diff --git a/build/Version.props b/build/Version.props
index 7178bdfc80..d37c328cda 100644
--- a/build/Version.props
+++ b/build/Version.props
@@ -3,7 +3,7 @@
   <!-- Integration tests will ensure they match across the board -->
   <Import Project="ControlPanelVersion.props" />
   <PropertyGroup>
-    <TgsCoreVersion>5.13.6</TgsCoreVersion>
+    <TgsCoreVersion>5.13.7</TgsCoreVersion>
     <TgsConfigVersion>4.7.1</TgsConfigVersion>
     <TgsApiVersion>9.11.0</TgsApiVersion>
     <TgsCommonLibraryVersion>6.0.0</TgsCommonLibraryVersion>
diff --git a/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs b/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
index 1b74ccfe08..087503d68c 100644
--- a/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
+++ b/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
@@ -236,7 +236,7 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 		}
 
 		/// <inheritdoc />
-		public async Task<IReadOnlyList<ConfigurationFileResponse>> ListDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
+		public async Task<IOrderedQueryable<ConfigurationFileResponse>> ListDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
 		{
 			await EnsureDirectories(cancellationToken);
 			var path = ValidateConfigRelativePath(configurationRelativePath);
@@ -252,14 +252,14 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 				{
 					IsDirectory = true,
 					Path = ioManager.ConcatPath(configurationRelativePath, x),
-				}).OrderBy(file => file.Path));
+				}));
 
 				enumerator = synchronousIOManager.GetFiles(path, cancellationToken);
 				result.AddRange(enumerator.Select(x => new ConfigurationFileResponse
 				{
 					IsDirectory = false,
 					Path = ioManager.ConcatPath(configurationRelativePath, x),
-				}).OrderBy(file => file.Path));
+				}));
 			}
 
 			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
@@ -276,7 +276,10 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 					await systemIdentity.RunImpersonated(ListImpl, cancellationToken);
 			}
 
-			return result;
+			return result
+				.AsQueryable()
+				.OrderBy(configFile => !configFile.IsDirectory)
+				.ThenBy(configFile => configFile.Path);
 		}
 
 		/// <inheritdoc />
diff --git a/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs b/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
index 4fece676c9..b4ed9f59f9 100644
--- a/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
+++ b/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
@@ -1,5 +1,5 @@
 using System;
-using System.Collections.Generic;
+using System.Linq;
 using System.Threading;
 using System.Threading.Tasks;
 
@@ -38,8 +38,8 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 		/// <param name="configurationRelativePath">The relative path in the Configuration directory.</param>
 		/// <param name="systemIdentity">The <see cref="ISystemIdentity"/> for the operation. If <see langword="null"/>, the operation will be performed as the user of the <see cref="Core.Application"/>.</param>
 		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
-		/// <returns>A <see cref="Task{TResult}"/> resulting in the <see cref="ConfigurationFileResponse"/>s for the items in the directory. <see cref="FileTicketResponse.FileTicket"/> and <see cref="IConfigurationFile.LastReadHash"/> will both be <see langword="null"/>. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
-		Task<IReadOnlyList<ConfigurationFileResponse>> ListDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
+		/// <returns>A <see cref="Task{TResult}"/> resulting in an <see cref="IOrderedQueryable{T}"/> of the <see cref="ConfigurationFileResponse"/>s for the items in the directory. <see cref="FileTicketResponse.FileTicket"/> and <see cref="IConfigurationFile.LastReadHash"/> will both be <see langword="null"/>. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
+		Task<IOrderedQueryable<ConfigurationFileResponse>> ListDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
 
 		/// <summary>
 		/// Reads a given <paramref name="configurationRelativePath"/>.
diff --git a/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs b/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
index 1a7e2dab49..6be4c6df5f 100644
--- a/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
+++ b/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
@@ -1,6 +1,5 @@
 using System;
 using System.IO;
-using System.Linq;
 using System.Threading;
 using System.Threading.Tasks;
 
@@ -190,10 +189,7 @@ namespace Tgstation.Server.Host.Controllers
 								return new PaginatableResult<ConfigurationFileResponse>(
 									Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess)));
 
-							return new PaginatableResult<ConfigurationFileResponse>(
-								result
-									.AsQueryable()
-									.OrderBy(x => x)); // ordering performed by IConfiguration
+							return new PaginatableResult<ConfigurationFileResponse>(result);
 						}
 						catch (NotImplementedException ex)
 						{
diff --git a/tests/Tgstation.Server.Host.Tests/Components/StaticFiles/TestConfiguration.cs b/tests/Tgstation.Server.Host.Tests/Components/StaticFiles/TestConfiguration.cs
index cec38f9875..68241988d1 100644
--- a/tests/Tgstation.Server.Host.Tests/Components/StaticFiles/TestConfiguration.cs
+++ b/tests/Tgstation.Server.Host.Tests/Components/StaticFiles/TestConfiguration.cs
@@ -1,5 +1,6 @@
 using System;
 using System.IO;
+using System.Linq;
 using System.Threading;
 using System.Threading.Tasks;
 
@@ -57,7 +58,7 @@ namespace Tgstation.Server.Host.Components.StaticFiles.Tests
 
 				await configuration.StartAsync(CancellationToken.None);
 
-				var listResponse = await configuration.ListDirectory(".", null, CancellationToken.None);
+				var listResponse = (await configuration.ListDirectory(".", null, CancellationToken.None)).ToList();
 				Assert.AreEqual(9, listResponse.Count);
 				Assert.AreEqual("a", listResponse[0].Path[2..]);
 				Assert.AreEqual("c", listResponse[1].Path[2..]);
@@ -76,7 +77,7 @@ namespace Tgstation.Server.Host.Components.StaticFiles.Tests
 				await ioManager.WriteAllBytes("GameStaticFiles/config/unbuyableshuttles.txt", Array.Empty<byte>(), CancellationToken.None);
 				await ioManager.WriteAllBytes("GameStaticFiles/config/spaceruinblacklist.txt", Array.Empty<byte>(), CancellationToken.None);
 
-				listResponse = await configuration.ListDirectory("GameStaticFiles/config", null, CancellationToken.None);
+				listResponse = (await configuration.ListDirectory("GameStaticFiles/config", null, CancellationToken.None)).ToList();
 				var substringStart = "GameStaticFiles/config".Length + 1;
 				Assert.AreEqual(6, listResponse.Count);
 				Assert.AreEqual("title_music", listResponse[0].Path[substringStart..]);
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
index c921b2c9cd..1008406cd7 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
@@ -1,9 +1,6 @@
 using System;
 using System.IO;
 using System.Linq;
-using System.Net.Http;
-using System.Net.Mime;
-using System.Reflection;
 using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
@@ -14,9 +11,7 @@ using Tgstation.Server.Api.Models;
 using Tgstation.Server.Api.Models.Request;
 using Tgstation.Server.Client;
 using Tgstation.Server.Client.Components;
-using Tgstation.Server.Common;
 using Tgstation.Server.Host.IO;
-using Tgstation.Server.Host.System;
 
 namespace Tgstation.Server.Tests.Live.Instance
 {
@@ -139,12 +134,49 @@ namespace Tgstation.Server.Tests.Live.Instance
 			TaskCreationOptions.LongRunning,
 			TaskScheduler.Current);
 
-		public Task RunPreWatchdog(CancellationToken cancellationToken)
+		async Task TestListing(CancellationToken cancellationToken)
 		{
-			return Task.WhenAll(
-				TestUploadDownloadAndDeleteDirectory(cancellationToken),
-				SetupDMApiTests(cancellationToken),
-				TestPregeneratedFilesExist(cancellationToken));
+			await using var uploadMs = new MemoryStream(Encoding.UTF8.GetBytes("Hello world!"));
+			await configurationClient.Write(
+				new ConfigurationFileRequest
+				{
+					Path = "f-TestFile.txt"
+				},
+				uploadMs,
+				cancellationToken);
+			uploadMs.Seek(0, SeekOrigin.Begin);
+			await configurationClient.Write(
+				new ConfigurationFileRequest
+				{
+					Path = "f-TestDir/f-TestFile.txt"
+				},
+				uploadMs,
+				cancellationToken);
+
+			var baseList = await configurationClient.List(null, ".", cancellationToken);
+			Assert.AreEqual(5, baseList.Count);
+
+			Assert.AreEqual($"/CodeModifications", baseList[0].Path);
+			Assert.IsTrue(baseList[0].IsDirectory);
+			Assert.AreEqual($"/EventScripts", baseList[1].Path);
+			Assert.IsTrue(baseList[1].IsDirectory);
+			Assert.AreEqual($"/f-TestDir", baseList[2].Path);
+			Assert.IsTrue(baseList[2].IsDirectory);
+			Assert.AreEqual($"/GameStaticFiles", baseList[3].Path);
+			Assert.IsTrue(baseList[3].IsDirectory);
+			Assert.AreEqual($"/f-TestFile.txt", baseList[4].Path);
+			Assert.IsFalse(baseList[4].IsDirectory);
 		}
+
+		async Task SequencedApiTests(CancellationToken cancellationToken)
+		{
+			await TestUploadDownloadAndDeleteDirectory(cancellationToken);
+			await TestListing(cancellationToken);
+		}
+
+		public Task RunPreWatchdog(CancellationToken cancellationToken) => Task.WhenAll(
+			SequencedApiTests(cancellationToken),
+			SetupDMApiTests(cancellationToken),
+			TestPregeneratedFilesExist(cancellationToken));
 	}
 }