diff --git a/build/Version.props b/build/Version.props
index 911e6616e3..a5d010ffb8 100644
--- a/build/Version.props
+++ b/build/Version.props
@@ -2,7 +2,7 @@
   <PropertyGroup>
     <!-- This is the authorative version list -->
     <!-- Integration tests will ensure they match across the board -->
-    <TgsCoreVersion>4.2.7</TgsCoreVersion>
+    <TgsCoreVersion>4.3.0</TgsCoreVersion>
     <TgsApiVersion>6.5.0</TgsApiVersion>
     <TgsClientVersion>7.1.0</TgsClientVersion>
     <TgsDmapiVersion>5.2.1</TgsDmapiVersion>
diff --git a/src/Tgstation.Server.Client/ApiClient.cs b/src/Tgstation.Server.Client/ApiClient.cs
index 539b3ce319..b9443b8897 100644
--- a/src/Tgstation.Server.Client/ApiClient.cs
+++ b/src/Tgstation.Server.Client/ApiClient.cs
@@ -162,22 +162,9 @@ namespace Tgstation.Server.Client
 				var headersToUse = tokenRefresh ? tokenRefreshHeaders! : headers;
 				headersToUse.SetRequestHeaders(request.Headers, instanceId);
 
-				// This is meant to be a gate against token refresh operations
-				await semaphoreSlim.WaitAsync(cancellationToken).ConfigureAwait(false);
-				if(!tokenRefresh)
-					semaphoreSlim.Release();
+				await Task.WhenAll(requestLoggers.Select(x => x.LogRequest(request, cancellationToken))).ConfigureAwait(false);
 
-				try
-				{
-					await Task.WhenAll(requestLoggers.Select(x => x.LogRequest(request, cancellationToken))).ConfigureAwait(false);
-
-					response = await httpClient.SendAsync(request, cancellationToken).ConfigureAwait(false);
-				}
-				finally
-				{
-					if (tokenRefresh)
-						semaphoreSlim.Release();
-				}
+				response = await httpClient.SendAsync(request, cancellationToken).ConfigureAwait(false);
 			}
 
 			using (response)
@@ -214,8 +201,13 @@ namespace Tgstation.Server.Client
 			if (tokenRefreshHeaders == null)
 				return false;
 
+			var startingToken = headers.Token;
+			await semaphoreSlim.WaitAsync(cancellationToken).ConfigureAwait(false);
 			try
 			{
+				if (startingToken != headers.Token)
+					return true;
+
 				var token = await RunRequest<Token>(Routes.Root, new object(), HttpMethod.Post, null, true, cancellationToken);
 				headers = new ApiHeaders(headers.UserAgent!, token.Bearer!);
 			}
@@ -223,6 +215,10 @@ namespace Tgstation.Server.Client
 			{
 				return false;
 			}
+			finally
+			{
+				semaphoreSlim.Release();
+			}
 
 			return true;
 		}
diff --git a/src/Tgstation.Server.Host/Configuration/GeneralConfiguration.cs b/src/Tgstation.Server.Host/Configuration/GeneralConfiguration.cs
index 9b5f34f5f6..e20d5cb3df 100644
--- a/src/Tgstation.Server.Host/Configuration/GeneralConfiguration.cs
+++ b/src/Tgstation.Server.Host/Configuration/GeneralConfiguration.cs
@@ -14,6 +14,11 @@ namespace Tgstation.Server.Host.Configuration
 		/// </summary>
 		public const string Section = "General";
 
+		/// <summary>
+		/// The default value of <see cref="ApiPort"/>.
+		/// </summary>
+		public const ushort DefaultApiPort = 5000;
+
 		/// <summary>
 		/// The default value for <see cref="ServerInformation.MinimumPasswordLength"/>.
 		/// </summary>
@@ -39,6 +44,11 @@ namespace Tgstation.Server.Host.Configuration
 		/// </summary>
 		const int DefaultRestartTimeout = 10000;
 
+		/// <summary>
+		/// The port the TGS API listens on.
+		/// </summary>
+		public ushort ApiPort { get; set; }
+
 		/// <summary>
 		/// A GitHub personal access token to use for bypassing rate limits on requests. Requires no scopes
 		/// </summary>
diff --git a/src/Tgstation.Server.Host/Core/ServerPortProivder.cs b/src/Tgstation.Server.Host/Core/ServerPortProivder.cs
index a71dc72a29..04c009949d 100644
--- a/src/Tgstation.Server.Host/Core/ServerPortProivder.cs
+++ b/src/Tgstation.Server.Host/Core/ServerPortProivder.cs
@@ -1,6 +1,9 @@
 using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
 using System;
 using System.Linq;
+using Tgstation.Server.Host.Configuration;
 
 namespace Tgstation.Server.Host.Core
 {
@@ -8,14 +11,25 @@ namespace Tgstation.Server.Host.Core
 	sealed class ServerPortProivder : IServerPortProvider
 	{
 		/// <inheritdoc />
-		public ushort HttpApiPort { get; }
+		public ushort HttpApiPort => generalConfiguration.ApiPort;
+
+		/// <summary>
+		/// The <see cref="GeneralConfiguration"/> for the <see cref="ServerPortProivder"/>.
+		/// </summary>
+		readonly GeneralConfiguration generalConfiguration;
 
 		/// <summary>
 		/// Initializes a new instance of the <see cref="ServerPortProivder"/> <see langword="class"/>.
 		/// </summary>
+		/// <param name="generalConfigurationOptions">The <see cref="IOptions{TOptions}"/> containing the value of <see cref="generalConfiguration"/>.</param>
 		/// <param name="configuration">The <see cref="IConfiguration"/> to use.</param>
-		public ServerPortProivder(IConfiguration configuration)
+		/// <param name="logger">The <see cref="ILogger"/> to use.</param>
+		public ServerPortProivder(
+			IOptions<GeneralConfiguration> generalConfigurationOptions,
+			IConfiguration configuration,
+			ILogger<ServerPortProivder> logger)
 		{
+			generalConfiguration = generalConfigurationOptions?.Value ?? throw new ArgumentNullException(nameof(generalConfigurationOptions));
 			if (configuration == null)
 				throw new ArgumentNullException(nameof(configuration));
 
@@ -26,8 +40,13 @@ namespace Tgstation.Server.Host.Core
 				.GetSection("Url")
 				.Value;
 
-			if (httpEndpoint == null)
-				throw new InvalidOperationException("Missing required configuration option Kestrel:EndPoints:Http:Url!");
+			if (generalConfiguration.ApiPort == default && httpEndpoint == null)
+				throw new InvalidOperationException("Missing required configuration option General:ApiPort!");
+
+			if (generalConfiguration.ApiPort != default)
+				return;
+
+			logger.LogWarning("The \"Kestrel\" configuration section is deprecated! Please set your API port using the \"General:ApiPort\" configuration option!");
 
 			var splits = httpEndpoint.Split(":", StringSplitOptions.RemoveEmptyEntries);
 			var portString = splits.Last();
@@ -36,7 +55,7 @@ namespace Tgstation.Server.Host.Core
 			if (!UInt16.TryParse(portString, out var result))
 				throw new InvalidOperationException($"Failed to parse HTTP EndPoint port: {httpEndpoint}");
 
-			HttpApiPort = result;
+			generalConfiguration.ApiPort = result;
 		}
 	}
 }
diff --git a/src/Tgstation.Server.Host/ServerFactory.cs b/src/Tgstation.Server.Host/ServerFactory.cs
index 32289426bc..6bb31a8948 100644
--- a/src/Tgstation.Server.Host/ServerFactory.cs
+++ b/src/Tgstation.Server.Host/ServerFactory.cs
@@ -1,10 +1,12 @@
 using Microsoft.AspNetCore.Hosting;
+using Microsoft.AspNetCore.Server.Kestrel.Core;
 using Microsoft.Extensions.Configuration;
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.Hosting;
 using System;
 using System.Threading;
 using System.Threading.Tasks;
+using Tgstation.Server.Host.Core;
 using Tgstation.Server.Host.Extensions;
 using Tgstation.Server.Host.IO;
 using Tgstation.Server.Host.Setup;
@@ -58,8 +60,17 @@ namespace Tgstation.Server.Host
 			}
 
 			var hostBuilder = CreateDefaultBuilder()
-				.ConfigureWebHostDefaults(webHostBuilder =>
+				.ConfigureWebHost(webHostBuilder =>
 					webHostBuilder
+						.UseKestrel(kestrelOptions =>
+						{
+							var serverPortProvider = kestrelOptions.ApplicationServices.GetRequiredService<IServerPortProvider>();
+							kestrelOptions.ListenAnyIP(
+								serverPortProvider.HttpApiPort,
+								listenOptions => listenOptions.Protocols = HttpProtocols.Http1AndHttp2);
+						})
+						.UseIIS()
+						.UseIISIntegration()
 						.UseApplication(postSetupServices)
 						.SuppressStatusMessages(true)
 						.UseShutdownTimeout(TimeSpan.FromMinutes(1)));
diff --git a/src/Tgstation.Server.Host/Setup/SetupWizard.cs b/src/Tgstation.Server.Host/Setup/SetupWizard.cs
index 72eb7e3509..9e54ac8f00 100644
--- a/src/Tgstation.Server.Host/Setup/SetupWizard.cs
+++ b/src/Tgstation.Server.Host/Setup/SetupWizard.cs
@@ -141,7 +141,11 @@ namespace Tgstation.Server.Host.Setup
 
 			do
 			{
-				await console.WriteAsync("API Port (leave blank for default): ", false, cancellationToken).ConfigureAwait(false);
+				await console.WriteAsync(
+					$"API Port (leave blank for default of {GeneralConfiguration.DefaultApiPort}): ",
+					false,
+					cancellationToken)
+					.ConfigureAwait(false);
 				var portString = await console.ReadLineAsync(false, cancellationToken).ConfigureAwait(false);
 				if (String.IsNullOrWhiteSpace(portString))
 					return null;
@@ -732,6 +736,7 @@ namespace Tgstation.Server.Host.Setup
 		{
 			await console.WriteAsync(String.Format(CultureInfo.InvariantCulture, "Configuration complete! Saving to {0}", userConfigFileName), true, cancellationToken).ConfigureAwait(false);
 
+			newGeneralConfiguration.ApiPort = hostingPort ?? GeneralConfiguration.DefaultApiPort;
 			var map = new Dictionary<string, object>()
 			{
 				{ DatabaseConfiguration.Section, databaseConfiguration },
@@ -740,18 +745,6 @@ namespace Tgstation.Server.Host.Setup
 				{ ControlPanelConfiguration.Section, controlPanelConfiguration }
 			};
 
-			if (hostingPort.HasValue)
-				map.Add("Kestrel", new
-				{
-					EndPoints = new
-					{
-						Http = new
-						{
-							Url = String.Format(CultureInfo.InvariantCulture, "http://0.0.0.0:{0}", hostingPort)
-						}
-					}
-				});
-
 			var json = JsonConvert.SerializeObject(map, Formatting.Indented);
 			var configBytes = Encoding.UTF8.GetBytes(json);
 
diff --git a/src/Tgstation.Server.Host/Tgstation.Server.Host.csproj b/src/Tgstation.Server.Host/Tgstation.Server.Host.csproj
index 09c0c09f16..4382558c26 100644
--- a/src/Tgstation.Server.Host/Tgstation.Server.Host.csproj
+++ b/src/Tgstation.Server.Host/Tgstation.Server.Host.csproj
@@ -83,7 +83,7 @@
     <PackageReference Include="Swashbuckle.AspNetCore.Newtonsoft" Version="5.4.1" />
     <PackageReference Include="System.Data.SqlClient" Version="4.8.1" />
     <PackageReference Include="System.DirectoryServices.AccountManagement" Version="4.7.0" />
-    <PackageReference Include="System.IdentityModel.Tokens.Jwt" Version="6.5.1" />
+    <PackageReference Include="System.IdentityModel.Tokens.Jwt" Version="6.6.0" />
     <PackageReference Include="System.Management" Version="4.7.0" />
     <PackageReference Include="Wangkanai.Detection.Browser" Version="2.0.0" />
     <PackageReference Include="Z.EntityFramework.Plus.EFCore" Version="3.0.50" />
diff --git a/src/Tgstation.Server.Host/appsettings.json b/src/Tgstation.Server.Host/appsettings.json
index 2457e64d56..e7f47e59b1 100644
--- a/src/Tgstation.Server.Host/appsettings.json
+++ b/src/Tgstation.Server.Host/appsettings.json
@@ -1,5 +1,6 @@
 {
   "General": {
+    "ApiPort": 5000,
     "MinimumPasswordLength": 15,
     "GitHubAccessToken": null,
     "SetupWizardMode": "AutoDetect",
@@ -17,13 +18,6 @@
     "LogLevel": "Debug",
     "MicrosoftLogLevel": "Warning"
   },
-  "Kestrel": {
-    "EndPoints": {
-      "Http": {
-        "Url": "http://0.0.0.0:5000"
-      }
-    }
-  },
   "Logging": {
     "IncludeScopes": false,
     "Debug": {
diff --git a/tests/Tgstation.Server.Tests/TestingServer.cs b/tests/Tgstation.Server.Tests/TestingServer.cs
index 7b7df505cc..c420bebd7f 100644
--- a/tests/Tgstation.Server.Tests/TestingServer.cs
+++ b/tests/Tgstation.Server.Tests/TestingServer.cs
@@ -72,7 +72,7 @@ namespace Tgstation.Server.Tests
 			var args = new List<string>()
 			{
 				String.Format(CultureInfo.InvariantCulture, "Database:DropDatabase={0}", true),
-				String.Format(CultureInfo.InvariantCulture, "Kestrel:EndPoints:Http:Url={0}", UrlString),
+				String.Format(CultureInfo.InvariantCulture, "General:ApiPort={0}", 5010),
 				String.Format(CultureInfo.InvariantCulture, "Database:DatabaseType={0}", DatabaseType),
 				String.Format(CultureInfo.InvariantCulture, "Database:ConnectionString={0}", connectionString),
 				String.Format(CultureInfo.InvariantCulture, "General:SetupWizardMode={0}", SetupWizardMode.Never),