diff --git a/Bukkit/src/main/java/com/plotsquared/bukkit/BukkitMain.java b/Bukkit/src/main/java/com/plotsquared/bukkit/BukkitMain.java
index c423d8102..1a40c51d5 100644
--- a/Bukkit/src/main/java/com/plotsquared/bukkit/BukkitMain.java
+++ b/Bukkit/src/main/java/com/plotsquared/bukkit/BukkitMain.java
@@ -392,6 +392,19 @@ public final class BukkitMain extends JavaPlugin implements Listener, IPlotMain<
         PlotSquared.log(
             Captions.PREFIX.getTranslated() + "Using platform world manager: " + this.worldManager
                 .getName());
+
+        // Clean up potential memory leak
+        Bukkit.getScheduler().runTaskTimer(this, () -> {
+            try {
+                for (final PlotPlayer<? extends Player> player : this.getPlayerManager().getPlayers()) {
+                    if (player.getPlatformPlayer() == null || !player.getPlatformPlayer().isOnline()) {
+                        this.getPlayerManager().removePlayer(player);
+                    }
+                }
+            } catch (final Exception e) {
+                getLogger().warning("Failed to clean up players: " + e.getMessage());
+            }
+        }, 100L, 100L);
     }
 
     private void unload() {
@@ -982,7 +995,7 @@ public final class BukkitMain extends JavaPlugin implements Listener, IPlotMain<
     }
 
     @Override public void unregister(@NonNull final PlotPlayer player) {
-        BukkitUtil.removePlayer(player.getName());
+        BukkitUtil.removePlayer(player.getUUID());
     }
 
     @Override public void registerChunkProcessor() {
diff --git a/Bukkit/src/main/java/com/plotsquared/bukkit/listener/PlayerEvents.java b/Bukkit/src/main/java/com/plotsquared/bukkit/listener/PlayerEvents.java
index f94c54638..643f80611 100644
--- a/Bukkit/src/main/java/com/plotsquared/bukkit/listener/PlayerEvents.java
+++ b/Bukkit/src/main/java/com/plotsquared/bukkit/listener/PlayerEvents.java
@@ -650,10 +650,10 @@ public class PlayerEvents extends PlotListener implements Listener {
         PlotSquared.get().getImpromptuUUIDPipeline().storeImmediately(event.getName(), uuid);
     }
 
-    @EventHandler(priority = EventPriority.LOWEST, ignoreCancelled = true)
+    @EventHandler(priority = EventPriority.HIGHEST, ignoreCancelled = true)
     public void onConnect(PlayerJoinEvent event) {
         final Player player = event.getPlayer();
-        BukkitUtil.removePlayer(player.getName());
+        BukkitUtil.removePlayer(player.getUniqueId());
         final PlotPlayer<Player> pp = BukkitUtil.getPlayer(player);
 
         Location location = pp.getLocation();
diff --git a/Bukkit/src/main/java/com/plotsquared/bukkit/util/BukkitUtil.java b/Bukkit/src/main/java/com/plotsquared/bukkit/util/BukkitUtil.java
index d73a11a54..5acdde298 100644
--- a/Bukkit/src/main/java/com/plotsquared/bukkit/util/BukkitUtil.java
+++ b/Bukkit/src/main/java/com/plotsquared/bukkit/util/BukkitUtil.java
@@ -116,9 +116,11 @@ public class BukkitUtil extends WorldUtil {
     private static Player lastPlayer = null;
     private static BukkitPlayer lastPlotPlayer = null;
 
-    public static void removePlayer(String player) {
+    public static void removePlayer(UUID uuid) {
         lastPlayer = null;
         lastPlotPlayer = null;
+        // Make sure that it's removed internally
+        PlotSquared.imp().getPlayerManager().removePlayer(uuid);
     }
 
     public static PlotPlayer<Player> getPlayer(@NonNull final OfflinePlayer op) {
diff --git a/Core/src/main/java/com/plotsquared/core/plot/Plot.java b/Core/src/main/java/com/plotsquared/core/plot/Plot.java
index 83e616e9f..0d756ac6c 100644
--- a/Core/src/main/java/com/plotsquared/core/plot/Plot.java
+++ b/Core/src/main/java/com/plotsquared/core/plot/Plot.java
@@ -2917,7 +2917,7 @@ public class Plot {
      */
     public void reEnter() {
         TaskManager.runTaskLater(() -> {
-            for (PlotPlayer pp : Plot.this.getPlayersInPlot()) {
+            for (PlotPlayer<?> pp : Plot.this.getPlayersInPlot()) {
                 PlotListener.plotExit(pp, Plot.this);
                 PlotListener.plotEntry(pp, Plot.this);
             }
@@ -2925,18 +2925,19 @@ public class Plot {
     }
 
     public void debug(@NotNull final String message) {
-        final Collection<PlotPlayer<?>> players = PlotPlayer.getDebugModePlayersInPlot(this);
-        if (players.isEmpty()) {
-            return;
-        }
-        final String string = Captions.PLOT_DEBUG.getTranslated().replace("%plot%", this.toString())
-            .replace("%message%", message);
-        for (final PlotPlayer<?> player : players) {
-            if (isOwner(player.getUUID()) ||
-                Permissions.hasPermission(player, Captions.PERMISSION_ADMIN_DEBUG_OTHER)) {
-                player.sendMessage(string);
+        try {
+            final Collection<PlotPlayer<?>> players = PlotPlayer.getDebugModePlayersInPlot(this);
+            if (players.isEmpty()) {
+                return;
             }
-        }
+            final String string =
+                Captions.PLOT_DEBUG.getTranslated().replace("%plot%", this.toString()).replace("%message%", message);
+            for (final PlotPlayer<?> player : players) {
+                if (isOwner(player.getUUID()) || Permissions.hasPermission(player, Captions.PERMISSION_ADMIN_DEBUG_OTHER)) {
+                    player.sendMessage(string);
+                }
+            }
+        } catch (final Exception ignored) {}
     }
 
     /**
diff --git a/Core/src/main/java/com/plotsquared/core/util/PlayerManager.java b/Core/src/main/java/com/plotsquared/core/util/PlayerManager.java
index 4af113ca6..8c4ec1bea 100644
--- a/Core/src/main/java/com/plotsquared/core/util/PlayerManager.java
+++ b/Core/src/main/java/com/plotsquared/core/util/PlayerManager.java
@@ -30,6 +30,7 @@ import com.plotsquared.core.player.PlotPlayer;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
+import java.util.ArrayList;
 import java.util.Collection;
 import java.util.Collections;
 import java.util.HashMap;
@@ -55,6 +56,17 @@ public abstract class PlayerManager<P extends PlotPlayer<? extends T>, T> {
         }
     }
 
+    /**
+     * Remove a player from the player map
+     *
+     * @param uuid Player to remove
+     */
+    public void removePlayer(@NotNull final UUID uuid) {
+        synchronized (playerLock) {
+            this.playerMap.remove(uuid);
+        }
+    }
+
     /**
      * Get the player from its UUID if it is stored in the player map.
      *
@@ -110,7 +122,7 @@ public abstract class PlayerManager<P extends PlotPlayer<? extends T>, T> {
         }
     }
 
-    @NotNull protected abstract P createPlayer(@NotNull final UUID uuid);
+    @NotNull public abstract P createPlayer(@NotNull final UUID uuid);
 
     /**
      * Get an an offline player object from the player's UUID
@@ -134,7 +146,7 @@ public abstract class PlayerManager<P extends PlotPlayer<? extends T>, T> {
      * @return Unmodifiable collection of players
      */
     public Collection<P> getPlayers() {
-        return Collections.unmodifiableCollection(this.playerMap.values());
+        return Collections.unmodifiableCollection(new ArrayList<>(this.playerMap.values()));
     }