diff --git a/stl/inc/chrono b/stl/inc/chrono
index 4a8e089c91a..67593076fb1 100644
--- a/stl/inc/chrono
+++ b/stl/inc/chrono
@@ -1944,65 +1944,75 @@ namespace chrono {
             return _Elapsed_offset;
         }
 
-    private:
-        sys_seconds _Date;
-        bool _Is_positive;
-        seconds _Elapsed_offset;
-    };
+        _NODISCARD friend constexpr bool operator==(const leap_second& _Left, const leap_second& _Right) noexcept {
+            return _Left.date() == _Right.date();
+        }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator==(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return _Left.date() == _Right;
+        }
 
-    _EXPORT_STD _NODISCARD constexpr bool operator==(const leap_second& _Left, const leap_second& _Right) noexcept {
-        return _Left.date() == _Right.date();
-    }
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator==(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return _Left.date() == _Right;
-    }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator<(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return _Left.date() < _Right;
+        }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator<(
+            const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
+            return _Left < _Right.date();
+        }
 
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator<(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return _Left.date() < _Right;
-    }
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator<(const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
-        return _Left < _Right.date();
-    }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator>(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return _Right < _Left.date();
+        }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator>(
+            const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
+            return _Right.date() < _Left;
+        }
 
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator>(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return _Right < _Left.date();
-    }
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator>(const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
-        return _Right.date() < _Left;
-    }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator<=(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return !(_Right < _Left.date());
+        }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator<=(
+            const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
+            return !(_Right.date() < _Left);
+        }
 
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator<=(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return !(_Right < _Left.date());
-    }
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator<=(const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
-        return !(_Right.date() < _Left);
-    }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator>=(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return !(_Left.date() < _Right);
+        }
+        template <class _Duration>
+        _NODISCARD friend constexpr bool operator>=(
+            const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
+            return !(_Left < _Right.date());
+        }
 
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator>=(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return !(_Left.date() < _Right);
-    }
-    _EXPORT_STD template <class _Duration>
-    _NODISCARD constexpr bool operator>=(const sys_time<_Duration>& _Left, const leap_second& _Right) noexcept {
-        return !(_Left < _Right.date());
-    }
+        template <class _Duration>
+            requires three_way_comparable_with<sys_seconds, sys_time<_Duration>>
+        _NODISCARD friend constexpr auto operator<=>(
+            const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
+            return _Left.date() <=> _Right;
+        }
+        _NODISCARD friend constexpr strong_ordering operator<=>(
+            const leap_second& _Left, const leap_second& _Right) noexcept {
+            return _Left.date() <=> _Right.date();
+        }
 
-    _EXPORT_STD template <class _Duration>
-        requires three_way_comparable_with<sys_seconds, sys_time<_Duration>>
-    _NODISCARD constexpr auto operator<=>(const leap_second& _Left, const sys_time<_Duration>& _Right) noexcept {
-        return _Left.date() <=> _Right;
-    }
-    _EXPORT_STD _NODISCARD constexpr strong_ordering operator<=>(
-        const leap_second& _Left, const leap_second& _Right) noexcept {
-        return _Left.date() <=> _Right.date();
-    }
+    private:
+        sys_seconds _Date;
+        bool _Is_positive;
+        seconds _Elapsed_offset;
+    };
 
     // [time.zone.link]
 
diff --git a/tests/std/tests/P0355R7_calendars_and_time_zones_clocks/test.cpp b/tests/std/tests/P0355R7_calendars_and_time_zones_clocks/test.cpp
index a0b24b0b320..eb4812739ba 100644
--- a/tests/std/tests/P0355R7_calendars_and_time_zones_clocks/test.cpp
+++ b/tests/std/tests/P0355R7_calendars_and_time_zones_clocks/test.cpp
@@ -7,10 +7,12 @@
 #include <cmath>
 #include <compare>
 #include <filesystem>
+#include <functional>
 #include <iterator>
 #include <type_traits>
 #include <utility>
 
+#include <is_permissive.hpp>
 #include <timezone_data.hpp>
 
 using namespace std;
@@ -475,6 +477,63 @@ void test() {
     }
 }
 
+// LWG-4139 "[time.zone.leap] recursive constraint in <=>"
+namespace lwg_4139 {
+    struct conv_to_leap_second : local_t {
+        operator leap_second() const noexcept;
+    };
+
+    static_assert(equality_comparable<conv_to_leap_second> == is_permissive);
+    static_assert(equality_comparable_with<conv_to_leap_second, leap_second> == is_permissive);
+    static_assert(totally_ordered<conv_to_leap_second> == is_permissive);
+    static_assert(totally_ordered_with<conv_to_leap_second, leap_second> == is_permissive);
+    static_assert(three_way_comparable<conv_to_leap_second> == is_permissive);
+    static_assert(three_way_comparable_with<conv_to_leap_second, leap_second> == is_permissive);
+
+    using ref_leap_second = reference_wrapper<leap_second>;
+
+    static_assert(equality_comparable<ref_leap_second>);
+    static_assert(equality_comparable_with<ref_leap_second, leap_second>);
+    static_assert(totally_ordered<ref_leap_second>);
+    static_assert(totally_ordered_with<ref_leap_second, leap_second>);
+    static_assert(three_way_comparable<ref_leap_second>);
+    static_assert(three_way_comparable_with<ref_leap_second, leap_second>);
+
+    template <class T, class U>
+    concept can_equality_compare_with = requires(const remove_reference_t<T>& t, const remove_reference_t<U>& u) {
+        t == u;
+        t != u;
+        u == t;
+        u != t;
+    };
+
+    template <class T, class U>
+    concept can_relation_compare_with = requires(const remove_reference_t<T>& t, const remove_reference_t<U>& u) {
+        t < u;
+        t > u;
+        t <= u;
+        t >= u;
+        u < t;
+        u > t;
+        u <= t;
+        u >= t;
+    };
+
+    template <class T, class U>
+    concept can_three_way_compare_with = requires(const remove_reference_t<T>& t, const remove_reference_t<U>& u) {
+        t <=> u;
+        u <=> t;
+    };
+
+    static_assert(!can_equality_compare_with<conv_to_leap_second, sys_seconds>);
+    static_assert(!can_relation_compare_with<conv_to_leap_second, sys_seconds>);
+    static_assert(!can_three_way_compare_with<conv_to_leap_second, sys_seconds>);
+
+    static_assert(can_equality_compare_with<ref_leap_second, sys_seconds>);
+    static_assert(can_relation_compare_with<ref_leap_second, sys_seconds>);
+    static_assert(can_three_way_compare_with<ref_leap_second, sys_seconds>);
+} // namespace lwg_4139
+
 int main() {
     run_tz_test([] { test(); });
 }