diff --git a/common/src/main/java/me/lucko/luckperms/common/core/PriorityComparator.java b/common/src/main/java/me/lucko/luckperms/common/core/PriorityComparator.java
index 63ef62eac..265f2cab9 100644
--- a/common/src/main/java/me/lucko/luckperms/common/core/PriorityComparator.java
+++ b/common/src/main/java/me/lucko/luckperms/common/core/PriorityComparator.java
@@ -40,7 +40,7 @@ import java.util.Locale;
 @NoArgsConstructor(access = AccessLevel.PRIVATE)
 public class PriorityComparator implements Comparator<LocalizedNode> {
     private static final PriorityComparator INSTANCE = new PriorityComparator();
-    public static Comparator<LocalizedNode> get() {
+    public static PriorityComparator get() {
         return INSTANCE;
     }
     public static Comparator<LocalizedNode> reverse() {
@@ -97,14 +97,17 @@ public class PriorityComparator implements Comparator<LocalizedNode> {
             return o1.getWildcardLevel() > o2.getWildcardLevel() ? 1 : -1;
         }
 
+        return compareStrings(o1.getPermission(), o2.getPermission()) == 1 ? -1 : 1;
+    }
+
+    public int compareStrings(String o1, String o2) {
         try {
-            CollationKey o1c = collationKeyCache.get(o1.getPermission());
-            CollationKey o2c = collationKeyCache.get(o2.getPermission());
-            return o1c.compareTo(o2c) == 1 ? -1 : 1;
+            CollationKey o1c = collationKeyCache.get(o1);
+            CollationKey o2c = collationKeyCache.get(o2);
+            return o1c.compareTo(o2c) == 1 ? 1 : -1;
         } catch (Exception e) {
             // ignored
         }
-
         return 1;
     }
 }
diff --git a/common/src/main/java/me/lucko/luckperms/common/core/model/PermissionHolder.java b/common/src/main/java/me/lucko/luckperms/common/core/model/PermissionHolder.java
index 4f67d03ab..3f8a93706 100644
--- a/common/src/main/java/me/lucko/luckperms/common/core/model/PermissionHolder.java
+++ b/common/src/main/java/me/lucko/luckperms/common/core/model/PermissionHolder.java
@@ -75,6 +75,7 @@ import java.util.Optional;
 import java.util.OptionalInt;
 import java.util.Set;
 import java.util.SortedSet;
+import java.util.TreeMap;
 import java.util.TreeSet;
 import java.util.concurrent.ConcurrentHashMap;
 import java.util.concurrent.TimeUnit;
@@ -1166,7 +1167,7 @@ public abstract class PermissionHolder {
     }
 
     public static Map<String, Boolean> exportToLegacy(Set<Node> nodes) {
-        Map<String, Boolean> m = new HashMap<>();
+        Map<String, Boolean> m = new TreeMap<>((o1, o2) -> PriorityComparator.get().compareStrings(o1, o2));
         for (Node node : nodes) {
             m.put(node.toSerializedNode(), node.getValue());
         }