlwaysTruthy
+        reveal_type(x)  # revealed: A | B
     else:
         reveal_type(x)  # revealed: A & ~AlwaysTruthy & ~AlwaysFalsy | B & ~AlwaysTruthy & ~AlwaysFalsy
 ```
@@ -214,10 +214,9 @@ if x and not x:
     reveal_type(y)  # revealed: A & ~AlwaysFalsy & ~AlwaysTruthy
 else:
     y = x
-    reveal_type(y)  # revealed: A & ~AlwaysTruthy | A & ~AlwaysFalsy
+    reveal_type(y)  # revealed: A
 
-# TODO: It should be A. We should improve UnionBuilder or IntersectionBuilder. (issue #15023)
-reveal_type(y)  # revealed: A & ~AlwaysTruthy | A & ~AlwaysFalsy
+reveal_type(y)  # revealed: A
 ```
 
 ## Truthiness of classes
diff --git a/crates/red_knot_python_semantic/src/types/builder.rs b/crates/red_knot_python_semantic/src/types/builder.rs
index 9671e1ba8d..c4599eb498 100644
--- a/crates/red_knot_python_semantic/src/types/builder.rs
+++ b/crates/red_knot_python_semantic/src/types/builder.rs
@@ -65,6 +65,8 @@ impl<'db> UnionBuilder<'db> {
 
                 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);
@@ -80,6 +82,17 @@ impl<'db> UnionBuilder<'db> {
                         return self;
                     } else if element.is_subtype_of(self.db, ty) {
                         to_remove.push(index);
+                    } else if ty_negated.is_subtype_of(self.db, *element) {
+                        // We add `ty` to the union. We just checked that `~ty` is a subtype of an existing `element`.
+                        // This also means that `~ty | ty` is a subtype of `element | ty`, because both elements in the
+                        // first union are subtypes of the corresponding elements in the second union. But `~ty | ty` is
+                        // just `object`. Since `object` is a subtype of `element | ty`, we can only conclude that
+                        // `element | ty` must be `object` (object has no other supertypes). This means we can simplify
+                        // the whole union to just `object`, since all other potential elements would also be subtypes of
+                        // `object`.
+                        self.elements.clear();
+                        self.elements.push(KnownClass::Object.to_instance(self.db));
+                        return self;
                     }
                 }
                 match to_remove[..] {