diff --git a/tests/DMAPI/LongRunning/Test.dm b/tests/DMAPI/LongRunning/Test.dm
index 657fadbfd0..f605c5ad59 100644
--- a/tests/DMAPI/LongRunning/Test.dm
+++ b/tests/DMAPI/LongRunning/Test.dm
@@ -31,6 +31,23 @@
 	if(!fexists("[DME_NAME].rsc"))
 		FailTest("Failed to create .rsc!")
 
+#ifdef RUN_STATIC_FILE_TESTS
+	if(params["expect_static_files"])
+		if(!fexists("test2.txt"))
+			FailTest("Missing test2.txt")
+
+		var/f2content = file2text("test2.txt")
+		if(f2content != "bbb")
+			FailTest("Unexpected test2.txt content: [f2content]")
+
+		if(!fexists("data/test.txt"))
+			FailTest("Missing data/test.txt")
+
+		var/f1content = file2text("data/test.txt")
+		if(f1content != "aaa")
+			FailTest("Unexpected data/test.txt content: [f1content]")
+#endif
+
 	StartAsync()
 
 /proc/dab()
diff --git a/tests/DMAPI/LongRunning/long_running_test_rooted.dme b/tests/DMAPI/LongRunning/long_running_test_rooted.dme
index d8e9d61c96..a2ff783588 100644
--- a/tests/DMAPI/LongRunning/long_running_test_rooted.dme
+++ b/tests/DMAPI/LongRunning/long_running_test_rooted.dme
@@ -11,6 +11,8 @@
 // END_PREFERENCES
 
 // BEGIN_INCLUDE
+#define RUN_STATIC_FILE_TESTS
+#define DME_NAME "long_running_test_rooted"
 #include "tests/DMAPI/LongRunning/Config.dm"
 #include "tests/DMAPI/test_prelude.dm"
 #include "tests/DMAPI/LongRunning/Test.dm"
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
index 2dea3e5b12..44c2f7246b 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/ConfigurationTest.cs
@@ -83,19 +83,40 @@ namespace Tgstation.Server.Tests.Live.Instance
 			var path = Path.Combine(instance.Path, "Configuration", tmp);
 			Assert.IsFalse(Directory.Exists(path));
 
-			// leave a directory there to test the deployment process
-			var staticDir = new ConfigurationFileRequest
-			{
-				Path = "/GameStaticFiles/data"
-			};
-
-			await configurationClient.CreateDirectory(staticDir, cancellationToken);
 		}
 
 		public Task SetupDMApiTests(bool includingRoot, CancellationToken cancellationToken)
 		{
 			// just use an I/O manager here
 			var ioManager = new DefaultIOManager();
+
+			async Task TestStaticFileAndDir()
+			{
+				// leave a file there to test the deployment process
+				var staticDir = new ConfigurationFileRequest
+				{
+					Path = "/GameStaticFiles/data"
+				};
+
+				await configurationClient.CreateDirectory(staticDir, cancellationToken);
+
+				var staticFile = new ConfigurationFileRequest
+				{
+					Path = "/GameStaticFiles/data/test.txt"
+				};
+
+				await using var memoryStream = new MemoryStream(Encoding.UTF8.GetBytes("aaa"));
+				await configurationClient.Write(staticFile, memoryStream, cancellationToken);
+
+				var staticFile2 = new ConfigurationFileRequest
+				{
+					Path = "/GameStaticFiles/test2.txt"
+				};
+
+				await using var memoryStream2 = new MemoryStream(Encoding.UTF8.GetBytes("bbb"));
+				await configurationClient.Write(staticFile2, memoryStream2, cancellationToken);
+			}
+
 			return Task.WhenAll(
 				ioManager.CopyDirectory(
 					Enumerable.Empty<string>(),
@@ -110,6 +131,9 @@ namespace Tgstation.Server.Tests.Live.Instance
 						ioManager.ConcatPath(instance.Path, "Repository", "long_running_test_rooted.dme"),
 						cancellationToken)
 					: Task.CompletedTask,
+				includingRoot
+					? TestStaticFileAndDir()
+					: Task.CompletedTask,
 				ioManager.CopyDirectory(
 					Enumerable.Empty<string>(),
 					null,
diff --git a/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs b/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
index 784fce5f67..35bd51fd11 100644
--- a/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
+++ b/tests/Tgstation.Server.Tests/Live/Instance/WatchdogTest.cs
@@ -114,7 +114,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 					Port = ddPort,
 					MapThreads = 2,
 					LogOutput = false,
-					AdditionalParameters = "expect_chat_channels=1"
+					AdditionalParameters = "expect_chat_channels=1&expect_static_files=1"
 				}, cancellationToken),
 				CheckByondVersions(),
 				ApiAssert.ThrowsException<ApiConflictException>(() => instanceClient.DreamDaemon.Update(new DreamDaemonRequest
@@ -157,8 +157,64 @@ namespace Tgstation.Server.Tests.Live.Instance
 			System.Console.WriteLine($"TEST: END WATCHDOG TESTS {instanceClient.Metadata.Name}");
 		}
 
+		async ValueTask RegressionTest1686(CancellationToken cancellationToken) 
+		{
+			async ValueTask RunTest(bool useTrusted)
+			{
+				System.Console.WriteLine($"TEST: RegressionTest1686 {useTrusted}...");
+				var ddUpdateTask = instanceClient.DreamDaemon.Update(new DreamDaemonRequest
+				{
+					SecurityLevel = useTrusted ? DreamDaemonSecurity.Trusted : DreamDaemonSecurity.Safe,
+					AdditionalParameters = "expect_chat_channels=1&expect_static_files=1",
+				}, cancellationToken);
+				var currentStatus = await DeployTestDme("long_running_test_rooted", DreamDaemonSecurity.Trusted, true, cancellationToken);
+				await ddUpdateTask;
+
+				Assert.AreEqual(WatchdogStatus.Offline, currentStatus.Status);
+
+				var startJob = await StartDD(cancellationToken);
+
+				await WaitForJob(startJob, 40, false, null, cancellationToken);
+
+				currentStatus = await instanceClient.DreamDaemon.Update(new DreamDaemonRequest
+				{
+					SoftShutdown = true,
+				}, cancellationToken);
+
+				Assert.AreEqual(WatchdogStatus.Online, currentStatus.Status);
+
+				// reimplement TellWorldToReboot because it expects a new deployment and we don't care
+				System.Console.WriteLine("TEST: Hack world reboot topic...");
+				var result = await topicClient.SendTopic(IPAddress.Loopback, "tgs_integration_test_special_tactics=1", ddPort, cancellationToken);
+				Assert.AreEqual("ack", result.StringData);
+
+				using var tempCts = CancellationTokenSource.CreateLinkedTokenSource(cancellationToken);
+				var tempToken = tempCts.Token;
+				using (tempToken.Register(() => System.Console.WriteLine("TEST ERROR: Timeout in RegressionTest1686!")))
+				{
+					tempCts.CancelAfter(TimeSpan.FromMinutes(2));
+
+					do
+					{
+						await Task.Delay(TimeSpan.FromSeconds(1), tempToken);
+						currentStatus = await instanceClient.DreamDaemon.Read(tempToken);
+					}
+					while (currentStatus.Status != WatchdogStatus.Offline);
+				}
+
+				await CheckDMApiFail(currentStatus.ActiveCompileJob, cancellationToken);
+			}
+
+			await RunTest(true);
+
+			if (new PlatformIdentifier().IsWindows || !usingBasicWatchdog)
+				await RunTest(false);
+		}
+
 		async Task InteropTestsForLongRunningDme(CancellationToken cancellationToken)
 		{
+			await RegressionTest1686(cancellationToken);
+
 			await StartAndLeaveRunning(cancellationToken);
 
 			await RegressionTest1550(cancellationToken);
@@ -191,8 +247,7 @@ namespace Tgstation.Server.Tests.Live.Instance
 		async ValueTask RegressionTest1550(CancellationToken cancellationToken)
 		{
 			// we need to cycle deployments twice because TGS holds the initial deployment
-			await DeployTestDme("LongRunning/long_running_test", DreamDaemonSecurity.Trusted, true, cancellationToken);
-			var currentStatus = await instanceClient.DreamDaemon.Read(cancellationToken);
+			var currentStatus = await DeployTestDme("LongRunning/long_running_test", DreamDaemonSecurity.Trusted, true, cancellationToken);
 
 			Assert.AreEqual(WatchdogStatus.Online, currentStatus.Status);
 			Assert.IsNotNull(currentStatus.StagedCompileJob);