diff --git a/src/main/java/org/mvplugins/multiverse/core/permissions/CorePermissions.java b/src/main/java/org/mvplugins/multiverse/core/permissions/CorePermissions.java
index 54060ced7..102fce8ac 100644
--- a/src/main/java/org/mvplugins/multiverse/core/permissions/CorePermissions.java
+++ b/src/main/java/org/mvplugins/multiverse/core/permissions/CorePermissions.java
@@ -13,6 +13,7 @@
 import org.mvplugins.multiverse.core.world.MultiverseWorld;
 
 import static org.mvplugins.multiverse.core.permissions.PermissionUtils.concatPermission;
+import static org.mvplugins.multiverse.core.permissions.PermissionUtils.registerPermissionWithWildcards;
 
 @Service
 public final class CorePermissions {
@@ -60,28 +61,34 @@ public final class CorePermissions {
 
     @PostConstruct
     void registerBasePermissions() {
-        pluginManager.addPermission(new Permission(JOINLOCATION_BYPASS, PermissionDefault.FALSE));
-        Logging.fine("Successfully registered base permissions");
+        Try.run(() -> {
+            registerPermissionWithWildcards(new Permission(JOINLOCATION_BYPASS, PermissionDefault.FALSE));
+        }).onSuccess(ignore -> {
+            Logging.fine("Successfully registered base permissions");
+        }).onFailure(e -> {
+            Logging.fine("Failed to register base permissions: %s", e.getMessage());
+        });
     }
 
     public Try<Void> addWorldPermissions(@NotNull MultiverseWorld world) {
         return Try.run(() -> {
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(WORLD_ACCESS, world.getName()), PermissionDefault.OP));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(WORLD_EXEMPT, world.getName()), PermissionDefault.OP));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(GAMEMODE_BYPASS, world.getName()), PermissionDefault.FALSE));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(PLAYERLIMIT_BYPASS, world.getName()), PermissionDefault.FALSE));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(SPAWN, world.getName()), PermissionDefault.OP));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(SPAWN, "self", world.getName()), PermissionDefault.OP));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(SPAWN, "other", world.getName()), PermissionDefault.OP));
             Logging.fine("Successfully registered permissions for world %s", world.getName());
-        });
+        }).onFailure(e -> Logging.fine("Failed to register permissions for world %s: %s",
+                world.getName(), e.getMessage()));
     }
 
     public Try<Void> removeWorldPermissions(@NotNull MultiverseWorld world) {
@@ -90,20 +97,23 @@ public Try<Void> removeWorldPermissions(@NotNull MultiverseWorld world) {
             pluginManager.removePermission(concatPermission(WORLD_EXEMPT, world.getName()));
             pluginManager.removePermission(concatPermission(GAMEMODE_BYPASS, world.getName()));
             pluginManager.removePermission(concatPermission(PLAYERLIMIT_BYPASS, world.getName()));
+            pluginManager.removePermission(concatPermission(SPAWN, world.getName()));
             pluginManager.removePermission(concatPermission(SPAWN, "self", world.getName()));
             pluginManager.removePermission(concatPermission(SPAWN, "other", world.getName()));
             Logging.fine("Successfully removed permissions for world %s", world.getName());
-        });
+        }).onFailure(e -> Logging.fine("Failed to remove permissions for world %s: %s",
+                world.getName(), e.getMessage()));
     }
 
     public Try<Void> addDestinationPermissions(@NotNull Destination destination) {
         return Try.run(() -> {
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(TELEPORT, "self", destination.getIdentifier()), PermissionDefault.OP));
-            pluginManager.addPermission(new Permission(
+            registerPermissionWithWildcards(new Permission(
                     concatPermission(TELEPORT, "other", destination.getIdentifier()), PermissionDefault.OP));
             Logging.fine("Successfully registered permissions for destination %s", destination.getIdentifier());
-        });
+        }).onFailure(e -> Logging.fine("Failed to register permissions for destination %s: %s",
+                destination.getIdentifier(), e.getMessage()));
     }
 
     public Try<Void> removeDestinationPermissions(@NotNull Destination destination) {
@@ -111,6 +121,7 @@ public Try<Void> removeDestinationPermissions(@NotNull Destination destination)
             pluginManager.removePermission(concatPermission(TELEPORT, "self", destination.getIdentifier()));
             pluginManager.removePermission(concatPermission(TELEPORT, "other", destination.getIdentifier()));
             Logging.fine("Successfully removed permissions for destination %s", destination.getIdentifier());
-        });
+        }).onFailure(e -> Logging.fine("Failed to remove permissions for destination %s: %s",
+                destination.getIdentifier(), e.getMessage()));
     }
 }
diff --git a/src/main/java/org/mvplugins/multiverse/core/permissions/PermissionUtils.java b/src/main/java/org/mvplugins/multiverse/core/permissions/PermissionUtils.java
index 97a707cbb..55cd65a05 100644
--- a/src/main/java/org/mvplugins/multiverse/core/permissions/PermissionUtils.java
+++ b/src/main/java/org/mvplugins/multiverse/core/permissions/PermissionUtils.java
@@ -1,8 +1,14 @@
 package org.mvplugins.multiverse.core.permissions;
 
 import com.dumptruckman.minecraft.util.Logging;
+import org.bukkit.Bukkit;
 import org.bukkit.command.CommandSender;
 import org.bukkit.command.ConsoleCommandSender;
+import org.bukkit.permissions.Permission;
+import org.bukkit.permissions.PermissionDefault;
+import org.jetbrains.annotations.ApiStatus;
+
+import java.util.Arrays;
 
 public final class PermissionUtils {
 
@@ -20,6 +26,37 @@ public static void setDebugPermissions(boolean debugPermissions) {
         PermissionUtils.debugPermissions = debugPermissions;
     }
 
+    /**
+     * Registers a permission along with all its wildcard parents.
+     * <br />
+     * For example, registering "mv.bypass.joinlocation" will also register "mv.*" and "mv.bypass.*" as parents.
+     *
+     * @param permission    The permission to register.
+     *
+     * @since 5.4
+     */
+    @ApiStatus.AvailableSince("5.4")
+    public static void registerPermissionWithWildcards(Permission permission) {
+        Bukkit.getServer().getPluginManager().addPermission(permission);
+        String[] split = permission.getName().split("\\.");
+        StringBuilder prefix = new StringBuilder();
+        // Skip the last element since it's the actual permission
+        Arrays.stream(Arrays.copyOfRange(split, 0, split.length - 1)).forEach(s -> {
+            prefix.append(s).append(".");
+            Permission perm = getOrAddPermission(prefix + "*");
+            permission.addParent(perm, true);
+        });
+    }
+
+    private static Permission getOrAddPermission(String permission) {
+        Permission perm = Bukkit.getServer().getPluginManager().getPermission(permission);
+        if (perm == null) {
+            perm = new Permission(permission, PermissionDefault.FALSE);
+            Bukkit.getServer().getPluginManager().addPermission(perm);
+        }
+        return perm;
+    }
+
     /**
      * Joins permissions with a dot.
      *