diff --git a/KfChatDotNetBot/ChatBot.cs b/KfChatDotNetBot/ChatBot.cs
index 75d5ce2..cd2f0bf 100644
--- a/KfChatDotNetBot/ChatBot.cs
+++ b/KfChatDotNetBot/ChatBot.cs
@@ -152,8 +152,22 @@ public class ChatBot
         // Reset value to 0 as we've now successfully joined
         if (_joinFailures > 0) _joinFailures = 0;
         var settings = Helpers.GetMultipleValues([BuiltIn.Keys.GambaSeshDetectEnabled,
-                BuiltIn.Keys.GambaSeshUserId, BuiltIn.Keys.KiwiFarmsUsername])
+                BuiltIn.Keys.GambaSeshUserId, BuiltIn.Keys.KiwiFarmsUsername, BuiltIn.Keys.BotDisconnectReplayLimit])
             .Result;
+        // Send messages if there are any to replay (Assuming we DC'd, and it's now the message flood)
+        foreach (var replayMsg in _sentMessages.Where(msg => msg.Status == SentMessageTrackerStatus.ChatDisconnected)
+                     .TakeLast(settings[BuiltIn.Keys.BotDisconnectReplayLimit].ToType<int>()))
+        {
+            // Bypass the helpful method we have for sending messages so we don't create new sent message items for them
+            // The validation of whether to send based on GambaSesh's presence etc. has already been performed for msgs here
+            KfClient.SendMessage(replayMsg.Message);
+            replayMsg.Status = SentMessageTrackerStatus.WaitingForResponse;
+            replayMsg.SentAt = DateTimeOffset.UtcNow;
+        }
+        foreach(var lostMsg in _sentMessages.Where(msg => msg.Status == SentMessageTrackerStatus.ChatDisconnected))
+        {
+            lostMsg.Status = SentMessageTrackerStatus.Lost;
+        }
         _logger.Debug($"Received {messages.Count} message(s)");
         foreach (var message in messages)
         {
@@ -203,7 +217,7 @@ public class ChatBot
         }
     }
 
-    public string SendChatMessage(string message, bool bypassSeshDetect = false)
+    public SentMessageTrackerModel SendChatMessage(string message, bool bypassSeshDetect = false)
     {
         var settings = Helpers
             .GetMultipleValues([BuiltIn.Keys.KiwiFarmsSuppressChatMessages, BuiltIn.Keys.GambaSeshDetectEnabled])
@@ -221,20 +235,28 @@ public class ChatBot
             _logger.Info($"Message was: {message}");
             messageTracker.Status = SentMessageTrackerStatus.NotSending;
             _sentMessages.Add(messageTracker);
-            return reference;
+            return messageTracker;
         }
         if (GambaSeshPresent && settings[BuiltIn.Keys.GambaSeshDetectEnabled].ToBoolean() && !bypassSeshDetect)
         {
             _logger.Info($"Not sending message '{message}' as GambaSesh is present");
             messageTracker.Status = SentMessageTrackerStatus.NotSending;
             _sentMessages.Add(messageTracker);
-            return reference;
+            return messageTracker;
+        }
+
+        if (!KfClient.IsConnected())
+        {
+            _logger.Info($"Not sending message '{message}' as Sneedchat is not connected");
+            messageTracker.Status = SentMessageTrackerStatus.ChatDisconnected;
+            _sentMessages.Add(messageTracker);
+            return messageTracker;
         }
         messageTracker.Status = SentMessageTrackerStatus.WaitingForResponse;
         messageTracker.SentAt = DateTimeOffset.UtcNow;
         _sentMessages.Add(messageTracker);
         KfClient.SendMessage(message);
-        return reference;
+        return messageTracker;
     }
 
     public SentMessageTrackerModel GetSentMessageStatus(string reference)
diff --git a/KfChatDotNetBot/Commands/TestCommands.cs b/KfChatDotNetBot/Commands/TestCommands.cs
index 3f561a5..d58bba8 100644
--- a/KfChatDotNetBot/Commands/TestCommands.cs
+++ b/KfChatDotNetBot/Commands/TestCommands.cs
@@ -25,14 +25,15 @@ public class EditTestCommand : ICommand
         var i = 0;
         var delay = 1000;
         var reference = botInstance.SendChatMessage($"{msg} {i}", true);
-        while (botInstance.GetSentMessageStatus(reference).Status == SentMessageTrackerStatus.WaitingForResponse)
+        while (reference.Status == SentMessageTrackerStatus.WaitingForResponse)
         {
             await Task.Delay(100, ctx);
         }
-        
-        var status = botInstance.GetSentMessageStatus(reference);
-        if (status.Status == SentMessageTrackerStatus.NotSending || status.Status == SentMessageTrackerStatus.Unknown ||
-            status.ChatMessageId == null)
+
+        if (reference.Status == SentMessageTrackerStatus.NotSending ||
+            reference.Status == SentMessageTrackerStatus.Unknown ||
+            reference.Status == SentMessageTrackerStatus.ChatDisconnected ||
+            reference.ChatMessageId == null)
         {
             logger.Error("Either message refused to send due to bot settings or something fucked up getting the message ID");
             return;
@@ -41,13 +42,13 @@ public class EditTestCommand : ICommand
         {
             i++;
             await Task.Delay(delay, ctx);
-            botInstance.KfClient.EditMessage(status.ChatMessageId!.Value, $"{msg} {i}");
+            botInstance.KfClient.EditMessage(reference.ChatMessageId!.Value, $"{msg} {i}");
         }
 
         await Task.Delay(delay, ctx);
-        botInstance.KfClient.EditMessage(status.ChatMessageId!.Value, "This message will self destruct in 1 second");
+        botInstance.KfClient.EditMessage(reference.ChatMessageId!.Value, "This message will self destruct in 1 second");
         await Task.Delay(delay, ctx);
-        botInstance.KfClient.DeleteMessage(status.ChatMessageId!.Value);
+        botInstance.KfClient.DeleteMessage(reference.ChatMessageId!.Value);
     }
 }
 
diff --git a/KfChatDotNetBot/Models/SentMessageTrackerModel.cs b/KfChatDotNetBot/Models/SentMessageTrackerModel.cs
index f6c858a..55d968e 100644
--- a/KfChatDotNetBot/Models/SentMessageTrackerModel.cs
+++ b/KfChatDotNetBot/Models/SentMessageTrackerModel.cs
@@ -19,5 +19,9 @@ public enum SentMessageTrackerStatus
     // If the bot is blocked from sending the message, e.g. due to suppress chat messages being enabled 
     NotSending,
     // Shouldn't happen normally, it's just set before the bot has made a decision on whether to send or not,
-    Unknown
+    Unknown,
+    // Means the chat was disconnected when you attempted to send the message
+    ChatDisconnected,
+    // Was held in the replay buffer due to a disconnect, but there were too many messages ahead of it and so was culled
+    Lost
 }
\ No newline at end of file
diff --git a/KfChatDotNetBot/Settings/BuiltIn.cs b/KfChatDotNetBot/Settings/BuiltIn.cs
index e948d17..ed2e263 100644
--- a/KfChatDotNetBot/Settings/BuiltIn.cs
+++ b/KfChatDotNetBot/Settings/BuiltIn.cs
@@ -516,6 +516,15 @@ public static class BuiltIn
             Default = "https://kiwifarms.st/attachments/winmanjack_bgr-png.6414050/",
             IsSecret = false,
             CacheDuration = TimeSpan.FromHours(1)
+        },
+        new BuiltInSettingsModel
+        {
+            Key = Keys.BotDisconnectReplayLimit,
+            Regex = @"\d+",
+            Description = "Limit of messages which could not be sent while bot was disconnected to replay on connect",
+            Default = "10",
+            IsSecret = false,
+            CacheDuration = TimeSpan.FromHours(1)
         }
     ];
     
@@ -565,5 +574,6 @@ public static class BuiltIn
         public static string CrackedZalgoFuckUpMode = "Cracked.ZalgoFuckUpMode";
         public static string CrackedZalgoFuckUpPosition = "Cracked.ZalgoFuckUpPosition";
         public static string WinmanjackImgUrl = "Winmanjack.ImgUrl";
+        public static string BotDisconnectReplayLimit = "Bot.DisconnectReplayLimit";
     }
 }
\ No newline at end of file