diff --git a/src/Tgstation.Server.Host/Components/InstanceManager.cs b/src/Tgstation.Server.Host/Components/InstanceManager.cs
index b9b558cba2..b68c16c63d 100644
--- a/src/Tgstation.Server.Host/Components/InstanceManager.cs
+++ b/src/Tgstation.Server.Host/Components/InstanceManager.cs
@@ -39,6 +39,11 @@ namespace Tgstation.Server.Host.Components
 		/// </summary>
 		readonly IJobManager jobManager;
 
+		/// <summary>
+		/// The <see cref="IServerControl"/> for the <see cref="InstanceManager"/>
+		/// </summary>
+		readonly IServerControl serverControl;
+
 		/// <summary>
 		/// The <see cref="ILogger"/> for the <see cref="InstanceManager"/>
 		/// </summary>
@@ -67,7 +72,7 @@ namespace Tgstation.Server.Host.Components
 		/// <param name="databaseContextFactory">The value of <paramref name="databaseContextFactory"/></param>
 		/// <param name="application">The value of <see cref="application"/></param>
 		/// <param name="jobManager">The value of <see cref="jobManager"/></param>
-		/// <param name="serverControl">The <see cref="IServerControl"/> used to register the <see cref="InstanceManager"/> as a <see cref="IRestartHandler"/></param>
+		/// <param name="serverControl">The value of <see cref="serverControl"/></param>
 		/// <param name="logger">The value of <see cref="logger"/></param>
 		public InstanceManager(IInstanceFactory instanceFactory, IIOManager ioManager, IDatabaseContextFactory databaseContextFactory, IApplication application, IJobManager jobManager, IServerControl serverControl, ILogger<InstanceManager> logger)
 		{
@@ -76,8 +81,7 @@ namespace Tgstation.Server.Host.Components
 			this.databaseContextFactory = databaseContextFactory ?? throw new ArgumentNullException(nameof(databaseContextFactory));
 			this.application = application ?? throw new ArgumentNullException(nameof(application));
 			this.jobManager = jobManager ?? throw new ArgumentNullException(nameof(jobManager));
-			if (serverControl == null)
-				throw new ArgumentNullException(nameof(serverControl));
+			this.serverControl = serverControl ?? throw new ArgumentNullException(nameof(serverControl));
 			this.logger = logger ?? throw new ArgumentNullException(nameof(logger));
 
 			serverControl.RegisterForRestart(this);
@@ -215,7 +219,7 @@ namespace Tgstation.Server.Host.Components
 				await factoryStartup.ConfigureAwait(false);
 				await dbInstances.ForEachAsync(metadata => tasks.Add(metadata.Online.Value ? OnlineInstance(metadata, cancellationToken) : Task.CompletedTask), cancellationToken).ConfigureAwait(false);
 				await Task.WhenAll(tasks).ConfigureAwait(false);
-				logger.LogInformation("Instance manager ready!");
+				logger.LogInformation("Server ready!");
 				application.Ready(null);
 			}
 			catch (OperationCanceledException)
@@ -226,6 +230,14 @@ namespace Tgstation.Server.Host.Components
 			{
 				logger.LogCritical("Instance manager startup error! Exception: {0}", e);
 				application.Ready(e);
+				try
+				{
+					await serverControl.Die(e).ConfigureAwait(false);
+				}
+				catch (Exception e2)
+				{
+					logger.LogCritical("Failed to kill server! Exception: {0}", e2);
+				}
 			}
 		});
 
diff --git a/src/Tgstation.Server.Host/Core/IServerControl.cs b/src/Tgstation.Server.Host/Core/IServerControl.cs
index 184280b033..03b5b10a67 100644
--- a/src/Tgstation.Server.Host/Core/IServerControl.cs
+++ b/src/Tgstation.Server.Host/Core/IServerControl.cs
@@ -36,5 +36,12 @@ namespace Tgstation.Server.Host.Core
 		/// </summary>
 		/// <returns>A <see cref="Task"/> representing the running operation</returns>
 		Task Restart();
+
+		/// <summary>
+		/// Kill the server with a fatal exception
+		/// </summary>
+		/// <param name="exception">The <see cref="Exception"/> to propagate to the watchdog if any</param>
+		/// <returns>A <see cref="Task"/> representing the running operation</returns>
+		Task Die(Exception exception);
 	}
 }
diff --git a/src/Tgstation.Server.Host/Server.cs b/src/Tgstation.Server.Host/Server.cs
index 1786fd6a19..cee0258581 100644
--- a/src/Tgstation.Server.Host/Server.cs
+++ b/src/Tgstation.Server.Host/Server.cs
@@ -48,6 +48,11 @@ namespace Tgstation.Server.Host
 		/// </summary>
 		CancellationTokenSource cancellationTokenSource;
 
+		/// <summary>
+		/// The <see cref="Exception"/> to propagate when the server terminates
+		/// </summary>
+		Exception propagatedException;
+
 		/// <summary>
 		/// If a server update has been or is being applied
 		/// </summary>
@@ -63,6 +68,8 @@ namespace Tgstation.Server.Host
 			this.webHostBuilder = webHostBuilder ?? throw new ArgumentNullException(nameof(webHostBuilder));
 			this.updatePath = updatePath;
 
+			webHostBuilder.ConfigureServices(serviceCollection => serviceCollection.AddSingleton<IServerControl>(this));
+
 			restartHandlers = new List<IRestartHandler>();
 		}
 
@@ -72,13 +79,22 @@ namespace Tgstation.Server.Host
 		/// <param name="checkWatchdog">If <see cref="WatchdogPresent"/> should be checked</param>
 		void CheckSanity(bool checkWatchdog)
 		{
-			if (checkWatchdog && !WatchdogPresent)
+			if (checkWatchdog && !WatchdogPresent && propagatedException == null)
 				throw new InvalidOperationException("Server restarts are not supported");
 
 			if (cancellationTokenSource == null || logger == null)
 				throw new InvalidOperationException("Tried to control a non-running Server!");
 		}
 
+		/// <summary>
+		/// Re-throw <see cref="propagatedException"/> if it exists
+		/// </summary>
+		void CheckExceptionPropagation()
+		{
+			if (propagatedException != null)
+				throw propagatedException;
+		}
+
 		/// <inheritdoc />
 		public async Task RunAsync(CancellationToken cancellationToken)
 		{
@@ -94,16 +110,20 @@ namespace Tgstation.Server.Host
 					};
 					fsWatcher.EnableRaisingEvents = true;
 				}
-				using (var webHost = webHostBuilder
-					.UseStartup<Application>()
-					.ConfigureServices(serviceCollection => serviceCollection.AddSingleton<IServerControl>(this))
-					.Build()
-				)
-				{
-					logger = webHost.Services.GetRequiredService<ILogger<Server>>();
-					await webHost.RunAsync(cancellationTokenSource.Token).ConfigureAwait(false);
-				}
+				
+				using (var webHost = webHostBuilder.Build())
+					try
+					{
+						logger = webHost.Services.GetRequiredService<ILogger<Server>>();
+						await webHost.RunAsync(cancellationTokenSource.Token).ConfigureAwait(false);
+					}
+					catch (OperationCanceledException)
+					{
+						CheckExceptionPropagation();
+						throw;
+					}
 			}
+			CheckExceptionPropagation();
 		}
 
 		/// <inheritdoc />
@@ -163,7 +183,7 @@ namespace Tgstation.Server.Host
 						throw;
 					}
 
-					await Restart(version).ConfigureAwait(false);
+					await Restart(version, null).ConfigureAwait(false);
 				}
 				catch (OperationCanceledException)
 				{
@@ -207,14 +227,15 @@ namespace Tgstation.Server.Host
 		}
 
 		/// <inheritdoc />
-		public Task Restart() => Restart(null);
+		public Task Restart() => Restart(null, null);
 
 		/// <summary>
 		/// Implements <see cref="Restart()"/>
 		/// </summary>
 		/// <param name="newVersion">The <see cref="Version"/> of any potential updates being applied</param>
+		/// <param name="exception">The potential value of <see cref="propagatedException"/></param>
 		/// <returns></returns>
-		async Task Restart(Version newVersion)
+		async Task Restart(Version newVersion, Exception exception)
 		{
 			CheckSanity(true);
 
@@ -228,33 +249,36 @@ namespace Tgstation.Server.Host
 					return;
 				}
 				RestartRequested = true;
+				propagatedException = exception;
 			}
 
-			logger.LogInformation("Restarting server...");
-
-			using (var cts = new CancellationTokenSource())
-			{
-				logger.LogTrace("Running restart handlers...");
-				var cancellationToken = cts.Token;
-				var eventsTask = Task.WhenAll(restartHandlers.Select(x => x.HandleRestart(newVersion, cancellationToken)).ToList());
-				//YA GOT 10 SECONDS
-				var expiryTask = Task.Delay(TimeSpan.FromSeconds(10));
-				await Task.WhenAny(eventsTask, expiryTask).ConfigureAwait(false);
-				logger.LogTrace("Joining restart handlers...");
-				cts.Cancel();
-				try
+			if (exception == null)
+				using (var cts = new CancellationTokenSource())
 				{
-					await eventsTask.ConfigureAwait(false);
+					logger.LogInformation("Restarting server...");
+					var cancellationToken = cts.Token;
+					var eventsTask = Task.WhenAll(restartHandlers.Select(x => x.HandleRestart(newVersion, cancellationToken)).ToList());
+					//YA GOT 10 SECONDS
+					var expiryTask = Task.Delay(TimeSpan.FromSeconds(10));
+					await Task.WhenAny(eventsTask, expiryTask).ConfigureAwait(false);
+					logger.LogTrace("Joining restart handlers...");
+					cts.Cancel();
+					try
+					{
+						await eventsTask.ConfigureAwait(false);
+					}
+					catch (OperationCanceledException) { }
+					catch (Exception e)
+					{
+						logger.LogError("Restart handlers error! Exception: {0}", e);
+					}
 				}
-				catch (OperationCanceledException) { }
-				catch (Exception e)
-				{
-					logger.LogError("Restart handlers error! Exception: {0}", e);
-				}
-			}
 
 			logger.LogTrace("Stopping host...");
 			cancellationTokenSource.Cancel();
 		}
+
+		/// <inheritdoc />
+		public Task Die(Exception exception) => Restart(null, exception);
 	}
 }
diff --git a/src/Tgstation.Server.Host/ServerFactory.cs b/src/Tgstation.Server.Host/ServerFactory.cs
index cefdfd8897..26d77ab31f 100644
--- a/src/Tgstation.Server.Host/ServerFactory.cs
+++ b/src/Tgstation.Server.Host/ServerFactory.cs
@@ -1,5 +1,10 @@
 using Microsoft.AspNetCore;
+using Microsoft.AspNetCore.Hosting;
+using Microsoft.Extensions.Configuration;
 using System;
+using System.IO;
+using System.Reflection;
+using Tgstation.Server.Host.Core;
 
 namespace Tgstation.Server.Host
 {
@@ -7,6 +12,18 @@ namespace Tgstation.Server.Host
 	public sealed class ServerFactory : IServerFactory
 	{
 		/// <inheritdoc />
-		public IServer CreateServer(string[] args, string updatePath) => new Server(WebHost.CreateDefaultBuilder(args ?? throw new ArgumentNullException(nameof(args))), updatePath);
+		public IServer CreateServer(string[] args, string updatePath) {
+
+			var webHost = WebHost.CreateDefaultBuilder(args ?? throw new ArgumentNullException(nameof(args)))
+				.ConfigureAppConfiguration((context, configurationBuilder) => configurationBuilder.SetBasePath(Directory.GetCurrentDirectory()))
+				.UseStartup<Application>()
+				.SuppressStatusMessages(true)
+				.UseShutdownTimeout(TimeSpan.FromMinutes(1));
+
+			if(updatePath != null)
+				webHost.UseContentRoot(Path.GetDirectoryName(Assembly.GetExecutingAssembly().Location));
+
+			return new Server(webHost, updatePath);
+		}
 	}
 }