diff --git a/lib/CMakeLists.txt b/lib/CMakeLists.txt
index 29cbf1e6..869d269d 100644
--- a/lib/CMakeLists.txt
+++ b/lib/CMakeLists.txt
@@ -13,6 +13,7 @@ endif ()
 
 add_library(libpl ${LIBRARY_TYPE}
         source/pl/helpers/utils.cpp
+        source/pl/helpers/sort_checks.cpp
 
         source/pl/pattern_language.cpp
 
diff --git a/lib/include/pl/core/token.hpp b/lib/include/pl/core/token.hpp
index 5c9198e4..e274d914 100644
--- a/lib/include/pl/core/token.hpp
+++ b/lib/include/pl/core/token.hpp
@@ -220,8 +220,10 @@ namespace pl::core {
             constexpr bool operator==(const Comment &) const = default;
         };
 
+        using LiteralVariantType = std::variant<char, bool, u128, i128, double, std::string, std::shared_ptr<ptrn::Pattern>>;
 
-        struct Literal : std::variant<char, bool, u128, i128, double, std::string, std::shared_ptr<ptrn::Pattern>> {
+
+        struct Literal : LiteralVariantType {
             using variant::variant;
 
             [[nodiscard]] std::shared_ptr<ptrn::Pattern> toPattern() const;
diff --git a/lib/include/pl/helpers/sort_checks.hpp b/lib/include/pl/helpers/sort_checks.hpp
new file mode 100644
index 00000000..74a51466
--- /dev/null
+++ b/lib/include/pl/helpers/sort_checks.hpp
@@ -0,0 +1,139 @@
+#pragma once
+
+//#define ENABLE_STD_SORT_CHECKS
+
+#ifdef ENABLE_STD_SORT_CHECKS
+#include <cstddef>
+#endif
+
+#include <algorithm>
+
+namespace  pl::hlp {
+
+#ifdef ENABLE_STD_SORT_CHECKS
+
+void sortPredicateError(const char *pMsg);
+void transitivityError(const char *pMsg, std::size_t b_idx, std::size_t e_idx, std::size_t x_idx, std::size_t y_idx);
+
+// Logical implication
+inline bool imp(bool l, bool r) {
+    return !(l && !r);
+}
+
+template <typename Predicate>
+auto checked_pedicate(const Predicate pred) {
+    return [=](const auto &l, const auto &r) {
+        // Irreflexivity: !(x<x)
+        if (pred(l,l))
+            sortPredicateError("Irreflexivity: pred(l,l) is false");
+        if (pred(r,r))
+            sortPredicateError("Irreflexivity: pred(r,r) is false");
+
+        // Asymmetry: if l<r not r<l
+        if (!imp(pred(l,r), !pred(r,l)))
+            sortPredicateError("Asymmetry: if pred(l,r) then !pred(r,l) is false");
+        if (!imp(pred(r,l), !pred(l,r)))
+            sortPredicateError("Asymmetry: if pred(r,l) then !pred(l,r) is false");
+
+        return pred(l, r);
+    };
+}
+
+namespace impl {
+
+// Transitivity:
+// For all x,y.z in [b, e)
+//  if pred(x,y) and pred(y,z) are true then pred(x,z) is true
+//
+// All elements in [b, e) should have already been sorted so
+// b[n]<b[n+1]. We'll assume this even though with a dogy predicate
+// it may not be the case.
+template <typename Iter, typename Predicate>
+void transitivity(const Iter cb, const Iter b, const Iter e, const Predicate pred)
+{
+    for (Iter l=b; l<e-2; ++l) {
+        for (Iter r=l+2; r<e; ++r) {
+            if (!pred(*l, *r)) {
+                transitivityError("Transitivity", b-cb, e-cb-1, l-cb, r-cb);
+                // For all x (at index n) in [b, e-1): 
+                //  pred(b[n], b[n+1]) == true
+                // pred(*l, *r) returned false however. This is in violation
+                // of a strict weak ordering.
+            }
+        }
+    }
+}
+
+// For all x,y.z in [b, e)
+//  if !pred(x,y) && !pred(y,x) && !pred(y,z) && !pred(z,y)
+//  then
+//  !pred(x,z) && !pred(z,x)
+//
+// Incomparability is perhaps better undersood as equality.
+template <typename Iter, typename Predicate>
+void transitivity_of_incomparability(const Iter cb, const Iter b, const Iter e, const Predicate pred)
+{
+    for (Iter l=b; l<e-2; ++l) {
+        for (Iter r=l+2; r<e; ++r) {
+            if (!(!pred(*l, *r) && !pred(*r, *l))) {
+                transitivityError("Transitivity of incomparability", b-cb, e-cb-1, l-cb, r-cb);
+                // For all x (at index n) in [b, e-1): 
+                //  pred(b[n], b[n+1]) == false && pred(b[n+1], b[n]) == false
+                // (!pred(*l, *r) && !pred(*r, *l)) returned false however. This is in violation
+                // of a strict weak ordering.
+            }
+        }
+    }
+}
+
+} // namespace impl
+
+template <typename Iter, typename Predicate>
+void post_sort_check(const Iter b, const Iter e, const Predicate pred) {
+    if (b==e)
+        return;
+
+    for (Iter l=b; l<e-1;) {
+        if (pred(*l, *(l+1))) {
+            Iter r = l+1;
+            for (; r<e-1 && pred(*r, *(r+1)); ++r) {}
+            impl::transitivity(b, l, r+1, pred);
+            l = r;
+        } else if (!pred(*(l+1), *l)) {
+            Iter r = l+1;
+            for (; r<e-1 && !pred(*(r+1), *r) && !pred(*r, *(r+1)); ++r) {}
+            impl::transitivity_of_incomparability(b, l, r+1, pred);
+            l = r;
+        }
+        else {
+            // !pred(*l, *(l+1)) && pred(*(l+1), *l)
+            // So l>=r && l>r
+            sortPredicateError("Not sorted"); // NOT sorted!
+            ++l;
+        }
+    }
+}
+
+#endif // ENABLE_STD_SORT_CHECKS
+
+template<typename RandomIt, typename Compare>
+void checked_sort(RandomIt first, RandomIt last, Compare comp) {
+#ifdef ENABLE_STD_SORT_CHECKS
+    std::sort(first, last, checked_pedicate(comp));
+    post_sort_check(first, last, comp);
+#else
+    std::sort(first, last, comp);
+#endif
+}
+
+template<typename RandomIt, typename Compare>
+void checked_stable_sort(RandomIt first, RandomIt last, Compare comp) {
+#ifdef ENABLE_STD_SORT_CHECKS
+    std::stable_sort(first, last, checked_pedicate(comp));
+    post_sort_check(first, last, comp);
+#else
+    std::stable_sort(first, last, comp);
+#endif
+}
+
+} // namespace pl::hlp
diff --git a/lib/include/pl/helpers/variant_type_index.hpp b/lib/include/pl/helpers/variant_type_index.hpp
new file mode 100644
index 00000000..5252edcf
--- /dev/null
+++ b/lib/include/pl/helpers/variant_type_index.hpp
@@ -0,0 +1,31 @@
+#pragma once
+
+#include <variant>
+#include <type_traits>
+#include <cstddef>
+
+namespace pl::hlp {
+
+template<typename T, typename Variant>
+struct variant_type_index;
+
+template<typename T, typename... Ts>
+struct variant_type_index<T, std::variant<Ts...>> {
+    static constexpr auto value = [] -> std::size_t {
+        static_assert(
+            (std::is_same_v<std::remove_cvref_t<T>, Ts> || ...),
+            "T not in std::variant");
+        constexpr bool matches[] = { std::is_same_v<std::remove_cvref_t<T>, Ts>... };
+
+        for (std::size_t i=0; i<sizeof...(Ts); ++i) {
+            if (matches[i]) { return i; }
+        }
+
+        return -1;
+    }();
+};
+
+template<class T, class Variant>
+inline constexpr std::size_t variant_type_index_v = variant_type_index<T, Variant>::value;
+
+} // namespace pl::hlp
\ No newline at end of file
diff --git a/lib/include/pl/patterns/pattern_bitfield.hpp b/lib/include/pl/patterns/pattern_bitfield.hpp
index 8cedee67..cc6d113f 100644
--- a/lib/include/pl/patterns/pattern_bitfield.hpp
+++ b/lib/include/pl/patterns/pattern_bitfield.hpp
@@ -2,6 +2,7 @@
 
 #include <pl/patterns/pattern.hpp>
 #include <pl/patterns/pattern_enum.hpp>
+#include <pl/helpers/sort_checks.hpp>
 
 namespace pl::ptrn {
 
@@ -497,7 +498,7 @@ namespace pl::ptrn {
             for (auto &member : this->m_entries)
                 this->m_sortedEntries.push_back(member.get());
 
-            std::sort(this->m_sortedEntries.begin(), this->m_sortedEntries.end(), comparator);
+            pl::hlp::checked_sort(this->m_sortedEntries.begin(), this->m_sortedEntries.end(), comparator);
             if (this->isReversed())
                 std::reverse(this->m_sortedEntries.begin(), this->m_sortedEntries.end());
 
@@ -774,7 +775,7 @@ namespace pl::ptrn {
             for (auto &member : this->m_fields)
                 this->m_sortedFields.push_back(member.get());
 
-            std::sort(this->m_sortedFields.begin(), this->m_sortedFields.end(), comparator);
+            pl::hlp::checked_sort(this->m_sortedFields.begin(), this->m_sortedFields.end(), comparator);
             if (this->isReversed())
                 std::reverse(this->m_sortedFields.begin(), this->m_sortedFields.end());
 
diff --git a/lib/include/pl/patterns/pattern_struct.hpp b/lib/include/pl/patterns/pattern_struct.hpp
index 900d517c..b0e2ca6b 100644
--- a/lib/include/pl/patterns/pattern_struct.hpp
+++ b/lib/include/pl/patterns/pattern_struct.hpp
@@ -1,6 +1,7 @@
 #pragma once
 
 #include <pl/patterns/pattern.hpp>
+#include <pl/helpers/sort_checks.hpp>
 
 namespace pl::ptrn {
 
@@ -160,8 +161,7 @@ namespace pl::ptrn {
             for (auto &member : this->m_members)
                 this->m_sortedMembers.push_back(member.get());
 
-            std::sort(this->m_sortedMembers.begin(), this->m_sortedMembers.end(), comparator);
-
+            pl::hlp::checked_sort(this->m_sortedMembers.begin(), this->m_sortedMembers.end(), comparator);
             for (auto &member : this->m_sortedMembers)
                 member->sort(comparator);
         }
diff --git a/lib/include/pl/patterns/pattern_union.hpp b/lib/include/pl/patterns/pattern_union.hpp
index a38be0f7..a911a5ba 100644
--- a/lib/include/pl/patterns/pattern_union.hpp
+++ b/lib/include/pl/patterns/pattern_union.hpp
@@ -1,6 +1,7 @@
 #pragma once
 
 #include <pl/patterns/pattern.hpp>
+#include <pl/helpers/sort_checks.hpp>
 
 namespace pl::ptrn {
 
@@ -159,7 +160,7 @@ namespace pl::ptrn {
             for (auto &member : this->m_members)
                 this->m_sortedMembers.push_back(member.get());
 
-            std::sort(this->m_sortedMembers.begin(), this->m_sortedMembers.end(), comparator);
+            pl::hlp::checked_sort(this->m_sortedMembers.begin(), this->m_sortedMembers.end(), comparator);
 
             for (auto &member : this->m_members)
                 member->sort(comparator);
diff --git a/lib/source/pl/core/token.cpp b/lib/source/pl/core/token.cpp
index 3bbddfe6..b8078423 100644
--- a/lib/source/pl/core/token.cpp
+++ b/lib/source/pl/core/token.cpp
@@ -5,6 +5,7 @@
 
 #include <pl/helpers/utils.hpp>
 #include <pl/helpers/concepts.hpp>
+#include <pl/helpers/variant_type_index.hpp>
 #include <variant>
 
 namespace pl::core {
@@ -160,8 +161,8 @@ namespace pl::core {
                     return std::strong_ordering::greater;
                 }
             },
-            [](auto, auto) -> std::strong_ordering {
-                return std::strong_ordering::equal;
+            []<typename TL, typename TR>(TL, TR) -> std::strong_ordering {
+                return hlp::variant_type_index_v<TL, LiteralVariantType> <=> hlp::variant_type_index_v<TR, LiteralVariantType>;
             }
         }, *this, other);
     }
diff --git a/lib/source/pl/helpers/sort_checks.cpp b/lib/source/pl/helpers/sort_checks.cpp
new file mode 100644
index 00000000..e92c8f45
--- /dev/null
+++ b/lib/source/pl/helpers/sort_checks.cpp
@@ -0,0 +1,25 @@
+#include <pl/helpers/sort_checks.hpp>
+
+#ifdef ENABLE_STD_SORT_CHECKS
+#include <cstddef>
+#include <iostream>
+
+using std::size_t;
+using std::cout;
+using std::endl;
+
+namespace pl::hlp {
+
+void sortPredicateError(const char *pMsg) {
+    cout << pMsg << endl;
+}
+
+void transitivityError(const char *pMsg, size_t b_idx, size_t e_idx, size_t x_idx, size_t y_idx) {
+    cout << pMsg << endl
+         << "   Run: " << "b_idx=" << b_idx << ", e_idx=" << e_idx << endl
+         << "   Error: " << "x_idx=" << x_idx << ", y_idx=" << y_idx << endl;
+}
+
+} // namespace pl::hlp
+
+#endif // ENABLE_STD_SORT_CHECKS