diff --git a/pom.xml b/pom.xml
index bc3dac7..7f7c102 100644
--- a/pom.xml
+++ b/pom.xml
@@ -86,7 +86,7 @@
         <dependency>
             <groupId>org.spigotmc</groupId>
             <artifactId>spigot-api</artifactId>
-            <version>1.19.4-R0.1-SNAPSHOT</version>
+            <version>1.20-R0.1-SNAPSHOT</version>
             <scope>provided</scope>
         </dependency>
         <dependency>
diff --git a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
index c298e04..971eece 100644
--- a/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/AbstractArenaSession.java
@@ -15,7 +15,7 @@ public abstract class AbstractArenaSession implements ArenaSession {
     private final @NotNull ArenaGameMode gameMode;
     private final @NotNull Player player;
     protected int deaths;
-    protected final long startTime;
+    protected long startTime;
     protected PlayerEntryState entryState;
 
     /**
@@ -47,6 +47,14 @@ public abstract class AbstractArenaSession implements ArenaSession {
         player.sendMessage(Message.SUCCESS_ARENA_QUIT.getMessage());
     }
 
+    @Override
+    public void reset() {
+        this.deaths = 0;
+        this.startTime = System.currentTimeMillis();
+        PlayerTeleporter.teleportPlayer(this.player, this.arena.getSpawnLocation(), false, false);
+        this.entryState.setArenaState();
+    }
+
     /**
      * Announces a record set by this player
      *
diff --git a/src/main/java/net/knarcraft/minigames/arena/ArenaSession.java b/src/main/java/net/knarcraft/minigames/arena/ArenaSession.java
index 22737bb..8003b62 100644
--- a/src/main/java/net/knarcraft/minigames/arena/ArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/ArenaSession.java
@@ -47,4 +47,9 @@ public interface ArenaSession {
      */
     @NotNull ArenaGUI getGUI();
 
+    /**
+     * Resets the session to allow a player to try again
+     */
+    void reset();
+
 }
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 1a1ae73..0f3d694 100644
--- a/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java
+++ b/src/main/java/net/knarcraft/minigames/arena/parkour/ParkourArenaSession.java
@@ -116,6 +116,12 @@ public class ParkourArenaSession extends AbstractArenaSession {
         return new ParkourGUI(player);
     }
 
+    @Override
+    public void reset() {
+        this.reachedCheckpoint = null;
+        super.reset();
+    }
+
     @Override
     protected void removeSession() {
         // Remove this session for game sessions to stop listeners from fiddling more with the player
diff --git a/src/main/java/net/knarcraft/minigames/command/parkour/JoinParkourArenaCommand.java b/src/main/java/net/knarcraft/minigames/command/parkour/JoinParkourArenaCommand.java
index 1d536db..26f9792 100644
--- a/src/main/java/net/knarcraft/minigames/command/parkour/JoinParkourArenaCommand.java
+++ b/src/main/java/net/knarcraft/minigames/command/parkour/JoinParkourArenaCommand.java
@@ -101,7 +101,7 @@ public class JoinParkourArenaCommand implements CommandExecutor {
         } else {
             // Update the player's state to follow the arena's rules
             newSession.getEntryState().setArenaState();
-            
+
             player.getInventory().addItem(GUIHelper.getGUIOpenItem());
             player.sendMessage(Message.SUCCESS_ARENA_JOINED.getMessage());
             return true;
diff --git a/src/main/java/net/knarcraft/minigames/gui/ArenaGUI.java b/src/main/java/net/knarcraft/minigames/gui/ArenaGUI.java
index fdca5c8..a00dc43 100644
--- a/src/main/java/net/knarcraft/minigames/gui/ArenaGUI.java
+++ b/src/main/java/net/knarcraft/minigames/gui/ArenaGUI.java
@@ -21,18 +21,29 @@ import java.util.List;
  */
 public abstract class ArenaGUI extends AbstractGUI {
 
-    protected final ArenaPlayerRegistry<?> playerRegistry;
-
     /**
      * Instantiates a new arena gui
      *
-     * @param inventorySize  <p>The size of the GUI's inventory</p>
-     * @param inventoryName  <p>The name of the inventory</p>
-     * @param playerRegistry <p>The player registry used for this GUI</p>
+     * @param inventorySize <p>The size of the GUI's inventory</p>
+     * @param inventoryName <p>The name of the inventory</p>
      */
-    public ArenaGUI(int inventorySize, String inventoryName, ArenaPlayerRegistry<?> playerRegistry) {
+    public ArenaGUI(int inventorySize, String inventoryName) {
         super(inventorySize, inventoryName, null);
-        this.playerRegistry = playerRegistry;
+    }
+
+    /**
+     * Gets an item describing a retry arena action
+     *
+     * @return <p>An arena restart item</p>
+     */
+    protected ItemStack getRestartItem() {
+        PlayerHeadGUIItemFactory restartItemFactory = new PlayerHeadGUIItemFactory();
+        restartItemFactory.useSkin("e23b225ed0443c4eec7cf30a034490485904e6eb3d53ef2ab9e39c73bdf22c30");
+        List<String> loreLines = getLoreLines();
+        loreLines.add(ChatColor.GRAY + "Use this item to retry the arena");
+        restartItemFactory.setName(ChatColor.BLUE + "Retry arena");
+        restartItemFactory.setLore(loreLines);
+        return restartItemFactory.build();
     }
 
     /**
@@ -108,7 +119,7 @@ public abstract class ArenaGUI extends AbstractGUI {
      *
      * @return <p>The leave action</p>
      */
-    protected GUIAction getLeaveAction() {
+    public static GUIAction getLeaveAction() {
         return (player) -> {
             ArenaSession session = MiniGames.getInstance().getSession(player.getUniqueId());
             if (session != null) {
@@ -117,12 +128,27 @@ public abstract class ArenaGUI extends AbstractGUI {
         };
     }
 
+    /**
+     * Gets the action to run when triggering the restart action
+     *
+     * @return <p>The action for triggering a session restart</p>
+     */
+    public static GUIAction getRestartAction() {
+        return (player -> {
+            ArenaSession session = MiniGames.getInstance().getSession(player.getUniqueId());
+            if (session != null) {
+                session.reset();
+            }
+        });
+    }
+
     /**
      * Gets the action to run when triggering the toggle players action
      *
+     * @param playerRegistry <p>The registry containing relevant players</p>
      * @return <p>The action for triggering player visibility</p>
      */
-    protected GUIAction getTogglePlayersAction() {
+    public GUIAction getTogglePlayersAction(ArenaPlayerRegistry<?> playerRegistry) {
         return (player) -> {
             PlayerVisibilityManager visibilityManager = MiniGames.getInstance().getPlayerVisibilityManager();
             visibilityManager.toggleHidePlayers(playerRegistry, player);
diff --git a/src/main/java/net/knarcraft/minigames/gui/DropperGUI.java b/src/main/java/net/knarcraft/minigames/gui/DropperGUI.java
index a280166..acf2324 100644
--- a/src/main/java/net/knarcraft/minigames/gui/DropperGUI.java
+++ b/src/main/java/net/knarcraft/minigames/gui/DropperGUI.java
@@ -14,16 +14,18 @@ public class DropperGUI extends ArenaGUI {
      * @param player <p>The player the GUI is created for</p>
      */
     public DropperGUI(Player player) {
-        super(9, "Dropper", MiniGames.getInstance().getDropperArenaPlayerRegistry());
+        super(9, "Dropper");
         if (MiniGames.getInstance().getPlayerVisibilityManager().isHidingPlayers(player)) {
             setItem(0, getTogglePlayersItemEnabled());
         } else {
             setItem(0, getTogglePlayersItemDisabled());
         }
         setItem(2, getLeaveItem());
+        setItem(4, getRestartItem());
 
-        setAnyClickAction(0, getTogglePlayersAction());
+        setAnyClickAction(0, getTogglePlayersAction(MiniGames.getInstance().getDropperArenaPlayerRegistry()));
         setAnyClickAction(2, getLeaveAction());
+        setAnyClickAction(4, getRestartAction());
     }
 
 }
diff --git a/src/main/java/net/knarcraft/minigames/gui/MiniGamesGUI.java b/src/main/java/net/knarcraft/minigames/gui/MiniGamesGUI.java
index 7b8f34e..4dca1f4 100644
--- a/src/main/java/net/knarcraft/minigames/gui/MiniGamesGUI.java
+++ b/src/main/java/net/knarcraft/minigames/gui/MiniGamesGUI.java
@@ -14,14 +14,14 @@ public class MiniGamesGUI extends ArenaGUI {
      * @param player <p>The player the GUI is created for</p>
      */
     public MiniGamesGUI(Player player) {
-        super(9, "MiniGames", null);
+        super(9, "MiniGames");
         if (MiniGames.getInstance().getPlayerVisibilityManager().isHidingPlayers(player)) {
             setItem(0, getTogglePlayersItemEnabled());
         } else {
             setItem(0, getTogglePlayersItemDisabled());
         }
 
-        setAnyClickAction(0, getTogglePlayersAction());
+        setAnyClickAction(0, getTogglePlayersAction(null));
     }
 
 }
diff --git a/src/main/java/net/knarcraft/minigames/gui/ParkourGUI.java b/src/main/java/net/knarcraft/minigames/gui/ParkourGUI.java
index ac6d4d0..1783cc3 100644
--- a/src/main/java/net/knarcraft/minigames/gui/ParkourGUI.java
+++ b/src/main/java/net/knarcraft/minigames/gui/ParkourGUI.java
@@ -23,7 +23,7 @@ public class ParkourGUI extends ArenaGUI {
      * @param player <p>The player the GUI is created for</p>
      */
     public ParkourGUI(Player player) {
-        super(9, "Parkour", MiniGames.getInstance().getParkourArenaPlayerRegistry());
+        super(9, "Parkour");
         if (MiniGames.getInstance().getPlayerVisibilityManager().isHidingPlayers(player)) {
             setItem(0, getTogglePlayersItemEnabled());
         } else {
@@ -31,10 +31,12 @@ public class ParkourGUI extends ArenaGUI {
         }
         setItem(2, getGiveUpItem());
         setItem(4, getLeaveItem());
+        setItem(6, getRestartItem());
 
-        setAnyClickAction(0, getTogglePlayersAction());
+        setAnyClickAction(0, getTogglePlayersAction(MiniGames.getInstance().getParkourArenaPlayerRegistry()));
         setAnyClickAction(2, getGiveUpAction());
         setAnyClickAction(4, getLeaveAction());
+        setAnyClickAction(6, getRestartAction());
     }
 
     /**
@@ -57,7 +59,7 @@ public class ParkourGUI extends ArenaGUI {
      *
      * @return <p>The give up action</p>
      */
-    private GUIAction getGiveUpAction() {
+    public static GUIAction getGiveUpAction() {
         return (player) -> {
             ArenaSession session = MiniGames.getInstance().getSession(player.getUniqueId());
             if (session instanceof ParkourArenaSession) {
diff --git a/src/main/java/net/knarcraft/minigames/listener/InteractListener.java b/src/main/java/net/knarcraft/minigames/listener/InteractListener.java
index f476b68..fe96318 100644
--- a/src/main/java/net/knarcraft/minigames/listener/InteractListener.java
+++ b/src/main/java/net/knarcraft/minigames/listener/InteractListener.java
@@ -1,6 +1,8 @@
 package net.knarcraft.minigames.listener;
 
 import net.knarcraft.minigames.MiniGames;
+import net.knarcraft.minigames.gui.ArenaGUI;
+import net.knarcraft.minigames.gui.ParkourGUI;
 import net.knarcraft.minigames.property.PersistentDataKey;
 import net.knarcraft.minigames.util.GUIHelper;
 import org.bukkit.NamespacedKey;
@@ -33,6 +35,20 @@ public class InteractListener implements Listener {
         if (persistentData != null && persistentData == PersistentDataKey.MENU_ITEM.getDataValue()) {
             event.setCancelled(true);
             GUIHelper.openGUI(event.getPlayer());
+            return;
+        }
+
+        persistentData = meta.getPersistentDataContainer().get(new NamespacedKey(MiniGames.getInstance(),
+                PersistentDataKey.LEAVE_ITEM.getKeyName()), PersistentDataType.INTEGER);
+        if (persistentData != null) {
+            event.setCancelled(true);
+            if (persistentData == PersistentDataKey.LEAVE_ITEM.getDataValue()) {
+                ArenaGUI.getLeaveAction().run(event.getPlayer());
+            } else if (persistentData == PersistentDataKey.GIVE_UP_ITEM.getDataValue()) {
+                ParkourGUI.getGiveUpAction().run(event.getPlayer());
+            } else if (persistentData == PersistentDataKey.TOGGLE_PLAYERS_ITEM.getDataValue()) {
+                //TODO: Figure out how in the world this should be done, as the existing code cannot be re-used
+            }
         }
     }
 
diff --git a/src/main/java/net/knarcraft/minigames/placeholder/RecordExpansion.java b/src/main/java/net/knarcraft/minigames/placeholder/RecordExpansion.java
index 9dca66c..93a0822 100644
--- a/src/main/java/net/knarcraft/minigames/placeholder/RecordExpansion.java
+++ b/src/main/java/net/knarcraft/minigames/placeholder/RecordExpansion.java
@@ -1,6 +1,7 @@
 package net.knarcraft.minigames.placeholder;
 
 import me.clip.placeholderapi.expansion.PlaceholderExpansion;
+import net.knarcraft.minigames.MiniGames;
 import net.knarcraft.minigames.arena.Arena;
 import net.knarcraft.minigames.arena.ArenaGameMode;
 import net.knarcraft.minigames.arena.ArenaGroup;
@@ -26,6 +27,7 @@ import java.util.Objects;
 import java.util.Set;
 import java.util.UUID;
 import java.util.function.Supplier;
+import java.util.logging.Level;
 
 /**
  * A placeholder expansion for parkour record placeholders
@@ -71,7 +73,14 @@ public abstract class RecordExpansion extends PlaceholderExpansion {
         ArenaGameMode gameMode = parseGameMode(parts[2]);
         SelectionType selectionType = SelectionType.getFromString(parts[3]);
         String identifier = parts[4];
-        int recordNumber = Integer.parseInt(parts[5]) - 1;
+        int recordNumber;
+        try {
+            recordNumber = Integer.parseInt(parts[5]) - 1;
+        } catch (NumberFormatException exception) {
+            MiniGames.log(Level.WARNING, "Invalid placeholder given. " + parts[5] +
+                    " supplied instead of record placement.");
+            return parameters;
+        }
         InfoType infoType = InfoType.getFromString(parts[6]);
 
         if (recordType == null || infoType == null) {
diff --git a/src/main/java/net/knarcraft/minigames/property/PersistentDataKey.java b/src/main/java/net/knarcraft/minigames/property/PersistentDataKey.java
index 2965f89..a3343ab 100644
--- a/src/main/java/net/knarcraft/minigames/property/PersistentDataKey.java
+++ b/src/main/java/net/knarcraft/minigames/property/PersistentDataKey.java
@@ -6,6 +6,9 @@ package net.knarcraft.minigames.property;
 public enum PersistentDataKey {
 
     MENU_ITEM("MiniGamesMenu", 1799804),
+    LEAVE_ITEM("MiniGamesAction", 1799871),
+    GIVE_UP_ITEM("MiniGamesAction", 1799872),
+    TOGGLE_PLAYERS_ITEM("MiniGamesAction", 1799873),
     ;
 
     private final String keyName;