diff --git a/.locale/en_US.yml b/.locale/en_US.yml
index ce23a897..e0e92a25 100644
--- a/.locale/en_US.yml
+++ b/.locale/en_US.yml
@@ -9,7 +9,7 @@ log-error: "&7&l[&bLuck&3Perms&7&l] &4[ERROR] {0}"
 empty: "{0}"
 player-online: "&aOnline"
 player-offline: "&cOffline"
-loading-error: "Permissions data could not be loaded. Please contact an administrator."
+loading-error: "Permissions data could not be loaded. Please try again later."
 op-disabled: "&bThe vanilla OP system is disabled on this server."
 op-disabled-sponge: "&2Server Operator status has no effect when a permission plugin is installed. Please edit user data directly."
 log: "&3LOG &3&l> {0}"
diff --git a/bukkit/src/main/java/me/lucko/luckperms/bukkit/BukkitListener.java b/bukkit/src/main/java/me/lucko/luckperms/bukkit/BukkitListener.java
index 5d9ff17b..36da2046 100644
--- a/bukkit/src/main/java/me/lucko/luckperms/bukkit/BukkitListener.java
+++ b/bukkit/src/main/java/me/lucko/luckperms/bukkit/BukkitListener.java
@@ -22,12 +22,15 @@
 
 package me.lucko.luckperms.bukkit;
 
+import lombok.RequiredArgsConstructor;
+
 import me.lucko.luckperms.bukkit.model.Injector;
 import me.lucko.luckperms.bukkit.model.LPPermissible;
+import me.lucko.luckperms.common.caching.UserCache;
 import me.lucko.luckperms.common.config.ConfigKeys;
 import me.lucko.luckperms.common.constants.Message;
 import me.lucko.luckperms.common.core.model.User;
-import me.lucko.luckperms.common.utils.AbstractListener;
+import me.lucko.luckperms.common.utils.LoginHelper;
 
 import org.bukkit.entity.Player;
 import org.bukkit.event.EventHandler;
@@ -39,62 +42,78 @@ import org.bukkit.event.player.PlayerCommandPreprocessEvent;
 import org.bukkit.event.player.PlayerLoginEvent;
 import org.bukkit.event.player.PlayerQuitEvent;
 import org.bukkit.event.server.PluginEnableEvent;
-import org.bukkit.scheduler.BukkitTask;
 
 import java.util.Collections;
-import java.util.HashMap;
 import java.util.HashSet;
-import java.util.Map;
 import java.util.Set;
 import java.util.UUID;
 
-class BukkitListener extends AbstractListener implements Listener {
+@RequiredArgsConstructor
+public class BukkitListener implements Listener {
     private final LPBukkitPlugin plugin;
 
     private final Set<UUID> deniedAsyncLogin = Collections.synchronizedSet(new HashSet<>());
-    private final Set<UUID> deniedLogin = new HashSet<>();
-
-    private final Map<UUID, BukkitTask> cleanupTasks = Collections.synchronizedMap(new HashMap<>());
-
-    BukkitListener(LPBukkitPlugin plugin) {
-        super(plugin);
-        this.plugin = plugin;
-    }
+    private final Set<UUID> deniedLogin = Collections.synchronizedSet(new HashSet<>());
 
     @EventHandler(priority = EventPriority.LOW)
     public void onPlayerPreLogin(AsyncPlayerPreLoginEvent e) {
+        /* Called when the player first attempts a connection with the server.
+           Listening on LOW priority to allow plugins to modify username / UUID data here. (auth plugins) */
+
+        /* the player was denied entry to the server before this priority.
+           log this, so we can handle appropriately later. */
         if (e.getLoginResult() != AsyncPlayerPreLoginEvent.Result.ALLOWED) {
+            plugin.getLog().warn("Connection from " + e.getUniqueId() + " was already denied. No permissions data will be loaded.");
             deniedAsyncLogin.add(e.getUniqueId());
             return;
         }
 
+        /* either the plugin hasn't finished starting yet, or there was an issue connecting to the DB, performing file i/o, etc.
+           we don't let players join in this case, because it means they can connect to the server without their permissions data.
+           some server admins rely on negating perms to stop users from causing damage etc, so it's really important that
+           this data is loaded. */
         if (!plugin.isStarted() || !plugin.getStorage().isAcceptingLogins()) {
+
+            // log that the user tried to login, but was denied at this stage.
             deniedAsyncLogin.add(e.getUniqueId());
 
-            // The datastore is disabled, prevent players from joining the server
-            plugin.getLog().warn("The plugin storage is not loaded. Denying connection from: " + e.getUniqueId() + " - " + e.getName());
-            e.disallow(AsyncPlayerPreLoginEvent.Result.KICK_OTHER, Message.LOADING_ERROR.toString());
+            // actually deny the connection.
+            plugin.getLog().warn("Permissions storage is not loaded yet. Denying connection from: " + e.getUniqueId() + " - " + e.getName());
+            e.disallow(AsyncPlayerPreLoginEvent.Result.KICK_OTHER, Message.LOADING_ERROR.asString(plugin.getLocaleManager()));
             return;
         }
 
-        // remove any pending cleanup tasks
-        BukkitTask task = cleanupTasks.remove(e.getUniqueId());
-        if (task != null) {
-            task.cancel();
-        }
+        /* Actually process the login for the connection.
+           We do this here to delay the login until the data is ready.
+           If the login gets cancelled later on, then this will be cleaned up.
 
-        // Process login
-        onAsyncLogin(e.getUniqueId(), e.getName());
+           This includes:
+           - loading uuid data
+           - loading permissions
+           - creating a user instance in the UserManager for this connection.
+           - setting up cached data. */
+        try {
+            LoginHelper.loadUser(plugin, e.getUniqueId(), e.getName());
+        } catch (Exception ex) {
+            ex.printStackTrace();
+
+            // there was some error loading data. deny the connection
+            deniedAsyncLogin.add(e.getUniqueId());
+            e.disallow(AsyncPlayerPreLoginEvent.Result.KICK_OTHER, Message.LOADING_ERROR.asString(plugin.getLocaleManager()));
+        }
     }
 
-    @EventHandler(priority = EventPriority.HIGHEST)
+    @EventHandler(priority = EventPriority.MONITOR)
     public void onPlayerPreLoginMonitor(AsyncPlayerPreLoginEvent e) {
-        // If they were denied before/at LOW, then don't bother handling here.
+        /* Listen to see if the event was cancelled after we initially handled the connection
+           If the connection was cancelled here, we need to do something to clean up the data that was loaded. */
+
+        // Check to see if this connection was denied at LOW.
         if (deniedAsyncLogin.remove(e.getUniqueId())) {
 
-            // this is a problem, as they were denied at low priority, but are now being allowed.
+            // This is a problem, as they were denied at low priority, but are now being allowed.
             if (e.getLoginResult() == AsyncPlayerPreLoginEvent.Result.ALLOWED) {
-                new IllegalStateException("Player connection was re-allowed for " + e.getUniqueId()).printStackTrace();
+                plugin.getLog().severe("Player connection was re-allowed for " + e.getUniqueId());
                 e.disallow(AsyncPlayerPreLoginEvent.Result.KICK_OTHER, "");
             }
 
@@ -102,14 +121,22 @@ class BukkitListener extends AbstractListener implements Listener {
         }
 
         // Login event was cancelled by another plugin
-        if (plugin.isStarted() && plugin.getStorage().isAcceptingLogins() && e.getLoginResult() != AsyncPlayerPreLoginEvent.Result.ALLOWED) {
-            cleanupUser(e.getUniqueId());
+        if (e.getLoginResult() != AsyncPlayerPreLoginEvent.Result.ALLOWED) {
+            // Schedule cleanup of this user.
+            plugin.getUserManager().scheduleUnload(e.getUniqueId());
         }
     }
 
     @EventHandler(priority = EventPriority.LOW)
     public void onPlayerLogin(PlayerLoginEvent e) {
+        /* Called when the player starts logging into the server.
+           At this point, the users data should be present and loaded.
+           Listening on LOW priority to allow plugins to further modify data here. (auth plugins, etc.) */
+
+        /* the player was denied entry to the server before this priority.
+           log this, so we can handle appropriately later. */
         if (e.getResult() != PlayerLoginEvent.Result.ALLOWED) {
+            plugin.getLog().warn("Login from " + e.getPlayer().getUniqueId() + " was denied before an attachment could be injected.");
             deniedLogin.add(e.getPlayer().getUniqueId());
             return;
         }
@@ -117,21 +144,17 @@ class BukkitListener extends AbstractListener implements Listener {
         final Player player = e.getPlayer();
         final User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(player.getUniqueId()));
 
+        /* User instance is null for whatever reason. Could be that it was unloaded between asyncpre and now. */
         if (user == null) {
             deniedLogin.add(e.getPlayer().getUniqueId());
 
-            // User wasn't loaded for whatever reason.
-            plugin.getLog().warn("User " + player.getUniqueId() + " - " + player.getName() + " could not be loaded. - denying login.");
-            e.disallow(PlayerLoginEvent.Result.KICK_OTHER, Message.LOADING_ERROR.toString());
+            plugin.getLog().warn("User " + player.getUniqueId() + " - " + player.getName() + " doesn't have data pre-loaded. - denying login.");
+            e.disallow(PlayerLoginEvent.Result.KICK_OTHER, Message.LOADING_ERROR.asString(plugin.getLocaleManager()));
             return;
         }
 
-        // remove any pending cleanup tasks
-        BukkitTask task = cleanupTasks.remove(e.getPlayer().getUniqueId());
-        if (task != null) {
-            task.cancel();
-        }
-
+        // User instance is there, now we can inject our custom Permissible into the player.
+        // Care should be taken at this stage to ensure that async tasks which manipulate bukkit data check that the player is still online.
         try {
             // Make a new permissible for the user
             LPPermissible lpPermissible = new LPPermissible(player, user, plugin);
@@ -147,30 +170,43 @@ class BukkitListener extends AbstractListener implements Listener {
 
         // We assume all users are not op, but those who are need extra calculation.
         if (player.isOp()) {
-            plugin.doAsync(() -> user.getUserData().preCalculate(plugin.getPreProcessContexts(true)));
+            plugin.doAsync(() -> {
+                UserCache userData = user.getUserData();
+                if (userData == null) {
+                    return;
+                }
+
+                userData.preCalculate(plugin.getPreProcessContexts(true));
+            });
         }
     }
 
-    @EventHandler(priority = EventPriority.HIGHEST)
+    @EventHandler(priority = EventPriority.MONITOR)
     public void onPlayerLoginMonitor(PlayerLoginEvent e) {
-        // If they were denied before/at LOW, then don't bother handling here.
+        /* Listen to see if the event was cancelled after we initially handled the login
+           If the connection was cancelled here, we need to do something to clean up the data that was loaded. */
+
+        // Check to see if this connection was denied at LOW.
         if (deniedLogin.remove(e.getPlayer().getUniqueId())) {
 
-            // this is a problem, as they were denied at low priority, but are now being allowed.
+            // This is a problem, as they were denied at low priority, but are now being allowed.
             if (e.getResult() == PlayerLoginEvent.Result.ALLOWED) {
-                new IllegalStateException("Player connection was re-allowed for " + e.getPlayer().getUniqueId()).printStackTrace();
+                plugin.getLog().severe("Player connection was re-allowed for " + e.getPlayer().getUniqueId());
                 e.disallow(PlayerLoginEvent.Result.KICK_OTHER, "");
             }
 
             return;
         }
 
+        // Login event was cancelled by another plugin
         if (e.getResult() != PlayerLoginEvent.Result.ALLOWED) {
-            // The player got denied on sync login.
-            cleanupUser(e.getPlayer().getUniqueId());
-        } else {
-            plugin.refreshAutoOp(e.getPlayer());
+            // Schedule cleanup of this user.
+            plugin.getUserManager().scheduleUnload(e.getPlayer().getUniqueId());
+            return;
         }
+
+        // everything is going well. login was processed ok, this is just to refresh auto-op status.
+        plugin.refreshAutoOp(e.getPlayer());
     }
 
     // Wait until the last priority to unload, so plugins can still perform permission checks on this event
@@ -186,21 +222,8 @@ class BukkitListener extends AbstractListener implements Listener {
             player.setOp(false);
         }
 
-        // Call internal leave handling
-        onLeave(player.getUniqueId());
-    }
-
-    private void cleanupUser(UUID uuid) {
-        if (cleanupTasks.containsKey(uuid)) {
-            return;
-        }
-
-        BukkitTask task = plugin.getServer().getScheduler().runTaskLater(plugin, () -> {
-            onLeave(uuid);
-            cleanupTasks.remove(uuid);
-        }, 60L);
-
-        cleanupTasks.put(uuid, task);
+        // Request that the users data is unloaded.
+        plugin.getUserManager().scheduleUnload(player.getUniqueId());
     }
 
     @EventHandler
@@ -209,7 +232,7 @@ class BukkitListener extends AbstractListener implements Listener {
             return;
         }
 
-        String s = e.getMessage()
+        String s = e.getMessage().toLowerCase()
                 .replace("/", "")
                 .replace("bukkit:", "")
                 .replace("spigot:", "")
@@ -217,7 +240,7 @@ class BukkitListener extends AbstractListener implements Listener {
 
         if (s.equals("op") || s.startsWith("op ") || s.equals("deop") || s.startsWith("deop ")) {
             e.setCancelled(true);
-            e.getPlayer().sendMessage(Message.OP_DISABLED.toString());
+            e.getPlayer().sendMessage(Message.OP_DISABLED.asString(plugin.getLocaleManager()));
         }
     }
 
diff --git a/bukkit/src/main/java/me/lucko/luckperms/bukkit/LPBukkitPlugin.java b/bukkit/src/main/java/me/lucko/luckperms/bukkit/LPBukkitPlugin.java
index 9df16e07..a8eef4de 100644
--- a/bukkit/src/main/java/me/lucko/luckperms/bukkit/LPBukkitPlugin.java
+++ b/bukkit/src/main/java/me/lucko/luckperms/bukkit/LPBukkitPlugin.java
@@ -39,6 +39,7 @@ import me.lucko.luckperms.bukkit.model.LPPermissible;
 import me.lucko.luckperms.bukkit.vault.VaultHook;
 import me.lucko.luckperms.common.api.ApiHandler;
 import me.lucko.luckperms.common.api.ApiProvider;
+import me.lucko.luckperms.common.caching.UserCache;
 import me.lucko.luckperms.common.caching.handlers.CachedStateManager;
 import me.lucko.luckperms.common.calculators.CalculatorFactory;
 import me.lucko.luckperms.common.commands.sender.Sender;
@@ -73,6 +74,7 @@ import me.lucko.luckperms.common.treeview.PermissionVault;
 import me.lucko.luckperms.common.utils.BufferedRequest;
 import me.lucko.luckperms.common.utils.FileWatcher;
 import me.lucko.luckperms.common.utils.LoggerImpl;
+import me.lucko.luckperms.common.utils.LoginHelper;
 import me.lucko.luckperms.common.verbose.VerboseHandler;
 
 import org.bukkit.World;
@@ -302,7 +304,7 @@ public class LPBukkitPlugin extends JavaPlugin implements LuckPermsPlugin {
         // Load any online users (in the case of a reload)
         for (Player player : getServer().getOnlinePlayers()) {
             scheduler.doAsync(() -> {
-                listener.onAsyncLogin(player.getUniqueId(), player.getName());
+                LoginHelper.loadUser(this, player.getUniqueId(), player.getName());
                 User user = getUserManager().get(getUuidCache().getUUID(player.getUniqueId()));
                 if (user != null) {
                     scheduler.doSync(() -> {
@@ -431,11 +433,21 @@ public class LPBukkitPlugin extends JavaPlugin implements LuckPermsPlugin {
         if (getConfiguration().get(ConfigKeys.AUTO_OP)) {
             try {
                 LPPermissible permissible = Injector.getPermissible(player.getUniqueId());
-                if (permissible == null) {
+                if (permissible == null || !permissible.getActive().get()) {
                     return;
                 }
 
-                Map<String, Boolean> backing = permissible.getUser().getUserData().getPermissionData(permissible.calculateContexts()).getImmutableBacking();
+                User user = permissible.getUser();
+                if (user == null) {
+                    return;
+                }
+
+                UserCache userData = user.getUserData();
+                if (userData == null) {
+                    return;
+                }
+
+                Map<String, Boolean> backing = userData.getPermissionData(permissible.calculateContexts()).getImmutableBacking();
                 boolean op = Optional.ofNullable(backing.get("luckperms.autoop")).orElse(false);
                 player.setOp(op);
             } catch (Exception ignored) {}
@@ -511,7 +523,8 @@ public class LPBukkitPlugin extends JavaPlugin implements LuckPermsPlugin {
 
     @Override
     public boolean isPlayerOnline(UUID external) {
-        return getServer().getPlayer(external) != null;
+        Player player = getServer().getPlayer(external);
+        return player != null && player.isOnline();
     }
 
     @Override
diff --git a/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/Injector.java b/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/Injector.java
index 1944446b..96494ed9 100644
--- a/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/Injector.java
+++ b/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/Injector.java
@@ -64,7 +64,7 @@ public class Injector {
             PermissibleBase existing = (PermissibleBase) HUMAN_ENTITY_FIELD.get(player);
             if (existing instanceof LPPermissible) {
                 // uh oh
-                throw new IllegalStateException();
+                throw new IllegalStateException("LPPermissible already injected into player " + player.toString());
             }
 
             // Move attachments over from the old permissible.
@@ -73,6 +73,7 @@ public class Injector {
             attachments.clear();
             existing.clearPermissions();
 
+            lpPermissible.getActive().set(true);
             lpPermissible.recalculatePermissions();
             lpPermissible.setOldPermissible(existing);
 
@@ -98,6 +99,8 @@ public class Injector {
                     ((LPPermissible) permissible).unsubscribeFromAllAsync();
                 }
 
+                ((LPPermissible) permissible).getActive().set(false);
+
                 if (dummy) {
                     HUMAN_ENTITY_FIELD.set(player, new DummyPermissibleBase());
                 } else {
diff --git a/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/LPPermissible.java b/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/LPPermissible.java
index 508ccc1f..eaceb72f 100644
--- a/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/LPPermissible.java
+++ b/bukkit/src/main/java/me/lucko/luckperms/bukkit/model/LPPermissible.java
@@ -49,6 +49,7 @@ import java.util.List;
 import java.util.Map;
 import java.util.Set;
 import java.util.concurrent.ConcurrentHashMap;
+import java.util.concurrent.atomic.AtomicBoolean;
 import java.util.logging.Level;
 import java.util.stream.Collectors;
 
@@ -66,6 +67,8 @@ public class LPPermissible extends PermissibleBase {
     @Setter
     private PermissibleBase oldPermissible = null;
 
+    private final AtomicBoolean active = new AtomicBoolean(false);
+
     // Attachment stuff.
     private final Map<String, PermissionAttachmentInfo> attachmentPermissions = new ConcurrentHashMap<>();
     private final List<PermissionAttachment> attachments = Collections.synchronizedList(new LinkedList<>());
@@ -81,10 +84,18 @@ public class LPPermissible extends PermissibleBase {
     }
 
     public void updateSubscriptionsAsync() {
+        if (!active.get()) {
+            return;
+        }
+
         plugin.doAsync(this::updateSubscriptions);
     }
 
     public void updateSubscriptions() {
+        if (!active.get()) {
+            return;
+        }
+
         UserCache cache = user.getUserData();
         if (cache == null) {
             return;
@@ -110,9 +121,7 @@ public class LPPermissible extends PermissibleBase {
     }
 
     public void addAttachments(List<PermissionAttachment> attachments) {
-        for (PermissionAttachment attachment : attachments) {
-            this.attachments.add(attachment);
-        }
+        this.attachments.addAll(attachments);
     }
 
     public Contexts calculateContexts() {
@@ -128,7 +137,7 @@ public class LPPermissible extends PermissibleBase {
     }
 
     private boolean hasData() {
-        return user.getUserData() != null;
+        return user != null && user.getUserData() != null;
     }
 
     @Override
diff --git a/bungee/src/main/java/me/lucko/luckperms/bungee/BungeeListener.java b/bungee/src/main/java/me/lucko/luckperms/bungee/BungeeListener.java
index 143a025c..0aab6299 100644
--- a/bungee/src/main/java/me/lucko/luckperms/bungee/BungeeListener.java
+++ b/bungee/src/main/java/me/lucko/luckperms/bungee/BungeeListener.java
@@ -22,6 +22,8 @@
 
 package me.lucko.luckperms.bungee;
 
+import lombok.RequiredArgsConstructor;
+
 import me.lucko.luckperms.api.Contexts;
 import me.lucko.luckperms.api.caching.UserData;
 import me.lucko.luckperms.api.context.MutableContextSet;
@@ -30,7 +32,6 @@ import me.lucko.luckperms.common.constants.Message;
 import me.lucko.luckperms.common.core.UuidCache;
 import me.lucko.luckperms.common.core.model.User;
 import me.lucko.luckperms.common.defaults.Rule;
-import me.lucko.luckperms.common.utils.AbstractListener;
 
 import net.md_5.bungee.api.chat.TextComponent;
 import net.md_5.bungee.api.connection.PendingConnection;
@@ -44,62 +45,61 @@ import net.md_5.bungee.api.plugin.Listener;
 import net.md_5.bungee.event.EventHandler;
 import net.md_5.bungee.event.EventPriority;
 
+import java.util.Collections;
+import java.util.HashSet;
+import java.util.Set;
 import java.util.UUID;
 import java.util.concurrent.TimeUnit;
 
-@SuppressWarnings("WeakerAccess")
-public class BungeeListener extends AbstractListener implements Listener {
-    private static final TextComponent WARN_MESSAGE = new TextComponent(Message.LOADING_ERROR.toString());
+@RequiredArgsConstructor
+public class BungeeListener implements Listener {
     private final LPBungeePlugin plugin;
 
-    BungeeListener(LPBungeePlugin plugin) {
-        super(plugin);
-        this.plugin = plugin;
-    }
+    private final Set<UUID> deniedLogin = Collections.synchronizedSet(new HashSet<>());
 
-    @EventHandler(priority = EventPriority.HIGH)
-    public void onPlayerPermissionCheck(PermissionCheckEvent e) {
-        if (!(e.getSender() instanceof ProxiedPlayer)) {
-            e.setHasPermission(true);
-            return;
-        }
-
-        final ProxiedPlayer player = ((ProxiedPlayer) e.getSender());
-
-        User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(player.getUniqueId()));
-        if (user == null) {
-            return;
-        }
-
-        UserData userData = user.getUserData();
-        if (userData == null) {
-            plugin.getLog().warn("Player " + player.getName() + " does not have any user data setup.");
-            return;
-        }
-
-        Contexts contexts = new Contexts(
-                plugin.getContextManager().getApplicableContext(player),
-                plugin.getConfiguration().get(ConfigKeys.INCLUDING_GLOBAL_PERMS),
-                plugin.getConfiguration().get(ConfigKeys.INCLUDING_GLOBAL_WORLD_PERMS),
-                true,
-                plugin.getConfiguration().get(ConfigKeys.APPLYING_GLOBAL_GROUPS),
-                plugin.getConfiguration().get(ConfigKeys.APPLYING_GLOBAL_WORLD_GROUPS),
-                false
-        );
-
-        e.setHasPermission(userData.getPermissionData(contexts).getPermissionValue(e.getPermission()).asBoolean());
-    }
-
-    @EventHandler(priority = EventPriority.LOWEST)
+    @EventHandler(priority = EventPriority.LOW)
     public void onPlayerLogin(LoginEvent e) {
-        /* Delay the login here, as we want to cache UUID data before the player is connected to a backend bukkit server.
+        /* Called when the player first attempts a connection with the server.
+           Listening on LOW priority to allow plugins to modify username / UUID data here. (auth plugins)
+
+           Delay the login here, as we want to cache UUID data before the player is connected to a backend bukkit server.
            This means that a player will have the same UUID across the network, even if parts of the network are running in
            Offline mode. */
+
+        // registers the plugins intent to modify this events state going forward.
+        // this will prevent the event from completing until we're finished handling.
         e.registerIntent(plugin);
+
+        final long startTime = System.currentTimeMillis();
+        final PendingConnection c = e.getConnection();
+
+        /* either the plugin hasn't finished starting yet, or there was an issue connecting to the DB, performing file i/o, etc.
+           as this is bungeecord, we will still allow the login, as players can't really do much harm without permissions data.
+           the proxy will just fallback to using the config file perms. */
+        if (!plugin.getStorage().isAcceptingLogins()) {
+            // log that the user tried to login, but was denied at this stage.
+            deniedLogin.add(c.getUniqueId());
+            return;
+        }
+
+        /* another plugin (or the proxy itself) has cancelled this connection already */
+        if (e.isCancelled()) {
+            plugin.getLog().warn("Connection from " + c.getUniqueId() + " was already denied. No permissions data will be loaded.");
+            deniedLogin.add(c.getUniqueId());
+            return;
+        }
+
+        /* Actually process the login for the connection.
+           We do this here to delay the login until the data is ready.
+           If the login gets cancelled later on, then this will be cleaned up.
+
+           This includes:
+           - loading uuid data
+           - loading permissions
+           - creating a user instance in the UserManager for this connection.
+           - setting up cached data. */
         plugin.doAsync(() -> {
-            final long startTime = System.currentTimeMillis();
             final UuidCache cache = plugin.getUuidCache();
-            final PendingConnection c = e.getConnection();
 
             if (!plugin.getConfiguration().get(ConfigKeys.USE_SERVER_UUIDS)) {
                 UUID uuid = plugin.getStorage().getUUID(c.getName()).join();
@@ -109,6 +109,8 @@ public class BungeeListener extends AbstractListener implements Listener {
                     // No previous data for this player
                     plugin.getApiProvider().getEventFactory().handleUserFirstLogin(c.getUniqueId(), c.getName());
                     cache.addToCache(c.getUniqueId(), c.getUniqueId());
+
+                    // Join this call, as we want this to be set for when the player connects to the backend.
                     plugin.getStorage().force().saveUUIDData(c.getName(), c.getUniqueId()).join();
                 }
             } else {
@@ -118,12 +120,14 @@ public class BungeeListener extends AbstractListener implements Listener {
                 }
 
                 // Online mode, no cache needed. This is just for name -> uuid lookup.
+                // Again, join this call so the data is available for the backend.
                 plugin.getStorage().force().saveUUIDData(c.getName(), c.getUniqueId()).join();
             }
 
-            // We have to make a new user on this thread whilst the connection is being held, or we get concurrency issues as the Bukkit server
-            // and the BungeeCord server try to make a new user at the same time.
+            /* We have to make a new user on this thread whilst the connection is being held, or we get concurrency issues
+               as the Bukkit server and the BungeeCord server try to make a new user at the same time. */
             plugin.getStorage().force().loadUser(cache.getUUID(c.getUniqueId()), c.getName()).join();
+
             User user = plugin.getUserManager().get(cache.getUUID(c.getUniqueId()));
             if (user == null) {
                 plugin.getLog().warn("Failed to load user: " + c.getName());
@@ -148,7 +152,13 @@ public class BungeeListener extends AbstractListener implements Listener {
             if (time >= 1000) {
                 plugin.getLog().warn("Processing login for " + c.getName() + " took " + time + "ms.");
             }
+
+            // finally, complete out intent to modify state, so the proxy can continue handling the connection.
             e.completeIntent(plugin);
+
+            // schedule a cleanup of the users data in a few seconds.
+            // this should cover the eventuality that the login fails.
+            plugin.getUserManager().scheduleUnload(c.getUniqueId());
         });
     }
 
@@ -158,17 +168,57 @@ public class BungeeListener extends AbstractListener implements Listener {
         final User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(e.getPlayer().getUniqueId()));
 
         if (user == null) {
-            plugin.getProxy().getScheduler().schedule(plugin, () -> player.sendMessage(WARN_MESSAGE), 3, TimeUnit.SECONDS);
+            plugin.getProxy().getScheduler().schedule(plugin, () -> {
+                if (!player.isConnected()) {
+                    return;
+                }
+
+                player.sendMessage(new TextComponent(Message.LOADING_ERROR.asString(plugin.getLocaleManager())));
+            }, 3, TimeUnit.SECONDS);
         }
     }
 
     // Wait until the last priority to unload, so plugins can still perform permission checks on this event
     @EventHandler(priority = EventPriority.HIGHEST)
     public void onPlayerQuit(PlayerDisconnectEvent e) {
-        onLeave(e.getPlayer().getUniqueId());
+        // Request that the users data is unloaded.
+        plugin.getUserManager().scheduleUnload(e.getPlayer().getUniqueId());
     }
 
-    // We don't preprocess all servers, so we may have to do it here.
+    @EventHandler(priority = EventPriority.HIGH)
+    public void onPlayerPermissionCheck(PermissionCheckEvent e) {
+        if (!(e.getSender() instanceof ProxiedPlayer)) {
+            return;
+        }
+
+        final ProxiedPlayer player = ((ProxiedPlayer) e.getSender());
+
+        User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(player.getUniqueId()));
+        if (user == null) {
+            return;
+        }
+
+        UserData userData = user.getUserData();
+        if (userData == null) {
+            plugin.getLog().warn("Player " + player.getName() + " does not have any user data setup.");
+            plugin.doAsync(() -> user.setupData(false));
+            return;
+        }
+
+        Contexts contexts = new Contexts(
+                plugin.getContextManager().getApplicableContext(player),
+                plugin.getConfiguration().get(ConfigKeys.INCLUDING_GLOBAL_PERMS),
+                plugin.getConfiguration().get(ConfigKeys.INCLUDING_GLOBAL_WORLD_PERMS),
+                true,
+                plugin.getConfiguration().get(ConfigKeys.APPLYING_GLOBAL_GROUPS),
+                plugin.getConfiguration().get(ConfigKeys.APPLYING_GLOBAL_WORLD_GROUPS),
+                false
+        );
+
+        e.setHasPermission(userData.getPermissionData(contexts).getPermissionValue(e.getPermission()).asBoolean());
+    }
+
+    // We don't pre-process all servers, so we have to do it here.
     @EventHandler(priority = EventPriority.LOWEST)
     public void onServerSwitch(ServerConnectEvent e) {
         String serverName = e.getTarget().getName();
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 c6eb92d7..1127857e 100644
--- a/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java
+++ b/bungee/src/main/java/me/lucko/luckperms/bungee/LPBungeePlugin.java
@@ -323,7 +323,8 @@ public class LPBungeePlugin extends Plugin implements LuckPermsPlugin {
 
     @Override
     public boolean isPlayerOnline(UUID external) {
-        return getProxy().getPlayer(external) != null;
+        ProxiedPlayer player = getProxy().getPlayer(external);
+        return player != null && player.isConnected();
     }
 
     @Override
diff --git a/common/src/main/java/me/lucko/luckperms/common/constants/Message.java b/common/src/main/java/me/lucko/luckperms/common/constants/Message.java
index d262055f..9e10a5f6 100644
--- a/common/src/main/java/me/lucko/luckperms/common/constants/Message.java
+++ b/common/src/main/java/me/lucko/luckperms/common/constants/Message.java
@@ -27,6 +27,7 @@ import lombok.Getter;
 
 import me.lucko.luckperms.common.commands.sender.Sender;
 import me.lucko.luckperms.common.commands.utils.Util;
+import me.lucko.luckperms.common.locale.LocaleManager;
 
 @SuppressWarnings("SpellCheckingInspection")
 @AllArgsConstructor
@@ -44,7 +45,7 @@ public enum Message {
     EMPTY("{0}", true),
     PLAYER_ONLINE("&aOnline", false),
     PLAYER_OFFLINE("&cOffline", false),
-    LOADING_ERROR("Permissions data could not be loaded. Please contact an administrator.", true),
+    LOADING_ERROR("Permissions data could not be loaded. Please try again later.", true),
     OP_DISABLED("&bThe vanilla OP system is disabled on this server.", false),
     OP_DISABLED_SPONGE("&2Server Operator status has no effect when a permission plugin is installed. Please edit user data directly.", true),
     LOG("&3LOG &3&l> {0}", true),
@@ -452,6 +453,21 @@ public enum Message {
         return Util.color(showPrefix ? PREFIX + message : message);
     }
 
+    public String asString(LocaleManager localeManager) {
+        String prefix = localeManager.getTranslation(PREFIX);
+        if (prefix == null) {
+            prefix = PREFIX.getMessage();
+        }
+
+        String s = localeManager.getTranslation(this);
+        if (s == null) {
+            s = message;
+        }
+
+        s = s.replace("{PREFIX}", prefix).replace("\\n", "\n");
+        return Util.color(showPrefix ? (prefix + s) : (s));
+    }
+
     public void send(Sender sender, Object... objects) {
         String prefix = sender.getPlatform().getLocaleManager().getTranslation(PREFIX);
         if (prefix == null) {
diff --git a/common/src/main/java/me/lucko/luckperms/common/managers/UserManager.java b/common/src/main/java/me/lucko/luckperms/common/managers/UserManager.java
index cc391b6e..b0a82195 100644
--- a/common/src/main/java/me/lucko/luckperms/common/managers/UserManager.java
+++ b/common/src/main/java/me/lucko/luckperms/common/managers/UserManager.java
@@ -60,6 +60,13 @@ public interface UserManager extends Manager<UserIdentifier, User> {
      */
     void cleanup(User user);
 
+    /**
+     * Schedules a task to cleanup a user after a certain period of time, if they're not on the server anymore.
+     *
+     * @param uuid external uuid of the player
+     */
+    void scheduleUnload(UUID uuid);
+
     /**
      * Reloads the data of all online users
      */
diff --git a/common/src/main/java/me/lucko/luckperms/common/managers/impl/GenericUserManager.java b/common/src/main/java/me/lucko/luckperms/common/managers/impl/GenericUserManager.java
index 9422dc1b..01a93770 100644
--- a/common/src/main/java/me/lucko/luckperms/common/managers/impl/GenericUserManager.java
+++ b/common/src/main/java/me/lucko/luckperms/common/managers/impl/GenericUserManager.java
@@ -134,6 +134,18 @@ public class GenericUserManager extends AbstractManager<UserIdentifier, User> im
         }
     }
 
+    @Override
+    public void scheduleUnload(UUID uuid) {
+        plugin.getScheduler().doAsyncLater(() -> {
+            User user = get(plugin.getUuidCache().getUUID(uuid));
+            if (user != null && !plugin.isPlayerOnline(uuid)) {
+                user.unregisterData();
+                unload(user);
+            }
+            plugin.getUuidCache().clearCache(uuid);
+        }, 40L);
+    }
+
     @Override
     public void updateAllUsers() {
         plugin.doSync(() -> {
diff --git a/common/src/main/java/me/lucko/luckperms/common/utils/AbstractListener.java b/common/src/main/java/me/lucko/luckperms/common/utils/LoginHelper.java
similarity index 84%
rename from common/src/main/java/me/lucko/luckperms/common/utils/AbstractListener.java
rename to common/src/main/java/me/lucko/luckperms/common/utils/LoginHelper.java
index 36b284df..a9d8b2e9 100644
--- a/common/src/main/java/me/lucko/luckperms/common/utils/AbstractListener.java
+++ b/common/src/main/java/me/lucko/luckperms/common/utils/LoginHelper.java
@@ -22,7 +22,7 @@
 
 package me.lucko.luckperms.common.utils;
 
-import lombok.AllArgsConstructor;
+import lombok.experimental.UtilityClass;
 
 import me.lucko.luckperms.common.config.ConfigKeys;
 import me.lucko.luckperms.common.core.UuidCache;
@@ -33,13 +33,12 @@ import me.lucko.luckperms.common.plugin.LuckPermsPlugin;
 import java.util.UUID;
 
 /**
- * An abstract listener shared by Bukkit & Sponge.
+ * Utilities for use in platform listeners
  */
-@AllArgsConstructor
-public class AbstractListener {
-    private final LuckPermsPlugin plugin;
+@UtilityClass
+public class LoginHelper {
 
-    public void onAsyncLogin(UUID u, String username) {
+    public static void loadUser(LuckPermsPlugin plugin, UUID u, String username) {
         final long startTime = System.currentTimeMillis();
 
         final UuidCache cache = plugin.getUuidCache();
@@ -67,6 +66,7 @@ public class AbstractListener {
         User user = plugin.getUserManager().get(cache.getUUID(u));
         if (user == null) {
             plugin.getLog().warn("Failed to load user: " + username);
+            throw new RuntimeException("Failed to load user");
         } else {
             // Setup defaults for the user
             boolean save = false;
@@ -90,20 +90,7 @@ public class AbstractListener {
         }
     }
 
-    protected void onLeave(UUID uuid) {
-        final UuidCache cache = plugin.getUuidCache();
-
-        final User user = plugin.getUserManager().get(cache.getUUID(uuid));
-        if (user != null) {
-            user.unregisterData();
-            plugin.getUserManager().unload(user);
-        }
-
-        // Unload the user from memory when they disconnect;
-        cache.clearCache(uuid);
-    }
-
-    protected void refreshPlayer(UUID uuid) {
+    public static void refreshPlayer(LuckPermsPlugin plugin, UUID uuid) {
         final User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(uuid));
         if (user != null) {
             user.getRefreshBuffer().requestDirectly();
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 e1be359a..bf86b2f0 100644
--- a/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java
+++ b/sponge/src/main/java/me/lucko/luckperms/sponge/LPSpongePlugin.java
@@ -440,7 +440,7 @@ public class LPSpongePlugin implements LuckPermsPlugin {
 
     @Override
     public boolean isPlayerOnline(UUID external) {
-        return game.getServer().getPlayer(external).isPresent();
+        return game.getServer().getPlayer(external).map(Player::isOnline).orElse(false);
     }
 
     @Override
diff --git a/sponge/src/main/java/me/lucko/luckperms/sponge/SpongeListener.java b/sponge/src/main/java/me/lucko/luckperms/sponge/SpongeListener.java
index b3ba259a..a2794581 100644
--- a/sponge/src/main/java/me/lucko/luckperms/sponge/SpongeListener.java
+++ b/sponge/src/main/java/me/lucko/luckperms/sponge/SpongeListener.java
@@ -22,12 +22,14 @@
 
 package me.lucko.luckperms.sponge;
 
+import lombok.RequiredArgsConstructor;
+
 import me.lucko.luckperms.api.caching.UserData;
 import me.lucko.luckperms.api.context.MutableContextSet;
 import me.lucko.luckperms.common.constants.Message;
 import me.lucko.luckperms.common.core.UuidCache;
 import me.lucko.luckperms.common.core.model.User;
-import me.lucko.luckperms.common.utils.AbstractListener;
+import me.lucko.luckperms.common.utils.LoginHelper;
 import me.lucko.luckperms.sponge.timings.LPTiming;
 
 import org.spongepowered.api.command.CommandSource;
@@ -35,49 +37,131 @@ import org.spongepowered.api.entity.living.player.Player;
 import org.spongepowered.api.event.Listener;
 import org.spongepowered.api.event.Order;
 import org.spongepowered.api.event.command.SendCommandEvent;
+import org.spongepowered.api.event.filter.IsCancelled;
 import org.spongepowered.api.event.network.ClientConnectionEvent;
 import org.spongepowered.api.profile.GameProfile;
 import org.spongepowered.api.text.serializer.TextSerializers;
+import org.spongepowered.api.util.Tristate;
 import org.spongepowered.api.world.World;
 
 import co.aikar.timings.Timing;
 
+import java.util.Collections;
+import java.util.HashSet;
 import java.util.List;
 import java.util.Optional;
+import java.util.Set;
+import java.util.UUID;
 import java.util.stream.Collectors;
 
-@SuppressWarnings("WeakerAccess")
-public class SpongeListener extends AbstractListener {
+@RequiredArgsConstructor
+public class SpongeListener {
     private final LPSpongePlugin plugin;
 
-    SpongeListener(LPSpongePlugin plugin) {
-        super(plugin);
-        this.plugin = plugin;
-    }
+    private final Set<UUID> deniedAsyncLogin = Collections.synchronizedSet(new HashSet<>());
+    private final Set<UUID> deniedLogin = Collections.synchronizedSet(new HashSet<>());
 
-    @Listener(order = Order.EARLY)
+    @Listener(order = Order.AFTER_PRE)
+    @IsCancelled(Tristate.UNDEFINED)
     public void onClientAuth(ClientConnectionEvent.Auth e) {
-        if (!plugin.getStorage().isAcceptingLogins()) {
-            /* Datastore is disabled, prevent players from joining the server
-               Just don't load their data, they will be kicked at login */
+        /* Called when the player first attempts a connection with the server.
+           Listening on AFTER_PRE priority to allow plugins to modify username / UUID data here. (auth plugins) */
+
+        final GameProfile p = e.getProfile();
+
+        /* the player was denied entry to the server before this priority.
+           log this, so we can handle appropriately later. */
+        if (e.isCancelled()) {
+            plugin.getLog().warn("Connection from " + p.getUniqueId() + " was already denied. No permissions data will be loaded.");
+            deniedAsyncLogin.add(p.getUniqueId());
             return;
         }
 
-        final GameProfile p = e.getProfile();
-        onAsyncLogin(p.getUniqueId(), p.getName().get()); // Load the user into LuckPerms
+        /* either the plugin hasn't finished starting yet, or there was an issue connecting to the DB, performing file i/o, etc.
+           we don't let players join in this case, because it means they can connect to the server without their permissions data.
+           some server admins rely on negating perms to stop users from causing damage etc, so it's really important that
+           this data is loaded. */
+        if (!plugin.getStorage().isAcceptingLogins()) {
+
+            // log that the user tried to login, but was denied at this stage.
+            deniedAsyncLogin.add(p.getUniqueId());
+
+            // actually deny the connection.
+            plugin.getLog().warn("Permissions storage is not loaded yet. Denying connection from: " + p.getUniqueId() + " - " + p.getName());
+            e.setCancelled(true);
+            e.setMessageCancelled(true);
+            //noinspection deprecation
+            e.setMessage(TextSerializers.LEGACY_FORMATTING_CODE.deserialize(Message.LOADING_ERROR.asString(plugin.getLocaleManager())));
+            return;
+        }
+
+        /* Actually process the login for the connection.
+           We do this here to delay the login until the data is ready.
+           If the login gets cancelled later on, then this will be cleaned up.
+
+           This includes:
+           - loading uuid data
+           - loading permissions
+           - creating a user instance in the UserManager for this connection.
+           - setting up cached data. */
+        try {
+            LoginHelper.loadUser(plugin, p.getUniqueId(), p.getName().orElseThrow(() -> new RuntimeException("No username present for user " + p.getUniqueId())));
+        } catch (Exception ex) {
+            ex.printStackTrace();
+
+            e.setCancelled(true);
+            e.setMessageCancelled(true);
+            //noinspection deprecation
+            e.setMessage(TextSerializers.LEGACY_FORMATTING_CODE.deserialize(Message.LOADING_ERROR.asString(plugin.getLocaleManager())));
+        }
     }
 
-    @SuppressWarnings("deprecation")
-    @Listener(order = Order.EARLY)
+    @Listener(order = Order.BEFORE_POST)
+    @IsCancelled(Tristate.UNDEFINED)
+    public void onClientAuthMonitor(ClientConnectionEvent.Auth e) {
+        /* Listen to see if the event was cancelled after we initially handled the connection
+           If the connection was cancelled here, we need to do something to clean up the data that was loaded. */
+
+        // Check to see if this connection was denied at LOW.
+        if (deniedAsyncLogin.remove(e.getProfile().getUniqueId())) {
+
+            // This is a problem, as they were denied at low priority, but are now being allowed.
+            if (e.isCancelled()) {
+                plugin.getLog().severe("Player connection was re-allowed for " + e.getProfile().getUniqueId());
+                e.setCancelled(true);
+            }
+        }
+    }
+
+    @Listener(order = Order.AFTER_PRE)
+    @IsCancelled(Tristate.UNDEFINED)
     public void onClientLogin(ClientConnectionEvent.Login e) {
         try (Timing ignored = plugin.getTimings().time(LPTiming.ON_CLIENT_LOGIN)) {
+            /* Called when the player starts logging into the server.
+               At this point, the users data should be present and loaded.
+               Listening on LOW priority to allow plugins to further modify data here. (auth plugins, etc.) */
+
             final GameProfile player = e.getProfile();
+
+            /* the player was denied entry to the server before this priority.
+               log this, so we can handle appropriately later. */
+            if (e.isCancelled()) {
+                plugin.getLog().warn("Login from " + player.getUniqueId() + " was denied before an attachment could be injected.");
+                deniedLogin.add(player.getUniqueId());
+                return;
+            }
+
             final User user = plugin.getUserManager().get(plugin.getUuidCache().getUUID(player.getUniqueId()));
 
-            // Check if the user was loaded successfully.
+            /* User instance is null for whatever reason. Could be that it was unloaded between asyncpre and now. */
             if (user == null) {
+                deniedLogin.add(player.getUniqueId());
+
+                plugin.getLog().warn("User " + player.getUniqueId() + " - " + player.getName() + " doesn't have data pre-loaded. - denying login.");
                 e.setCancelled(true);
-                e.setMessage(TextSerializers.LEGACY_FORMATTING_CODE.deserialize(Message.LOADING_ERROR.toString()));
+                e.setMessageCancelled(true);
+                //noinspection deprecation
+                e.setMessage(TextSerializers.LEGACY_FORMATTING_CODE.deserialize(Message.LOADING_ERROR.asString(plugin.getLocaleManager())));
                 return;
             }
 
@@ -108,7 +192,7 @@ public class SpongeListener extends AbstractListener {
     @Listener(order = Order.EARLY)
     public void onClientJoin(ClientConnectionEvent.Join e) {
         // Refresh permissions again
-        plugin.doAsync(() -> refreshPlayer(e.getTargetEntity().getUniqueId()));
+        plugin.doAsync(() -> LoginHelper.refreshPlayer(plugin, e.getTargetEntity().getUniqueId()));
     }
 
     @Listener(order = Order.LAST)
diff --git a/sponge/src/main/java/me/lucko/luckperms/sponge/managers/SpongeUserManager.java b/sponge/src/main/java/me/lucko/luckperms/sponge/managers/SpongeUserManager.java
index 9ca1574b..acdf34db 100644
--- a/sponge/src/main/java/me/lucko/luckperms/sponge/managers/SpongeUserManager.java
+++ b/sponge/src/main/java/me/lucko/luckperms/sponge/managers/SpongeUserManager.java
@@ -205,6 +205,11 @@ public class SpongeUserManager implements UserManager, LPSubjectCollection {
         // Do nothing - this instance uses other means in order to cleanup
     }
 
+    @Override
+    public void scheduleUnload(UUID uuid) {
+        // Do nothing - this instance uses other means in order to cleanup
+    }
+
     @Override
     public void updateAllUsers() {
         plugin.doSync(() -> {