diff --git a/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs b/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
index 25807b4d2f..93e8971229 100644
--- a/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
+++ b/src/Tgstation.Server.Host/Components/Chat/ChatManager.cs
@@ -111,6 +111,11 @@ namespace Tgstation.Server.Host.Components.Chat
 		/// </summary>
 		Task initialProviderConnectionsTask;
 
+		/// <summary>
+		/// A <see cref="Task"/> that represents all sent messages.
+		/// </summary>
+		Task messageSendTask;
+
 		/// <summary>
 		/// The <see cref="TaskCompletionSource{TResult}"/> that completes when <see cref="ChatBot"/>s change
 		/// </summary>
@@ -159,6 +164,8 @@ namespace Tgstation.Server.Host.Components.Chat
 			trackingContexts = new List<IChatTrackingContext>();
 			handlerCts = new CancellationTokenSource();
 			connectionsUpdated = new TaskCompletionSource<object>();
+
+			messageSendTask = Task.CompletedTask;
 			channelIdCounter = 1;
 		}
 
@@ -170,6 +177,8 @@ namespace Tgstation.Server.Host.Components.Chat
 			handlerCts.Dispose();
 			foreach (var I in providers)
 				await I.Value.DisposeAsync().ConfigureAwait(false);
+
+			await messageSendTask.ConfigureAwait(false);
 		}
 
 		/// <summary>
@@ -614,16 +623,29 @@ namespace Tgstation.Server.Host.Components.Chat
 		}
 
 		/// <inheritdoc />
-		public async Task SendMessage(string message, IEnumerable<ulong> channelIds, CancellationToken cancellationToken)
+		public void QueueMessage(string message, IEnumerable<ulong> channelIds)
 		{
 			if (message == null)
 				throw new ArgumentNullException(nameof(message));
 			if (channelIds == null)
 				throw new ArgumentNullException(nameof(channelIds));
 
+			var task = SendMessage(message, channelIds, handlerCts.Token);
+			AddMessageTask(task);
+		}
+
+		/// <summary>
+		/// Asynchronously send a given <paramref name="message"/> to a set of <paramref name="channelIds"/>.
+		/// </summary>
+		/// <param name="message">The message to send.</param>
+		/// <param name="channelIds">The <see cref="Models.ChatChannel.Id"/>s of the <see cref="Models.ChatChannel"/>s to send to.</param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
+		/// <returns>A <see cref="Task"/> representing the running operation.</returns>
+		Task SendMessage(string message, IEnumerable<ulong> channelIds, CancellationToken cancellationToken)
+		{
 			logger.LogTrace("Chat send \"{0}\" to channels: {1}", message, String.Join(", ", channelIds));
 
-			await Task.WhenAll(
+			return Task.WhenAll(
 				channelIds.Select(x =>
 				{
 					ChannelMapping channelMapping;
@@ -635,12 +657,11 @@ namespace Tgstation.Server.Host.Components.Chat
 						if (!providers.TryGetValue(channelMapping.ProviderId, out provider))
 							return Task.CompletedTask;
 					return provider.SendMessage(channelMapping.ProviderChannelId, message, cancellationToken);
-				}))
-				.ConfigureAwait(false);
+				}));
 		}
 
 		/// <inheritdoc />
-		public async Task SendWatchdogMessage(string message, CancellationToken cancellationToken)
+		public async Task QueueWatchdogMessage(string message, CancellationToken cancellationToken)
 		{
 			List<ulong> wdChannels = null;
 			message = String.Format(CultureInfo.InvariantCulture, "WD: {0}", message);
@@ -654,18 +675,17 @@ namespace Tgstation.Server.Host.Components.Chat
 			lock (mappedChannels)
 				wdChannels = mappedChannels.Where(x => x.Value.IsWatchdogChannel).Select(x => x.Key).ToList();
 
-			await SendMessage(message, wdChannels, cancellationToken).ConfigureAwait(false);
+			QueueMessage(message, wdChannels);
 		}
 
 		/// <inheritdoc />
-		public async Task<Func<string, string, Task>> SendDeploymentMessage(
+		public Action<string, string> QueueDeploymentMessage(
 			Models.RevisionInformation revisionInformation,
 			Version byondVersion,
 			DateTimeOffset? estimatedCompletionTime,
 			string gitHubOwner,
 			string gitHubRepo,
-			bool localCommitPushed,
-			CancellationToken cancellationToken)
+			bool localCommitPushed)
 		{
 			List<ulong> wdChannels;
 			lock (mappedChannels) // so it doesn't change while we're using it
@@ -675,7 +695,7 @@ namespace Tgstation.Server.Host.Components.Chat
 
 			var callbacks = new List<Func<string, string, Task>>();
 
-			await Task.WhenAll(
+			var task = Task.WhenAll(
 				wdChannels.Select(
 					async x =>
 					{
@@ -697,7 +717,7 @@ namespace Tgstation.Server.Host.Components.Chat
 								gitHubRepo,
 								channelMapping.ProviderChannelId,
 								localCommitPushed,
-								cancellationToken)
+								handlerCts.Token)
 								.ConfigureAwait(false);
 
 							callbacks.Add(callback);
@@ -709,10 +729,16 @@ namespace Tgstation.Server.Host.Components.Chat
 								"Error sending deploy message to provider {0}!",
 								channelMapping.ProviderId);
 						}
-					}))
-				.ConfigureAwait(false);
+					}));
 
-			return (errorMessage, dreamMakerOutput) => Task.WhenAll(callbacks.Select(x => x(errorMessage, dreamMakerOutput)));
+			AddMessageTask(task);
+
+			return (errorMessage, dreamMakerOutput) => AddMessageTask(
+				Task.WhenAll(
+					callbacks.Select(
+						x => x(
+							errorMessage,
+							dreamMakerOutput))));
 		}
 
 		/// <inheritdoc />
@@ -744,6 +770,7 @@ namespace Tgstation.Server.Host.Components.Chat
 			if (chatHandler != null)
 				await chatHandler.ConfigureAwait(false);
 			await Task.WhenAll(providers.Select(x => x.Value).Select(x => x.Disconnect(cancellationToken))).ConfigureAwait(false);
+			await messageSendTask.ConfigureAwait(false);
 		}
 
 		/// <inheritdoc />
@@ -800,7 +827,32 @@ namespace Tgstation.Server.Host.Components.Chat
 			List<ulong> wdChannels;
 			lock (mappedChannels) // so it doesn't change while we're using it
 				wdChannels = mappedChannels.Select(x => x.Key).ToList();
-			return SendMessage(message, wdChannels, cancellationToken);
+
+			QueueMessage(message, wdChannels);
+			return Task.CompletedTask;
+		}
+
+		/// <summary>
+		/// Adds a given <paramref name="task"/> to <see cref="messageSendTask"/>.
+		/// </summary>
+		/// <param name="task">The <see cref="Task"/> to add.</param>
+		void AddMessageTask(Task task)
+		{
+			async Task Wrap(Task originalTask)
+			{
+				await originalTask.ConfigureAwait(false);
+				try
+				{
+					await task.ConfigureAwait(false);
+				}
+				catch (Exception ex)
+				{
+					logger.LogWarning(ex, "Error in asynchronous chat message!");
+				}
+			}
+
+			lock (handlerCts)
+				messageSendTask = Wrap(messageSendTask);
 		}
 	}
 }
diff --git a/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs b/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
index 3cfe424951..367274d8b2 100644
--- a/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
+++ b/src/Tgstation.Server.Host/Components/Chat/IChatManager.cs
@@ -44,21 +44,19 @@ namespace Tgstation.Server.Host.Components.Chat
 		Task ChangeChannels(long connectionId, IEnumerable<Api.Models.ChatChannel> newChannels, CancellationToken cancellationToken);
 
 		/// <summary>
-		/// Send a chat <paramref name="message"/> to a given set of <paramref name="channelIds"/>
+		/// Queue a chat <paramref name="message"/> to a given set of <paramref name="channelIds"/>.
 		/// </summary>
-		/// <param name="message">The message being sent</param>
-		/// <param name="channelIds">The <see cref="Models.ChatChannel.Id"/>s of the <see cref="Models.ChatChannel"/>s to send to</param>
-		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
-		/// <returns>A <see cref="Task"/> representing the running operation</returns>
-		Task SendMessage(string message, IEnumerable<ulong> channelIds, CancellationToken cancellationToken);
+		/// <param name="message">The message being sent.</param>
+		/// <param name="channelIds">The <see cref="Models.ChatChannel.Id"/>s of the <see cref="Models.ChatChannel"/>s to send to.</param>
+		void QueueMessage(string message, IEnumerable<ulong> channelIds);
 
 		/// <summary>
-		/// Send a chat <paramref name="message"/> to configured watchdog channels
+		/// Queue a chat <paramref name="message"/> to configured watchdog channels.
 		/// </summary>
-		/// <param name="message">The message being sent</param>
-		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
-		/// <returns>A <see cref="Task"/> representing the running operation</returns>
-		Task SendWatchdogMessage(string message, CancellationToken cancellationToken);
+		/// <param name="message">The message being sent.</param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
+		/// <returns>A <see cref="Task"/> representing the running operation.</returns>
+		Task QueueWatchdogMessage(string message, CancellationToken cancellationToken);
 
 		/// <summary>
 		/// Send the message for a deployment to configured deployment channels.
@@ -69,16 +67,14 @@ namespace Tgstation.Server.Host.Components.Chat
 		/// <param name="gitHubOwner">The repository GitHub owner, if any.</param>
 		/// <param name="gitHubRepo">The repository GitHub name, if any.</param>
 		/// <param name="localCommitPushed"><see langword="true"/> if the local deployment commit was pushed to the remote repository.</param>
-		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
-		/// <returns>A <see cref="Task{TResult}"/> resulting in a <see cref="Func{T1, T2, TResult}"/> to call to update the message at the deployment's conclusion. Parameters: Error message if any, DreamMaker output if any.</returns>
-		Task<Func<string, string, Task>> SendDeploymentMessage(
+		/// <returns>An <see cref="Action{T1, T2}"/> to call to update the message at the deployment's conclusion. Parameters: Error message if any, DreamMaker output if any.</returns>
+		Action<string, string> QueueDeploymentMessage(
 			Models.RevisionInformation revisionInformation,
 			Version byondVersion,
 			DateTimeOffset? estimatedCompletionTime,
 			string gitHubOwner,
 			string gitHubRepo,
-			bool localCommitPushed,
-			CancellationToken cancellationToken);
+			bool localCommitPushed);
 
 		/// <summary>
 		/// Start tracking <see cref="Commands.CustomCommand"/>s and <see cref="ChannelRepresentation"/>s.
diff --git a/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs b/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
index a7fb801b9e..c031f55a4d 100644
--- a/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
+++ b/src/Tgstation.Server.Host/Components/Deployment/DreamMaker.cs
@@ -101,8 +101,14 @@ namespace Tgstation.Server.Host.Components.Deployment
 		/// </summary>
 		readonly object deploymentLock;
 
-		Func<string, string, Task> currentChatCallback;
+		/// <summary>
+		/// The active callback from <see cref="IChatManager.QueueDeploymentMessage"/>.
+		/// </summary>
+		Action<string, string> currentChatCallback;
 
+		/// <summary>
+		/// Cached for <see cref="currentChatCallback"/>.
+		/// </summary>
 		string currentDreamMakerOutput;
 
 		/// <summary>
@@ -716,25 +722,26 @@ namespace Tgstation.Server.Host.Components.Deployment
 
 				var eventTask = eventConsumer.HandleEvent(EventType.DeploymentComplete, null, cancellationToken);
 
-				var chatTask = currentChatCallback(null, compileJob.Output);
-				currentChatCallback = null;
-
 				try
 				{
-					await Task.WhenAll(commentsTask, eventTask, chatTask).ConfigureAwait(false);
+					currentChatCallback(null, compileJob.Output);
+
+					await Task.WhenAll(commentsTask, eventTask).ConfigureAwait(false);
 				}
 				catch (Exception ex)
 				{
 					throw new JobException(ErrorCode.PostDeployFailure, ex);
 				}
+				finally
+				{
+					currentChatCallback = null;
+				}
 			}
 			catch (Exception ex)
 			{
-				if (currentChatCallback != null)
-					await currentChatCallback(
-						FormatExceptionForUsers(ex),
-						currentDreamMakerOutput)
-						.ConfigureAwait(false);
+				currentChatCallback?.Invoke(
+					FormatExceptionForUsers(ex),
+					currentDreamMakerOutput);
 
 				throw;
 			}
@@ -797,15 +804,13 @@ namespace Tgstation.Server.Host.Components.Deployment
 			try
 			{
 				using var byondLock = await byond.UseExecutables(null, cancellationToken).ConfigureAwait(false);
-				currentChatCallback = await chatManager.SendDeploymentMessage(
+				currentChatCallback = chatManager.QueueDeploymentMessage(
 					revisionInformation,
 					byondLock.Version,
 					DateTimeOffset.Now + estimatedDuration,
 					repository.RemoteRepositoryOwner,
 					repository.RemoteRepositoryName,
-					localCommitExistsOnRemote,
-					cancellationToken)
-					.ConfigureAwait(false);
+					localCommitExistsOnRemote);
 
 				var job = new Models.CompileJob
 				{
diff --git a/src/Tgstation.Server.Host/Components/Session/SessionController.cs b/src/Tgstation.Server.Host/Components/Session/SessionController.cs
index 79b17c930b..1e068f0188 100644
--- a/src/Tgstation.Server.Host/Components/Session/SessionController.cs
+++ b/src/Tgstation.Server.Host/Components/Session/SessionController.cs
@@ -343,7 +343,7 @@ namespace Tgstation.Server.Host.Components.Session
 		}
 
 		/// <inheritdoc />
-		public async Task<BridgeResponse> ProcessBridgeRequest(BridgeParameters parameters, CancellationToken cancellationToken)
+		public Task<BridgeResponse> ProcessBridgeRequest(BridgeParameters parameters, CancellationToken cancellationToken)
 		{
 			if (parameters == null)
 				throw new ArgumentNullException(nameof(parameters));
@@ -358,34 +358,36 @@ namespace Tgstation.Server.Host.Components.Session
 				{
 					case BridgeCommandType.ChatSend:
 						if (parameters.ChatMessage == null)
-							return new BridgeResponse
-							{
-								ErrorMessage = "Missing chatMessage field!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Missing chatMessage field!"
+								});
 
 						if (parameters.ChatMessage.ChannelIds == null)
-							return new BridgeResponse
-							{
-								ErrorMessage = "Missing channelIds field in chatMessage!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Missing channelIds field in chatMessage!"
+								});
 
 						if (parameters.ChatMessage.ChannelIds.Any(channelIdString => !UInt64.TryParse(channelIdString, out var _)))
-							return new BridgeResponse
-							{
-								ErrorMessage = "Invalid channelIds in chatMessage!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Invalid channelIds in chatMessage!"
+								});
 
 						if (parameters.ChatMessage.Text == null)
-							return new BridgeResponse
-							{
-								ErrorMessage = "Missing message field in chatMessage!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Missing message field in chatMessage!"
+								});
 
-						await chat.SendMessage(
+						chat.QueueMessage(
 							parameters.ChatMessage.Text,
-							parameters.ChatMessage.ChannelIds.Select(UInt64.Parse),
-							cancellationToken)
-							.ConfigureAwait(false);
+							parameters.ChatMessage.ChannelIds.Select(UInt64.Parse));
 						break;
 					case BridgeCommandType.Prime:
 						var oldPrimeTcs = primeTcs;
@@ -404,10 +406,11 @@ namespace Tgstation.Server.Host.Components.Session
 							{
 								/////UHHHH
 								logger.LogWarning("DreamDaemon sent new port command without providing it's own!");
-								return new BridgeResponse
-								{
-									ErrorMessage = "Missing stringified port as data parameter!"
-								};
+								return Task.FromResult(
+									new BridgeResponse
+									{
+										ErrorMessage = "Missing stringified port as data parameter!"
+									});
 							}
 
 							var currentPort = parameters.CurrentPort.Value;
@@ -434,19 +437,21 @@ namespace Tgstation.Server.Host.Components.Session
 					case BridgeCommandType.Startup:
 						apiValidationStatus = ApiValidationStatus.BadValidationRequest;
 						if (parameters.Version == null)
-							return new BridgeResponse
-							{
-								ErrorMessage = "Missing dmApiVersion field!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Missing dmApiVersion field!"
+								});
 
 						DMApiVersion = parameters.Version;
 						if (DMApiVersion.Major != DMApiConstants.Version.Major)
 						{
 							apiValidationStatus = ApiValidationStatus.Incompatible;
-							return new BridgeResponse
-							{
-								ErrorMessage = "Incompatible dmApiVersion!"
-							};
+							return Task.FromResult(
+								new BridgeResponse
+								{
+									ErrorMessage = "Incompatible dmApiVersion!"
+								});
 						}
 
 						switch (parameters.MinimumSecurityLevel)
@@ -461,15 +466,17 @@ namespace Tgstation.Server.Host.Components.Session
 								apiValidationStatus = ApiValidationStatus.RequiresTrusted;
 								break;
 							case null:
-								return new BridgeResponse
-								{
-									ErrorMessage = "Missing minimumSecurityLevel field!"
-								};
+								return Task.FromResult(
+									new BridgeResponse
+									{
+										ErrorMessage = "Missing minimumSecurityLevel field!"
+									});
 							default:
-								return new BridgeResponse
-								{
-									ErrorMessage = "Invalid minimumSecurityLevel!"
-								};
+								return Task.FromResult(
+									new BridgeResponse
+									{
+										ErrorMessage = "Invalid minimumSecurityLevel!"
+									});
 						}
 
 						response.RuntimeInformation = new RuntimeInformation(
@@ -504,7 +511,7 @@ namespace Tgstation.Server.Host.Components.Session
 						break;
 				}
 
-				return response;
+				return Task.FromResult(response);
 			}
 		}
 
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs b/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
index 48098d98de..c364a8cf65 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/BasicWatchdog.cs
@@ -95,7 +95,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 					if (Server.RebootState == Session.RebootState.Shutdown)
 					{
 						// the time for graceful shutdown is now
-						await Chat.SendWatchdogMessage(
+						await Chat.QueueWatchdogMessage(
 							String.Format(
 								CultureInfo.InvariantCulture,
 								"Server {0}! Shutting down due to graceful termination request...",
@@ -105,7 +105,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 						return MonitorAction.Exit;
 					}
 
-					await Chat.SendWatchdogMessage(
+					await Chat.QueueWatchdogMessage(
 						String.Format(
 							CultureInfo.InvariantCulture,
 							"Server {0}! Rebooting...",
@@ -132,7 +132,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 							return MonitorAction.Restart;
 						case Session.RebootState.Shutdown:
 							// graceful shutdown time
-							await Chat.SendWatchdogMessage(
+							await Chat.QueueWatchdogMessage(
 								"Active server rebooted! Shutting down due to graceful termination request...",
 								cancellationToken)
 								.ConfigureAwait(false);
@@ -265,7 +265,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		{
 			gracefulRebootRequired = true;
 			if (Server.CompileJob.DMApiVersion == null)
-				return Chat.SendWatchdogMessage(
+				return Chat.QueueWatchdogMessage(
 					"A new deployment has been made but cannot be applied automatically as the currently running server has no DMAPI. Please manually reboot the server to apply the update.",
 					cancellationToken);
 			return Server.SetRebootState(Session.RebootState.Restart, cancellationToken);
diff --git a/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs b/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
index 8275f6df83..cf873601f4 100644
--- a/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
+++ b/src/Tgstation.Server.Host/Components/Watchdog/WatchdogBase.cs
@@ -269,7 +269,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 			{
 				var eventTask = eventConsumer.HandleEvent(releaseServers ? EventType.WatchdogDetach : EventType.WatchdogShutdown, null, cancellationToken);
 
-				var chatTask = announce ? Chat.SendWatchdogMessage("Shutting down...", cancellationToken) : Task.CompletedTask;
+				var chatTask = announce ? Chat.QueueWatchdogMessage("Shutting down...", cancellationToken) : Task.CompletedTask;
 
 				await eventTask.ConfigureAwait(false);
 
@@ -314,7 +314,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 					case 2:
 						var message2 = "DEFCON 3: DreamDaemon has missed 2 heartbeats!";
 						Logger.LogInformation(message2);
-						await Chat.SendWatchdogMessage(message2, cancellationToken).ConfigureAwait(false);
+						await Chat.QueueWatchdogMessage(message2, cancellationToken).ConfigureAwait(false);
 						break;
 					case 3:
 						var actionToTake = shouldShutdown
@@ -322,7 +322,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 							: "be restarted";
 						var message3 = $"DEFCON 2: DreamDaemon has missed 3 heartbeats! If it does not respond to the next one, the watchdog will {actionToTake}!";
 						Logger.LogWarning(message3);
-						await Chat.SendWatchdogMessage(message3, cancellationToken).ConfigureAwait(false);
+						await Chat.QueueWatchdogMessage(message3, cancellationToken).ConfigureAwait(false);
 						break;
 					case 4:
 						var actionTaken = shouldShutdown
@@ -330,7 +330,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 							: "Restarting";
 						var message4 = $"DEFCON 1: Four heartbeats have been missed! {actionTaken}...";
 						Logger.LogWarning(message4);
-						await Chat.SendWatchdogMessage(message4, cancellationToken).ConfigureAwait(false);
+						await Chat.QueueWatchdogMessage(message4, cancellationToken).ConfigureAwait(false);
 						await DisposeAndNullControllers(cancellationToken).ConfigureAwait(false);
 						return shouldShutdown ? MonitorAction.Exit : MonitorAction.Restart;
 					default:
@@ -371,7 +371,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 			Task announceTask;
 			if (announce)
 			{
-				announceTask = Chat.SendWatchdogMessage(
+				announceTask = Chat.QueueWatchdogMessage(
 					reattachInfo == null
 						? "Launching..."
 						: "Reattaching...",
@@ -405,7 +405,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 				{
 					await originalChatTask.ConfigureAwait(false);
 					if (announceFailure)
-						await Chat.SendWatchdogMessage("Startup failed!", cancellationToken).ConfigureAwait(false);
+						await Chat.QueueWatchdogMessage("Startup failed!", cancellationToken).ConfigureAwait(false);
 				}
 
 				announceTask = ChainChatTaskWithErrorMessage();
@@ -487,7 +487,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 			const string FailReattachMessage = "Unable to properly reattach to server! Restarting watchdog...";
 			Logger.LogWarning(FailReattachMessage);
 
-			var chatTask = Chat.SendWatchdogMessage(FailReattachMessage, cancellationToken);
+			var chatTask = Chat.QueueWatchdogMessage(FailReattachMessage, cancellationToken);
 			await InitControllers(chatTask, null, cancellationToken).ConfigureAwait(false);
 		}
 
@@ -591,7 +591,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 						Math.Pow(2, retryAttempts)),
 					TimeSpan.FromHours(1).TotalSeconds); // max of one hour, increasing by a power of 2 each time
 
-				chatTask = Chat.SendWatchdogMessage(
+				chatTask = Chat.QueueWatchdogMessage(
 					$"Failed to restart (Attempt: {retryAttempts}), retrying in {retryDelay}s...",
 					cancellationToken);
 
@@ -733,7 +733,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 							var nextActionMessage = nextAction != MonitorAction.Exit
 								? "Recovering"
 								: "Shutting down";
-							var chatTask = Chat.SendWatchdogMessage(
+							var chatTask = Chat.QueueWatchdogMessage(
 								$"Monitor crashed, this should NEVER happen! Please report this, full details in logs! {nextActionMessage}. Error: {e.Message}",
 								cancellationToken);
 
@@ -811,22 +811,19 @@ namespace Tgstation.Server.Host.Components.Watchdog
 				.ConfigureAwait(false);
 
 			if (result?.InteropResponse?.ChatResponses != null)
-				await Task.WhenAll(
-					result.InteropResponse.ChatResponses.Select(
-						x => Chat.SendMessage(
-							x.Text,
-							x.ChannelIds
-								.Select(channelIdString =>
-								{
-									if (UInt64.TryParse(channelIdString, out var channelId))
-										return (ulong?)channelId;
+				foreach (var response in result.InteropResponse.ChatResponses)
+					Chat.QueueMessage(
+						response.Text,
+						response.ChannelIds
+							.Select(channelIdString =>
+							{
+								if (UInt64.TryParse(channelIdString, out var channelId))
+									return (ulong?)channelId;
 
-									return null;
-								})
-								.Where(nullableChannelId => nullableChannelId.HasValue)
-								.Select(nullableChannelId => nullableChannelId.Value),
-							cancellationToken)))
-					.ConfigureAwait(false);
+								return null;
+							})
+							.Where(nullableChannelId => nullableChannelId.HasValue)
+							.Select(nullableChannelId => nullableChannelId.Value));
 		}
 
 		/// <inheritdoc />
@@ -888,7 +885,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 			{
 				if (!graceful)
 				{
-					var chatTask = Chat.SendWatchdogMessage("Manual restart triggered...", cancellationToken);
+					var chatTask = Chat.QueueWatchdogMessage("Manual restart triggered...", cancellationToken);
 					await TerminateNoLock(false, false, cancellationToken).ConfigureAwait(false);
 					await LaunchNoLock(true, false, true, null, cancellationToken).ConfigureAwait(false);
 					await chatTask.ConfigureAwait(false);
@@ -966,7 +963,7 @@ namespace Tgstation.Server.Host.Components.Watchdog
 		{
 			releaseServers = true;
 			if (Status == WatchdogStatus.Online)
-				await Chat.SendWatchdogMessage("Detaching...", cancellationToken).ConfigureAwait(false);
+				await Chat.QueueWatchdogMessage("Detaching...", cancellationToken).ConfigureAwait(false);
 			else
 				Logger.LogTrace("Not sending detach chat message as status is: {0}", Status);
 		}
diff --git a/tools/ReleaseNotes/Program.cs b/tools/ReleaseNotes/Program.cs
index 28cafa17a7..65760f4b8d 100644
--- a/tools/ReleaseNotes/Program.cs
+++ b/tools/ReleaseNotes/Program.cs
@@ -60,7 +60,6 @@ namespace ReleaseNotes
 				{
 					Milestone = $"v{versionString}",
 					Type = IssueTypeQualifier.PullRequest,
-					State = ItemState.Closed,
 					Repos = { { RepoOwner, RepoName } }
 				}).ConfigureAwait(false);