diff --git a/src/Tgstation.Server.Host/Components/Configuration.cs b/src/Tgstation.Server.Host/Components/Configuration.cs
index 9c5a127316..4c31b9eadd 100644
--- a/src/Tgstation.Server.Host/Components/Configuration.cs
+++ b/src/Tgstation.Server.Host/Components/Configuration.cs
@@ -33,6 +33,11 @@ namespace Tgstation.Server.Host.Components
 		/// </summary>
 		readonly ISynchronousIOManager synchronousIOManager;
 
+		/// <summary>
+		/// The <see cref="ISymlinkFactory"/> for <see cref="Configuration"/>
+		/// </summary>
+		readonly ISymlinkFactory symlinkFactory;
+
 		/// <summary>
 		/// The <see cref="ILogger"/> for <see cref="Configuration"/>
 		/// </summary>
@@ -43,11 +48,13 @@ namespace Tgstation.Server.Host.Components
 		/// </summary>
 		/// <param name="ioManager">The value of <see cref="ioManager"/></param>
 		/// <param name="synchronousIOManager">The value of <see cref="synchronousIOManager"/></param>
+		/// <param name="symlinkFactory">The value of <see cref="symlinkFactory"/></param>
 		/// <param name="logger">The value of <see cref="logger"/></param>
-		public Configuration(IIOManager ioManager, ISynchronousIOManager synchronousIOManager, ILogger<Configuration> logger)
+		public Configuration(IIOManager ioManager, ISynchronousIOManager synchronousIOManager, ISymlinkFactory symlinkFactory, ILogger<Configuration> logger)
 		{
 			this.ioManager = ioManager ?? throw new ArgumentNullException(nameof(ioManager));
 			this.synchronousIOManager = synchronousIOManager ?? throw new ArgumentNullException(nameof(synchronousIOManager));
+			this.symlinkFactory = symlinkFactory ?? throw new ArgumentNullException(nameof(symlinkFactory));
 			this.logger = logger ?? throw new ArgumentNullException(nameof(logger));
 		}
 
@@ -171,7 +178,18 @@ namespace Tgstation.Server.Host.Components
 		/// <inheritdoc />
 		public Task SymlinkStaticFilesTo(string destination, CancellationToken cancellationToken)
 		{
-			throw new NotImplementedException();
+			async Task SymlinkBase(bool files)
+			{
+				Task<IReadOnlyList<string>> task;
+				if (files)
+					task = ioManager.GetFiles(GameStaticFilesSubdirectory, cancellationToken);
+				else
+					task = ioManager.GetDirectories(GameStaticFilesSubdirectory, cancellationToken);
+				var entries = await task.ConfigureAwait(false);
+				await Task.WhenAll(entries.Select(x => symlinkFactory.CreateSymbolicLink(ioManager.ResolvePath(x), ioManager.ConcatPath(destination, x), cancellationToken))).ConfigureAwait(false);
+			}
+
+			return Task.WhenAll(SymlinkBase(true), SymlinkBase(false));
 		}
 
 		/// <inheritdoc />
diff --git a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
index 21cf9db515..5a4bb9654f 100644
--- a/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/DefaultIOManager.cs
@@ -213,10 +213,25 @@ namespace Tgstation.Server.Host.IO
 		{
 			path = ResolvePath(path);
 			var results = new List<string>();
-			foreach(var I in Directory.EnumerateDirectories(path))
+			cancellationToken.ThrowIfCancellationRequested();
+			foreach (var I in Directory.EnumerateDirectories(path))
 			{
-				cancellationToken.ThrowIfCancellationRequested();
 				results.Add(I);
+				cancellationToken.ThrowIfCancellationRequested();
+			}
+			return (IReadOnlyList<string>)results;
+		}, cancellationToken, TaskCreationOptions.LongRunning, TaskScheduler.Current);
+
+		/// <inheritdoc />
+		public Task<IReadOnlyList<string>> GetFiles(string path, CancellationToken cancellationToken) => Task.Factory.StartNew(() =>
+		{
+			path = ResolvePath(path);
+			var results = new List<string>();
+			cancellationToken.ThrowIfCancellationRequested();
+			foreach (var I in Directory.EnumerateFiles(path))
+			{
+				results.Add(I);
+				cancellationToken.ThrowIfCancellationRequested();
 			}
 			return (IReadOnlyList<string>)results;
 		}, cancellationToken, TaskCreationOptions.LongRunning, TaskScheduler.Current);
diff --git a/src/Tgstation.Server.Host/IO/IIOManager.cs b/src/Tgstation.Server.Host/IO/IIOManager.cs
index c317e70789..e5b6cdefde 100644
--- a/src/Tgstation.Server.Host/IO/IIOManager.cs
+++ b/src/Tgstation.Server.Host/IO/IIOManager.cs
@@ -72,6 +72,14 @@ namespace Tgstation.Server.Host.IO
 		/// <returns>A <see cref="Task{TResult}"/> resulting in the directories in <paramref name="path"/></returns>
 		Task<IReadOnlyList<string>> GetDirectories(string path, CancellationToken cancellationToken);
 
+		/// <summary>
+		/// Returns file names in a given <paramref name="path"/>
+		/// </summary>
+		/// <param name="path">The path to search for files</param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
+		/// <returns>A <see cref="Task{TResult}"/> resulting in the files in <paramref name="path"/></returns>
+		Task<IReadOnlyList<string>> GetFiles(string path, CancellationToken cancellationToken);
+
 		/// <summary>
 		/// Writes some <paramref name="contents"/> to a file at <paramref name="path"/> overwriting previous content
 		/// </summary>
diff --git a/src/Tgstation.Server.Host/IO/ISymlinkFactory.cs b/src/Tgstation.Server.Host/IO/ISymlinkFactory.cs
new file mode 100644
index 0000000000..b92269404b
--- /dev/null
+++ b/src/Tgstation.Server.Host/IO/ISymlinkFactory.cs
@@ -0,0 +1,20 @@
+using System.Threading;
+using System.Threading.Tasks;
+
+namespace Tgstation.Server.Host.IO
+{
+	/// <summary>
+	/// For creating filesystem symbolic links
+	/// </summary>
+	interface ISymlinkFactory
+	{
+		/// <summary>
+		/// Create a symbolic link
+		/// </summary>
+		/// <param name="targetPath">The path to the hard target</param>
+		/// <param name="linkPath">The path to the link</param>
+		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation</param>
+		/// <returns>A <see cref="Task"/> representing the running operation</returns>
+		Task CreateSymbolicLink(string targetPath, string linkPath, CancellationToken cancellationToken);
+	}
+}