diff --git a/Content.Client/Administration/AdminSystem.cs b/Content.Client/Administration/AdminSystem.cs
index 3b4b0a9240..b9ae77f754 100644
--- a/Content.Client/Administration/AdminSystem.cs
+++ b/Content.Client/Administration/AdminSystem.cs
@@ -24,6 +24,14 @@ namespace Content.Client.Administration
             }
         }
 
+        public List<PlayerInfo> GetSortedPlayerList(Comparison<PlayerInfo> comparison)
+        {
+            if (_playerList == null) return new List<PlayerInfo>();
+            var list = _playerList.Values.ToList();
+            list.Sort(comparison);
+            return list;
+        }
+
         public override void Initialize()
         {
             base.Initialize();
diff --git a/Content.Client/Administration/BwoinkSystem.cs b/Content.Client/Administration/BwoinkSystem.cs
index f207c9e75c..bf6ca9ca2f 100644
--- a/Content.Client/Administration/BwoinkSystem.cs
+++ b/Content.Client/Administration/BwoinkSystem.cs
@@ -36,7 +36,7 @@ namespace Content.Client.Administration
             LogBwoink(message);
             // Actual line
             var window = EnsurePanel(message.ChannelId);
-            window.ReceiveLine($"[color=gray]{message.SentAt.ToShortTimeString()}[/color] {message.Text}");
+            window.ReceiveLine(message);
             // Play a sound if we didn't send it
             var localPlayer = _playerManager.LocalPlayer;
             if (localPlayer?.UserId != message.TrueSender)
@@ -62,7 +62,7 @@ namespace Content.Client.Administration
                     _adminWindow.BwoinkArea.AddChild(existingPanel);
             }
 
-            _adminWindow.Open();
+            if(!_adminWindow.IsOpen) _adminWindow.Open();
 
             return existingPanel;
         }
diff --git a/Content.Client/Administration/UI/BwoinkWindow.xaml.cs b/Content.Client/Administration/UI/BwoinkWindow.xaml.cs
index ccd2b3ef6e..ababb5e8c3 100644
--- a/Content.Client/Administration/UI/BwoinkWindow.xaml.cs
+++ b/Content.Client/Administration/UI/BwoinkWindow.xaml.cs
@@ -54,13 +54,20 @@ namespace Content.Client.Administration.UI
                 li.Text = FormatTabTitle(li, pl);
             };
 
-            ChannelSelector.SortKey = (PlayerInfo pl) =>
+            ChannelSelector.Comparison = (a, b) =>
             {
-               if (_bwoinkSystem.TryGetChannel(pl.SessionId, out var ch))
-               {
-                   return ch.Unread;
-               }
-               return 0;
+                var aChannelExists = _bwoinkSystem.TryGetChannel(a.SessionId, out var ach);
+                var bChannelExists = _bwoinkSystem.TryGetChannel(b.SessionId, out var bch);
+                if (!aChannelExists && !bChannelExists)
+                    return 0;
+
+                if (!aChannelExists)
+                    return -1;
+
+                if (!bChannelExists)
+                    return 1;
+
+                return bch!.LastMessage.CompareTo(ach!.LastMessage);
             };
 
             // ew
@@ -152,7 +159,8 @@ namespace Content.Client.Administration.UI
         public void SwitchToChannel(NetUserId ch)
         {
             foreach (var bw in BwoinkArea.Children)
-                bw.Visible = (bw as BwoinkPanel)?.ChannelId == ch;
+                bw.Visible = false;
+            _bwoinkSystem.EnsurePanel(ch).Visible = true;
         }
     }
 }
diff --git a/Content.Client/Administration/UI/CustomControls/BwoinkPanel.xaml.cs b/Content.Client/Administration/UI/CustomControls/BwoinkPanel.xaml.cs
index c59198d21a..86540a3f27 100644
--- a/Content.Client/Administration/UI/CustomControls/BwoinkPanel.xaml.cs
+++ b/Content.Client/Administration/UI/CustomControls/BwoinkPanel.xaml.cs
@@ -1,4 +1,6 @@
 #nullable enable
+using System;
+using Content.Shared.Administration;
 using Robust.Client.AutoGenerated;
 using Robust.Client.UserInterface.Controls;
 using Robust.Client.UserInterface.XAML;
@@ -14,6 +16,7 @@ namespace Content.Client.Administration.UI.CustomControls
         public readonly NetUserId ChannelId;
 
         public int Unread { get; private set; } = 0;
+        public DateTime LastMessage { get; private set; }
 
         public BwoinkPanel(BwoinkSystem bwoinkSys, NetUserId userId)
         {
@@ -37,13 +40,15 @@ namespace Content.Client.Administration.UI.CustomControls
             SenderLineEdit.Clear();
         }
 
-        public void ReceiveLine(string text)
+        public void ReceiveLine(SharedBwoinkSystem.BwoinkTextMessage message)
         {
             if (!Visible)
                 Unread++;
+
             var formatted = new FormattedMessage(1);
-            formatted.AddMarkup(text);
+            formatted.AddMarkup($"[color=gray]{message.SentAt.ToShortTimeString()}[/color] {message.Text}");
             TextOutput.AddMessage(formatted);
+            LastMessage = message.SentAt;
         }
     }
 }
diff --git a/Content.Client/Administration/UI/CustomControls/PlayerListControl.xaml.cs b/Content.Client/Administration/UI/CustomControls/PlayerListControl.xaml.cs
index 88273fc9ee..48b0ca65a7 100644
--- a/Content.Client/Administration/UI/CustomControls/PlayerListControl.xaml.cs
+++ b/Content.Client/Administration/UI/CustomControls/PlayerListControl.xaml.cs
@@ -18,7 +18,7 @@ namespace Content.Client.Administration.UI.CustomControls
         public event Action<PlayerInfo?>? OnSelectionChanged;
 
         public Action<PlayerInfo, ItemList.Item>? DecoratePlayer;
-        public Func<PlayerInfo, int>? SortKey;
+        public Comparison<PlayerInfo>? Comparison;
 
         public PlayerListControl()
         {
@@ -59,11 +59,7 @@ namespace Content.Client.Administration.UI.CustomControls
         {
             PlayerItemList.Clear();
 
-            IEnumerable<PlayerInfo> iter = _adminSystem.PlayerList;
-            if (SortKey is not null)
-                iter = _adminSystem.PlayerList.OrderByDescending(SortKey);
-
-            foreach (var info in iter)
+            foreach (var info in Comparison == null ? _adminSystem.PlayerList : _adminSystem.GetSortedPlayerList(Comparison))
             {
                 var displayName = $"{info.CharacterName} ({info.Username})";
                 if (!string.IsNullOrEmpty(FilterLineEdit.Text) &&