diff --git a/common/src/main/java/me/lucko/luckperms/common/api/delegate/PermissionHolderDelegate.java b/common/src/main/java/me/lucko/luckperms/common/api/delegate/PermissionHolderDelegate.java
index 9b99da4be..16de2565a 100644
--- a/common/src/main/java/me/lucko/luckperms/common/api/delegate/PermissionHolderDelegate.java
+++ b/common/src/main/java/me/lucko/luckperms/common/api/delegate/PermissionHolderDelegate.java
@@ -68,7 +68,7 @@ public class PermissionHolderDelegate implements PermissionHolder {
 
     @Override
     public SortedSet<? extends Node> getPermissions() {
-        return ImmutableSortedSet.copyOf(master.getPermissions(false));
+        return ImmutableSortedSet.copyOfSorted(master.getPermissions(false));
     }
 
     @Override
diff --git a/common/src/main/java/me/lucko/luckperms/common/data/Log.java b/common/src/main/java/me/lucko/luckperms/common/data/Log.java
index d714381d0..59bd3dea4 100644
--- a/common/src/main/java/me/lucko/luckperms/common/data/Log.java
+++ b/common/src/main/java/me/lucko/luckperms/common/data/Log.java
@@ -83,7 +83,7 @@ public class Log {
     private final SortedSet<LogEntry> content;
 
     public Log(SortedSet<LogEntry> content) {
-        this.content = ImmutableSortedSet.copyOf(content);
+        this.content = ImmutableSortedSet.copyOfSorted(content);
     }
 
     public SortedSet<LogEntry> getRecent() {