diff --git a/src/Tgstation.Server.Host/Utils/GitHub/GitHubClientFactory.cs b/src/Tgstation.Server.Host/Utils/GitHub/GitHubClientFactory.cs
index a424e1b4d5..2a1554f0e9 100644
--- a/src/Tgstation.Server.Host/Utils/GitHub/GitHubClientFactory.cs
+++ b/src/Tgstation.Server.Host/Utils/GitHub/GitHubClientFactory.cs
@@ -2,6 +2,7 @@
 using System.Collections.Generic;
 using System.IdentityModel.Tokens.Jwt;
 using System.Linq;
+using System.Net.Http;
 using System.Security.Cryptography;
 using System.Text;
 using System.Threading;
@@ -12,6 +13,7 @@ using Microsoft.Extensions.Options;
 using Microsoft.IdentityModel.Tokens;
 
 using Octokit;
+using Octokit.Internal;
 
 using Tgstation.Server.Api.Models;
 using Tgstation.Server.Host.Configuration;
@@ -38,6 +40,11 @@ namespace Tgstation.Server.Host.Utils.GitHub
 		/// </summary>
 		readonly IAssemblyInformationProvider assemblyInformationProvider;
 
+		/// <summary>
+		/// The <see cref="IHttpMessageHandlerFactory"/> for the <see cref="GitHubClientFactory"/>.
+		/// </summary>
+		readonly IHttpMessageHandlerFactory httpMessageHandlerFactory;
+
 		/// <summary>
 		/// The <see cref="ILogger"/> for the <see cref="GitHubClientFactory"/>.
 		/// </summary>
@@ -62,14 +69,17 @@ namespace Tgstation.Server.Host.Utils.GitHub
 		/// Initializes a new instance of the <see cref="GitHubClientFactory"/> class.
 		/// </summary>
 		/// <param name="assemblyInformationProvider">The value of <see cref="assemblyInformationProvider"/>.</param>
+		/// <param name="httpMessageHandlerFactory">The value of <see cref="httpMessageHandlerFactory"/>.</param>
 		/// <param name="logger">The value of <see cref="logger"/>.</param>
 		/// <param name="generalConfigurationOptions">The <see cref="IOptions{TOptions}"/> containing the value of <see cref="generalConfiguration"/>.</param>
 		public GitHubClientFactory(
 			IAssemblyInformationProvider assemblyInformationProvider,
+			IHttpMessageHandlerFactory httpMessageHandlerFactory,
 			ILogger<GitHubClientFactory> logger,
 			IOptions<GeneralConfiguration> generalConfigurationOptions)
 		{
 			this.assemblyInformationProvider = assemblyInformationProvider ?? throw new ArgumentNullException(nameof(assemblyInformationProvider));
+			this.httpMessageHandlerFactory = httpMessageHandlerFactory ?? throw new ArgumentNullException(nameof(httpMessageHandlerFactory));
 			this.logger = logger ?? throw new ArgumentNullException(nameof(logger));
 			generalConfiguration = generalConfigurationOptions?.Value ?? throw new ArgumentNullException(nameof(generalConfigurationOptions));
 
@@ -315,10 +325,33 @@ namespace Tgstation.Server.Host.Utils.GitHub
 		GitHubClient CreateUnauthenticatedClient()
 		{
 			var product = assemblyInformationProvider.ProductInfoHeaderValue.Product!;
-			return new GitHubClient(
-				new ProductHeaderValue(
-					product.Name,
-					product.Version));
+#pragma warning disable CA2000 // Dispose objects before losing scope
+			var handler = httpMessageHandlerFactory.CreateHandler();
+			try
+			{
+				var clientAdapter = new HttpClientAdapter(() => handler);
+#pragma warning restore CA2000 // Dispose objects before losing scope
+				handler = null;
+				try
+				{
+					return new GitHubClient(
+						new Connection(
+							new ProductHeaderValue(
+								product.Name,
+								product.Version),
+							clientAdapter));
+				}
+				catch
+				{
+					clientAdapter.Dispose();
+					throw;
+				}
+			}
+			catch
+			{
+				handler?.Dispose();
+				throw;
+			}
 		}
 	}
 }
diff --git a/tests/Tgstation.Server.Host.Tests/BasicHttpMessageHandlerFactory.cs b/tests/Tgstation.Server.Host.Tests/BasicHttpMessageHandlerFactory.cs
new file mode 100644
index 0000000000..94dd57d3ea
--- /dev/null
+++ b/tests/Tgstation.Server.Host.Tests/BasicHttpMessageHandlerFactory.cs
@@ -0,0 +1,19 @@
+using System;
+using System.Net.Http;
+
+namespace Tgstation.Server.Host.Tests
+{
+	/// <summary>
+	/// Basic <see cref="IHttpMessageHandlerFactory"/> implementation for testiong
+	/// </summary>
+	public sealed class BasicHttpMessageHandlerFactory : IHttpMessageHandlerFactory, IDisposable
+	{
+		readonly HttpClientHandler handler = new();
+
+		public HttpMessageHandler CreateHandler(string name)
+			=> handler;
+
+		public void Dispose()
+			=> handler.Dispose();
+	}
+}
diff --git a/tests/Tgstation.Server.Host.Tests/Utils/GitHub/TestGitHubClientFactory.cs b/tests/Tgstation.Server.Host.Tests/Utils/GitHub/TestGitHubClientFactory.cs
index 5132f8ab01..01bb7bac1f 100644
--- a/tests/Tgstation.Server.Host.Tests/Utils/GitHub/TestGitHubClientFactory.cs
+++ b/tests/Tgstation.Server.Host.Tests/Utils/GitHub/TestGitHubClientFactory.cs
@@ -1,4 +1,5 @@
 using System;
+using System.Net.Http;
 using System.Net.Http.Headers;
 using System.Text;
 using System.Threading;
@@ -15,6 +16,7 @@ using Octokit;
 using Tgstation.Server.Api.Models;
 using Tgstation.Server.Host.Configuration;
 using Tgstation.Server.Host.System;
+using Tgstation.Server.Host.Tests;
 
 namespace Tgstation.Server.Host.Utils.GitHub.Tests
 {
@@ -42,9 +44,10 @@ namespace Tgstation.Server.Host.Utils.GitHub.Tests
 		[TestMethod]
 		public void TestContructionThrows()
 		{
-			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(null, null, null));
-			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(Mock.Of<IAssemblyInformationProvider>(), null, null));
-			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(Mock.Of<IAssemblyInformationProvider>(), Mock.Of<ILogger<GitHubClientFactory>>(), null));
+			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(null, null, null, null));
+			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(Mock.Of<IAssemblyInformationProvider>(), null, null, null));
+			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(Mock.Of<IAssemblyInformationProvider>(), Mock.Of<IHttpMessageHandlerFactory>(), null, null));
+			Assert.ThrowsException<ArgumentNullException>(() => new GitHubClientFactory(Mock.Of<IAssemblyInformationProvider>(), Mock.Of<IHttpMessageHandlerFactory>(), Mock.Of<ILogger<GitHubClientFactory>>(), null));
 		}
 
 		[TestMethod]
@@ -58,7 +61,7 @@ namespace Tgstation.Server.Host.Utils.GitHub.Tests
 			var gc = new GeneralConfiguration();
 			Assert.IsNull(gc.GitHubAccessToken);
 			mockOptions.SetupGet(x => x.Value).Returns(gc);
-			var factory = new GitHubClientFactory(mockApp.Object, loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
+			var factory = new GitHubClientFactory(mockApp.Object, new BasicHttpMessageHandlerFactory(), loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
 
 			var client = await factory.CreateClient(CancellationToken.None);
 			Assert.IsNotNull(client);
@@ -84,7 +87,7 @@ namespace Tgstation.Server.Host.Utils.GitHub.Tests
 
 			var mockOptions = new Mock<IOptions<GeneralConfiguration>>();
 			mockOptions.SetupGet(x => x.Value).Returns(new GeneralConfiguration());
-			var factory = new GitHubClientFactory(mockApp.Object, loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
+			var factory = new GitHubClientFactory(mockApp.Object, new BasicHttpMessageHandlerFactory(), loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
 
 			await Assert.ThrowsExceptionAsync<ArgumentNullException>(() => factory.CreateClient(null, CancellationToken.None).AsTask());
 
@@ -106,7 +109,7 @@ namespace Tgstation.Server.Host.Utils.GitHub.Tests
 
 			var mockOptions = new Mock<IOptions<GeneralConfiguration>>();
 			mockOptions.SetupGet(x => x.Value).Returns(new GeneralConfiguration());
-			var factory = new GitHubClientFactory(mockApp.Object, loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
+			var factory = new GitHubClientFactory(mockApp.Object, new BasicHttpMessageHandlerFactory(), loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
 
 			var appID = Environment.GetEnvironmentVariable("TGS_TEST_APP_ID");
 			var privateKey = Environment.GetEnvironmentVariable("TGS_TEST_APP_PRIVATE_KEY");
@@ -144,7 +147,7 @@ namespace Tgstation.Server.Host.Utils.GitHub.Tests
 
 			var mockOptions = new Mock<IOptions<GeneralConfiguration>>();
 			mockOptions.SetupGet(x => x.Value).Returns(new GeneralConfiguration());
-			var factory = new GitHubClientFactory(mockApp.Object, loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
+			var factory = new GitHubClientFactory(mockApp.Object, new BasicHttpMessageHandlerFactory(), loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
 
 			await Assert.ThrowsExceptionAsync<ArgumentNullException>(() => factory.CreateClient(null, CancellationToken.None).AsTask());
 
@@ -192,7 +195,7 @@ vTdVAoGBAI/jjUMdjkY43zhe3w2piwT0fhGfqm9ikdAB9IcgcptuS0ML0ZaWV/eO
 
 			var mockOptions = new Mock<IOptions<GeneralConfiguration>>();
 			mockOptions.SetupGet(x => x.Value).Returns(new GeneralConfiguration());
-			var factory = new GitHubClientFactory(mockApp.Object, loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
+			var factory = new GitHubClientFactory(mockApp.Object, new BasicHttpMessageHandlerFactory(), loggerFactory.CreateLogger<GitHubClientFactory>(), mockOptions.Object);
 
 			var client1 = await factory.CreateClient(CancellationToken.None);
 			var client2 = await factory.CreateClient("asdf", CancellationToken.None);
diff --git a/tests/Tgstation.Server.Tests/Live/TestingGitHubService.cs b/tests/Tgstation.Server.Tests/Live/TestingGitHubService.cs
index 585dd56999..48434bd142 100644
--- a/tests/Tgstation.Server.Tests/Live/TestingGitHubService.cs
+++ b/tests/Tgstation.Server.Tests/Live/TestingGitHubService.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.Linq;
+using System.Net.Http;
 using System.Threading;
 using System.Threading.Tasks;
 
@@ -38,7 +39,7 @@ namespace Tgstation.Server.Tests.Live
 				GitHubAccessToken = Environment.GetEnvironmentVariable("TGS_TEST_GITHUB_TOKEN")
 			});
 
-			var gitHubClientFactory = new GitHubClientFactory(new AssemblyInformationProvider(), Mock.Of<ILogger<GitHubClientFactory>>(), mockOptions.Object);
+			var gitHubClientFactory = new GitHubClientFactory(new AssemblyInformationProvider(), Mock.Of<IHttpMessageHandlerFactory>(), Mock.Of<ILogger<GitHubClientFactory>>(), mockOptions.Object);
 			RealClient = gitHubClientFactory.CreateClient(CancellationToken.None).GetAwaiter().GetResult();
 		}
 
diff --git a/tests/Tgstation.Server.Tests/Tgstation.Server.Tests.csproj b/tests/Tgstation.Server.Tests/Tgstation.Server.Tests.csproj
index 32edf3de15..342d841f8e 100644
--- a/tests/Tgstation.Server.Tests/Tgstation.Server.Tests.csproj
+++ b/tests/Tgstation.Server.Tests/Tgstation.Server.Tests.csproj
@@ -13,6 +13,7 @@
     <ProjectReference Include="..\..\src\Tgstation.Server.Client.GraphQL\Tgstation.Server.Client.GraphQL.csproj" />
     <ProjectReference Include="..\..\src\Tgstation.Server.Host.Watchdog\Tgstation.Server.Host.Watchdog.csproj" />
     <ProjectReference Include="..\..\src\Tgstation.Server.Host\Tgstation.Server.Host.csproj" />
+    <ProjectReference Include="..\Tgstation.Server.Host.Tests\Tgstation.Server.Host.Tests.csproj" />
   </ItemGroup>
 
   <ItemGroup>