diff --git a/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml b/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml
index 433807e7b1..5c3e7f667d 100644
--- a/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml
+++ b/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml
@@ -1,7 +1,9 @@
 <BoxContainer
     xmlns="https://spacestation14.io"
+    xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
     Orientation="Vertical"
-    HorizontalExpand="true">
+    HorizontalExpand="True">
     <OutputPanel Name="TextOutput" VerticalExpand="true" />
     <HistoryLineEdit Name="SenderLineEdit" />
+    <RichTextLabel Name="RelayedToDiscordLabel" Access="Public" Visible="False" />
 </BoxContainer>
diff --git a/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml.cs b/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml.cs
index f545aff422..ee345cb51c 100644
--- a/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml.cs
+++ b/Content.Client/Administration/UI/Bwoink/BwoinkPanel.xaml.cs
@@ -3,7 +3,6 @@ using Robust.Client.AutoGenerated;
 using Robust.Client.UserInterface.Controls;
 using Robust.Client.UserInterface.XAML;
 using Robust.Shared.Utility;
-using Content.Client.Administration.UI.CustomControls;
 
 namespace Content.Client.Administration.UI.Bwoink
 {
@@ -18,6 +17,13 @@ namespace Content.Client.Administration.UI.Bwoink
         public BwoinkPanel(Action<string> messageSender)
         {
             RobustXamlLoader.Load(this);
+
+            var msg = new FormattedMessage();
+            msg.PushColor(Color.LightGray);
+            msg.AddText(Loc.GetString("bwoink-system-messages-being-relayed-to-discord"));
+            msg.Pop();
+            RelayedToDiscordLabel.SetMessage(msg);
+
             _messageSender = messageSender;
 
             OnVisibilityChanged += c =>
diff --git a/Content.Client/UserInterface/Systems/Bwoink/AHelpUIController.cs b/Content.Client/UserInterface/Systems/Bwoink/AHelpUIController.cs
index 21b3c9d0ff..871708a711 100644
--- a/Content.Client/UserInterface/Systems/Bwoink/AHelpUIController.cs
+++ b/Content.Client/UserInterface/Systems/Bwoink/AHelpUIController.cs
@@ -29,9 +29,18 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
     [Dependency] private readonly IPlayerManager _playerManager = default!;
     [Dependency] private readonly IClyde _clyde = default!;
     [Dependency] private readonly IUserInterfaceManager _uiManager = default!;
+
     private BwoinkSystem? _bwoinkSystem;
     private MenuButton? AhelpButton => UIManager.GetActiveUIWidgetOrNull<MenuBar.Widgets.GameTopMenuBar>()?.AHelpButton;
     public IAHelpUIHandler? UIHelper;
+    private bool _discordRelayActive;
+
+    public override void Initialize()
+    {
+        base.Initialize();
+
+        SubscribeNetworkEvent<SharedBwoinkSystem.BwoinkDiscordRelayUpdated>(DiscordRelayUpdated);
+    }
 
     public void OnStateEntered(GameplayState state)
     {
@@ -71,7 +80,6 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
         EnsureUIHelper();
     }
 
-
     private void AHelpButtonPressed(BaseButton.ButtonEventArgs obj)
     {
         EnsureUIHelper();
@@ -129,6 +137,12 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
         UIHelper!.Receive(message);
     }
 
+    private void DiscordRelayUpdated(SharedBwoinkSystem.BwoinkDiscordRelayUpdated args, EntitySessionEventArgs session)
+    {
+        _discordRelayActive = args.DiscordRelayEnabled;
+        UIHelper?.DiscordRelayChanged(_discordRelayActive);
+    }
+
     public void EnsureUIHelper()
     {
         var isAdmin = _adminManager.HasFlag(AdminFlags.Adminhelp);
@@ -139,6 +153,7 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
         UIHelper?.Dispose();
         var ownerUserId = _playerManager.LocalPlayer!.UserId;
         UIHelper = isAdmin ? new AdminAHelpUIHandler(ownerUserId) : new UserAHelpUIHandler(ownerUserId);
+        UIHelper.DiscordRelayChanged(_discordRelayActive);
 
         UIHelper.SendMessageAction = (userId, textMessage) => _bwoinkSystem?.Send(userId, textMessage);
         UIHelper.OnClose += () => { SetAHelpPressed(false); };
@@ -161,14 +176,15 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
         EnsureUIHelper();
         if (UIHelper!.IsOpen)
             return;
-        UIHelper!.Open(localPlayer.UserId);
+        UIHelper!.Open(localPlayer.UserId, _discordRelayActive);
     }
+
     public void Open(NetUserId userId)
     {
         EnsureUIHelper();
         if (!UIHelper!.IsAdmin)
             return;
-        UIHelper?.Open(userId);
+        UIHelper?.Open(userId, _discordRelayActive);
     }
 
     public void ToggleWindow()
@@ -177,7 +193,6 @@ public sealed class AHelpUIController: UIController, IOnStateChanged<GameplaySta
         UIHelper?.ToggleWindow();
     }
 
-
     public void PopOut()
     {
         EnsureUIHelper();
@@ -223,8 +238,9 @@ public interface IAHelpUIHandler : IDisposable
     public bool IsOpen { get; }
     public void Receive(SharedBwoinkSystem.BwoinkTextMessage message);
     public void Close();
-    public void Open(NetUserId netUserId);
+    public void Open(NetUserId netUserId, bool relayActive);
     public void ToggleWindow();
+    public void DiscordRelayChanged(bool active);
     public event Action OnClose;
     public event Action OnOpen;
     public Action<NetUserId, string>? SendMessageAction { get; set; }
@@ -298,11 +314,15 @@ public sealed class AdminAHelpUIHandler : IAHelpUIHandler
             OpenWindow();
     }
 
+    public void DiscordRelayChanged(bool active)
+    {
+    }
+
     public event Action? OnClose;
     public event Action? OnOpen;
     public Action<NetUserId, string>? SendMessageAction { get; set; }
 
-    public void Open(NetUserId channelId)
+    public void Open(NetUserId channelId, bool relayActive)
     {
         SelectChannel(channelId);
         OpenWindow();
@@ -381,11 +401,12 @@ public sealed class UserAHelpUIHandler : IAHelpUIHandler
     public bool IsOpen => _window is { Disposed: false, IsOpen: true };
     private DefaultWindow? _window;
     private BwoinkPanel? _chatPanel;
+    private bool _discordRelayActive;
 
     public void Receive(SharedBwoinkSystem.BwoinkTextMessage message)
     {
         DebugTools.Assert(message.UserId == _ownerId);
-        EnsureInit();
+        EnsureInit(_discordRelayActive);
         _chatPanel!.ReceiveLine(message);
         _window!.OpenCentered();
     }
@@ -397,7 +418,7 @@ public sealed class UserAHelpUIHandler : IAHelpUIHandler
 
     public void ToggleWindow()
     {
-        EnsureInit();
+        EnsureInit(_discordRelayActive);
         if (_window!.IsOpen)
         {
             _window.Close();
@@ -413,27 +434,38 @@ public sealed class UserAHelpUIHandler : IAHelpUIHandler
     {
     }
 
+    public void DiscordRelayChanged(bool active)
+    {
+        _discordRelayActive = active;
+
+        if (_chatPanel != null)
+        {
+            _chatPanel.RelayedToDiscordLabel.Visible = active;
+        }
+    }
+
     public event Action? OnClose;
     public event Action? OnOpen;
     public Action<NetUserId, string>? SendMessageAction { get; set; }
 
-    public void Open(NetUserId channelId)
+    public void Open(NetUserId channelId, bool relayActive)
     {
-        EnsureInit();
+        EnsureInit(relayActive);
         _window!.OpenCentered();
     }
 
-    private void EnsureInit()
+    private void EnsureInit(bool relayActive)
     {
         if (_window is { Disposed: false })
             return;
         _chatPanel = new BwoinkPanel(text => SendMessageAction?.Invoke(_ownerId, text));
+        _chatPanel.RelayedToDiscordLabel.Visible = relayActive;
         _window = new DefaultWindow()
         {
             TitleClass="windowTitleAlert",
             HeaderClass="windowHeaderAlert",
             Title=Loc.GetString("bwoink-user-title"),
-            SetSize=(400, 200),
+            MinSize=(500, 200),
         };
         _window.OnClose += () => { OnClose?.Invoke(); };
         _window.OnOpen += () => { OnOpen?.Invoke(); };
diff --git a/Content.Server/Administration/Systems/BwoinkSystem.cs b/Content.Server/Administration/Systems/BwoinkSystem.cs
index 0d42407b15..2cc3d2d3c7 100644
--- a/Content.Server/Administration/Systems/BwoinkSystem.cs
+++ b/Content.Server/Administration/Systems/BwoinkSystem.cs
@@ -109,6 +109,8 @@ namespace Content.Server.Administration.Systems
         {
             _webhookUrl = url;
 
+            RaiseNetworkEvent(new BwoinkDiscordRelayUpdated(!string.IsNullOrWhiteSpace(url)));
+
             if (url == string.Empty)
                 return;
 
@@ -395,13 +397,11 @@ namespace Content.Server.Administration.Systems
                 _messageQueues[msg.UserId].Enqueue(GenerateAHelpMessage(senderSession.Name, str, !personalChannel, admins.Count == 0));
             }
 
-            if (admins.Count != 0)
+            if (admins.Count != 0 || sendsWebhook)
                 return;
 
             // No admin online, let the player know
-            var systemText = sendsWebhook ?
-                Loc.GetString("bwoink-system-starmute-message-no-other-users-webhook") :
-                Loc.GetString("bwoink-system-starmute-message-no-other-users");
+            var systemText = Loc.GetString("bwoink-system-starmute-message-no-other-users");
             var starMuteMsg = new BwoinkTextMessage(message.UserId, SystemUserId, systemText);
             RaiseNetworkEvent(starMuteMsg, senderSession.ConnectedClient);
         }
diff --git a/Content.Shared/Administration/SharedBwoinkSystem.cs b/Content.Shared/Administration/SharedBwoinkSystem.cs
index 2df0e3a7d7..597d2c0a6c 100644
--- a/Content.Shared/Administration/SharedBwoinkSystem.cs
+++ b/Content.Shared/Administration/SharedBwoinkSystem.cs
@@ -29,7 +29,9 @@ namespace Content.Shared.Administration
         public sealed class BwoinkTextMessage : EntityEventArgs
         {
             public DateTime SentAt { get; }
+
             public NetUserId UserId { get; }
+
             // This is ignored from the client.
             // It's checked by the client when receiving a message from the server for bwoink noises.
             // This could be a boolean "Incoming", but that would require making a second instance.
@@ -44,5 +46,20 @@ namespace Content.Shared.Administration
                 Text = text;
             }
         }
+
+        /// <summary>
+        ///     Sent by the server to notify all clients when the webhook url is sent.
+        ///     The webhook url itself is not and should not be sent.
+        /// </summary>
+        [Serializable, NetSerializable]
+        public sealed class BwoinkDiscordRelayUpdated : EntityEventArgs
+        {
+            public bool DiscordRelayEnabled { get; }
+
+            public BwoinkDiscordRelayUpdated(bool enabled)
+            {
+                DiscordRelayEnabled = enabled;
+            }
+        }
     }
 }
diff --git a/Resources/Locale/en-US/administration/bwoink.ftl b/Resources/Locale/en-US/administration/bwoink.ftl
index cb9230e2da..dd96f8a3b7 100644
--- a/Resources/Locale/en-US/administration/bwoink.ftl
+++ b/Resources/Locale/en-US/administration/bwoink.ftl
@@ -2,5 +2,4 @@ bwoink-user-title = Admin Message
 
 bwoink-system-starmute-message-no-other-users = *System: Nobody is available to receive your message. Try pinging Game Admins on Discord.
 
-bwoink-system-starmute-message-no-other-users-webhook = *System: Your message has been relayed to the admins via discord.
-
+bwoink-system-messages-being-relayed-to-discord = Your messages are being relayed to the admins via Discord.