diff --git a/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs b/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
index 5faa30dbd2..2aeca4f8f3 100644
--- a/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
+++ b/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
@@ -351,28 +351,11 @@ namespace Tgstation.Server.Host.Components.Chat
 
 		/// <inheritdoc />
 		public void QueueWatchdogMessage(string message)
-		{
-			ArgumentNullException.ThrowIfNull(message);
+			=> QueueMessageGeneric(mapping => mapping.IsWatchdogChannel, message, "WD");
 
-			message = String.Format(CultureInfo.InvariantCulture, "WD: {0}", message);
-
-			if (!initialProviderConnectionsTask!.IsCompleted)
-				logger.LogTrace("Waiting for initial provider connections before sending watchdog message...");
-
-			// Reimplementing QueueMessage
-			QueueMessageInternal(
-				new MessageContent
-				{
-					Text = message,
-				},
-				() =>
-				{
-					// so it doesn't change while we're using it
-					lock (mappedChannels)
-						return mappedChannels.Where(x => x.Value.IsWatchdogChannel).Select(x => x.Key).ToList();
-				},
-				true);
-		}
+		/// <inheritdoc />
+		public void QueueRawDeploymentMessage(string message)
+			=> QueueMessageGeneric(mapping => mapping.IsUpdatesChannel, message, null);
 
 		/// <inheritdoc />
 		public Func<string?, string, Action<bool>> QueueDeploymentMessage(
@@ -1111,5 +1094,38 @@ namespace Tgstation.Server.Host.Components.Chat
 
 			AddMessageTask(SendMessageTask());
 		}
+
+		/// <summary>
+		/// Queues a message to a selected set of <see cref="ChannelMapping"/>s.
+		/// </summary>
+		/// <param name="channelSelector">A <see cref="Predicate{T}"/> for selecting the <see cref="ChannelMapping"/>s to send to.</param>
+		/// <param name="message">The message to send.</param>
+		/// <param name="prefix">The optional prefix to the message to be sent.</param>
+		void QueueMessageGeneric(Predicate<ChannelMapping> channelSelector, string message, string? prefix)
+		{
+			ArgumentNullException.ThrowIfNull(message);
+
+			if (prefix != null)
+			{
+				message = $"{prefix}: {message}";
+			}
+
+			if (!initialProviderConnectionsTask!.IsCompleted)
+				logger.LogTrace("Waiting for initial provider connections before sending chat message...");
+
+			// Reimplementing QueueMessage
+			QueueMessageInternal(
+				new MessageContent
+				{
+					Text = message,
+				},
+				() =>
+				{
+					// so it doesn't change while we're using it
+					lock (mappedChannels)
+						return mappedChannels.Where(x => channelSelector(x.Value)).Select(x => x.Key).ToList();
+				},
+				true);
+		}
 	}
 }
diff --git a/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs b/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
index 669f21b305..4f112afb69 100644
--- a/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
+++ b/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
@@ -57,6 +57,12 @@ namespace Tgstation.Server.Host.Components.Chat
 		/// <param name="message">The message being sent.</param>
 		void QueueWatchdogMessage(string message);
 
+		/// <summary>
+		/// Queue a chat <paramref name="message"/> to configured deployment channels.
+		/// </summary>
+		/// <param name="message">The message being sent.</param>
+		void QueueRawDeploymentMessage(string message);
+
 		/// <summary>
 		/// Send the message for a deployment to configured deployment channels.
 		/// </summary>
diff --git a/src/Tgstation.Server.Host/Components/Instance.cs b/src/Tgstation.Server.Host/Components/Instance.cs
index f0fd27f661..37454b7dbc 100644
--- a/src/Tgstation.Server.Host/Components/Instance.cs
+++ b/src/Tgstation.Server.Host/Components/Instance.cs
@@ -531,7 +531,10 @@ namespace Tgstation.Server.Host.Components
 						}
 					}
 					else if (preserveTestMerges)
+					{
+						Chat.QueueRawDeploymentMessage("Automatic update has failed due to a conflicting testmerge!");
 						throw new JobException(Api.Models.ErrorCode.InstanceUpdateTestMergeConflict);
+					}
 
 					if (!preserveTestMerges)
 					{