diff --git a/libcxx/include/__expected/expected.h b/libcxx/include/__expected/expected.h
index 045370a486fae6..bf16c8f720d268 100644
--- a/libcxx/include/__expected/expected.h
+++ b/libcxx/include/__expected/expected.h
@@ -119,9 +119,7 @@ class expected {
   _LIBCPP_HIDE_FROM_ABI constexpr expected()
     noexcept(is_nothrow_default_constructible_v<_Tp>) // strengthened
     requires is_default_constructible_v<_Tp>
-      : __has_val_(true) {
-    std::construct_at(std::addressof(__union_.__val_));
-  }
+      : __union_(std::in_place), __has_val_(true) {}
 
   _LIBCPP_HIDE_FROM_ABI constexpr expected(const expected&) = delete;
 
@@ -136,14 +134,7 @@ class expected {
     noexcept(is_nothrow_copy_constructible_v<_Tp> && is_nothrow_copy_constructible_v<_Err>) // strengthened
     requires(is_copy_constructible_v<_Tp> && is_copy_constructible_v<_Err> &&
              !(is_trivially_copy_constructible_v<_Tp> && is_trivially_copy_constructible_v<_Err>))
-      : __has_val_(__other.__has_val_) {
-    if (__has_val_) {
-      std::construct_at(std::addressof(__union_.__val_), __other.__union_.__val_);
-    } else {
-      std::construct_at(std::addressof(__union_.__unex_), __other.__union_.__unex_);
-    }
-  }
-
+      : __union_(__other.__has_val_, __other.__union_), __has_val_(__other.__has_val_) { }
 
   _LIBCPP_HIDE_FROM_ABI constexpr expected(expected&&)
     requires(is_move_constructible_v<_Tp> && is_move_constructible_v<_Err>
@@ -154,13 +145,7 @@ class expected {
     noexcept(is_nothrow_move_constructible_v<_Tp> && is_nothrow_move_constructible_v<_Err>)
     requires(is_move_constructible_v<_Tp> && is_move_constructible_v<_Err> &&
              !(is_trivially_move_constructible_v<_Tp> && is_trivially_move_constructible_v<_Err>))
-      : __has_val_(__other.__has_val_) {
-    if (__has_val_) {
-      std::construct_at(std::addressof(__union_.__val_), std::move(__other.__union_.__val_));
-    } else {
-      std::construct_at(std::addressof(__union_.__unex_), std::move(__other.__union_.__unex_));
-    }
-  }
+      : __union_(__other.__has_val_, std::move(__other.__union_)), __has_val_(__other.__has_val_) { }
 
 private:
   template <class _Up, class _OtherErr, class _UfQual, class _OtherErrQual>
@@ -200,26 +185,14 @@ class expected {
   expected(const expected<_Up, _OtherErr>& __other)
     noexcept(is_nothrow_constructible_v<_Tp, const _Up&> &&
              is_nothrow_constructible_v<_Err, const _OtherErr&>) // strengthened
-      : __has_val_(__other.__has_val_) {
-    if (__has_val_) {
-      std::construct_at(std::addressof(__union_.__val_), __other.__union_.__val_);
-    } else {
-      std::construct_at(std::addressof(__union_.__unex_), __other.__union_.__unex_);
-    }
-  }
+      : __union_(__other.__has_val_, __other.__union_), __has_val_(__other.__has_val_) {}
 
   template <class _Up, class _OtherErr>
     requires __can_convert<_Up, _OtherErr, _Up, _OtherErr>::value
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<_Up, _Tp> || !is_convertible_v<_OtherErr, _Err>)
   expected(expected<_Up, _OtherErr>&& __other)
     noexcept(is_nothrow_constructible_v<_Tp, _Up> && is_nothrow_constructible_v<_Err, _OtherErr>) // strengthened
-      : __has_val_(__other.__has_val_) {
-    if (__has_val_) {
-      std::construct_at(std::addressof(__union_.__val_), std::move(__other.__union_.__val_));
-    } else {
-      std::construct_at(std::addressof(__union_.__unex_), std::move(__other.__union_.__unex_));
-    }
-  }
+      : __union_(__other.__has_val_, std::move(__other.__union_)), __has_val_(__other.__has_val_) {}
 
   template <class _Up = _Tp>
     requires(!is_same_v<remove_cvref_t<_Up>, in_place_t> && !is_same_v<expected, remove_cvref_t<_Up>> &&
@@ -227,61 +200,47 @@ class expected {
              (!is_same_v<remove_cv_t<_Tp>, bool> || !__is_std_expected<remove_cvref_t<_Up>>::value))
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<_Up, _Tp>)
       expected(_Up&& __u) noexcept(is_nothrow_constructible_v<_Tp, _Up>) // strengthened
-      : __has_val_(true) {
-    std::construct_at(std::addressof(__union_.__val_), std::forward<_Up>(__u));
-  }
+      : __union_(std::in_place, std::forward<_Up>(__u)), __has_val_(true) {}
 
   template <class _OtherErr>
     requires is_constructible_v<_Err, const _OtherErr&>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<const _OtherErr&, _Err>)
   expected(const unexpected<_OtherErr>& __unex)
     noexcept(is_nothrow_constructible_v<_Err, const _OtherErr&>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), __unex.error());
-  }
+      : __union_(std::unexpect, __unex.error()), __has_val_(false) {}
 
   template <class _OtherErr>
     requires is_constructible_v<_Err, _OtherErr>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<_OtherErr, _Err>)
   expected(unexpected<_OtherErr>&& __unex)
     noexcept(is_nothrow_constructible_v<_Err, _OtherErr>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), std::move(__unex.error()));
-  }
+      : __union_(std::unexpect, std::move(__unex.error())), __has_val_(false) {}
 
   template <class... _Args>
     requires is_constructible_v<_Tp, _Args...>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit expected(in_place_t, _Args&&... __args)
     noexcept(is_nothrow_constructible_v<_Tp, _Args...>) // strengthened
-      : __has_val_(true) {
-    std::construct_at(std::addressof(__union_.__val_), std::forward<_Args>(__args)...);
-  }
+      : __union_(std::in_place, std::forward<_Args>(__args)...), __has_val_(true) {}
 
   template <class _Up, class... _Args>
     requires is_constructible_v< _Tp, initializer_list<_Up>&, _Args... >
   _LIBCPP_HIDE_FROM_ABI constexpr explicit
   expected(in_place_t, initializer_list<_Up> __il, _Args&&... __args)
     noexcept(is_nothrow_constructible_v<_Tp, initializer_list<_Up>&, _Args...>) // strengthened
-      : __has_val_(true) {
-    std::construct_at(std::addressof(__union_.__val_), __il, std::forward<_Args>(__args)...);
-  }
+      : __union_(std::in_place, __il, std::forward<_Args>(__args)...), __has_val_(true) {}
 
   template <class... _Args>
     requires is_constructible_v<_Err, _Args...>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit expected(unexpect_t, _Args&&... __args)
-    noexcept(is_nothrow_constructible_v<_Err, _Args...>)  // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), std::forward<_Args>(__args)...);
-  }
+    noexcept(is_nothrow_constructible_v<_Err, _Args...>) // strengthened
+      : __union_(std::unexpect, std::forward<_Args>(__args)...), __has_val_(false) {}
 
   template <class _Up, class... _Args>
     requires is_constructible_v< _Err, initializer_list<_Up>&, _Args... >
   _LIBCPP_HIDE_FROM_ABI constexpr explicit
   expected(unexpect_t, initializer_list<_Up> __il, _Args&&... __args)
     noexcept(is_nothrow_constructible_v<_Err, initializer_list<_Up>&, _Args...>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), __il, std::forward<_Args>(__args)...);
-  }
+      : __union_(std::unexpect, __il, std::forward<_Args>(__args)...), __has_val_(false) {}
 
   // [expected.object.dtor], destructor
 
@@ -440,9 +399,10 @@ class expected {
       std::destroy_at(std::addressof(__union_.__val_));
     } else {
       std::destroy_at(std::addressof(__union_.__unex_));
-      __has_val_ = true;
     }
-    return *std::construct_at(std::addressof(__union_.__val_), std::forward<_Args>(__args)...);
+    std::construct_at(std::addressof(__union_.__val_), std::forward<_Args>(__args)...);
+    __has_val_ = true;
+    return __union_.__val_;
   }
 
   template <class _Up, class... _Args>
@@ -452,9 +412,10 @@ class expected {
       std::destroy_at(std::addressof(__union_.__val_));
     } else {
       std::destroy_at(std::addressof(__union_.__unex_));
-      __has_val_ = true;
     }
-    return *std::construct_at(std::addressof(__union_.__val_), __il, std::forward<_Args>(__args)...);
+    std::construct_at(std::addressof(__union_.__val_), __il, std::forward<_Args>(__args)...);
+    __has_val_ = true;
+    return __union_.__val_;
   }
 
 
@@ -893,11 +854,15 @@ class expected {
   }
 
 private:
-  struct __empty_t {};
-
   template <class _ValueType, class _ErrorType>
   union __union_t {
-    _LIBCPP_HIDE_FROM_ABI constexpr __union_t() {}
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::in_place_t, _Args&&... __args)
+        : __val_(std::forward<_Args>(__args)...) {}
+
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::unexpect_t, _Args&&... __args)
+        : __unex_(std::forward<_Args>(__args)...) {}
 
     template <class _Func, class... _Args>
     _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(
@@ -909,6 +874,14 @@ class expected {
         std::__expected_construct_unexpected_from_invoke_tag, _Func&& __f, _Args&&... __args)
         : __unex_(std::invoke(std::forward<_Func>(__f), std::forward<_Args>(__args)...)) {}
 
+    template <class _Union>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(bool __has_val, _Union&& __other) {
+      if (__has_val)
+        std::construct_at(std::addressof(__val_), std::forward<_Union>(__other).__val_);
+      else
+        std::construct_at(std::addressof(__unex_), std::forward<_Union>(__other).__unex_);
+    }
+
     _LIBCPP_HIDE_FROM_ABI constexpr ~__union_t()
       requires(is_trivially_destructible_v<_ValueType> && is_trivially_destructible_v<_ErrorType>)
     = default;
@@ -927,10 +900,17 @@ class expected {
   template <class _ValueType, class _ErrorType>
     requires(is_trivially_move_constructible_v<_ValueType> && is_trivially_move_constructible_v<_ErrorType>)
   union __union_t<_ValueType, _ErrorType> {
-    _LIBCPP_HIDE_FROM_ABI constexpr __union_t() : __empty_() {}
     _LIBCPP_HIDE_FROM_ABI constexpr __union_t(const __union_t&) = default;
     _LIBCPP_HIDE_FROM_ABI constexpr __union_t& operator=(const __union_t&) = default;
 
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::in_place_t, _Args&&... __args)
+        : __val_(std::forward<_Args>(__args)...) {}
+
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::unexpect_t, _Args&&... __args)
+        : __unex_(std::forward<_Args>(__args)...) {}
+
     template <class _Func, class... _Args>
     _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(
         std::__expected_construct_in_place_from_invoke_tag, _Func&& __f, _Args&&... __args)
@@ -941,6 +921,14 @@ class expected {
         std::__expected_construct_unexpected_from_invoke_tag, _Func&& __f, _Args&&... __args)
         : __unex_(std::invoke(std::forward<_Func>(__f), std::forward<_Args>(__args)...)) {}
 
+    template <class _Union>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(bool __has_val, _Union&& __other) {
+      if (__has_val)
+        std::construct_at(std::addressof(__val_), std::forward<_Union>(__other).__val_);
+      else
+        std::construct_at(std::addressof(__unex_), std::forward<_Union>(__other).__unex_);
+    }
+
     _LIBCPP_HIDE_FROM_ABI constexpr ~__union_t()
       requires(is_trivially_destructible_v<_ValueType> && is_trivially_destructible_v<_ErrorType>)
     = default;
@@ -950,7 +938,6 @@ class expected {
       requires(!is_trivially_destructible_v<_ValueType> || !is_trivially_destructible_v<_ErrorType>)
     {}
 
-    _LIBCPP_NO_UNIQUE_ADDRESS __empty_t __empty_;
     _LIBCPP_NO_UNIQUE_ADDRESS _ValueType __val_;
     _LIBCPP_NO_UNIQUE_ADDRESS _ErrorType __unex_;
   };
@@ -998,11 +985,7 @@ class expected<_Tp, _Err> {
   _LIBCPP_HIDE_FROM_ABI constexpr expected(const expected& __rhs)
     noexcept(is_nothrow_copy_constructible_v<_Err>) // strengthened
     requires(is_copy_constructible_v<_Err> && !is_trivially_copy_constructible_v<_Err>)
-      : __has_val_(__rhs.__has_val_) {
-    if (!__rhs.__has_val_) {
-      std::construct_at(std::addressof(__union_.__unex_), __rhs.__union_.__unex_);
-    }
-  }
+      : __union_(__rhs.__has_val_, __rhs.__union_), __has_val_(__rhs.__has_val_) {}
 
   _LIBCPP_HIDE_FROM_ABI constexpr expected(expected&&)
     requires(is_move_constructible_v<_Err> && is_trivially_move_constructible_v<_Err>)
@@ -1011,51 +994,35 @@ class expected<_Tp, _Err> {
   _LIBCPP_HIDE_FROM_ABI constexpr expected(expected&& __rhs)
     noexcept(is_nothrow_move_constructible_v<_Err>)
     requires(is_move_constructible_v<_Err> && !is_trivially_move_constructible_v<_Err>)
-      : __has_val_(__rhs.__has_val_) {
-    if (!__rhs.__has_val_) {
-      std::construct_at(std::addressof(__union_.__unex_), std::move(__rhs.__union_.__unex_));
-    }
-  }
+      : __union_(__rhs.__has_val_, std::move(__rhs.__union_)), __has_val_(__rhs.__has_val_) {}
 
   template <class _Up, class _OtherErr>
     requires __can_convert<_Up, _OtherErr, const _OtherErr&>::value
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<const _OtherErr&, _Err>)
   expected(const expected<_Up, _OtherErr>& __rhs)
     noexcept(is_nothrow_constructible_v<_Err, const _OtherErr&>) // strengthened
-      : __has_val_(__rhs.__has_val_) {
-    if (!__rhs.__has_val_) {
-      std::construct_at(std::addressof(__union_.__unex_), __rhs.__union_.__unex_);
-    }
-  }
+      : __union_(__rhs.__has_val_, __rhs.__union_), __has_val_(__rhs.__has_val_) {}
 
   template <class _Up, class _OtherErr>
     requires __can_convert<_Up, _OtherErr, _OtherErr>::value
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<_OtherErr, _Err>)
   expected(expected<_Up, _OtherErr>&& __rhs)
     noexcept(is_nothrow_constructible_v<_Err, _OtherErr>) // strengthened
-      : __has_val_(__rhs.__has_val_) {
-    if (!__rhs.__has_val_) {
-      std::construct_at(std::addressof(__union_.__unex_), std::move(__rhs.__union_.__unex_));
-    }
-  }
+      : __union_(__rhs.__has_val_, std::move(__rhs.__union_)), __has_val_(__rhs.__has_val_) {}
 
   template <class _OtherErr>
     requires is_constructible_v<_Err, const _OtherErr&>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<const _OtherErr&, _Err>)
   expected(const unexpected<_OtherErr>& __unex)
     noexcept(is_nothrow_constructible_v<_Err, const _OtherErr&>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), __unex.error());
-  }
+      : __union_(std::unexpect, __unex.error()), __has_val_(false) {}
 
   template <class _OtherErr>
     requires is_constructible_v<_Err, _OtherErr>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit(!is_convertible_v<_OtherErr, _Err>)
   expected(unexpected<_OtherErr>&& __unex)
     noexcept(is_nothrow_constructible_v<_Err, _OtherErr>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), std::move(__unex.error()));
-  }
+      : __union_(std::unexpect, std::move(__unex.error())), __has_val_(false) {}
 
   _LIBCPP_HIDE_FROM_ABI constexpr explicit expected(in_place_t) noexcept : __has_val_(true) {}
 
@@ -1063,17 +1030,13 @@ class expected<_Tp, _Err> {
     requires is_constructible_v<_Err, _Args...>
   _LIBCPP_HIDE_FROM_ABI constexpr explicit expected(unexpect_t, _Args&&... __args)
     noexcept(is_nothrow_constructible_v<_Err, _Args...>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), std::forward<_Args>(__args)...);
-  }
+      : __union_(std::unexpect, std::forward<_Args>(__args)...), __has_val_(false) {}
 
   template <class _Up, class... _Args>
     requires is_constructible_v< _Err, initializer_list<_Up>&, _Args... >
   _LIBCPP_HIDE_FROM_ABI constexpr explicit expected(unexpect_t, initializer_list<_Up> __il, _Args&&... __args)
     noexcept(is_nothrow_constructible_v<_Err, initializer_list<_Up>&, _Args...>) // strengthened
-      : __has_val_(false) {
-    std::construct_at(std::addressof(__union_.__unex_), __il, std::forward<_Args>(__args)...);
-  }
+      : __union_(std::unexpect, __il, std::forward<_Args>(__args)...), __has_val_(false) {}
 
 private:
   template <class _Func>
@@ -1507,11 +1470,23 @@ class expected<_Tp, _Err> {
   union __union_t {
     _LIBCPP_HIDE_FROM_ABI constexpr __union_t() : __empty_() {}
 
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::unexpect_t, _Args&&... __args)
+        : __unex_(std::forward<_Args>(__args)...) {}
+
     template <class _Func, class... _Args>
     _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(
         __expected_construct_unexpected_from_invoke_tag, _Func&& __f, _Args&&... __args)
         : __unex_(std::invoke(std::forward<_Func>(__f), std::forward<_Args>(__args)...)) {}
 
+    template <class _Union>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(bool __has_val, _Union&& __other) {
+      if (__has_val)
+        std::construct_at(std::addressof(__empty_));
+      else
+        std::construct_at(std::addressof(__unex_), std::forward<_Union>(__other).__unex_);
+    }
+
     _LIBCPP_HIDE_FROM_ABI constexpr ~__union_t()
       requires(is_trivially_destructible_v<_ErrorType>)
     = default;
@@ -1534,11 +1509,23 @@ class expected<_Tp, _Err> {
     _LIBCPP_HIDE_FROM_ABI constexpr __union_t(const __union_t&) = default;
     _LIBCPP_HIDE_FROM_ABI constexpr __union_t& operator=(const __union_t&) = default;
 
+    template <class... _Args>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(std::unexpect_t, _Args&&... __args)
+        : __unex_(std::forward<_Args>(__args)...) {}
+
     template <class _Func, class... _Args>
     _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(
         __expected_construct_unexpected_from_invoke_tag, _Func&& __f, _Args&&... __args)
         : __unex_(std::invoke(std::forward<_Func>(__f), std::forward<_Args>(__args)...)) {}
 
+    template <class _Union>
+    _LIBCPP_HIDE_FROM_ABI constexpr explicit __union_t(bool __has_val, _Union&& __other) {
+      if (__has_val)
+        std::construct_at(std::addressof(__empty_));
+      else
+        std::construct_at(std::addressof(__unex_), std::forward<_Union>(__other).__unex_);
+    }
+
     _LIBCPP_HIDE_FROM_ABI constexpr ~__union_t()
       requires(is_trivially_destructible_v<_ErrorType>)
     = default;
diff --git a/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.intializer_list.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.intializer_list.pass.cpp
index 3cdfcde3f4d694..922200a8c0263d 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.intializer_list.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.intializer_list.pass.cpp
@@ -81,6 +81,14 @@ constexpr bool test() {
     assert(e.value().i == 10);
   }
 
+  // TailClobberer
+  {
+    std::expected<TailClobberer<0>, bool> e(std::unexpect);
+    auto list = {4, 5, 6};
+    e.emplace(list);
+    assert(e.has_value());
+  }
+
   return true;
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.pass.cpp
index c62e6289350201..491de2dff03312 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/assign/emplace.pass.cpp
@@ -73,6 +73,13 @@ constexpr bool test() {
     assert(e.value() == 10);
   }
 
+  // TailClobberer
+  {
+    std::expected<TailClobberer<0>, bool> e(std::unexpect);
+    e.emplace();
+    assert(e.has_value());
+  }
+
   return true;
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.copy.pass.cpp
index 9274b9a2c030e5..16de28d9703961 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.copy.pass.cpp
@@ -45,6 +45,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 template <class T1, class Err1, class T2, class Err2>
@@ -161,13 +162,19 @@ constexpr bool test() {
     assert(e1.error() == 5);
   }
 
+  // convert TailClobberer
+  {
+    const std::expected<TailClobbererNonTrivialMove<0>, char> e1;
+    std::expected<TailClobberer<0>, char> e2 = e1;
+    assert(e2.has_value());
+    assert(e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct ThrowingInt {
     ThrowingInt(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.move.pass.cpp
index 71979311bfd103..0e30ea2c7fe0b4 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.convert.move.pass.cpp
@@ -46,6 +46,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 template <class T1, class Err1, class T2, class Err2>
@@ -160,13 +161,19 @@ constexpr bool test() {
     assert(e1.error().get() == 0);
   }
 
+  // convert TailClobberer
+  {
+    std::expected<TailClobbererNonTrivialMove<0>, char> e1;
+    std::expected<TailClobberer<0>, char> e2 = std::move(e1);
+    assert(e2.has_value());
+    assert(e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct ThrowingInt {
     ThrowingInt(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.copy.pass.cpp
index 77d73485025ab6..581df51207da29 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.copy.pass.cpp
@@ -30,6 +30,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 struct NonCopyable {
   NonCopyable(const NonCopyable&) = delete;
@@ -93,13 +94,26 @@ constexpr bool test() {
     assert(!e2.has_value());
     assert(e2.error() == 5);
   }
+
+  // copy TailClobberer as value
+  {
+    const std::expected<TailClobberer<0>, bool> e1;
+    auto e2 = e1;
+    assert(e2.has_value());
+  }
+
+  // copy TailClobberer as error
+  {
+    const std::expected<bool, TailClobberer<1>> e1(std::unexpect);
+    auto e2 = e1;
+    assert(!e2.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing() = default;
     Throwing(const Throwing&) { throw Except{}; }
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.default.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.default.pass.cpp
index 431e604e8b692f..dcd046bdd9d893 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.default.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.default.pass.cpp
@@ -22,6 +22,7 @@
 #include <type_traits>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 struct NoDedefaultCtor {
   NoDedefaultCtor() = delete;
@@ -45,6 +46,7 @@ constexpr void testDefaultCtor() {
 
 template <class T>
 constexpr void testTypes() {
+  testDefaultCtor<T, bool>();
   testDefaultCtor<T, int>();
   testDefaultCtor<T, NoDedefaultCtor>();
 }
@@ -52,13 +54,12 @@ constexpr void testTypes() {
 constexpr bool test() {
   testTypes<int>();
   testTypes<MyInt>();
+  testTypes<TailClobberer<0>>();
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing() { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace.pass.cpp
index 92952551711e04..88ec41939439af 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace.pass.cpp
@@ -26,6 +26,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(std::is_constructible_v<std::expected<int, int>, std::in_place_t>);
@@ -54,24 +55,24 @@ struct CopyOnly {
   friend constexpr bool operator==(const CopyOnly& mi, int ii) { return mi.i == ii; }
 };
 
-template <class T>
+template <class T, class E = int>
 constexpr void testInt() {
-  std::expected<T, int> e(std::in_place, 5);
+  std::expected<T, E> e(std::in_place, 5);
   assert(e.has_value());
   assert(e.value() == 5);
 }
 
-template <class T>
+template <class T, class E = int>
 constexpr void testLValue() {
   T t(5);
-  std::expected<T, int> e(std::in_place, t);
+  std::expected<T, E> e(std::in_place, t);
   assert(e.has_value());
   assert(e.value() == 5);
 }
 
-template <class T>
+template <class T, class E = int>
 constexpr void testRValue() {
-  std::expected<T, int> e(std::in_place, T(5));
+  std::expected<T, E> e(std::in_place, T(5));
   assert(e.has_value());
   assert(e.value() == 5);
 }
@@ -80,10 +81,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<CopyOnly>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<0>, bool>();
   testLValue<int>();
   testLValue<CopyOnly>();
+  testLValue<TailClobberer<0>, bool>();
   testRValue<int>();
   testRValue<MoveOnly>();
+  testRValue<TailClobberer<0>, bool>();
 
   // no arg
   {
@@ -111,8 +115,6 @@ constexpr bool test() {
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace_init_list.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace_init_list.pass.cpp
index b4cad54b860e92..a97086fcc9195b 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace_init_list.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.inplace_init_list.pass.cpp
@@ -28,6 +28,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(
@@ -90,13 +91,17 @@ constexpr bool test() {
     assert(m.get() == 0);
   }
 
+  // TailClobberer
+  {
+    std::expected<TailClobberer<0>, bool> e(std::in_place, {1, 2, 3});
+    assert(e.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(std::initializer_list<int>, int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.move.pass.cpp
index 5e6749e50c16c9..cd89e2445860a2 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.move.pass.cpp
@@ -32,6 +32,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 struct NonMovable {
   NonMovable(NonMovable&&) = delete;
@@ -112,13 +113,28 @@ constexpr bool test() {
     assert(e2.error() == 5);
     assert(!e1.has_value());
   }
+
+  // move TailClobbererNonTrivialMove as value
+  {
+    std::expected<TailClobbererNonTrivialMove<0>, bool> e1;
+    auto e2 = std::move(e1);
+    assert(e2.has_value());
+    assert(e1.has_value());
+  }
+
+  // move TailClobbererNonTrivialMove as error
+  {
+    std::expected<bool, TailClobbererNonTrivialMove<1>> e1(std::unexpect);
+    auto e2 = std::move(e1);
+    assert(!e2.has_value());
+    assert(!e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing() = default;
     Throwing(Throwing&&) { throw Except{}; }
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.u.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.u.pass.cpp
index 9e82943f9f314d..1cf3d9cc2ef49c 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.u.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.u.pass.cpp
@@ -29,6 +29,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(std::is_constructible_v<std::expected<int, int>, int>);
@@ -70,24 +71,24 @@ struct CopyOnly {
 struct BaseError {};
 struct DerivedError : BaseError {};
 
-template <class T>
+template <class T, class E = int>
 constexpr void testInt() {
-  std::expected<T, int> e(5);
+  std::expected<T, E> e(5);
   assert(e.has_value());
   assert(e.value() == 5);
 }
 
-template <class T>
+template <class T, class E = int>
 constexpr void testLValue() {
   T t(5);
-  std::expected<T, int> e(t);
+  std::expected<T, E> e(t);
   assert(e.has_value());
   assert(e.value() == 5);
 }
 
-template <class T>
+template <class T, class E = int>
 constexpr void testRValue() {
-  std::expected<T, int> e(T(5));
+  std::expected<T, E> e(T(5));
   assert(e.has_value());
   assert(e.value() == 5);
 }
@@ -96,10 +97,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<CopyOnly>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<0>, bool>();
   testLValue<int>();
   testLValue<CopyOnly>();
+  testLValue<TailClobberer<0>, bool>();
   testRValue<int>();
   testRValue<MoveOnly>();
+  testRValue<TailClobberer<0>, bool>();
 
   // Test default template argument.
   // Without it, the template parameter cannot be deduced from an initializer list
@@ -153,8 +157,6 @@ constexpr bool test() {
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect.pass.cpp
index 5a78e41dfcae25..27ce97737d288b 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect.pass.cpp
@@ -26,6 +26,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(std::is_constructible_v<std::expected<int, int>, std::unexpect_t>);
@@ -54,24 +55,24 @@ struct CopyOnly {
   friend constexpr bool operator==(const CopyOnly& mi, int ii) { return mi.i == ii; }
 };
 
-template <class T>
+template <class T, class V = int>
 constexpr void testInt() {
-  std::expected<int, T> e(std::unexpect, 5);
+  std::expected<V, T> e(std::unexpect, 5);
   assert(!e.has_value());
   assert(e.error() == 5);
 }
 
-template <class T>
+template <class T, class V = int>
 constexpr void testLValue() {
   T t(5);
-  std::expected<int, T> e(std::unexpect, t);
+  std::expected<V, T> e(std::unexpect, t);
   assert(!e.has_value());
   assert(e.error() == 5);
 }
 
-template <class T>
+template <class T, class V = int>
 constexpr void testRValue() {
-  std::expected<int, T> e(std::unexpect, T(5));
+  std::expected<V, T> e(std::unexpect, T(5));
   assert(!e.has_value());
   assert(e.error() == 5);
 }
@@ -80,10 +81,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<CopyOnly>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<1>, bool>();
   testLValue<int>();
   testLValue<CopyOnly>();
+  testLValue<TailClobberer<1>, bool>();
   testRValue<int>();
   testRValue<MoveOnly>();
+  testRValue<TailClobberer<1>, bool>();
 
   // no arg
   {
@@ -111,8 +115,6 @@ constexpr bool test() {
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect_init_list.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect_init_list.pass.cpp
index 7cc36b51e41534..4f5d3d1492d37a 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect_init_list.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpect_init_list.pass.cpp
@@ -28,6 +28,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(
@@ -90,13 +91,17 @@ constexpr bool test() {
     assert(m.get() == 0);
   }
 
+  // TailClobberer
+  {
+    std::expected<bool, TailClobberer<1>> e(std::unexpect, {1, 2, 3});
+    assert(!e.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(std::initializer_list<int>, int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.copy.pass.cpp
index 09ac91182b3b89..bbfd3048533c79 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.copy.pass.cpp
@@ -27,6 +27,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints
 static_assert(std::is_constructible_v<std::expected<int, int>, const std::unexpected<int>&>);
@@ -49,10 +50,10 @@ struct MyInt {
   friend constexpr bool operator==(const MyInt&, const MyInt&) = default;
 };
 
-template <class T>
+template <class T, class V = int>
 constexpr void testUnexpected() {
   const std::unexpected<int> u(5);
-  std::expected<int, T> e(u);
+  std::expected<V, T> e(u);
   assert(!e.has_value());
   assert(e.error() == 5);
 }
@@ -60,13 +61,12 @@ constexpr void testUnexpected() {
 constexpr bool test() {
   testUnexpected<int>();
   testUnexpected<MyInt>();
+  testUnexpected<TailClobberer<1>, bool>();
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.move.pass.cpp
index 9aaaa3fe1a448d..800d47bda69587 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/ctor/ctor.unexpected.move.pass.cpp
@@ -27,6 +27,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints
 static_assert(std::is_constructible_v<std::expected<int, int>, std::unexpected<int>>);
@@ -49,10 +50,10 @@ struct MyInt {
   friend constexpr bool operator==(const MyInt&, const MyInt&) = default;
 };
 
-template <class Err>
+template <class Err, class V = int>
 constexpr void testInt() {
   std::unexpected<int> u(5);
-  std::expected<int, Err> e(std::move(u));
+  std::expected<V, Err> e(std::move(u));
   assert(!e.has_value());
   assert(e.error() == 5);
 }
@@ -69,14 +70,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<MyInt>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<1>, bool>();
   testMoveOnly();
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.expected/observers/has_value.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/observers/has_value.pass.cpp
index 27d657a065699e..2b24b0ac24ddb8 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/observers/has_value.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/observers/has_value.pass.cpp
@@ -12,10 +12,12 @@
 #include <cassert>
 #include <concepts>
 #include <expected>
+#include <optional>
 #include <type_traits>
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test noexcept
 template <class T>
@@ -43,6 +45,36 @@ constexpr bool test() {
     assert(!e.has_value());
   }
 
+  // The following tests check that the "has_value" flag is not overwritten
+  // by the constructor of the value. This could happen because the flag is
+  // stored in the tail padding of the value.
+  //
+  // The first test is a simplified version of the real code where this was
+  // first observed.
+  //
+  // The other tests use a synthetic struct that clobbers its tail padding
+  // on construction, making the issue easier to reproduce.
+  //
+  // See https://github.com/llvm/llvm-project/issues/68552 and the linked PR.
+  {
+    auto f1 = [] -> std::expected<std::optional<int>, long> { return 0; };
+
+    auto f2 = [&f1] -> std::expected<std::optional<int>, int> {
+      return f1().transform_error([](auto) { return 0; });
+    };
+
+    auto e = f2();
+    assert(e.has_value());
+  }
+  {
+    const std::expected<TailClobberer<0>, bool> e = {};
+    // clang-cl does not support [[no_unique_address]] yet.
+#if !(defined(TEST_COMPILER_CLANG) && defined(_MSC_VER))
+    LIBCPP_STATIC_ASSERT(sizeof(TailClobberer<0>) == sizeof(e));
+#endif
+    assert(e.has_value());
+  }
+
   return true;
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.expected/swap/free.swap.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/swap/free.swap.pass.cpp
index 15c66d2b75076e..3c03efd8329196 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/swap/free.swap.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/swap/free.swap.pass.cpp
@@ -129,7 +129,7 @@ constexpr bool test() {
     std::expected<TrackedMove<true>, TrackedMove<false>> e1(std::in_place, 5);
     std::expected<TrackedMove<true>, TrackedMove<false>> e2(std::unexpect, 10);
 
-    e1.swap(e2);
+    swap(e1, e2);
 
     assert(!e1.has_value());
     assert(e1.error().i == 10);
@@ -180,6 +180,35 @@ constexpr bool test() {
     assert(!e2.error().swapCalled);
   }
 
+  // TailClobberer
+  {
+    // is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, true>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, true>> y(std::unexpect);
+
+      swap(x, y);
+
+      // Both of these would fail if adjusting the "has value" flags happened
+      // _before_ constructing the member objects inside the `swap`.
+      assert(!x.has_value());
+      assert(y.has_value());
+    }
+
+    // !is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, false>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, false>> y(std::unexpect);
+
+      swap(x, y);
+
+      // Both of these would fail if adjusting the "has value" flags happened
+      // _before_ constructing the member objects inside the `swap`.
+      assert(!x.has_value());
+      assert(y.has_value());
+    }
+  }
+
   return true;
 }
 
@@ -210,6 +239,39 @@ void testException() {
       assert(*e1 == 5);
     }
   }
+
+  // TailClobberer
+  {
+    // is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, false, true>, TailClobbererNonTrivialMove<1>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, false, true>, TailClobbererNonTrivialMove<1>> y(std::unexpect);
+      try {
+        swap(x, y);
+        assert(false);
+      } catch (Except) {
+        assert(x.has_value());
+        // This would fail if `TailClobbererNonTrivialMove<1>` clobbered the
+        // flag when rolling back the swap.
+        assert(!y.has_value());
+      }
+    }
+
+    // !is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0>, TailClobbererNonTrivialMove<1, false, true>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0>, TailClobbererNonTrivialMove<1, false, true>> y(std::unexpect);
+      try {
+        swap(x, y);
+        assert(false);
+      } catch (Except) {
+        // This would fail if `TailClobbererNonTrivialMove<0>` clobbered the
+        // flag when rolling back the swap.
+        assert(x.has_value());
+        assert(!y.has_value());
+      }
+    }
+  }
 #endif // TEST_HAS_NO_EXCEPTIONS
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.expected/swap/member.swap.pass.cpp b/libcxx/test/std/utilities/expected/expected.expected/swap/member.swap.pass.cpp
index d2d4a099220927..b6b112cfbeb8ba 100644
--- a/libcxx/test/std/utilities/expected/expected.expected/swap/member.swap.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.expected/swap/member.swap.pass.cpp
@@ -70,7 +70,7 @@ static_assert(!HasMemberSwap<MoveMayThrow, MoveMayThrow>);
 
 // Test noexcept
 template <class T, class E>
-concept MemberSwapNoexcept =
+concept MemberSwapNoexcept = //
     requires(std::expected<T, E> x, std::expected<T, E> y) {
       { x.swap(y) } noexcept;
     };
@@ -198,6 +198,35 @@ constexpr bool test() {
     assert(!e2.error().swapCalled);
   }
 
+  // TailClobberer
+  {
+    // is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, true>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, true>> y(std::unexpect);
+
+      x.swap(y);
+
+      // Both of these would fail if adjusting the "has value" flags happened
+      // _before_ constructing the member objects inside the `swap`.
+      assert(!x.has_value());
+      assert(y.has_value());
+    }
+
+    // !is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, false>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, true>, TailClobbererNonTrivialMove<1, false>> y(std::unexpect);
+
+      x.swap(y);
+
+      // Both of these would fail if adjusting the "has value" flags happened
+      // _before_ constructing the member objects inside the `swap`.
+      assert(!x.has_value());
+      assert(y.has_value());
+    }
+  }
+
   return true;
 }
 
@@ -228,6 +257,39 @@ void testException() {
       assert(*e1 == 5);
     }
   }
+
+  // TailClobberer
+  {
+    // is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0, false, true>, TailClobbererNonTrivialMove<1>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0, false, true>, TailClobbererNonTrivialMove<1>> y(std::unexpect);
+      try {
+        x.swap(y);
+        assert(false);
+      } catch (Except) {
+        assert(x.has_value());
+        // This would fail if `TailClobbererNonTrivialMove<1>` clobbered the
+        // flag when rolling back the swap.
+        assert(!y.has_value());
+      }
+    }
+
+    // !is_nothrow_move_constructible_v<E>
+    {
+      std::expected<TailClobbererNonTrivialMove<0>, TailClobbererNonTrivialMove<1, false, true>> x(std::in_place);
+      std::expected<TailClobbererNonTrivialMove<0>, TailClobbererNonTrivialMove<1, false, true>> y(std::unexpect);
+      try {
+        x.swap(y);
+        assert(false);
+      } catch (Except) {
+        // This would fail if `TailClobbererNonTrivialMove<0>` clobbered the
+        // flag when rolling back the swap.
+        assert(x.has_value());
+        assert(!y.has_value());
+      }
+    }
+  }
 #endif // TEST_HAS_NO_EXCEPTIONS
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.copy.pass.cpp
index 40f8efa5f94bf9..05f556e25eac14 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.copy.pass.cpp
@@ -33,6 +33,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 template <class T1, class Err1, class T2, class Err2>
@@ -97,13 +98,19 @@ constexpr bool test() {
     assert(e1.error() == 5);
   }
 
+  // convert TailClobberer
+  {
+    const std::expected<void, TailClobbererNonTrivialMove<1>> e1(std::unexpect);
+    std::expected<void, TailClobberer<1>> e2 = e1;
+    assert(!e2.has_value());
+    assert(!e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct ThrowingInt {
     ThrowingInt(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.move.pass.cpp
index b28fc7a03bb344..a48888be53ee07 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.convert.move.pass.cpp
@@ -34,6 +34,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 template <class T1, class Err1, class T2, class Err2>
@@ -98,13 +99,19 @@ constexpr bool test() {
     assert(e1.error().get() == 0);
   }
 
+  // convert TailClobberer
+  {
+    std::expected<void, TailClobbererNonTrivialMove<1>> e1(std::unexpect);
+    std::expected<void, TailClobberer<1>> e2 = std::move(e1);
+    assert(!e2.has_value());
+    assert(!e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct ThrowingInt {
     ThrowingInt(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.copy.pass.cpp
index 689f152a3ac554..7c04a5fa9d0440 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.copy.pass.cpp
@@ -25,6 +25,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 struct NonCopyable {
   NonCopyable(const NonCopyable&) = delete;
@@ -62,13 +63,19 @@ constexpr bool test() {
     assert(!e2.has_value());
     assert(e2.error() == 5);
   }
+
+  // copy TailClobberer as error
+  {
+    const std::expected<void, TailClobberer<1>> e1(std::unexpect);
+    auto e2 = e1;
+    assert(!e2.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing() = default;
     Throwing(const Throwing&) { throw Except{}; }
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.move.pass.cpp
index 61bce2be4897f0..bfb5028c9264d0 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.move.pass.cpp
@@ -25,6 +25,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 struct NonMovable {
   NonMovable(NonMovable&&) = delete;
@@ -76,13 +77,20 @@ constexpr bool test() {
     assert(e2.error() == 5);
     assert(!e1.has_value());
   }
+
+  // move TailClobbererNonTrivialMove as error
+  {
+    std::expected<void, TailClobbererNonTrivialMove<1>> e1(std::unexpect);
+    auto e2 = std::move(e1);
+    assert(!e2.has_value());
+    assert(!e1.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing() = default;
     Throwing(Throwing&&) { throw Except{}; }
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect.pass.cpp
index 0a857c77d9c7a6..85bc98d7f462de 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect.pass.cpp
@@ -26,6 +26,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(std::is_constructible_v<std::expected<void, int>, std::unexpect_t>);
@@ -80,10 +81,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<CopyOnly>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<1>>();
   testLValue<int>();
   testLValue<CopyOnly>();
+  testLValue<TailClobberer<1>>();
   testRValue<int>();
   testRValue<MoveOnly>();
+  testRValue<TailClobberer<1>>();
 
   // no arg
   {
@@ -111,8 +115,6 @@ constexpr bool test() {
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect_init_list.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect_init_list.pass.cpp
index a73921225f1fae..4128668a6b07bc 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect_init_list.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpect_init_list.pass.cpp
@@ -28,6 +28,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints:
 static_assert(
@@ -89,13 +90,17 @@ constexpr bool test() {
     assert(m.get() == 0);
   }
 
+  // TailClobberer
+  {
+    std::expected<void, TailClobberer<1>> e(std::unexpect, {1, 2, 3});
+    assert(!e.has_value());
+  }
+
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(std::initializer_list<int>, int) { throw Except{}; };
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.copy.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.copy.pass.cpp
index 89e1c9275e3e06..ba738a3e339de7 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.copy.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.copy.pass.cpp
@@ -27,6 +27,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints
 static_assert(std::is_constructible_v<std::expected<void, int>, const std::unexpected<int>&>);
@@ -60,13 +61,12 @@ constexpr void testUnexpected() {
 constexpr bool test() {
   testUnexpected<int>();
   testUnexpected<MyInt>();
+  testUnexpected<TailClobberer<1>>();
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.move.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.move.pass.cpp
index 2ddcb63c085f05..33a5e7293df214 100644
--- a/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.move.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/ctor/ctor.unexpected.move.pass.cpp
@@ -27,6 +27,7 @@
 
 #include "MoveOnly.h"
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test Constraints
 static_assert(std::is_constructible_v<std::expected<void, int>, std::unexpected<int>>);
@@ -69,14 +70,13 @@ constexpr bool test() {
   testInt<int>();
   testInt<MyInt>();
   testInt<MoveOnly>();
+  testInt<TailClobberer<1>>();
   testMoveOnly();
   return true;
 }
 
 void testException() {
 #ifndef TEST_HAS_NO_EXCEPTIONS
-  struct Except {};
-
   struct Throwing {
     Throwing(int) { throw Except{}; }
   };
diff --git a/libcxx/test/std/utilities/expected/expected.void/observers/has_value.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/observers/has_value.pass.cpp
index 42a173d60c898c..fe92bb401643d8 100644
--- a/libcxx/test/std/utilities/expected/expected.void/observers/has_value.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/observers/has_value.pass.cpp
@@ -16,6 +16,7 @@
 #include <utility>
 
 #include "test_macros.h"
+#include "../../types.h"
 
 // Test noexcept
 template <class T>
@@ -43,6 +44,17 @@ constexpr bool test() {
     assert(!e.has_value());
   }
 
+  // See comments of the corresponding test in
+  // "expected.expected/observers/has_value.pass.cpp".
+  {
+    const std::expected<void, TailClobberer<1>> e(std::unexpect);
+    // clang-cl does not support [[no_unique_address]] yet.
+#if !(defined(TEST_COMPILER_CLANG) && defined(_MSC_VER))
+    LIBCPP_STATIC_ASSERT(sizeof(TailClobberer<1>) == sizeof(e));
+#endif
+    assert(!e.has_value());
+  }
+
   return true;
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.void/swap/free.swap.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/swap/free.swap.pass.cpp
index ad1eb3f0bd20d0..f7314c79fa6db7 100644
--- a/libcxx/test/std/utilities/expected/expected.void/swap/free.swap.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/swap/free.swap.pass.cpp
@@ -91,7 +91,7 @@ constexpr bool test() {
     std::expected<void, Traced> e1(std::in_place);
     std::expected<void, Traced> e2(std::unexpect, s, 10);
 
-    e1.swap(e2);
+    swap(e1, e2);
 
     assert(!e1.has_value());
     assert(e1.error().data_ == 10);
@@ -107,7 +107,7 @@ constexpr bool test() {
     std::expected<void, Traced> e1(std::unexpect, s, 10);
     std::expected<void, Traced> e2(std::in_place);
 
-    e1.swap(e2);
+    swap(e1, e2);
 
     assert(e1.has_value());
     assert(!e2.has_value());
@@ -117,6 +117,19 @@ constexpr bool test() {
     assert(s.dtorCalled);
   }
 
+  // TailClobberer
+  {
+    std::expected<void, TailClobbererNonTrivialMove<1>> x(std::in_place);
+    std::expected<void, TailClobbererNonTrivialMove<1>> y(std::unexpect);
+
+    swap(x, y);
+
+    // The next line would fail if adjusting the "has value" flag happened
+    // _before_ constructing the member object inside the `swap`.
+    assert(!x.has_value());
+    assert(y.has_value());
+  }
+
   return true;
 }
 
@@ -151,6 +164,21 @@ void testException() {
       assert(!e2Destroyed);
     }
   }
+
+  // TailClobberer
+  {
+    std::expected<void, TailClobbererNonTrivialMove<0, false, true>> x(std::in_place);
+    std::expected<void, TailClobbererNonTrivialMove<0, false, true>> y(std::unexpect);
+    try {
+      swap(x, y);
+      assert(false);
+    } catch (Except) {
+      // This would fail if `TailClobbererNonTrivialMove<0, false, true>`
+      // clobbered the flag before throwing the exception.
+      assert(x.has_value());
+      assert(!y.has_value());
+    }
+  }
 #endif // TEST_HAS_NO_EXCEPTIONS
 }
 
diff --git a/libcxx/test/std/utilities/expected/expected.void/swap/member.swap.pass.cpp b/libcxx/test/std/utilities/expected/expected.void/swap/member.swap.pass.cpp
index a71c701a469303..70e004abef684a 100644
--- a/libcxx/test/std/utilities/expected/expected.void/swap/member.swap.pass.cpp
+++ b/libcxx/test/std/utilities/expected/expected.void/swap/member.swap.pass.cpp
@@ -52,7 +52,7 @@ struct MoveMayThrow {
 };
 
 template <class E>
-concept MemberSwapNoexcept =
+concept MemberSwapNoexcept = //
     requires(std::expected<void, E> x, std::expected<void, E> y) {
       { x.swap(y) } noexcept;
     };
@@ -126,6 +126,19 @@ constexpr bool test() {
     assert(s.dtorCalled);
   }
 
+  // TailClobberer
+  {
+    std::expected<void, TailClobbererNonTrivialMove<1>> x(std::in_place);
+    std::expected<void, TailClobbererNonTrivialMove<1>> y(std::unexpect);
+
+    x.swap(y);
+
+    // The next line would fail if adjusting the "has value" flag happened
+    // _before_ constructing the member object inside the `swap`.
+    assert(!x.has_value());
+    assert(y.has_value());
+  }
+
   return true;
 }
 
@@ -160,6 +173,21 @@ void testException() {
       assert(!e2Destroyed);
     }
   }
+
+  // TailClobberer
+  {
+    std::expected<void, TailClobbererNonTrivialMove<0, false, true>> x(std::in_place);
+    std::expected<void, TailClobbererNonTrivialMove<0, false, true>> y(std::unexpect);
+    try {
+      x.swap(y);
+      assert(false);
+    } catch (Except) {
+      // This would fail if `TailClobbererNonTrivialMove<0, false, true>`
+      // clobbered the flag before throwing the exception.
+      assert(x.has_value());
+      assert(!y.has_value());
+    }
+  }
 #endif // TEST_HAS_NO_EXCEPTIONS
 }
 
diff --git a/libcxx/test/std/utilities/expected/types.h b/libcxx/test/std/utilities/expected/types.h
index 7c7e517785b4f7..ac4a82f2baf78b 100644
--- a/libcxx/test/std/utilities/expected/types.h
+++ b/libcxx/test/std/utilities/expected/types.h
@@ -9,7 +9,9 @@
 #ifndef TEST_STD_UTILITIES_EXPECTED_TYPES_H
 #define TEST_STD_UTILITIES_EXPECTED_TYPES_H
 
+#include <cstring>
 #include <utility>
+#include <type_traits>
 #include "test_macros.h"
 
 template <bool copyMoveNoexcept, bool convertNoexcept = true>
@@ -150,4 +152,51 @@ struct MoveOnlyErrorType {
   MoveOnlyErrorType& operator=(const MoveOnlyErrorType&) = delete;
 };
 
+// This type has one byte of tail padding where `std::expected` may put its
+// "has value" flag. The constructor will clobber all bytes including the
+// tail padding. With this type we can check that `std::expected` handles
+// the case where the "has value" flag is an overlapping subobject correctly.
+//
+// See https://github.com/llvm/llvm-project/issues/68552 for details.
+template <int Constant>
+struct TailClobberer {
+  constexpr TailClobberer() noexcept {
+    if (!std::is_constant_evaluated()) {
+      std::memset(this, Constant, sizeof(*this));
+    }
+    // Always set `b` itself to `false` so that the comparison works.
+    b = false;
+  }
+  constexpr TailClobberer(const TailClobberer&) : TailClobberer() {}
+  constexpr TailClobberer(TailClobberer&&) = default;
+  // Converts from `int`/`std::initializer_list<int>, used in some tests.
+  constexpr TailClobberer(int) : TailClobberer() {}
+  constexpr TailClobberer(std::initializer_list<int>) noexcept : TailClobberer() {}
+
+  friend constexpr bool operator==(const TailClobberer&, const TailClobberer&) = default;
+
+  friend constexpr void swap(TailClobberer&, TailClobberer&){};
+
+private:
+  alignas(2) bool b;
+};
+static_assert(!std::is_trivially_copy_constructible_v<TailClobberer<0>>);
+static_assert(std::is_trivially_move_constructible_v<TailClobberer<0>>);
+
+template <int Constant, bool Noexcept = true, bool ThrowOnMove = false>
+struct TailClobbererNonTrivialMove : TailClobberer<Constant> {
+  using TailClobberer<Constant>::TailClobberer;
+  constexpr TailClobbererNonTrivialMove(TailClobbererNonTrivialMove&&) noexcept(Noexcept) : TailClobberer<Constant>() {
+#ifndef TEST_HAS_NO_EXCEPTIONS
+    if constexpr (!Noexcept && ThrowOnMove)
+      throw Except{};
+#endif
+  }
+};
+static_assert(!std::is_trivially_copy_constructible_v<TailClobbererNonTrivialMove<0>>);
+static_assert(std::is_move_constructible_v<TailClobbererNonTrivialMove<0>>);
+static_assert(!std::is_trivially_move_constructible_v<TailClobbererNonTrivialMove<0>>);
+static_assert(std::is_nothrow_move_constructible_v<TailClobbererNonTrivialMove<0, true>>);
+static_assert(!std::is_nothrow_move_constructible_v<TailClobbererNonTrivialMove<0, false>>);
+
 #endif // TEST_STD_UTILITIES_EXPECTED_TYPES_H