diff --git a/src/Tgstation.Server.Host.Startup/IServer.cs b/src/Tgstation.Server.Host.Startup/IServer.cs
index 1fd97d4930..3ab78291f5 100644
--- a/src/Tgstation.Server.Host.Startup/IServer.cs
+++ b/src/Tgstation.Server.Host.Startup/IServer.cs
@@ -12,13 +12,13 @@ namespace Tgstation.Server.Host.Startup
         /// <summary>
         /// The path to the updated assembly to run if any. Populated once <see cref="RunAsync(CancellationToken)"/> returns
         /// </summary>
-        Guid UpdateGuid { get; }
+        Guid? UpdateGuid { get; }
 
 		/// <summary>
 		/// Runs the <see cref="IServer"/>
 		/// </summary>
 		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
 		/// <returns>A <see cref="Task"/> representing the running operation</returns>
-		Task RunAsync(string updatesPath, CancellationToken cancellationToken);
+		Task RunAsync(CancellationToken cancellationToken);
 	}
 }
diff --git a/src/Tgstation.Server.Host.Startup/IServerFactory.cs b/src/Tgstation.Server.Host.Startup/IServerFactory.cs
index ed92399240..a787e083f8 100644
--- a/src/Tgstation.Server.Host.Startup/IServerFactory.cs
+++ b/src/Tgstation.Server.Host.Startup/IServerFactory.cs
@@ -9,7 +9,8 @@
         /// Create a <see cref="IServer"/>
         /// </summary>
         /// <param name="args">The arguments for the <see cref="IServer"/></param>
+		/// <param name="updatePath">The directory in which to install server updates</param>
         /// <returns>A new <see cref="IServer"/></returns>
-        IServer CreateServer(string[] args);
+        IServer CreateServer(string[] args, string updatePath);
 	}
 }
diff --git a/src/Tgstation.Server.Host/Components/ByondManager.cs b/src/Tgstation.Server.Host/Components/ByondManager.cs
index e046bcf56c..4b85832126 100644
--- a/src/Tgstation.Server.Host/Components/ByondManager.cs
+++ b/src/Tgstation.Server.Host/Components/ByondManager.cs
@@ -86,12 +86,9 @@ namespace Tgstation.Server.Host.Components
 			await ioManager.DeleteDirectory(versionKey, cancellationToken).ConfigureAwait(false);
 			await ioManager.CreateDirectory(versionKey, cancellationToken).ConfigureAwait(false);
 
-			var resolvedPath = ioManager.ResolvePath(versionKey);
-			using (var zipBytes = new MemoryStream(await downloadTask.ConfigureAwait(false)))
-			using (var archive = new ZipArchive(zipBytes))
-				await Task.Factory.StartNew(() => archive.ExtractToDirectory(resolvedPath), cancellationToken, TaskCreationOptions.LongRunning, TaskScheduler.Current).ConfigureAwait(false);
+			await ioManager.ZipToDirectory(versionKey, await downloadTask.ConfigureAwait(false), cancellationToken).ConfigureAwait(false);
 
-			await byondInstaller.InstallByond(resolvedPath, version, cancellationToken).ConfigureAwait(false);
+			await byondInstaller.InstallByond(ioManager.ResolvePath(versionKey), version, cancellationToken).ConfigureAwait(false);
 
 			//make sure to do this last because this is what tells us we have a valid version
 			await ioManager.WriteAllBytes(ioManager.ConcatPath(versionKey, VersionFileName), Encoding.UTF8.GetBytes(version.ToString()), cancellationToken).ConfigureAwait(false);
diff --git a/src/Tgstation.Server.Host/Core/IServerUpdater.cs b/src/Tgstation.Server.Host/Core/IServerUpdater.cs
index c4b43eb1b2..ed5a4e76f0 100644
--- a/src/Tgstation.Server.Host/Core/IServerUpdater.cs
+++ b/src/Tgstation.Server.Host/Core/IServerUpdater.cs
@@ -1,4 +1,7 @@
 using System;
+using System.Threading;
+using System.Threading.Tasks;
+using Tgstation.Server.Host.IO;
 
 namespace Tgstation.Server.Host.Core
 {
@@ -10,8 +13,11 @@ namespace Tgstation.Server.Host.Core
 		/// <summary>
 		/// Run a new <see cref="Host"/> assembly and stop the current one. This will likely trigger all active <see cref="System.Threading.CancellationToken"/>s
 		/// </summary>
-		/// <param name="updatePath">The path to the new <see cref="Host"/> assembly</param>
-		void ApplyUpdate(string updatePath);
+		/// <param name="updateZipData">The <see cref="byte"/>s of the .zip file that contains the new <see cref="Host"/> assembly</param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
+		/// <param name="ioManager">The <see cref="IIOManager"/> for the operation</param>
+		/// <returns>A <see cref="Task"/> representing the running operation</returns>
+		Task ApplyUpdate(byte[] updateZipData, IIOManager ioManager, CancellationToken cancellationToken);
 
 		/// <summary>
 		/// Register a given <paramref name="action"/> to run before stopping the server for updates
diff --git a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
index 793b5881e2..b24653f8fe 100644
--- a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
@@ -2,6 +2,7 @@
 using System.Collections.Generic;
 using System.Globalization;
 using System.IO;
+using System.IO.Compression;
 using System.Linq;
 using System.Net;
 using System.Text;
@@ -46,6 +47,12 @@ namespace Tgstation.Server.Host.IO
 			dir.Delete(true);
 		}
 
+		/// <summary>
+		/// Opens a <see cref="FileStream"/> for async writing at a given <paramref name="path"/>
+		/// </summary>
+		/// <param name="path">The path to open the <see cref="FileStream"/> at</param>
+		/// <returns>A new <see cref="FileStream"/> ready for async writing</returns>
+		static FileStream OpenWriteStream(string path) => new FileStream(path, FileMode.Create, FileAccess.Write, FileShare.ReadWrite, DefaultBufferSize, true);
 
 		/// <summary>
 		/// Copies a directory from <paramref name="src"/> to <paramref name="dest"/>
@@ -205,7 +212,7 @@ namespace Tgstation.Server.Host.IO
 		public async Task WriteAllBytes(string path, byte[] contents, CancellationToken cancellationToken)
 		{
 			path = ResolvePath(path);
-			using (var file = File.Open(path, FileMode.Create, FileAccess.Write))
+			using (var file = OpenWriteStream(path))
 				await file.WriteAsync(contents, 0, contents.Length, cancellationToken).ConfigureAwait(false);
 		}
 
@@ -252,5 +259,32 @@ namespace Tgstation.Server.Host.IO
 			using (cancellationToken.Register(() => wc.CancelAsync()))
 				return await wc.DownloadDataTaskAsync(url).ConfigureAwait(false);
 		}
+
+		/// <inheritdoc />
+		public async Task ZipToDirectory(string path, byte[] zipFileBytes, CancellationToken cancellationToken)
+		{
+			path = ResolvePath(path);
+			if (zipFileBytes == null)
+				throw new ArgumentNullException(nameof(zipFileBytes));
+
+			using (var ms = new MemoryStream(zipFileBytes))
+			{
+				zipFileBytes = null;
+				using (var archive = new ZipArchive(ms))
+				{
+					string GetEntryName(ZipArchiveEntry entry) => ConcatPath(path, GetDirectoryName(entry.FullName));
+					//create directories first
+					await Task.WhenAll(archive.Entries.Where(x => x.Name.Length == 0).Select(x => CreateDirectory(GetEntryName(x), cancellationToken))).ConfigureAwait(false);
+					//extract files
+					await Task.WhenAll(archive.Entries.Where(x => x.Name.Length > 0).Select(async x =>
+					{
+						var entryPath = GetEntryName(x);
+						using (var stream = x.Open())
+						using (var file = OpenWriteStream(entryPath))
+							await stream.CopyToAsync(file).ConfigureAwait(false);
+					})).ConfigureAwait(false);
+				}
+			}
+		}
 	}
 }
diff --git a/src/Tgstation.Server.Host/IO/IIOManager.cs b/src/Tgstation.Server.Host/IO/IIOManager.cs
index ad320805d3..3654fed7f5 100644
--- a/src/Tgstation.Server.Host/IO/IIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/IIOManager.cs
@@ -162,5 +162,14 @@ namespace Tgstation.Server.Host.IO
 		/// <param name="cancellationToken">A <see cref="CancellationToken"/> for the operation</param>
 		/// <returns>A <see cref="Task{TResult}"/> resulting in the <see cref="byte"/>s of the downloaded file</returns>
 		Task<byte[]> DownloadFile(Uri url, CancellationToken cancellationToken);
+
+		/// <summary>
+		/// Extract a set of <paramref name="zipFileBytes"/> to a given <paramref name="path"/>
+		/// </summary>
+		/// <param name="path">The path to unzip to</param>
+		/// <param name="zipFileBytes">The <see cref="byte"/>s of the <see cref="System.IO.Compression.ZipArchive"/></param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
+		/// <returns>A <see cref="Task"/> representing the running operation</returns>
+		Task ZipToDirectory(string path, byte[] zipFileBytes, CancellationToken cancellationToken);
 	}
 }
diff --git a/src/Tgstation.Server.Host/Server.cs b/src/Tgstation.Server.Host/Server.cs
index 5516c3287f..42f9cafeae 100644
--- a/src/Tgstation.Server.Host/Server.cs
+++ b/src/Tgstation.Server.Host/Server.cs
@@ -75,9 +75,9 @@ namespace Tgstation.Server.Host
 				UpdateGuid = Guid.NewGuid();
 				try
 				{
-					await ioManager.WriteAllBytes(serverUpdatePath, updateData, cancellationToken).ConfigureAwait(false);
+					await ioManager.ZipToDirectory(updatePath, updateZipData, cancellationToken).ConfigureAwait(false);
 				}
-				catch (OperationCanceledException)
+				catch
 				{
 					UpdateGuid = null;
 					throw;