diff --git a/bukkit/src/main/java/me/lucko/luckperms/bukkit/WorldCalculator.java b/bukkit/src/main/java/me/lucko/luckperms/bukkit/WorldCalculator.java
index 5d87a6dbc..1a953ed1d 100644
--- a/bukkit/src/main/java/me/lucko/luckperms/bukkit/WorldCalculator.java
+++ b/bukkit/src/main/java/me/lucko/luckperms/bukkit/WorldCalculator.java
@@ -27,8 +27,6 @@ package me.lucko.luckperms.bukkit;
 
 import lombok.RequiredArgsConstructor;
 
-import com.google.common.collect.Maps;
-
 import me.lucko.luckperms.api.context.ContextCalculator;
 import me.lucko.luckperms.api.context.MutableContextSet;
 import me.lucko.luckperms.common.config.ConfigKeys;
@@ -44,11 +42,10 @@ public class WorldCalculator implements ContextCalculator<Player> {
 
     @Override
     public MutableContextSet giveApplicableContext(Player subject, MutableContextSet accumulator) {
-        String world = subject.getWorld().getName();
-        world = plugin.getConfiguration().get(ConfigKeys.WORLD_REWRITES).getOrDefault(world, world);
-
-        if (world != null) {
-            accumulator.add(Maps.immutableEntry(WORLD_KEY, world.toLowerCase()));
+        String world = subject.getWorld().getName().toLowerCase();
+        while (!accumulator.has(WORLD_KEY, world)) {
+            accumulator.add(WORLD_KEY, world);
+            world = plugin.getConfiguration().get(ConfigKeys.WORLD_REWRITES).getOrDefault(world, world).toLowerCase();
         }
 
         return accumulator;
diff --git a/bungee/src/main/java/me/lucko/luckperms/bungee/BackendServerCalculator.java b/bungee/src/main/java/me/lucko/luckperms/bungee/BackendServerCalculator.java
index dac61606e..c6f806aae 100644
--- a/bungee/src/main/java/me/lucko/luckperms/bungee/BackendServerCalculator.java
+++ b/bungee/src/main/java/me/lucko/luckperms/bungee/BackendServerCalculator.java
@@ -25,13 +25,16 @@
 
 package me.lucko.luckperms.bungee;
 
-import com.google.common.collect.Maps;
+import lombok.RequiredArgsConstructor;
 
 import me.lucko.luckperms.api.context.ContextCalculator;
 import me.lucko.luckperms.api.context.MutableContextSet;
+import me.lucko.luckperms.common.config.ConfigKeys;
+import me.lucko.luckperms.common.plugin.LuckPermsPlugin;
 
 import net.md_5.bungee.api.connection.ProxiedPlayer;
 
+@RequiredArgsConstructor
 public class BackendServerCalculator implements ContextCalculator<ProxiedPlayer> {
     private static final String WORLD_KEY = "world";
 
@@ -39,12 +42,14 @@ public class BackendServerCalculator implements ContextCalculator<ProxiedPlayer>
         return player.getServer() == null ? null : (player.getServer().getInfo() == null ? null : player.getServer().getInfo().getName());
     }
 
+    private final LuckPermsPlugin plugin;
+
     @Override
     public MutableContextSet giveApplicableContext(ProxiedPlayer subject, MutableContextSet accumulator) {
         String server = getServer(subject);
-
-        if (server != null) {
-            accumulator.add(Maps.immutableEntry(WORLD_KEY, server.toLowerCase()));
+        while (server != null && !accumulator.has(WORLD_KEY, server)) {
+            accumulator.add(WORLD_KEY, server);
+            server = plugin.getConfiguration().get(ConfigKeys.WORLD_REWRITES).getOrDefault(server, server);
         }
 
         return accumulator;
diff --git a/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java b/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java
index 89769f529..299d08025 100644
--- a/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java
+++ b/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java
@@ -218,7 +218,7 @@ public class LPBungeePlugin extends Plugin implements LuckPermsPlugin {
         cachedStateManager = new CachedStateManager(this);
 
         contextManager = new ContextManager<>();
-        BackendServerCalculator serverCalculator = new BackendServerCalculator();
+        BackendServerCalculator serverCalculator = new BackendServerCalculator(this);
         contextManager.registerCalculator(serverCalculator);
 
         StaticCalculator<ProxiedPlayer> staticCalculator = new StaticCalculator<>(getConfiguration());
diff --git a/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java b/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java
index f4c062c27..029628a86 100644
--- a/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java
+++ b/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java
@@ -267,7 +267,7 @@ public class LPSpongePlugin implements LuckPermsPlugin {
         cachedStateManager = new CachedStateManager(this);
 
         contextManager = new ContextManager<>();
-        contextManager.registerCalculator(new WorldCalculator());
+        contextManager.registerCalculator(new WorldCalculator(this));
 
         StaticCalculator<Subject> staticCalculator = new StaticCalculator<>(getConfiguration());
         contextManager.registerCalculator(staticCalculator);
diff --git a/sponge/src/main/java/me/lucko/luckperms/sponge/contexts/WorldCalculator.java b/sponge/src/main/java/me/lucko/luckperms/sponge/contexts/WorldCalculator.java
index 460cf1ddf..0ccc4c93e 100644
--- a/sponge/src/main/java/me/lucko/luckperms/sponge/contexts/WorldCalculator.java
+++ b/sponge/src/main/java/me/lucko/luckperms/sponge/contexts/WorldCalculator.java
@@ -29,14 +29,18 @@ import lombok.RequiredArgsConstructor;
 
 import me.lucko.luckperms.api.context.ContextCalculator;
 import me.lucko.luckperms.api.context.MutableContextSet;
+import me.lucko.luckperms.common.config.ConfigKeys;
+import me.lucko.luckperms.common.plugin.LuckPermsPlugin;
 
 import org.spongepowered.api.command.CommandSource;
 import org.spongepowered.api.entity.living.player.Player;
-import org.spongepowered.api.service.context.Context;
 import org.spongepowered.api.service.permission.Subject;
 
 @RequiredArgsConstructor
 public class WorldCalculator implements ContextCalculator<Subject> {
+    private static final String WORLD_KEY = "world";
+
+    private final LuckPermsPlugin plugin;
 
     @Override
     public MutableContextSet giveApplicableContext(Subject subject, MutableContextSet accumulator) {
@@ -46,7 +50,12 @@ public class WorldCalculator implements ContextCalculator<Subject> {
         }
 
         Player p = ((Player) source);
-        accumulator.add(Context.WORLD_KEY, p.getWorld().getName().toLowerCase());
+        String world = p.getWorld().getName().toLowerCase();
+        while (!accumulator.has(WORLD_KEY, world)) {
+            accumulator.add(WORLD_KEY, world);
+            world = plugin.getConfiguration().get(ConfigKeys.WORLD_REWRITES).getOrDefault(world, world).toLowerCase();
+        }
+
         return accumulator;
     }