diff --git a/build.gradle.kts b/build.gradle.kts
index e15499c..e67401c 100644
--- a/build.gradle.kts
+++ b/build.gradle.kts
@@ -108,6 +108,7 @@ project(":duels-plugin") {
         compileOnly("org.spigotmc:spigot-api:1.14.4-R0.1-SNAPSHOT")
         compileOnly("com.mojang:authlib:1.5.21")
         compileOnly("me.clip:placeholderapi:2.11.6")
+        compileOnly("net.luckperms:api:5.4")
         compileOnly("com.SirBlobman.combatlogx:CombatLogX-API:10.0.0.0-SNAPSHOT")
 
         compileOnly("net.essentialsx:EssentialsX:2.19.2") {
diff --git a/duels-plugin/src/main/java/me/realized/duels/command/commands/duel/DuelCommand.java b/duels-plugin/src/main/java/me/realized/duels/command/commands/duel/DuelCommand.java
index 48cc32f..2316088 100644
--- a/duels-plugin/src/main/java/me/realized/duels/command/commands/duel/DuelCommand.java
+++ b/duels-plugin/src/main/java/me/realized/duels/command/commands/duel/DuelCommand.java
@@ -185,6 +185,13 @@ public class DuelCommand extends BaseCommand {
                     return true;
                 }
 
+                // Reject a bet the opponent cannot cover so the match is not doomed to fail on start.
+                if (!diamondBank.has(amount, target)) {
+                    lang.sendMessage(sender, "ERROR.command.opponent-not-enough-money",
+                        "name", target.getName(), "max", diamondBank.getDiamonds(target), "bet_amount", amount);
+                    return true;
+                }
+
                 settings.setBet(amount);
             }
 
diff --git a/duels-plugin/src/main/java/me/realized/duels/gui/settings/SettingsGui.java b/duels-plugin/src/main/java/me/realized/duels/gui/settings/SettingsGui.java
index fd31c79..53f3916 100644
--- a/duels-plugin/src/main/java/me/realized/duels/gui/settings/SettingsGui.java
+++ b/duels-plugin/src/main/java/me/realized/duels/gui/settings/SettingsGui.java
@@ -15,6 +15,7 @@ import me.realized.duels.gui.settings.buttons.MirrorTheirInventoryButton;
 import me.realized.duels.gui.settings.buttons.OwnInventoryButton;
 import me.realized.duels.gui.settings.buttons.RequestDetailsButton;
 import me.realized.duels.gui.settings.buttons.RequestSendButton;
+import me.realized.duels.gui.settings.buttons.ShuffleAllButton;
 import me.realized.duels.util.compat.Items;
 import me.realized.duels.util.gui.SinglePageGui;
 import me.realized.duels.util.inventory.Slots;
@@ -22,16 +23,16 @@ import org.bukkit.inventory.ItemStack;
 
 public class SettingsGui extends SinglePageGui<DuelsPlugin> {
 
-    // Option buttons are centered in the middle row (slots 9-16). Center is slot 13.
+    // Option buttons flank the middle row around the center slot 13, which is reserved for Shuffle All.
     // The bottom row is reserved for SEND / CANCEL, so options never collide with them.
     private static final int[][] PATTERNS = {
-        {13},
+        {12},
         {12, 14},
-        {12, 13, 14},
+        {11, 12, 14},
         {11, 12, 14, 15},
-        {11, 12, 13, 14, 15},
+        {10, 11, 12, 14, 15},
         {10, 11, 12, 14, 15, 16},
-        {10, 11, 12, 13, 14, 15, 16}
+        {9, 10, 11, 12, 14, 15, 16}
     };
 
     public SettingsGui(final DuelsPlugin plugin) {
@@ -71,7 +72,7 @@ public class SettingsGui extends SinglePageGui<DuelsPlugin> {
             buttons.add(new ItemBettingButton(plugin));
         }
 
-        // Middle row: option buttons, centered. PATTERNS supports up to 7 options (the max possible).
+        // Middle row: option buttons flanking the center. PATTERNS supports up to 7 options (the max possible).
         if (!buttons.isEmpty()) {
             final int[] pattern = PATTERNS[buttons.size() - 1];
 
@@ -80,6 +81,9 @@ public class SettingsGui extends SinglePageGui<DuelsPlugin> {
             }
         }
 
+        // Center of the window: Shuffle All (randomizes every option except the Diamond bet).
+        set(13, new ShuffleAllButton(plugin));
+
         // Bottom row: SEND on the left half, CANCEL on the right half, divider in the center.
         set(18, 22, 1, new RequestSendButton(plugin));
         set(23, 27, 1, new CancelButton(plugin));
diff --git a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorMyInventoryButton.java b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorMyInventoryButton.java
index ddedaf5..f9d77a8 100644
--- a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorMyInventoryButton.java
+++ b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorMyInventoryButton.java
@@ -3,6 +3,7 @@ package me.realized.duels.gui.settings.buttons;
 import me.realized.duels.DuelsPlugin;
 import me.realized.duels.Permissions;
 import me.realized.duels.gui.BaseButton;
+import me.realized.duels.hook.hooks.LuckPermsHook;
 import me.realized.duels.setting.Settings;
 import me.realized.duels.util.compat.Items;
 import me.realized.duels.util.inventory.ItemBuilder;
@@ -21,12 +22,15 @@ public class MirrorMyInventoryButton extends BaseButton {
             return;
         }
 
-        // Display the request sender's (challenger's) head so it is obvious whose inventory is cloned.
+        // Display the request sender's (challenger's) head and rank-colored name so it is obvious whose inventory is cloned.
         setOwner(player);
 
+        final String name = LuckPermsHook.coloredName(plugin, player);
+        setDisplayName(lang.getMessage("GUI.settings.buttons.use-mirror-my-inventory.name", "name", name));
+
         final Settings settings = settingManager.getSafely(player);
         final String value = settings.isMirrorMyInventory() ? lang.getMessage("GENERAL.enabled") : lang.getMessage("GENERAL.disabled");
-        final String lore = plugin.getLang().getMessage("GUI.settings.buttons.use-mirror-my-inventory.lore", "mirror_my_inventory", value);
+        final String lore = plugin.getLang().getMessage("GUI.settings.buttons.use-mirror-my-inventory.lore", "name", name, "mirror_my_inventory", value);
         setLore(lore.split("\n"));
     }
 
diff --git a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorTheirInventoryButton.java b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorTheirInventoryButton.java
index 5fe3b78..e07b575 100644
--- a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorTheirInventoryButton.java
+++ b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/MirrorTheirInventoryButton.java
@@ -3,6 +3,7 @@ package me.realized.duels.gui.settings.buttons;
 import me.realized.duels.DuelsPlugin;
 import me.realized.duels.Permissions;
 import me.realized.duels.gui.BaseButton;
+import me.realized.duels.hook.hooks.LuckPermsHook;
 import me.realized.duels.setting.Settings;
 import me.realized.duels.util.compat.Items;
 import me.realized.duels.util.inventory.ItemBuilder;
@@ -25,18 +26,19 @@ public class MirrorTheirInventoryButton extends BaseButton {
 
         final Settings settings = settingManager.getSafely(player);
 
-        // Display the opponent's head so it is obvious whose inventory is cloned.
+        // Display the opponent's head and rank-colored name so it is obvious whose inventory is cloned.
         final UUID targetId = settings.getTarget();
+        final Player target = targetId != null ? Bukkit.getPlayer(targetId) : null;
+        final String name = target != null ? LuckPermsHook.coloredName(plugin, target) : lang.getMessage("GENERAL.none");
 
-        if (targetId != null) {
-            final Player target = Bukkit.getPlayer(targetId);
-
-            if (target != null) {
-                setOwner(target);
-            }
+        if (target != null) {
+            setOwner(target);
         }
+
+        setDisplayName(lang.getMessage("GUI.settings.buttons.use-mirror-their-inventory.name", "name", name));
+
         final String value = settings.isMirrorTheirInventory() ? lang.getMessage("GENERAL.enabled") : lang.getMessage("GENERAL.disabled");
-        final String lore = plugin.getLang().getMessage("GUI.settings.buttons.use-mirror-their-inventory.lore", "mirror_their_inventory", value);
+        final String lore = plugin.getLang().getMessage("GUI.settings.buttons.use-mirror-their-inventory.lore", "name", name, "mirror_their_inventory", value);
         setLore(lore.split("\n"));
     }
 
diff --git a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/RequestDetailsButton.java b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/RequestDetailsButton.java
index 1a3d3b3..4f8a9b8 100644
--- a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/RequestDetailsButton.java
+++ b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/RequestDetailsButton.java
@@ -2,6 +2,7 @@ package me.realized.duels.gui.settings.buttons;
 
 import me.realized.duels.DuelsPlugin;
 import me.realized.duels.gui.BaseButton;
+import me.realized.duels.hook.hooks.LuckPermsHook;
 import me.realized.duels.setting.Settings;
 import me.realized.duels.util.compat.Items;
 import me.realized.duels.util.inventory.ItemBuilder;
@@ -27,7 +28,8 @@ public class RequestDetailsButton extends BaseButton {
         }
 
         final String lore = lang.getMessage("GUI.settings.buttons.details.lore",
-            "opponent", target.getName(),
+            "opponent", LuckPermsHook.coloredName(plugin, target),
+            "challenger", LuckPermsHook.coloredName(plugin, player),
             "kit", settings.getKit() != null ? settings.getKit().getName() : lang.getMessage("GENERAL.not-selected"),
             "own_inventory", settings.isOwnInventory() ? lang.getMessage("GENERAL.enabled") : lang.getMessage("GENERAL.disabled"),
             "mirror_my_inventory", settings.isMirrorMyInventory() ? lang.getMessage("GENERAL.enabled") : lang.getMessage("GENERAL.disabled"),
diff --git a/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/ShuffleAllButton.java b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/ShuffleAllButton.java
new file mode 100644
index 0000000..7052144
--- /dev/null
+++ b/duels-plugin/src/main/java/me/realized/duels/gui/settings/buttons/ShuffleAllButton.java
@@ -0,0 +1,96 @@
+package me.realized.duels.gui.settings.buttons;
+
+import java.util.ArrayList;
+import java.util.List;
+import java.util.concurrent.ThreadLocalRandom;
+import me.realized.duels.DuelsPlugin;
+import me.realized.duels.Permissions;
+import me.realized.duels.api.kit.Kit;
+import me.realized.duels.gui.BaseButton;
+import me.realized.duels.kit.KitImpl;
+import me.realized.duels.setting.Settings;
+import me.realized.duels.util.inventory.ItemBuilder;
+import org.bukkit.Material;
+import org.bukkit.entity.Player;
+
+public class ShuffleAllButton extends BaseButton {
+
+    public ShuffleAllButton(final DuelsPlugin plugin) {
+        super(plugin, ItemBuilder.of(Material.NETHER_STAR).name(plugin.getLang().getMessage("GUI.settings.buttons.shuffle-all.name")).build());
+    }
+
+    @Override
+    public void update(final Player player) {
+        setLore(lang.getMessage("GUI.settings.buttons.shuffle-all.lore").split("\n"));
+    }
+
+    @Override
+    public void onClick(final Player player) {
+        final Settings settings = settingManager.getSafely(player);
+        final ThreadLocalRandom random = ThreadLocalRandom.current();
+
+        // Randomly pick one of the enabled and permitted inventory/kit modes. They are mutually exclusive.
+        final List<Runnable> modes = new ArrayList<>();
+
+        if (config.isKitSelectingEnabled() && allowed(player, config.isKitSelectingUsePermission(), Permissions.KIT_SELECTING)) {
+            final KitImpl kit = randomKit(player, random);
+
+            if (kit != null) {
+                modes.add(() -> settings.setKit(kit));
+            }
+        }
+
+        if (config.isOwnInventoryEnabled() && allowed(player, config.isOwnInventoryUsePermission(), Permissions.OWN_INVENTORY)) {
+            modes.add(() -> settings.setOwnInventory(true));
+        }
+
+        if (config.isMirrorInventoryEnabled() && allowed(player, config.isMirrorInventoryUsePermission(), Permissions.MIRROR_INVENTORY)) {
+            modes.add(() -> settings.setMirrorMyInventory(true));
+            modes.add(() -> settings.setMirrorTheirInventory(true));
+        }
+
+        if (!modes.isEmpty()) {
+            modes.get(random.nextInt(modes.size())).run();
+        }
+
+        // Random arena for the chosen mode (null = Random, chosen when the match starts).
+        if (config.isArenaSelectingEnabled() && allowed(player, config.isArenaSelectingUsePermission(), Permissions.ARENA_SELECTING)) {
+            settings.setArena(arenaManager.randomArena(settings.getKit()));
+        }
+
+        // Random item betting toggle. Diamond betting is intentionally left untouched.
+        if (config.isItemBettingEnabled() && allowed(player, config.isItemBettingUsePermission(), Permissions.ITEM_BETTING)) {
+            settings.setItemBetting(random.nextBoolean());
+        }
+
+        settings.updateGui(player);
+        lang.sendMessage(player, "GUI.settings.buttons.shuffle-all.shuffled");
+    }
+
+    private boolean allowed(final Player player, final boolean usePermission, final String permission) {
+        return !usePermission || player.hasPermission(permission) || player.hasPermission(Permissions.SETTING_ALL);
+    }
+
+    private KitImpl randomKit(final Player player, final ThreadLocalRandom random) {
+        final List<KitImpl> usable = new ArrayList<>();
+
+        for (final Kit kit : kitManager.getKits()) {
+            final KitImpl impl = (KitImpl) kit;
+
+            if (canUseKit(player, impl)) {
+                usable.add(impl);
+            }
+        }
+
+        return usable.isEmpty() ? null : usable.get(random.nextInt(usable.size()));
+    }
+
+    private boolean canUseKit(final Player player, final KitImpl kit) {
+        if (!kit.isUsePermission()) {
+            return true;
+        }
+
+        final String permission = String.format(Permissions.KIT, kit.getName().replace(" ", "-").toLowerCase());
+        return player.hasPermission(Permissions.KIT_ALL) || player.hasPermission(permission);
+    }
+}
diff --git a/duels-plugin/src/main/java/me/realized/duels/hook/HookManager.java b/duels-plugin/src/main/java/me/realized/duels/hook/HookManager.java
index 92bf80d..dabeac3 100644
--- a/duels-plugin/src/main/java/me/realized/duels/hook/HookManager.java
+++ b/duels-plugin/src/main/java/me/realized/duels/hook/HookManager.java
@@ -9,6 +9,7 @@ import me.realized.duels.hook.hooks.EternalCombatHook;
 import me.realized.duels.hook.hooks.FactionsHook;
 import me.realized.duels.hook.hooks.GameModeInventoriesHook;
 import me.realized.duels.hook.hooks.LeaderHeadsHook;
+import me.realized.duels.hook.hooks.LuckPermsHook;
 import me.realized.duels.hook.hooks.MVdWPlaceholderHook;
 import me.realized.duels.hook.hooks.McMMOHook;
 import me.realized.duels.hook.hooks.PlaceholderHook;
@@ -30,6 +31,7 @@ public class HookManager extends AbstractHookManager<DuelsPlugin> {
         register(FactionsHook.NAME, FactionsHook.class);
         register(GameModeInventoriesHook.NAME, GameModeInventoriesHook.class);
         register(LeaderHeadsHook.NAME, LeaderHeadsHook.class);
+        register(LuckPermsHook.NAME, LuckPermsHook.class);
         register(McMMOHook.NAME, McMMOHook.class);
         register(MVdWPlaceholderHook.NAME, MVdWPlaceholderHook.class);
         register(PlaceholderHook.NAME, PlaceholderHook.class);
diff --git a/duels-plugin/src/main/java/me/realized/duels/hook/hooks/DiamondBankHook.java b/duels-plugin/src/main/java/me/realized/duels/hook/hooks/DiamondBankHook.java
index 9399b6b..3e483ef 100644
--- a/duels-plugin/src/main/java/me/realized/duels/hook/hooks/DiamondBankHook.java
+++ b/duels-plugin/src/main/java/me/realized/duels/hook/hooks/DiamondBankHook.java
@@ -67,6 +67,18 @@ public class DiamondBankHook extends PluginHook<DuelsPlugin> {
         }
     }
 
+    /**
+     * @return the whole number of Diamonds the given player can currently spend (bank + inventory), or 0 on failure.
+     */
+    public int getDiamonds(final Player player) {
+        try {
+            return ((Number) invoke(shardsToDiamonds, totalShards(player))).intValue();
+        } catch (ReflectiveOperationException | RuntimeException ex) {
+            Log.warn("Failed to read DiamondBank-OG balance: " + ex.getMessage());
+            return 0;
+        }
+    }
+
     public boolean add(final int amount, final Player... players) {
         try {
             final long shards = toShards(amount);
diff --git a/duels-plugin/src/main/java/me/realized/duels/hook/hooks/LuckPermsHook.java b/duels-plugin/src/main/java/me/realized/duels/hook/hooks/LuckPermsHook.java
new file mode 100644
index 0000000..59bf844
--- /dev/null
+++ b/duels-plugin/src/main/java/me/realized/duels/hook/hooks/LuckPermsHook.java
@@ -0,0 +1,55 @@
+package me.realized.duels.hook.hooks;
+
+import me.realized.duels.DuelsPlugin;
+import me.realized.duels.util.StringUtil;
+import me.realized.duels.util.hook.PluginHook;
+import net.luckperms.api.LuckPerms;
+import net.luckperms.api.LuckPermsProvider;
+import org.bukkit.ChatColor;
+import org.bukkit.entity.Player;
+
+public class LuckPermsHook extends PluginHook<DuelsPlugin> {
+
+    public static final String NAME = "LuckPerms";
+
+    private final LuckPerms api;
+
+    public LuckPermsHook(final DuelsPlugin plugin) {
+        super(plugin, NAME);
+        this.api = LuckPermsProvider.get();
+    }
+
+    /**
+     * @return the player's name colored with the formatting of their LuckPerms prefix (e.g. their rank color).
+     */
+    public String getColoredName(final Player player) {
+        return getColor(player) + player.getName();
+    }
+
+    private String getColor(final Player player) {
+        try {
+            final String prefix = api.getPlayerAdapter(Player.class).getMetaData(player).getPrefix();
+
+            if (prefix == null || prefix.isEmpty()) {
+                return "";
+            }
+
+            // Apply whatever color/format the prefix ends with to the name (e.g. "&c[Admin] " -> a red name).
+            return ChatColor.getLastColors(StringUtil.color(prefix));
+        } catch (final Exception ex) {
+            return "";
+        }
+    }
+
+    /**
+     * Returns the player's rank-colored name if LuckPerms is hooked, otherwise their plain name. Null-safe.
+     */
+    public static String coloredName(final DuelsPlugin plugin, final Player player) {
+        if (player == null) {
+            return "";
+        }
+
+        final LuckPermsHook hook = plugin.getHookManager().getHook(LuckPermsHook.class);
+        return hook != null ? hook.getColoredName(player) : player.getName();
+    }
+}
diff --git a/duels-plugin/src/main/java/me/realized/duels/request/RequestManager.java b/duels-plugin/src/main/java/me/realized/duels/request/RequestManager.java
index 7f4fff1..4e5f0f8 100644
--- a/duels-plugin/src/main/java/me/realized/duels/request/RequestManager.java
+++ b/duels-plugin/src/main/java/me/realized/duels/request/RequestManager.java
@@ -7,6 +7,7 @@ import me.realized.duels.DuelsPlugin;
 import me.realized.duels.api.event.request.RequestSendEvent;
 import me.realized.duels.config.Config;
 import me.realized.duels.config.Lang;
+import me.realized.duels.hook.hooks.LuckPermsHook;
 import me.realized.duels.setting.Settings;
 import me.realized.duels.util.Loadable;
 import me.realized.duels.util.TextBuilder;
@@ -20,11 +21,13 @@ import org.bukkit.event.player.PlayerQuitEvent;
 
 public class RequestManager implements Loadable, Listener {
 
+    private final DuelsPlugin plugin;
     private final Config config;
     private final Lang lang;
     private final Map<UUID, Map<UUID, RequestImpl>> requests = new HashMap<>();
 
     public RequestManager(final DuelsPlugin plugin) {
+        this.plugin = plugin;
         this.config = plugin.getConfiguration();
         this.lang = plugin.getLang();
         Bukkit.getPluginManager().registerEvents(this, plugin);
@@ -66,13 +69,15 @@ public class RequestManager implements Loadable, Listener {
         final String arena = settings.getArena() != null ? settings.getArena().getName() : lang.getMessage("GENERAL.random");
         final int betAmount = settings.getBet();
         final String itemBetting = settings.isItemBetting() ? lang.getMessage("GENERAL.enabled") : lang.getMessage("GENERAL.disabled");
+        final String challengerName = LuckPermsHook.coloredName(plugin, sender);
+        final String opponentName = LuckPermsHook.coloredName(plugin, target);
 
         lang.sendMessage(sender, "COMMAND.duel.request.send.sender",
-            "name", target.getName(), "kit", kit,
+            "name", opponentName, "challenger", challengerName, "opponent", opponentName, "kit", kit,
             "own_inventory", ownInventory, "mirror_my_inventory", mirrorMyInventory, "mirror_their_inventory", mirrorTheirInventory,
             "arena", arena, "bet_amount", betAmount, "item_betting", itemBetting);
         lang.sendMessage(target, "COMMAND.duel.request.send.receiver",
-            "name", sender.getName(), "kit", kit,
+            "name", challengerName, "challenger", challengerName, "opponent", opponentName, "kit", kit,
             "own_inventory", ownInventory, "mirror_my_inventory", mirrorMyInventory, "mirror_their_inventory", mirrorTheirInventory,
             "arena", arena, "bet_amount", betAmount, "item_betting", itemBetting);
 
diff --git a/duels-plugin/src/main/java/me/realized/duels/setting/SettingsManager.java b/duels-plugin/src/main/java/me/realized/duels/setting/SettingsManager.java
index e45a630..22dd8d9 100644
--- a/duels-plugin/src/main/java/me/realized/duels/setting/SettingsManager.java
+++ b/duels-plugin/src/main/java/me/realized/duels/setting/SettingsManager.java
@@ -22,6 +22,8 @@ public class SettingsManager implements Loadable, Listener {
     private final DuelsPlugin plugin;
     private final Map<UUID, Settings> cache = new HashMap<>();
     private final Set<UUID> awaitingBetInput = ConcurrentHashMap.newKeySet();
+    // Players who have already used their single "too high" retry for the current bet-input sequence.
+    private final Set<UUID> betInputRetried = ConcurrentHashMap.newKeySet();
 
     public SettingsManager(final DuelsPlugin plugin) {
         this.plugin = plugin;
@@ -35,6 +37,7 @@ public class SettingsManager implements Loadable, Listener {
     public void handleUnload() {
         cache.clear();
         awaitingBetInput.clear();
+        betInputRetried.clear();
     }
 
     // Only one Settings instance stays in memory while player is online; no need for manual removal of gui from GuiListener
@@ -43,9 +46,18 @@ public class SettingsManager implements Loadable, Listener {
     }
 
     public void requestBetInput(final Player player) {
+        // Clicking the bet button starts a fresh sequence, so the one-time retry is available again.
+        betInputRetried.remove(player.getUniqueId());
         awaitingBetInput.add(player.getUniqueId());
         player.closeInventory();
-        plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.prompt");
+
+        final Settings settings = getSafely(player);
+        final Player target = settings.getTarget() != null ? Bukkit.getPlayer(settings.getTarget()) : null;
+        final DiamondBankHook diamondBank = plugin.getHookManager().getHook(DiamondBankHook.class);
+        // The maximum bet is limited by the opponent's balance, since a bet they cannot cover is rejected.
+        final int max = (target != null && diamondBank != null) ? diamondBank.getDiamonds(target) : 0;
+        final String name = target != null ? target.getName() : plugin.getLang().getMessage("GENERAL.none");
+        plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.prompt", "name", name, "max", max);
     }
 
     @EventHandler(priority = EventPriority.LOWEST)
@@ -67,6 +79,7 @@ public class SettingsManager implements Loadable, Listener {
         final UUID uuid = event.getPlayer().getUniqueId();
         cache.remove(uuid);
         awaitingBetInput.remove(uuid);
+        betInputRetried.remove(uuid);
     }
 
     private void handleBetInput(final UUID uuid, final String message) {
@@ -79,6 +92,7 @@ public class SettingsManager implements Loadable, Listener {
         final Settings settings = getSafely(player);
 
         if (message.equalsIgnoreCase("cancel")) {
+            betInputRetried.remove(uuid);
             plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.cancelled");
             settings.openGui(player);
             return;
@@ -87,21 +101,49 @@ public class SettingsManager implements Loadable, Listener {
         final int bet = NumberUtil.parseInt(message).orElse(-1);
 
         if (bet < 0) {
+            betInputRetried.remove(uuid);
             plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.invalid");
             settings.openGui(player);
             return;
         }
 
-        final DiamondBankHook diamondBank = plugin.getHookManager().getHook(DiamondBankHook.class);
+        if (bet > 0) {
+            final DiamondBankHook diamondBank = plugin.getHookManager().getHook(DiamondBankHook.class);
 
-        if (bet > 0 && (diamondBank == null || !diamondBank.has(bet, player))) {
-            plugin.getLang().sendMessage(player, "ERROR.command.not-enough-money");
-            settings.openGui(player);
-            return;
+            if (diamondBank == null || !diamondBank.has(bet, player)) {
+                betTooHigh(player, () -> plugin.getLang().sendMessage(player, "ERROR.command.not-enough-money"));
+                return;
+            }
+
+            final Player target = settings.getTarget() != null ? Bukkit.getPlayer(settings.getTarget()) : null;
+
+            // Reject a bet the opponent cannot cover so the match is not doomed to fail on start.
+            if (target != null && !diamondBank.has(bet, target)) {
+                betTooHigh(player, () -> plugin.getLang().sendMessage(player, "ERROR.command.opponent-not-enough-money",
+                    "name", target.getName(), "max", diamondBank.getDiamonds(target), "bet_amount", bet));
+                return;
+            }
         }
 
+        betInputRetried.remove(uuid);
         settings.setBet(bet);
         plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.set", "bet_amount", bet);
         settings.openGui(player);
     }
+
+    // A bet that exceeds either balance gives the player one more chance to type an amount in chat.
+    // Once that single retry is used, they must send a new duel request rather than reopening the GUI.
+    private void betTooHigh(final Player player, final Runnable reasonMessage) {
+        final UUID uuid = player.getUniqueId();
+        reasonMessage.run();
+
+        if (betInputRetried.add(uuid)) {
+            awaitingBetInput.add(uuid);
+            plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.retry");
+            return;
+        }
+
+        betInputRetried.remove(uuid);
+        plugin.getLang().sendMessage(player, "GUI.settings.buttons.diamond-bet.retry-failed");
+    }
 }
diff --git a/duels-plugin/src/main/resources/lang.yml b/duels-plugin/src/main/resources/lang.yml
index a1941a0..ae1cc3d 100644
--- a/duels-plugin/src/main/resources/lang.yml
+++ b/duels-plugin/src/main/resources/lang.yml
@@ -63,7 +63,7 @@ ERROR:
       target: '{PREFIX} &c%name% is already in a duel.'
     already-in-queue: '{PREFIX} &cYou cannot do this while in a queue.'
     prevent-teleportation: '{PREFIX} &cCannot teleport to a player in a duel.'
-    mode-unselected: '{PREFIX} &cChoose a kit or enable one of: Each Uses Own Inventory, Both Use My Inventory, Both Use Their Inventory.'
+    mode-unselected: '{PREFIX} &cChoose a kit or enable an inventory option (each their own, yours, or your opponent''s).'
     mode-fixed: '{PREFIX} &cYou are not allowed to change inventory mode here.'
   spectate:
     already-spectating:
@@ -95,6 +95,7 @@ ERROR:
     invalid-option: '{PREFIX} &c''%option%'' is not a valid option. Available options are: %available_options%'
     invalid-action: '{PREFIX} &c''%action%'' is not a valid action. Available actions are: %available_actions%'
     not-enough-money: '{PREFIX} &cYou do not have enough Diamonds to bet!'
+    opponent-not-enough-money: '{PREFIX} &c%name% only has %max% Diamond(s) and cannot cover a bet of &B%bet_amount% Diamond(s)&c.'
     lobby-save-failure: '{PREFIX} &cCould not save lobby location. Please check the console for more information.'
     name-not-alphanumeric: '{PREFIX} &c''%name%'' is not alphanumeric.'
 
@@ -114,21 +115,21 @@ COMMAND:
       send:
         sender:
         - '{LINE}'
-        - '&7Duel request sent to &4%name%&7.'
+        - '&7Duel request sent to %opponent%&7.'
         - '&6- &7Kit: &d%kit%'
         - '&6- &7Each Uses Own Inventory: &r%own_inventory%'
-        - '&6- &7Both Use My Inventory: &r%mirror_my_inventory%'
-        - '&6- &7Both Use Their Inventory: &r%mirror_their_inventory%'
+        - '&6- &7Both Use %challenger%&7''s Inventory: &r%mirror_my_inventory%'
+        - '&6- &7Both Use %opponent%&7''s Inventory: &r%mirror_their_inventory%'
         - '&6- &7Arena: &e%arena%'
         - '&6- &7Bet: &B%bet_amount% Diamond(s)'
         - '{LINE}'
         receiver:
         - '{LINE}'
-        - '&7Duel request received from &4%name%&7.'
+        - '&7Duel request received from %challenger%&7.'
         - '&6- &7Kit: &d%kit%'
         - '&6- &7Each Uses Own Inventory: &r%own_inventory%'
-        - '&6- &7Both Use My Inventory: &r%mirror_my_inventory%'
-        - '&6- &7Both Use Their Inventory: &r%mirror_their_inventory%'
+        - '&6- &7Both Use %challenger%&7''s Inventory: &r%mirror_my_inventory%'
+        - '&6- &7Both Use %opponent%&7''s Inventory: &r%mirror_their_inventory%'
         - '&6- &7Arena: &e%arena%'
         - '&6- &7Bet: &B%bet_amount% Diamond(s)'
         clickable-text:
@@ -293,7 +294,7 @@ COMMAND:
 
 DUEL:
   start-failure:
-    mode-unselected: '{FAIL_PREFIX} &cChoose a kit or enable one of: Each Uses Own Inventory, Both Use My Inventory, Both Use Their Inventory.'
+    mode-unselected: '{FAIL_PREFIX} &cChoose a kit or enable an inventory option (each their own, yours, or your opponent''s).'
     player-is-dead: '{FAIL_PREFIX} You or your opponent is not alive!'
     in-blacklisted-world: '{FAIL_PREFIX} You or your opponent is in a blacklisted world!'
     is-tagged: '{FAIL_PREFIX} You or your opponent is in combat!'
@@ -357,11 +358,11 @@ GUI:
       details:
         name: '&9Request Details'
         lore:
-        - '&7Opponent: &4%opponent%'
+        - '&7Opponent: %opponent%'
         - '&7Kit: &d%kit%'
         - '&7Each Uses Own Inventory: &r%own_inventory%'
-        - '&7Both Use My Inventory: &r%mirror_my_inventory%'
-        - '&7Both Use Their Inventory: &r%mirror_their_inventory%'
+        - '&7Both Use %challenger%&7''s Inventory: &r%mirror_my_inventory%'
+        - '&7Both Use %opponent%&7''s Inventory: &r%mirror_their_inventory%'
         - '&7Arena: &e%arena%'
         - '&7Bet: &B%bet_amount% Diamond(s)'
       kit-selector:
@@ -389,11 +390,11 @@ GUI:
           - '&cYou do not have permission to'
           - '&cuse this option.'
       use-mirror-my-inventory:
-        name: '&bBoth Use My Inventory &7(Your Head)'
+        name: '&bBoth Use %name%&b''s Inventory'
         lore:
           - '&7Both duelists fight with a CLONE of'
-          - '&7YOUR inventory and armor (the challenger).'
-          - '&7You both get the same gear: yours.'
+          - '&7%name%&7''s inventory and armor (you, the challenger).'
+          - '&7You both get the same gear.'
           - '&7Originals are restored after the match.'
           - ' '
           - '&7Currently: &r%mirror_my_inventory%'
@@ -402,11 +403,11 @@ GUI:
           - '&cYou do not have permission to'
           - '&cuse this option.'
       use-mirror-their-inventory:
-        name: '&eBoth Use Their Inventory &7(Opponent Head)'
+        name: '&eBoth Use %name%&e''s Inventory'
         lore:
           - '&7Both duelists fight with a CLONE of'
-          - '&7the OPPONENT''s inventory and armor.'
-          - '&7You both get the same gear: theirs.'
+          - '&7%name%&7''s inventory and armor (your opponent).'
+          - '&7You both get the same gear.'
           - '&7Originals are restored after the match.'
           - ' '
           - '&7Currently: &r%mirror_their_inventory%'
@@ -429,8 +430,10 @@ GUI:
         - '&7Bet: &B%bet_amount% Diamond(s)'
         - ' '
         - '&aClick to enter a bet amount.'
-        prompt: '{PREFIX} &7Type the Diamond bet amount in chat, or type &ccancel &7to keep the current amount.'
+        prompt: '{PREFIX} &7Type the Diamond bet amount in chat, or type &ccancel &7to keep the current amount. &7Max bet vs &4%name%&7: &B%max% Diamond(s) &7(their balance).'
         invalid: '{PREFIX} &cPlease enter a whole number of Diamonds.'
+        retry: '{PREFIX} &7Type a lower Diamond bet in chat, or type &ccancel&7. &cThis is your last try before you must send a new duel request.'
+        retry-failed: '{PREFIX} &cThat bet is still too high. Send a new duel request to try betting again.'
         cancelled: '{PREFIX} &7Diamond bet unchanged.'
         set: '{PREFIX} &7Diamond bet set to &B%bet_amount% Diamond(s)&7.'
         lore-no-permission:
@@ -445,6 +448,15 @@ GUI:
         lore-no-permission:
         - '&cYou do not have permission to'
         - '&cuse this option.'
+      shuffle-all:
+        name: '&d&lShuffle All'
+        lore:
+        - '&7Randomly picks an inventory mode,'
+        - '&7arena, and item betting for you.'
+        - '&7Your Diamond bet is left unchanged.'
+        - ' '
+        - '&aClick to shuffle!'
+        shuffled: '{PREFIX} &7Randomized all settings except your Diamond bet.'
       send:
         name: '&a&lSEND REQUEST'
       cancel:
diff --git a/duels-plugin/src/main/resources/plugin.yml b/duels-plugin/src/main/resources/plugin.yml
index 11042a0..fed4905 100644
--- a/duels-plugin/src/main/resources/plugin.yml
+++ b/duels-plugin/src/main/resources/plugin.yml
@@ -1,7 +1,7 @@
 name: Duels-OG
 main: me.realized.duels.DuelsPlugin
 version: @VERSION@
-softdepend: [BetterChairs-OG, CombatLogX, CombatTagPlus, DiamondBank-OG, Essentials, EternalCombat, Factions, GameModeInventories-OG, LeaderHeads, mcMMO, MVdWPlaceholderAPI, MyWorlds, PlaceholderAPI, ProtocolLib, PvPManager, SimpleClans, WorldGuard]
+softdepend: [BetterChairs-OG, CombatLogX, CombatTagPlus, DiamondBank-OG, Essentials, EternalCombat, Factions, GameModeInventories-OG, LeaderHeads, LuckPerms, mcMMO, MVdWPlaceholderAPI, MyWorlds, PlaceholderAPI, ProtocolLib, PvPManager, SimpleClans, WorldGuard]
 # MyWorlds added as soft-depend due to locations being null when Duels is loaded before managed worlds.
 # Add any world management plugins to softdepend list if arena doesn't load properly in the generated world.
 api-version: 1.14