diff --git a/src/Tgstation.Server.Host/Controllers/DreamDaemonController.cs b/src/Tgstation.Server.Host/Controllers/DreamDaemonController.cs
index 069b272959..cce77f0dc3 100644
--- a/src/Tgstation.Server.Host/Controllers/DreamDaemonController.cs
+++ b/src/Tgstation.Server.Host/Controllers/DreamDaemonController.cs
@@ -174,6 +174,11 @@ namespace Tgstation.Server.Host.Controllers
 
 			if (model.Port.HasValue && model.Port.Value != current.Port!.Value)
 			{
+				Logger.LogTrace(
+					"Triggering port allocator for DD-I:{instanceId} because model port {modelPort} doesn't match DB port {dbPort}...",
+					Instance.Id,
+					model.Port,
+					current.Port);
 				var verifiedPort = await portAllocator
 					.GetAvailablePort(
 						model.Port.Value,
diff --git a/src/Tgstation.Server.Host/Controllers/DreamMakerController.cs b/src/Tgstation.Server.Host/Controllers/DreamMakerController.cs
index 419bc9c90d..8b4cfce563 100644
--- a/src/Tgstation.Server.Host/Controllers/DreamMakerController.cs
+++ b/src/Tgstation.Server.Host/Controllers/DreamMakerController.cs
@@ -175,6 +175,7 @@ namespace Tgstation.Server.Host.Controllers
 		[ProducesResponseType(typeof(DreamMakerResponse), 200)]
 		[ProducesResponseType(204)]
 		[ProducesResponseType(typeof(ErrorMessageResponse), 410)]
+#pragma warning disable CA1506 // TODO: Decomplexify
 		public async ValueTask<IActionResult> Update([FromBody] DreamMakerRequest model, CancellationToken cancellationToken)
 		{
 			ArgumentNullException.ThrowIfNull(model);
@@ -208,6 +209,11 @@ namespace Tgstation.Server.Host.Controllers
 
 				if (model.ApiValidationPort.Value != hostModel.ApiValidationPort!.Value)
 				{
+					Logger.LogTrace(
+						"Triggering port allocator for DM-I:{instanceId} because model port {modelPort} doesn't match DB port {dbPort}...",
+						Instance.Id,
+						model.ApiValidationPort,
+						hostModel.ApiValidationPort);
 					var verifiedPort = await portAllocator
 						.GetAvailablePort(
 							model.ApiValidationPort.Value,
@@ -248,6 +254,7 @@ namespace Tgstation.Server.Host.Controllers
 
 			return await Read(cancellationToken);
 		}
+#pragma warning restore CA1506
 
 		/// <summary>
 		/// Base query for pulling in all required <see cref="CompileJob"/> fields.
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/DeploymentTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/DeploymentTest.cs
index 0cd00f5330..28485a7732 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/DeploymentTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/DeploymentTest.cs
@@ -118,6 +118,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 		{
 			Assert.IsNotNull(vpTest);
 			// by alphabetization rules, it should discover api_free here
+			Console.WriteLine($"PORT REUSE BUG 5: Setting I-{instanceClient.Metadata.Id} DM to {dmPort}");
 			if (!new PlatformIdentifier().IsWindows)
 			{
 				var updatedDM = await dreamMakerClient.Update(new DreamMakerRequest
@@ -137,6 +138,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 				Assert.AreEqual(dmPort, updatedDM.ApiValidationPort);
 			}
 
+			Console.WriteLine($"PORT REUSE BUG 1: Setting I-{instanceClient.Metadata.Id} DD to {ddPort}");
 			var updatedDD = await dreamDaemonClient.Update(new DreamDaemonRequest
 			{
 				StartupTimeout = 60,
@@ -157,10 +159,12 @@ namespace Tgstation.Server.Tests.Live.Instance
 
 			await CheckDreamDaemonPriority(deploymentJobWaitTask, cancellationToken);
 
+			Console.WriteLine($"PORT REUSE BUG 2: Expect Conflict, Setting I-{instanceClient.Metadata.Id} DD to {dmPort}");
 			var t1 = ApiAssert.ThrowsException<ConflictException, DreamDaemonResponse>(() => dreamDaemonClient.Update(new DreamDaemonRequest
 			{
 				Port = dmPort,
 			}, cancellationToken), ErrorCode.PortNotAvailable);
+			Console.WriteLine($"PORT REUSE BUG 3: Expect Conflict, Setting I-{instanceClient.Metadata.Id} DM to {ddPort}");
 			var t2 = ApiAssert.ThrowsException<ConflictException, DreamMakerResponse>(() => dreamMakerClient.Update(new DreamMakerRequest
 			{
 				ApiValidationPort = ddPort
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/InstanceTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/InstanceTest.cs
index 571e3d88c7..a37ceb26e1 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/InstanceTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/InstanceTest.cs
@@ -164,6 +164,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 				for (var i = 0; i < 10; ++i)
 					try
 					{
+						global::System.Console.WriteLine($"PORT REUSE BUG 6: Setting I-{instanceClient.Metadata.Id} DM to {dmPort}");
 						await instanceClient.DreamMaker.Update(new DreamMakerRequest
 						{
 							ApiValidationPort = dmPort,
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
index 5b18b2417e..ceb8e80fe7 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
@@ -135,6 +135,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 					try
 					{
 						// Increase startup timeout, disable heartbeats, enable map threads because we've tested without for years
+						global::System.Console.WriteLine($"PORT REUSE BUG 4: Setting I-{instanceClient.Metadata.Id} DD to {ddPort}");
 						await instanceClient.DreamDaemon.Update(new DreamDaemonRequest
 						{
 							StartupTimeout = 60,
@@ -155,6 +156,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 					}
 			}
 
+			global::System.Console.WriteLine($"PORT REUSE BUG 4: Expect error. Setting I-{instanceClient.Metadata.Id} DD to 0");
 			await Task.WhenAll(
 				UpdateDDSettings(),
 				CheckByondVersions(),