diff --git a/src/Tgstation.Server.Api/Models/ErrorCode.cs b/src/Tgstation.Server.Api/Models/ErrorCode.cs
index a2e59a6856..23f8be21af 100644
--- a/src/Tgstation.Server.Api/Models/ErrorCode.cs
+++ b/src/Tgstation.Server.Api/Models/ErrorCode.cs
@@ -288,9 +288,8 @@ namespace Tgstation.Server.Api.Models
 		/// <summary>
 		/// Currently unused.
 		/// </summary>
-		[Obsolete("Unused", true)]
-		[Description("Unknown error code.")]
-		UnusedErrorCode3,
+		[Description("IO operation could not start contended access to the instance's configuration directory!")]
+		ConfigurationContendedAccess,
 
 		/// <summary>
 		/// Attempted to add a chat bot when at or above the <see cref="Instance.ChatBotLimit"/> or it was set to something lower than the existing amount of chat bots.
diff --git a/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs b/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
index 350d701880..1e7f082fe8 100644
--- a/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
+++ b/src/Tgstation.Server.Host/Components/StaticFiles/Configuration.cs
@@ -237,35 +237,34 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 
 			void ListImpl()
 			{
-				try
+				var enumerator = synchronousIOManager.GetDirectories(path, cancellationToken);
+				result.AddRange(enumerator.Select(x => new ConfigurationFileResponse
 				{
-					var enumerator = synchronousIOManager.GetDirectories(path, cancellationToken);
-					result.AddRange(enumerator.Select(x => new ConfigurationFileResponse
-					{
-						IsDirectory = true,
-						Path = ioManager.ConcatPath(configurationRelativePath, x),
-					}).OrderBy(file => file.Path));
+					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));
-				}
-				catch (IOException ex)
+				enumerator = synchronousIOManager.GetFiles(path, cancellationToken);
+				result.AddRange(enumerator.Select(x => new ConfigurationFileResponse
 				{
-					logger.LogDebug(ex, "IOException while enumerating direcotry!");
-					result = null;
-					return;
-				}
+					IsDirectory = false,
+					Path = ioManager.ConcatPath(configurationRelativePath, x),
+				}).OrderBy(file => file.Path));
 			}
 
-			using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
+			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+			{
+				if (!locked)
+				{
+					logger.LogDebug("Contention when attempting to enumerate directory!");
+					return null;
+				}
+
 				if (systemIdentity == null)
 					ListImpl();
 				else
 					await systemIdentity.RunImpersonated(ListImpl, cancellationToken);
+			}
 
 			return result;
 		}
@@ -280,90 +279,102 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 
 			void ReadImpl()
 			{
-				lock (semaphore)
+				try
+				{
+					string GetFileSha()
+					{
+						var content = synchronousIOManager.ReadFile(path);
+						using var sha1 = SHA1.Create();
+						return String.Join(String.Empty, sha1.ComputeHash(content).Select(b => b.ToString("x2", CultureInfo.InvariantCulture)));
+					}
+
+					var originalSha = GetFileSha();
+
+					var disposeToken = disposeCts.Token;
+					var fileTicket = fileTransferService.CreateDownload(
+						new FileDownloadProvider(
+							() =>
+							{
+								if (disposeToken.IsCancellationRequested)
+									return ErrorCode.InstanceOffline;
+
+								var newSha = GetFileSha();
+								if (newSha != originalSha)
+									return ErrorCode.ConfigurationFileUpdated;
+
+								return null;
+							},
+							async cancellationToken =>
+							{
+								FileStream result = null;
+								void GetFileStream()
+								{
+									result = ioManager.GetFileStream(path, false);
+								}
+
+								using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+								{
+									if (!locked)
+										return null;
+
+									if (systemIdentity == null)
+										await Task.Factory.StartNew(GetFileStream, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
+									else
+										await systemIdentity.RunImpersonated(GetFileStream, cancellationToken);
+								}
+
+								return result;
+							},
+							path,
+							false));
+
+					result = new ConfigurationFileResponse
+					{
+						FileTicket = fileTicket.FileTicket,
+						IsDirectory = false,
+						LastReadHash = originalSha,
+						AccessDenied = false,
+						Path = configurationRelativePath,
+					};
+				}
+				catch (UnauthorizedAccessException)
+				{
+					// this happens on windows, dunno about linux
+					bool isDirectory;
 					try
 					{
-						string GetFileSha()
-						{
-							var content = synchronousIOManager.ReadFile(path);
-							using var sha1 = SHA1.Create();
-							return String.Join(String.Empty, sha1.ComputeHash(content).Select(b => b.ToString("x2", CultureInfo.InvariantCulture)));
-						}
-
-						var originalSha = GetFileSha();
-
-						var disposeToken = disposeCts.Token;
-						var fileTicket = fileTransferService.CreateDownload(
-							new FileDownloadProvider(
-								() =>
-								{
-									if (disposeToken.IsCancellationRequested)
-										return ErrorCode.InstanceOffline;
-
-									var newSha = GetFileSha();
-									if (newSha != originalSha)
-										return ErrorCode.ConfigurationFileUpdated;
-
-									return null;
-								},
-								async cancellationToken =>
-								{
-									FileStream result = null;
-									void GetFileStream()
-									{
-										result = ioManager.GetFileStream(path, false);
-									}
-
-									using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
-										if (systemIdentity == null)
-											await Task.Factory.StartNew(GetFileStream, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
-										else
-											await systemIdentity.RunImpersonated(GetFileStream, cancellationToken);
-
-									return result;
-								},
-								path,
-								false));
-
-						result = new ConfigurationFileResponse
-						{
-							FileTicket = fileTicket.FileTicket,
-							IsDirectory = false,
-							LastReadHash = originalSha,
-							AccessDenied = false,
-							Path = configurationRelativePath,
-						};
+						isDirectory = synchronousIOManager.IsDirectory(path);
 					}
-					catch (UnauthorizedAccessException)
+					catch (Exception ex)
 					{
-						// this happens on windows, dunno about linux
-						bool isDirectory;
-						try
-						{
-							isDirectory = synchronousIOManager.IsDirectory(path);
-						}
-						catch (Exception ex)
-						{
-							logger.LogDebug(ex, "IsDirectory exception!");
-							isDirectory = false;
-						}
-
-						result = new ConfigurationFileResponse
-						{
-							Path = configurationRelativePath,
-						};
-						if (!isDirectory)
-							result.AccessDenied = true;
-
-						result.IsDirectory = isDirectory;
+						logger.LogDebug(ex, "IsDirectory exception!");
+						isDirectory = false;
 					}
+
+					result = new ConfigurationFileResponse
+					{
+						Path = configurationRelativePath,
+					};
+					if (!isDirectory)
+						result.AccessDenied = true;
+
+					result.IsDirectory = isDirectory;
+				}
 			}
 
-			using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
+			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+			{
+				if (!locked)
+				{
+					logger.LogDebug("Contention when attempting to read file!");
+					return null;
+				}
+
 				if (systemIdentity == null)
 					await Task.Factory.StartNew(ReadImpl, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
 				else
 					await systemIdentity.RunImpersonated(ReadImpl, cancellationToken);
+			}
 
 			return result;
 		}
@@ -448,93 +459,108 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 
 			void WriteImpl()
 			{
-				lock (semaphore)
-					try
+				try
+				{
+					var fileTicket = fileTransferService.CreateUpload(FileUploadStreamKind.ForSynchronousIO);
+					var uploadCancellationToken = disposeCts.Token;
+					async Task UploadHandler()
 					{
-						var fileTicket = fileTransferService.CreateUpload(FileUploadStreamKind.ForSynchronousIO);
-						var uploadCancellationToken = disposeCts.Token;
-						async Task UploadHandler()
+						await using (fileTicket)
 						{
-							await using (fileTicket)
+							var fileHash = previousHash;
+							var uploadStream = await fileTicket.GetResult(uploadCancellationToken);
+							if (uploadStream == null)
+								return; // expired
+
+							bool success = false;
+							void WriteCallback()
 							{
-								var fileHash = previousHash;
-								var uploadStream = await fileTicket.GetResult(uploadCancellationToken);
-								if (uploadStream == null)
-									return; // expired
+								success = synchronousIOManager.WriteFileChecked(path, uploadStream, ref fileHash, cancellationToken);
+							}
 
-								bool success = false;
-								void WriteCallback()
-								{
-									success = synchronousIOManager.WriteFileChecked(path, uploadStream, ref fileHash, cancellationToken);
-								}
+							if (fileTicket == null)
+							{
+								logger.LogDebug("File upload ticket for {path} expired!", path);
+								return;
+							}
 
-								if (fileTicket == null)
+							using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+							{
+								if (!locked)
 								{
-									logger.LogDebug("File upload ticket for {path} expired!", path);
+									fileTicket.SetError(ErrorCode.ConfigurationContendedAccess, null);
 									return;
 								}
 
-								using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
-									if (systemIdentity == null)
-										await Task.Factory.StartNew(WriteCallback, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
-									else
-										await systemIdentity.RunImpersonated(WriteCallback, cancellationToken);
-
-								if (!success)
-									fileTicket.SetError(ErrorCode.ConfigurationFileUpdated, fileHash);
-								else if (uploadStream.Length > 0)
-									postWriteHandler.HandleWrite(path);
+								if (systemIdentity == null)
+									await Task.Factory.StartNew(WriteCallback, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
+								else
+									await systemIdentity.RunImpersonated(WriteCallback, cancellationToken);
 							}
+
+							if (!success)
+								fileTicket.SetError(ErrorCode.ConfigurationFileUpdated, fileHash);
+							else if (uploadStream.Length > 0)
+								postWriteHandler.HandleWrite(path);
 						}
-
-						result = new ConfigurationFileResponse
-						{
-							FileTicket = fileTicket.Ticket.FileTicket,
-							LastReadHash = previousHash,
-							IsDirectory = false,
-							AccessDenied = false,
-							Path = configurationRelativePath,
-						};
-
-						lock (disposeCts)
-							uploadTasks = Task.WhenAll(uploadTasks, UploadHandler());
 					}
-					catch (UnauthorizedAccessException)
+
+					result = new ConfigurationFileResponse
 					{
-						// this happens on windows, dunno about linux
-						bool isDirectory;
-						try
-						{
-							isDirectory = synchronousIOManager.IsDirectory(path);
-						}
-						catch (Exception ex)
-						{
-							logger.LogDebug(ex, "IsDirectory exception!");
-							isDirectory = false;
-						}
+						FileTicket = fileTicket.Ticket.FileTicket,
+						LastReadHash = previousHash,
+						IsDirectory = false,
+						AccessDenied = false,
+						Path = configurationRelativePath,
+					};
 
-						result = new ConfigurationFileResponse
-						{
-							Path = configurationRelativePath,
-						};
-						if (!isDirectory)
-							result.AccessDenied = true;
-
-						result.IsDirectory = isDirectory;
+					lock (disposeCts)
+						uploadTasks = Task.WhenAll(uploadTasks, UploadHandler());
+				}
+				catch (UnauthorizedAccessException)
+				{
+					// this happens on windows, dunno about linux
+					bool isDirectory;
+					try
+					{
+						isDirectory = synchronousIOManager.IsDirectory(path);
 					}
+					catch (Exception ex)
+					{
+						logger.LogDebug(ex, "IsDirectory exception!");
+						isDirectory = false;
+					}
+
+					result = new ConfigurationFileResponse
+					{
+						Path = configurationRelativePath,
+					};
+					if (!isDirectory)
+						result.AccessDenied = true;
+
+					result.IsDirectory = isDirectory;
+				}
 			}
 
-			using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
+			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+			{
+				if (!locked)
+				{
+					logger.LogDebug("Contention when attempting to write file!");
+					return null;
+				}
+
 				if (systemIdentity == null)
 					await Task.Factory.StartNew(WriteImpl, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
 				else
 					await systemIdentity.RunImpersonated(WriteImpl, cancellationToken);
+			}
 
 			return result;
 		}
 
 		/// <inheritdoc />
-		public async Task<bool> CreateDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
+		public async Task<bool?> CreateDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
 		{
 			await EnsureDirectories(cancellationToken);
 			var path = ValidateConfigRelativePath(configurationRelativePath);
@@ -542,11 +568,19 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 			bool? result = null;
 			void DoCreate() => result = synchronousIOManager.CreateDirectory(path, cancellationToken);
 
-			using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
+			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
+			{
+				if (!locked)
+				{
+					logger.LogDebug("Contention when attempting to create directory!");
+					return null;
+				}
+
 				if (systemIdentity == null)
 					await Task.Factory.StartNew(DoCreate, cancellationToken, DefaultIOManager.BlockingTaskCreationOptions, TaskScheduler.Current);
 				else
 					await systemIdentity.RunImpersonated(DoCreate, cancellationToken);
+			}
 
 			return result.Value;
 		}
@@ -618,14 +652,20 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 		}
 
 		/// <inheritdoc />
-		public async Task<bool> DeleteDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
+		public async Task<bool?> DeleteDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken)
 		{
 			await EnsureDirectories(cancellationToken);
 			var path = ValidateConfigRelativePath(configurationRelativePath);
 
 			var result = false;
-			using (await SemaphoreSlimContext.Lock(semaphore, cancellationToken))
+			using (SemaphoreSlimContext.TryLock(semaphore, out var locked))
 			{
+				if (!locked)
+				{
+					logger.LogDebug("Contention when attempting to enumerate directory!");
+					return null;
+				}
+
 				void CheckDeleteImpl() => result = synchronousIOManager.DeleteDirectory(path);
 
 				if (systemIdentity != null)
diff --git a/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs b/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
index bc8b2be171..4fece676c9 100644
--- a/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
+++ b/src/Tgstation.Server.Host/Components/StaticFiles/IConfiguration.cs
@@ -38,7 +38,7 @@ 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"/>.</returns>
+		/// <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);
 
 		/// <summary>
@@ -47,7 +47,7 @@ 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"/> of the file.</returns>
+		/// <returns>A <see cref="Task{TResult}"/> resulting in the <see cref="ConfigurationFileResponse"/> of the file. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
 		Task<ConfigurationFileResponse> Read(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
 
 		/// <summary>
@@ -56,8 +56,8 @@ 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. Usage may result in partial writes.</param>
-		/// <returns>A <see cref="Task{TResult}"/> resulting in <see langword="true"/> if the directory already existed, <see langword="false"/> otherwise.</returns>
-		Task<bool> CreateDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
+		/// <returns>A <see cref="Task{TResult}"/> resulting in <see langword="true"/> if the directory already existed, <see langword="false"/> otherwise. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
+		Task<bool?> CreateDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
 
 		/// <summary>
 		/// Attempt to delete an empty directory at <paramref name="configurationRelativePath"/>.
@@ -65,8 +65,8 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 		/// <param name="configurationRelativePath">The path of the empty directory to delete.</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><see langword="true"/> if the directory was empty and deleted, <see langword="false"/> otherwise.</returns>
-		Task<bool> DeleteDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
+		/// <returns><see langword="true"/> if the directory was empty and deleted, <see langword="false"/> otherwise. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
+		Task<bool?> DeleteDirectory(string configurationRelativePath, ISystemIdentity systemIdentity, CancellationToken cancellationToken);
 
 		/// <summary>
 		/// Writes to a given <paramref name="configurationRelativePath"/>.
@@ -75,7 +75,7 @@ namespace Tgstation.Server.Host.Components.StaticFiles
 		/// <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="previousHash">The hash any existing file must match in order for the write to succeed.</param>
 		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation. Usage may result in partial writes.</param>
-		/// <returns>A <see cref="Task{TResult}"/> resulting in the updated <see cref="ConfigurationFileResponse"/> or <see langword="null"/> if the write failed due to <see cref="IConfigurationFile.LastReadHash"/> conflicts.</returns>
+		/// <returns>A <see cref="Task{TResult}"/> resulting in the updated <see cref="ConfigurationFileResponse"/> and associated writing <see cref="FileTicketResponse"/>. <see langword="null"/> will be returned if the operation failed due to access contention.</returns>
 		Task<ConfigurationFileResponse> Write(string configurationRelativePath, ISystemIdentity systemIdentity, string previousHash, CancellationToken cancellationToken);
 	}
 }
diff --git a/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs b/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
index 373554c928..52819df9ab 100644
--- a/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
+++ b/src/Tgstation.Server.Host/Controllers/ConfigurationController.cs
@@ -14,7 +14,6 @@ using Tgstation.Server.Api.Models.Response;
 using Tgstation.Server.Api.Rights;
 using Tgstation.Server.Host.Components;
 using Tgstation.Server.Host.Database;
-using Tgstation.Server.Host.Extensions;
 using Tgstation.Server.Host.IO;
 using Tgstation.Server.Host.Models;
 using Tgstation.Server.Host.Security;
@@ -86,6 +85,9 @@ namespace Tgstation.Server.Host.Controllers
 								model.LastReadHash,
 								cancellationToken);
 
+						if (newFile == null)
+							return Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess));
+
 						return model.LastReadHash == null ? Accepted(newFile) : Json(newFile);
 					});
 			}
@@ -114,6 +116,7 @@ namespace Tgstation.Server.Host.Controllers
 		[HttpGet(Routes.File + "/{*filePath}")]
 		[TgsAuthorize(ConfigurationRights.Read)]
 		[ProducesResponseType(typeof(ConfigurationFileResponse), 200)]
+		[ProducesResponseType(typeof(ErrorMessageResponse), 409)]
 		[ProducesResponseType(typeof(ErrorMessageResponse), 410)]
 		public async Task<IActionResult> File(string filePath, CancellationToken cancellationToken)
 		{
@@ -128,8 +131,9 @@ namespace Tgstation.Server.Host.Controllers
 						var result = await instance
 							.Configuration
 							.Read(filePath, systemIdentity, cancellationToken);
+
 						if (result == null)
-							return this.Gone();
+							return Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess));
 
 						return Json(result);
 					});
@@ -161,6 +165,7 @@ namespace Tgstation.Server.Host.Controllers
 		[HttpGet(Routes.List + "/{*directoryPath}")]
 		[TgsAuthorize(ConfigurationRights.List)]
 		[ProducesResponseType(typeof(PaginatedResponse<ConfigurationFileResponse>), 200)]
+		[ProducesResponseType(typeof(ErrorMessageResponse), 409)]
 		[ProducesResponseType(typeof(ErrorMessageResponse), 410)]
 		public Task<IActionResult> Directory(
 			string directoryPath,
@@ -180,8 +185,10 @@ namespace Tgstation.Server.Host.Controllers
 							var result = await instance
 								.Configuration
 								.ListDirectory(directoryPath, systemIdentity, cancellationToken);
+
 							if (result == null)
-								return new PaginatableResult<ConfigurationFileResponse>(this.Gone());
+								return new PaginatableResult<ConfigurationFileResponse>(
+									Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess)));
 
 							return new PaginatableResult<ConfigurationFileResponse>(
 								result
@@ -198,6 +205,15 @@ namespace Tgstation.Server.Host.Controllers
 							return new PaginatableResult<ConfigurationFileResponse>(
 								Forbid());
 						}
+						catch (IOException ex)
+						{
+							Logger.LogInformation(ex, "IOException while enumerating directory!");
+							return new PaginatableResult<ConfigurationFileResponse>(
+								Conflict(new ErrorMessageResponse(ErrorCode.IOError)
+								{
+									AdditionalData = ex.Message,
+								}));
+						}
 					},
 					null,
 					page,
@@ -231,6 +247,7 @@ namespace Tgstation.Server.Host.Controllers
 		[TgsAuthorize(ConfigurationRights.Write)]
 		[ProducesResponseType(typeof(ConfigurationFileResponse), 200)]
 		[ProducesResponseType(typeof(ConfigurationFileResponse), 201)]
+		[ProducesResponseType(typeof(ErrorMessageResponse), 409)]
 		public async Task<IActionResult> CreateDirectory([FromBody] ConfigurationFileRequest model, CancellationToken cancellationToken)
 		{
 			ArgumentNullException.ThrowIfNull(model);
@@ -247,11 +264,19 @@ namespace Tgstation.Server.Host.Controllers
 				};
 
 				return await WithComponentInstance(
-					async instance => await instance
-						.Configuration
-						.CreateDirectory(model.Path, systemIdentity, cancellationToken)
+					async instance =>
+					{
+						var result = await instance
+							.Configuration
+							.CreateDirectory(model.Path, systemIdentity, cancellationToken);
+
+						if (!result.HasValue)
+							return Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess));
+
+						return result.Value
 							? Json(resultModel)
-							: Created(resultModel));
+							: Created(resultModel);
+					});
 			}
 			catch (IOException e)
 			{
@@ -281,6 +306,7 @@ namespace Tgstation.Server.Host.Controllers
 		[HttpDelete]
 		[TgsAuthorize(ConfigurationRights.Delete)]
 		[ProducesResponseType(204)]
+		[ProducesResponseType(typeof(ErrorMessageResponse), 409)]
 		public async Task<IActionResult> DeleteDirectory([FromBody] ConfigurationFileRequest directory, CancellationToken cancellationToken)
 		{
 			ArgumentNullException.ThrowIfNull(directory);
@@ -294,11 +320,19 @@ namespace Tgstation.Server.Host.Controllers
 			try
 			{
 				return await WithComponentInstance(
-					async instance => await instance
-					.Configuration
-					.DeleteDirectory(directory.Path, systemIdentity, cancellationToken)
-						? NoContent()
-						: Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationDirectoryNotEmpty)));
+					async instance =>
+					{
+						var result = await instance
+							.Configuration
+							.DeleteDirectory(directory.Path, systemIdentity, cancellationToken);
+
+						if (!result.HasValue)
+							return Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationContendedAccess));
+
+						return result.Value
+							? NoContent()
+							: Conflict(new ErrorMessageResponse(ErrorCode.ConfigurationDirectoryNotEmpty));
+					});
 			}
 			catch (NotImplementedException ex)
 			{
@@ -308,6 +342,14 @@ namespace Tgstation.Server.Host.Controllers
 			{
 				return Forbid();
 			}
+			catch (IOException ex)
+			{
+				Logger.LogInformation(ex, "IOException while deleting directory!");
+				return Conflict(new ErrorMessageResponse(ErrorCode.IOError)
+				{
+					Message = ex.Message,
+				});
+			}
 		}
 
 		/// <summary>
diff --git a/src/Tgstation.Server.Host/Utils/SemaphoreSlimContext.cs b/src/Tgstation.Server.Host/Utils/SemaphoreSlimContext.cs
index cdbe250071..25f070cc4b 100644
--- a/src/Tgstation.Server.Host/Utils/SemaphoreSlimContext.cs
+++ b/src/Tgstation.Server.Host/Utils/SemaphoreSlimContext.cs
@@ -7,7 +7,7 @@ namespace Tgstation.Server.Host.Utils
 	/// <summary>
 	/// Async lock context helper.
 	/// </summary>
-	public sealed class SemaphoreSlimContext : IDisposable
+	sealed class SemaphoreSlimContext : IDisposable
 	{
 		/// <summary>
 		/// Asyncronously locks a <paramref name="semaphore"/>.
@@ -15,14 +15,28 @@ namespace Tgstation.Server.Host.Utils
 		/// <param name="semaphore">The <see cref="SemaphoreSlim"/> to lock.</param>
 		/// <param name="cancellationToken">The <see cref="CancellationToken"/> for the operation.</param>
 		/// <returns>A <see cref="Task{TResult}"/> resulting in the <see cref="SemaphoreSlimContext"/> for the lock.</returns>
-		public static async Task<SemaphoreSlimContext> Lock(SemaphoreSlim semaphore, CancellationToken cancellationToken)
+		public static async ValueTask<SemaphoreSlimContext> Lock(SemaphoreSlim semaphore, CancellationToken cancellationToken)
 		{
 			ArgumentNullException.ThrowIfNull(semaphore);
-			cancellationToken.ThrowIfCancellationRequested();
 			await semaphore.WaitAsync(cancellationToken);
 			return new SemaphoreSlimContext(semaphore);
 		}
 
+		/// <summary>
+		/// Asyncronously attempts to lock a <paramref name="semaphore"/>.
+		/// </summary>
+		/// <param name="semaphore">The <see cref="SemaphoreSlim"/> to lock.</param>
+		/// <param name="locked">The <see cref="bool"/> result of the lock attempt.</param>
+		/// <returns>A <see cref="SemaphoreSlimContext"/> for the lock on success, or <see langword="null"/> if it was not acquired.</returns>
+		public static SemaphoreSlimContext TryLock(SemaphoreSlim semaphore, out bool locked)
+		{
+			ArgumentNullException.ThrowIfNull(semaphore);
+			locked = semaphore.Wait(TimeSpan.Zero);
+			return locked
+				? new SemaphoreSlimContext(semaphore)
+				: null;
+		}
+
 		/// <summary>
 		/// The locked <see cref="SemaphoreSlim"/>.
 		/// </summary>