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 83579a0e06..ebb350ee28 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
@@ -133,6 +133,11 @@ class Single(Enum):
     VALUE = 1
 
 static_assert(is_equivalent_to(P | Q | Single, Literal[Single.VALUE] | Q | P))
+
+static_assert(is_equivalent_to(Any, Any | Intersection[Any, str]))
+static_assert(is_equivalent_to(Any, Intersection[str, Any] | Any))
+static_assert(is_equivalent_to(Any, Any | Intersection[Any, Not[None]]))
+static_assert(is_equivalent_to(Any, Intersection[Not[None], Any] | Any))
 ```
 
 ## Tuples
diff --git a/crates/ty_python_semantic/src/types.rs b/crates/ty_python_semantic/src/types.rs
index b2cb2d61f1..7b643a168a 100644
--- a/crates/ty_python_semantic/src/types.rs
+++ b/crates/ty_python_semantic/src/types.rs
@@ -1050,6 +1050,13 @@ impl<'db> Type<'db> {
         }
     }
 
+    pub(crate) const fn into_intersection(self) -> Option<IntersectionType<'db>> {
+        match self {
+            Type::Intersection(intersection_type) => Some(intersection_type),
+            _ => None,
+        }
+    }
+
     #[cfg(test)]
     #[track_caller]
     pub(crate) fn expect_union(self) -> UnionType<'db> {
diff --git a/crates/ty_python_semantic/src/types/builder.rs b/crates/ty_python_semantic/src/types/builder.rs
index cc1c35790a..556edcb368 100644
--- a/crates/ty_python_semantic/src/types/builder.rs
+++ b/crates/ty_python_semantic/src/types/builder.rs
@@ -504,9 +504,16 @@ impl<'db> UnionBuilder<'db> {
             if should_simplify_full && !matches!(element_type, Type::TypeAlias(_)) {
                 if ty.is_equivalent_to(self.db, element_type)
                     || ty.is_subtype_of(self.db, element_type)
+                    || ty.into_intersection().is_some_and(|intersection| {
+                        intersection.positive(self.db).contains(&element_type)
+                    })
                 {
                     return;
-                } else if element_type.is_subtype_of(self.db, ty) {
+                } else if element_type.is_subtype_of(self.db, ty)
+                    || element_type
+                        .into_intersection()
+                        .is_some_and(|intersection| intersection.positive(self.db).contains(&ty))
+                {
                     to_remove.push(index);
                 } else if ty_negated.is_subtype_of(self.db, element_type) {
                     // We add `ty` to the union. We just checked that `~ty` is a subtype of an