diff --git a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaPlayerRegistry.java b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaPlayerRegistry.java
index 0844f12..c9b17d7 100644
--- a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaPlayerRegistry.java
+++ b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaPlayerRegistry.java
@@ -42,9 +42,19 @@ public abstract class AbstractArenaPlayerRegistry<K extends Arena> implements Ar
     }
 
     @Override
-    public boolean removePlayer(@NotNull UUID playerId) {
-        this.entryStates.remove(playerId);
-        this.saveEntryStates();
+    public boolean removePlayer(@NotNull UUID playerId, boolean restoreState) {
+        // Try and restore the state. If it cannot be restored, retain the entry state
+        PlayerEntryState entryState = this.entryStates.remove(playerId);
+        if (restoreState) {
+            if (entryState.restore()) {
+                this.saveEntryStates();
+            } else {
+                this.entryStates.put(playerId, entryState);
+            }
+        } else {
+            this.saveEntryStates();
+        }
+
         return this.arenaPlayers.remove(playerId) != null;
     }
 
@@ -89,7 +99,7 @@ public abstract class AbstractArenaPlayerRegistry<K extends Arena> implements Ar
         }
         if (this.entryStates.size() > 0) {
             MiniGames.log(Level.WARNING, entryStates.size() + " un-exited sessions found. This happens if " +
-                    "players are leaving in the middle of a game, or the server crashes. MiniGames will do its best " +
+                    "players leave in the middle of a game, or if the server crashes. MiniGames will do its best " +
                     "to fix the players' states.");
         }
     }
diff --git a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
index 8000243..e95e41a 100644
--- a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
@@ -35,7 +35,7 @@ public abstract class AbstractArenaSession implements ArenaSession {
     @Override
     public void triggerQuit(boolean immediately) {
         // Stop this session
-        stopSession();
+        removeSession();
         // Teleport the player out of the arena
         teleportToExit(immediately);
 
@@ -92,17 +92,6 @@ public abstract class AbstractArenaSession implements ArenaSession {
         PlayerTeleporter.teleportPlayer(this.player, exitLocation, true, immediately);
     }
 
-    /**
-     * Stops this session, and disables flight mode
-     */
-    protected void stopSession() {
-        // Remove this session from game sessions to stop listeners from fiddling more with the player
-        removeSession();
-
-        // Remove flight mode
-        entryState.restore();
-    }
-
     /**
      * Gets the string representation of the session's game-mode
      *
diff --git a/src/main/java/net/knarcraft/minigames/arena/AbstractPlayerEntryState.java b/src/main/java/net/knarcraft/minigames/arena/AbstractPlayerEntryState.java
index 4c29cce..d1bf53b 100644
--- a/src/main/java/net/knarcraft/minigames/arena/AbstractPlayerEntryState.java
+++ b/src/main/java/net/knarcraft/minigames/arena/AbstractPlayerEntryState.java
@@ -94,20 +94,17 @@ public abstract class AbstractPlayerEntryState implements PlayerEntryState {
     }
 
     @Override
-    public void restore() {
+    public boolean restore() {
         Player player = getPlayer();
         if (player == null) {
-            return;
+            return false;
         }
         restore(player);
+        return true;
     }
 
-    /**
-     * Restores the state of the given player
-     *
-     * @param player <p>The player to restore the state for</p>
-     */
-    public void restore(Player player) {
+    @Override
+    public void restore(@NotNull Player player) {
         player.setFlying(this.originalIsFlying);
         player.setGameMode(this.originalGameMode);
         player.setAllowFlight(this.originalAllowFlight);
diff --git a/src/main/java/net/knarcraft/minigames/arena/ArenaPlayerRegistry.java b/src/main/java/net/knarcraft/minigames/arena/ArenaPlayerRegistry.java
index 5588433..cb10111 100644
--- a/src/main/java/net/knarcraft/minigames/arena/ArenaPlayerRegistry.java
+++ b/src/main/java/net/knarcraft/minigames/arena/ArenaPlayerRegistry.java
@@ -31,9 +31,10 @@ public interface ArenaPlayerRegistry<K extends Arena> {
     /**
      * Removes this player from players currently playing
      *
-     * @param playerId <p>The id of the player to remove</p>
+     * @param playerId     <p>The id of the player to remove</p>
+     * @param restoreState <p>Whether to restore the state of the player as part of the removal</p>
      */
-    boolean removePlayer(@NotNull UUID playerId);
+    boolean removePlayer(@NotNull UUID playerId, boolean restoreState);
 
     /**
      * Gets the player's active dropper arena session
diff --git a/src/main/java/net/knarcraft/minigames/arena/PlayerEntryState.java b/src/main/java/net/knarcraft/minigames/arena/PlayerEntryState.java
index 16f8edf..da3f8d8 100644
--- a/src/main/java/net/knarcraft/minigames/arena/PlayerEntryState.java
+++ b/src/main/java/net/knarcraft/minigames/arena/PlayerEntryState.java
@@ -19,7 +19,7 @@ public interface PlayerEntryState extends ConfigurationSerializable {
     /**
      * Restores the stored state for the stored player
      */
-    void restore();
+    boolean restore();
 
     /**
      * Restores the stored state for the given player
diff --git a/src/main/java/net/knarcraft/minigames/arena/dropper/DropperArenaSession.java b/src/main/java/net/knarcraft/minigames/arena/dropper/DropperArenaSession.java
index 45aac7f..9d995b5 100644
--- a/src/main/java/net/knarcraft/minigames/arena/dropper/DropperArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/dropper/DropperArenaSession.java
@@ -68,7 +68,7 @@ public class DropperArenaSession extends AbstractArenaSession {
     @Override
     public void triggerWin() {
         // Stop this session
-        stopSession();
+        removeSession();
 
         // Check for, and display, records
         MiniGames miniGames = MiniGames.getInstance();
@@ -104,7 +104,8 @@ public class DropperArenaSession extends AbstractArenaSession {
     @Override
     protected void removeSession() {
         // Remove this session for game sessions to stop listeners from fiddling more with the player
-        boolean removedSession = MiniGames.getInstance().getDropperArenaPlayerRegistry().removePlayer(player.getUniqueId());
+        boolean removedSession = MiniGames.getInstance().getDropperArenaPlayerRegistry().removePlayer(
+                player.getUniqueId(), true);
         if (!removedSession) {
             MiniGames.log(Level.SEVERE, "Unable to remove dropper arena session for " + player.getName() + ". " +
                     "This will have unintended consequences.");
diff --git a/src/main/java/net/knarcraft/minigames/arena/dropper/DropperPlayerEntryState.java b/src/main/java/net/knarcraft/minigames/arena/dropper/DropperPlayerEntryState.java
index 9385fdd..3a8e993 100644
--- a/src/main/java/net/knarcraft/minigames/arena/dropper/DropperPlayerEntryState.java
+++ b/src/main/java/net/knarcraft/minigames/arena/dropper/DropperPlayerEntryState.java
@@ -84,12 +84,18 @@ public class DropperPlayerEntryState extends AbstractPlayerEntryState {
     }
 
     @Override
-    public void restore() {
-        super.restore();
+    public boolean restore() {
         Player player = getPlayer();
         if (player == null) {
-            return;
+            return false;
         }
+        this.restore(player);
+        return true;
+    }
+
+    @Override
+    public void restore(@NotNull Player player) {
+        super.restore(player);
         player.setFlySpeed(this.originalFlySpeed);
     }
 
diff --git a/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java b/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java
index 7947098..6ed5aac 100644
--- a/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java
@@ -69,7 +69,7 @@ public class ParkourArenaSession extends AbstractArenaSession {
     @Override
     public void triggerWin() {
         // Stop this session
-        stopSession();
+        removeSession();
 
         // Check for, and display, records
         MiniGames miniGames = MiniGames.getInstance();
@@ -106,7 +106,8 @@ public class ParkourArenaSession extends AbstractArenaSession {
     @Override
     protected void removeSession() {
         // Remove this session for game sessions to stop listeners from fiddling more with the player
-        boolean removedSession = MiniGames.getInstance().getParkourArenaPlayerRegistry().removePlayer(player.getUniqueId());
+        boolean removedSession = MiniGames.getInstance().getParkourArenaPlayerRegistry().removePlayer(
+                player.getUniqueId(), true);
         if (!removedSession) {
             MiniGames.log(Level.SEVERE, "Unable to remove parkour arena session for " + player.getName() + ". " +
                     "This will have unintended consequences.");
diff --git a/src/main/java/net/knarcraft/minigames/listener/PlayerStateChangeListener.java b/src/main/java/net/knarcraft/minigames/listener/PlayerStateChangeListener.java
index 14987b0..e3831fa 100644
--- a/src/main/java/net/knarcraft/minigames/listener/PlayerStateChangeListener.java
+++ b/src/main/java/net/knarcraft/minigames/listener/PlayerStateChangeListener.java
@@ -79,7 +79,7 @@ public class PlayerStateChangeListener implements Listener {
         if (entryState != null) {
             MiniGames.log(Level.INFO, "Found existing state for joining player " + player +
                     ". Attempting to restore the player's state.");
-            playerRegistry.removePlayer(player.getUniqueId());
+            playerRegistry.removePlayer(player.getUniqueId(), false);
 
             entryState.restore(player);
             return entryState.getEntryLocation();