diff --git a/build/Version.props b/build/Version.props
index 21e5da987b..02bbc0e30a 100644
--- a/build/Version.props
+++ b/build/Version.props
@@ -12,7 +12,7 @@
     <TgsClientVersion>19.3.0</TgsClientVersion>
     <TgsDmapiVersion>7.3.0</TgsDmapiVersion>
     <TgsInteropVersion>5.10.0</TgsInteropVersion>
-    <TgsHostWatchdogVersion>1.5.0</TgsHostWatchdogVersion>
+    <TgsHostWatchdogVersion>1.6.0</TgsHostWatchdogVersion>
     <TgsSwarmProtocolVersion>8.0.0</TgsSwarmProtocolVersion>
     <TgsContainerScriptVersion>1.2.1</TgsContainerScriptVersion>
     <TgsMigratorVersion>2.0.0</TgsMigratorVersion>
diff --git a/src/Tgstation.Server.Host.Console/Tgstation.Server.Host.Console.csproj b/src/Tgstation.Server.Host.Console/Tgstation.Server.Host.Console.csproj
index ff23533a16..9804e251e3 100644
--- a/src/Tgstation.Server.Host.Console/Tgstation.Server.Host.Console.csproj
+++ b/src/Tgstation.Server.Host.Console/Tgstation.Server.Host.Console.csproj
@@ -4,6 +4,7 @@
   <PropertyGroup>
     <OutputType>Exe</OutputType>
     <TargetFramework>$(TgsFrameworkVersion)</TargetFramework>
+    <!-- Important that this is core and not host watchdog. Bootstrapping depends on it -->
     <Version>$(TgsCoreVersion)</Version>
     <Nullable>enable</Nullable>
     <UseAppHost>false</UseAppHost>
diff --git a/src/Tgstation.Server.Host.Service/Tgstation.Server.Host.Service.csproj b/src/Tgstation.Server.Host.Service/Tgstation.Server.Host.Service.csproj
index 417e03092c..e1f04e898b 100644
--- a/src/Tgstation.Server.Host.Service/Tgstation.Server.Host.Service.csproj
+++ b/src/Tgstation.Server.Host.Service/Tgstation.Server.Host.Service.csproj
@@ -7,6 +7,7 @@
     <Nullable>enable</Nullable>
     <!-- DO NOT ADD THE -windows SUFFIX, It makes the service require the desktop runtime instead of the ASP NET Core Hosting Bundle -->
     <TargetFramework>$(TgsFrameworkVersion)</TargetFramework>
+    <!-- Important that this is core and not host watchdog. Bootstrapping depends on it -->
     <Version>$(TgsCoreVersion)</Version>
     <!-- DO NOT ENABLE THIS, It makes the service require the desktop runtime instead of the ASP NET Core Hosting Bundle -->
     <UseWindowsForms>false</UseWindowsForms>
diff --git a/src/Tgstation.Server.Host.Watchdog/BootstrapSettings.cs b/src/Tgstation.Server.Host.Watchdog/BootstrapSettings.cs
new file mode 100644
index 0000000000..10c9ab11b4
--- /dev/null
+++ b/src/Tgstation.Server.Host.Watchdog/BootstrapSettings.cs
@@ -0,0 +1,38 @@
+using System;
+using System.Reflection;
+
+using Tgstation.Server.Common.Extensions;
+
+namespace Tgstation.Server.Host.Watchdog
+{
+	/// <summary>
+	/// Settings for the bootstrapper feature.
+	/// </summary>
+	sealed class BootstrapSettings
+	{
+		/// <summary>
+		/// The current supported major version of <see cref="FileVersion"/>.
+		/// </summary>
+		public const int FileMajorVersion = 1;
+
+		/// <summary>
+		/// The token used to substitute <see cref="ServerUpdatePackageUrlFormatter"/>.
+		/// </summary>
+		public const string VersionSubstitutionToken = "${version}";
+
+		/// <summary>
+		/// The version of the boostrapper file.
+		/// </summary>
+		public Version FileVersion { get; set; } = new Version(FileMajorVersion, 0, 0);
+
+		/// <summary>
+		/// The <see cref="Version"/> of TGS last launched in the lib/Default directory.
+		/// </summary>
+		public Version TgsVersion { get; set; } = Assembly.GetEntryAssembly()!.GetName().Version!.Semver();
+
+		/// <summary>
+		/// The URL to format with <see cref="TgsVersion"/> to get the download URL.
+		/// </summary>
+		public string ServerUpdatePackageUrlFormatter { get; set; } = $"https://github.com/tgstation/tgstation-server/releases/download/tgstation-server-v{VersionSubstitutionToken}/ServerUpdatePackage.zip";
+	}
+}
diff --git a/src/Tgstation.Server.Host.Watchdog/Watchdog.cs b/src/Tgstation.Server.Host.Watchdog/Watchdog.cs
index 4813383440..c139b9ac36 100644
--- a/src/Tgstation.Server.Host.Watchdog/Watchdog.cs
+++ b/src/Tgstation.Server.Host.Watchdog/Watchdog.cs
@@ -3,9 +3,12 @@ using System.Collections.Generic;
 using System.Diagnostics;
 using System.Globalization;
 using System.IO;
+using System.IO.Compression;
 using System.Linq;
+using System.Net.Http;
 using System.Reflection;
 using System.Runtime.InteropServices;
+using System.Text.Json;
 using System.Threading;
 using System.Threading.Tasks;
 
@@ -119,6 +122,49 @@ namespace Tgstation.Server.Host.Watchdog
 				else
 					Directory.CreateDirectory(assemblyStoragePath);
 
+				var bootstrappable = args.Contains("--bootstrap", StringComparer.OrdinalIgnoreCase);
+				var homeDirectory = Environment.GetFolderPath(Environment.SpecialFolder.UserProfile);
+				var bootstrapperSettingsFile = Path.Combine(homeDirectory, ".tgstation-server-bootstrap.json");
+				BootstrapSettings? bootstrapSettings = null;
+				if (!Directory.Exists(defaultAssemblyPath))
+				{
+					if (!bootstrappable)
+					{
+						logger.LogCritical("Unable to locate host assembly directory!");
+						return false;
+					}
+
+					if (File.Exists(bootstrapperSettingsFile))
+					{
+						logger.LogInformation("Loading bootstrap settings...");
+						var bootstrapperSettingsJson = await File.ReadAllTextAsync(bootstrapperSettingsFile, cancellationToken);
+						bootstrapSettings = JsonSerializer.Deserialize<BootstrapSettings>(bootstrapperSettingsJson);
+						if (bootstrapSettings == null)
+						{
+							logger.LogCritical("Failed to deserialize {settingsFile}!", bootstrapperSettingsFile);
+							return false;
+						}
+					}
+					else
+					{
+						logger.LogInformation("Using default bootstrap settings...");
+						bootstrapSettings = new BootstrapSettings(); // defaults
+					}
+
+					if (bootstrapSettings.FileVersion.Major != BootstrapSettings.FileMajorVersion)
+					{
+						logger.LogCritical("Unable to parse bootstrapper file! Expected version: {expected}.X.X", BootstrapSettings.FileMajorVersion);
+						return false;
+					}
+
+					string downloadUrl = bootstrapSettings.ServerUpdatePackageUrlFormatter.Replace(BootstrapSettings.VersionSubstitutionToken, bootstrapSettings.TgsVersion.ToString(), StringComparison.Ordinal);
+					logger.LogInformation("Bootstrapping from: {url}", downloadUrl);
+					using var httpClient = new HttpClient();
+					await using var zipData = await httpClient.GetStreamAsync(new Uri(downloadUrl), cancellationToken);
+					using var archive = new ZipArchive(zipData, ZipArchiveMode.Read, true);
+					archive.ExtractToDirectory(defaultAssemblyPath);
+				}
+
 				var assemblyName = String.Join(".", nameof(Tgstation), nameof(Server), nameof(Host), "dll");
 				var assemblyPath = Path.Combine(defaultAssemblyPath, assemblyName);
 
@@ -128,28 +174,59 @@ namespace Tgstation.Server.Host.Watchdog
 					return false;
 				}
 
-				if (!File.Exists(assemblyPath))
-				{
-					logger.LogCritical("Unable to locate host assembly!");
-					return false;
-				}
-
-				var fileVersion = FileVersionInfo.GetVersionInfo(assemblyPath).FileVersion;
-				if (fileVersion == null)
-				{
-					logger.LogCritical("Failed to parse version info from {assemblyPath}!", assemblyPath);
-					return false;
-				}
-
-				initialHostVersionTcs.SetResult(
-					Version.Parse(
-						fileVersion));
-
 				var watchdogVersion = executingAssembly.GetName().Version?.Semver().ToString();
 
 				while (!cancellationToken.IsCancellationRequested)
+				{
+					if (!File.Exists(assemblyPath))
+					{
+						logger.LogCritical("Unable to locate host assembly!");
+						return false;
+					}
+
+					var fileVersion = FileVersionInfo.GetVersionInfo(assemblyPath).FileVersion;
+					if (fileVersion == null)
+					{
+						logger.LogCritical("Failed to parse version info from {assemblyPath}!", assemblyPath);
+						return false;
+					}
+
+					if (bootstrappable)
+					{
+						if (!Version.TryParse(fileVersion, out var bootstrappedVersion))
+						{
+							logger.LogCritical("Failed to parse bootstrapped version prior to launch: {fileVersion}", fileVersion);
+						}
+						else
+						{
+							// save bootstrapper settings
+							var oldUrl = bootstrapSettings?.ServerUpdatePackageUrlFormatter;
+							bootstrapSettings = new BootstrapSettings
+							{
+								TgsVersion = bootstrappedVersion.Semver(),
+							};
+
+							bootstrapSettings.ServerUpdatePackageUrlFormatter = oldUrl ?? bootstrapSettings.ServerUpdatePackageUrlFormatter;
+
+							Directory.CreateDirectory(homeDirectory);
+							await File.WriteAllTextAsync(
+								bootstrapperSettingsFile,
+								JsonSerializer.Serialize(
+									bootstrapSettings,
+									new JsonSerializerOptions
+									{
+										WriteIndented = true,
+									}),
+								cancellationToken);
+						}
+					}
+
 					using (logger.BeginScope("Host invocation"))
 					{
+						initialHostVersionTcs.SetResult(
+							Version.Parse(
+								fileVersion));
+
 						updateDirectory = Path.GetFullPath(Path.Combine(assemblyStoragePath, Guid.NewGuid().ToString()));
 						logger.LogInformation("Update path set to {updateDirectory}", updateDirectory);
 						using (var process = new Process())
@@ -358,6 +435,7 @@ namespace Tgstation.Server.Host.Watchdog
 							}
 						}
 					}
+				}
 			}
 			catch (OperationCanceledException ex)
 			{