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 6456b7764b..f9de673a17 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/eq.md
@@ -238,3 +238,20 @@ def _(s: LiteralString | None, t: LiteralString | Any):
         # TODO could be `Literal["foo"] | Any`
         reveal_type(t)  # revealed: LiteralString | Any
 ```
+
+## Narrowing with tuple types
+
+We assume that tuple subclasses don't override `tuple.__eq__`, which only returns True for other
+tuples. So they are excluded from the narrowed type when comparing to non-tuple values.
+
+```py
+from typing import Literal
+
+def _(x: Literal["a", "b"] | tuple[int, int]):
+    if x == "a":
+        # tuple type is excluded because it's disjoint from the string literal
+        reveal_type(x)  # revealed: Literal["a"]
+    else:
+        # tuple type remains in the else branch
+        reveal_type(x)  # revealed: Literal["b"] | tuple[int, int]
+```
diff --git a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/in.md b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/in.md
index 14e2f6eab4..79bb4c1d92 100644
--- a/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/in.md
+++ b/crates/ty_python_semantic/resources/mdtest/narrow/conditionals/in.md
@@ -191,3 +191,20 @@ def test(x: Status | int):
     else:
         reveal_type(x)  # revealed: Literal[Status.REJECTED] | int
 ```
+
+## Union with tuple and `Literal`
+
+We assume that tuple subclasses don't override `tuple.__eq__`, which only returns True for other
+tuples. So they are excluded from the narrowed type when disjoint from the RHS values.
+
+```py
+from typing import Literal
+
+def test(x: Literal["none", "auto", "required"] | tuple[list[str], Literal["auto", "required"]]):
+    if x in ("auto", "required"):
+        # tuple type is excluded because it's disjoint from the string literals
+        reveal_type(x)  # revealed: Literal["auto", "required"]
+    else:
+        # tuple type remains in the else branch
+        reveal_type(x)  # revealed: Literal["none"] | tuple[list[str], Literal["auto", "required"]]
+```
diff --git a/crates/ty_python_semantic/src/types/narrow.rs b/crates/ty_python_semantic/src/types/narrow.rs
index cc9c0ca0f6..ae36ea47ed 100644
--- a/crates/ty_python_semantic/src/types/narrow.rs
+++ b/crates/ty_python_semantic/src/types/narrow.rs
@@ -324,6 +324,39 @@ fn place_expr(expr: &ast::Expr) -> Option<PlaceExpr> {
     }
 }
 
+/// Return `true` if it is possible for any two inhabitants of the given types to
+/// compare equal to each other; otherwise return `false`.
+fn could_compare_equal<'db>(db: &'db dyn Db, left_ty: Type<'db>, right_ty: Type<'db>) -> bool {
+    if !left_ty.is_disjoint_from(db, right_ty) {
+        // If types overlap, they have inhabitants in common; it's definitely possible
+        // for an object to compare equal to itself.
+        return true;
+    }
+    match (left_ty, right_ty) {
+        // In order to be sure a union type cannot compare equal to another type, it
+        // must be true that no element of the union can compare equal to that type.
+        (Type::Union(union), _) => union
+            .elements(db)
+            .iter()
+            .any(|ty| could_compare_equal(db, *ty, right_ty)),
+        (_, Type::Union(union)) => union
+            .elements(db)
+            .iter()
+            .any(|ty| could_compare_equal(db, left_ty, *ty)),
+        // Boolean literals and int literals are disjoint, and single valued, and yet
+        // `True == 1` and `False == 0`.
+        (Type::BooleanLiteral(b), Type::IntLiteral(i))
+        | (Type::IntLiteral(i), Type::BooleanLiteral(b)) => i64::from(b) == i,
+        // We assume that tuples use `tuple.__eq__` which only returns True
+        // for other tuples, so they cannot compare equal to non-tuple types.
+        (Type::NominalInstance(instance), _) if instance.tuple_spec(db).is_some() => false,
+        (_, Type::NominalInstance(instance)) if instance.tuple_spec(db).is_some() => false,
+        // Other than the above cases, two single-valued disjoint types cannot compare
+        // equal.
+        _ => !(left_ty.is_single_valued(db) && right_ty.is_single_valued(db)),
+    }
+}
+
 struct NarrowingConstraintsBuilder<'db, 'ast> {
     db: &'db dyn Db,
     module: &'ast ParsedModuleRef,
@@ -573,39 +606,6 @@ impl<'db, 'ast> NarrowingConstraintsBuilder<'db, 'ast> {
             // something that is not a type, and handle this not-a-type in `symbol_from_bindings`,
             // instead of intersecting with a type.)
 
-            // Return `true` if it is possible for any two inhabitants of the given types to
-            // compare equal to each other; otherwise return `false`.
-            fn could_compare_equal<'db>(
-                db: &'db dyn Db,
-                left_ty: Type<'db>,
-                right_ty: Type<'db>,
-            ) -> bool {
-                if !left_ty.is_disjoint_from(db, right_ty) {
-                    // If types overlap, they have inhabitants in common; it's definitely possible
-                    // for an object to compare equal to itself.
-                    return true;
-                }
-                match (left_ty, right_ty) {
-                    // In order to be sure a union type cannot compare equal to another type, it
-                    // must be true that no element of the union can compare equal to that type.
-                    (Type::Union(union), _) => union
-                        .elements(db)
-                        .iter()
-                        .any(|ty| could_compare_equal(db, *ty, right_ty)),
-                    (_, Type::Union(union)) => union
-                        .elements(db)
-                        .iter()
-                        .any(|ty| could_compare_equal(db, left_ty, *ty)),
-                    // Boolean literals and int literals are disjoint, and single valued, and yet
-                    // `True == 1` and `False == 0`.
-                    (Type::BooleanLiteral(b), Type::IntLiteral(i))
-                    | (Type::IntLiteral(i), Type::BooleanLiteral(b)) => i64::from(b) == i,
-                    // Other than the above cases, two single-valued disjoint types cannot compare
-                    // equal.
-                    _ => !(left_ty.is_single_valued(db) && right_ty.is_single_valued(db)),
-                }
-            }
-
             // Return `true` if `lhs_ty` consists only of `LiteralString` and types that cannot
             // compare equal to `rhs_ty`.
             fn can_narrow_to_rhs<'db>(
@@ -660,7 +660,8 @@ impl<'db, 'ast> NarrowingConstraintsBuilder<'db, 'ast> {
                         )
                     }
                     _ => {
-                        if ty.is_single_valued(db) && !could_compare_equal(db, ty, rhs_ty) {
+                        if !could_compare_equal(db, ty, rhs_ty) {
+                            // Cannot compare equal to rhs, so keep this type
                             ty
                         } else {
                             Type::Never
@@ -721,14 +722,22 @@ impl<'db, 'ast> NarrowingConstraintsBuilder<'db, 'ast> {
 
             if let Some(lhs_union) = lhs_ty.as_union() {
                 for element in lhs_union.elements(self.db) {
-                    // Keep only the non-single-valued portion of the original type.
-                    if !element.is_single_valued(self.db)
-                        && !element.is_literal_string()
-                        && !element.is_bool(self.db)
-                        && (!element.is_enum(self.db) || element.overrides_equality(self.db))
-                    {
-                        builder = builder.add(*element);
+                    // Skip single-valued types (handled via RHS matching).
+                    if element.is_single_valued(self.db) {
+                        continue;
                     }
+                    // Skip types that are handled specially (LiteralString, bool, enum).
+                    if element.is_literal_string()
+                        || element.is_bool(self.db)
+                        || (element.is_enum(self.db) && !element.overrides_equality(self.db))
+                    {
+                        continue;
+                    }
+                    // Skip types that cannot compare equal to any RHS value.
+                    if !could_compare_equal(self.db, *element, rhs_values) {
+                        continue;
+                    }
+                    builder = builder.add(*element);
                 }
             }
             Some(builder.build())