diff --git a/Content.Client/Administration/UI/Bwoink/BwoinkControl.xaml.cs b/Content.Client/Administration/UI/Bwoink/BwoinkControl.xaml.cs
index 18aa02e9d67cde..dd8e3e22121e83 100644
--- a/Content.Client/Administration/UI/Bwoink/BwoinkControl.xaml.cs
+++ b/Content.Client/Administration/UI/Bwoink/BwoinkControl.xaml.cs
@@ -92,13 +92,18 @@ public BwoinkControl()
                 if (a.IsPinned != b.IsPinned)
                     return a.IsPinned ? -1 : 1;
 
-                // First, sort by unread. Any chat with unread messages appears first. We just sort based on unread
-                // status, not number of unread messages, so that more recent unread messages take priority.
+                // First, sort by unread. Any chat with unread messages appears first.
                 var aUnread = ach.Unread > 0;
                 var bUnread = bch.Unread > 0;
                 if (aUnread != bUnread)
                     return aUnread ? -1 : 1;
 
+                // Sort by recent messages during the current round.
+                var aRecent = a.ActiveThisRound && ach.LastMessage != DateTime.MinValue;
+                var bRecent = b.ActiveThisRound && bch.LastMessage != DateTime.MinValue;
+                if (aRecent != bRecent)
+                    return aRecent ? -1 : 1;
+
                 // Next, sort by connection status. Any disconnected players are grouped towards the end.
                 if (a.Connected != b.Connected)
                     return a.Connected ? -1 : 1;