diff --git a/test/IntegrationTests/MSTest.VstestConsoleWrapper.IntegrationTests/DeploymentTests.cs b/test/IntegrationTests/MSTest.VstestConsoleWrapper.IntegrationTests/DeploymentTests.cs
index d8e63758fe..a37e8041d6 100644
--- a/test/IntegrationTests/MSTest.VstestConsoleWrapper.IntegrationTests/DeploymentTests.cs
+++ b/test/IntegrationTests/MSTest.VstestConsoleWrapper.IntegrationTests/DeploymentTests.cs
@@ -53,4 +53,16 @@ public void ValidateDirectoryDeployment(string targetFramework)
         InvokeVsTestForExecution(new string[] { TestAssetPreserveNewest }, testCaseFilter: "DirectoryDeploymentTests", targetFramework: targetFramework);
         ValidatePassedTestsContain("DeploymentTestProject.PreserveNewest.DirectoryDeploymentTests.DirectoryWithForwardSlash", "DeploymentTestProject.PreserveNewest.DirectoryDeploymentTests.DirectoryWithBackSlash");
     }
+
+    public void ValidateFileDeployment_net462()
+        => ValidateFileDeployment("net462");
+
+    public void ValidateFileDeployment_netcoreapp31()
+        => ValidateFileDeployment("netcoreapp3.1");
+
+    public void ValidateFileDeployment(string targetFramework)
+    {
+        InvokeVsTestForExecution(new string[] { TestAssetPreserveNewest }, testCaseFilter: "FileDeploymentTests", targetFramework: targetFramework);
+        ValidatePassedTestsContain("DeploymentTestProject.PreserveNewest.FileDeploymentTests.FileWithForwardSlash", "DeploymentTestProject.PreserveNewest.FileDeploymentTests.FileWithBackSlash");
+    }
 }
diff --git a/test/IntegrationTests/TestAssets/DeploymentTestProject.PreserveNewest/FileDeploymentTests.cs b/test/IntegrationTests/TestAssets/DeploymentTestProject.PreserveNewest/FileDeploymentTests.cs
new file mode 100644
index 0000000000..e143dc0c0c
--- /dev/null
+++ b/test/IntegrationTests/TestAssets/DeploymentTestProject.PreserveNewest/FileDeploymentTests.cs
@@ -0,0 +1,27 @@
+// Copyright (c) Microsoft Corporation. All rights reserved.
+// Licensed under the MIT license. See LICENSE file in the project root for full license information.
+
+using System.IO;
+
+using Microsoft.VisualStudio.TestTools.UnitTesting;
+
+namespace DeploymentTestProject.PreserveNewest;
+[TestClass]
+public class FileDeploymentTests
+{
+    [TestMethod]
+    [DeploymentItem(@"TestFiles1/some_file1")]
+    public void FileWithForwardSlash()
+    {
+        var fs = File.Open(@"some_file1", FileMode.Open);
+        fs.Close();
+    }
+
+    [TestMethod]
+    [DeploymentItem(@"TestFiles2\some_file2")]
+    public void FileWithBackSlash()
+    {
+        var fs = File.Open(@"some_file2", FileMode.Open);
+        fs.Close();
+    }
+}