diff --git a/test/E2ETests/RemoteDeploymentConfig.cs b/test/E2ETests/RemoteDeploymentConfig.cs
index ba33a5ae0d..49465131fd 100644
--- a/test/E2ETests/RemoteDeploymentConfig.cs
+++ b/test/E2ETests/RemoteDeploymentConfig.cs
@@ -2,14 +2,42 @@
 {
     public class RemoteDeploymentConfig
     {
+        /// <summary>
+        /// Name or IP address of the server to deploy to
+        /// </summary>
         public string ServerName { get; set; }
 
+        /// <summary>
+        /// Account name for the credentials required to setup a powershell session to the target server
+        /// </summary>
         public string AccountName { get; set; }
 
+        /// <summary>
+        /// Account password for the credentials required to setup a powershell session to the target server
+        /// </summary>
         public string AccountPassword { get; set; }
 
+        /// <summary>
+        /// The file share on the target server to copy the files to
+        /// </summary>
         public string FileSharePath { get; set; }
 
-        public string ExecutableRelativePath { get; set; }
+        /// <summary>
+        /// Location of the dotnet runtime zip file which is required for testing portable apps.
+        /// When both <see cref="DotnetRuntimeZipFilePath"/> and <see cref="DotnetRuntimeFolderPath"/> properties
+        /// are provided, the <see cref="DotnetRuntimeZipFilePath"/> property is preferred.
+        /// </summary>
+        public string DotnetRuntimeZipFilePath { get; set; }
+
+        /// <summary>
+        /// Location of the dotnet runtime folder which is required for testing portable apps.
+        /// This property is probably more useful for users as they can point their local 'dotnet' runtime folder.
+        /// </summary>
+        public string DotnetRuntimeFolderPath { get; set; }
+
+        /// <summary>
+        /// Path to the parent folder containing 'dotnet.exe' on remote server's file share
+        /// </summary>
+        public string DotnetRuntimePathOnShare { get; set; }
     }
 }
diff --git a/test/E2ETests/SmokeTestsOnNanoServer.cs b/test/E2ETests/SmokeTestsOnNanoServer.cs
index 20221f2c10..d6b8d9b0e3 100644
--- a/test/E2ETests/SmokeTestsOnNanoServer.cs
+++ b/test/E2ETests/SmokeTestsOnNanoServer.cs
@@ -1,6 +1,7 @@
 using System;
 using System.Collections.Generic;
 using System.IO;
+using System.IO.Compression;
 using System.Threading.Tasks;
 using E2ETests.Common;
 using Microsoft.AspNetCore.Server.Testing;
@@ -12,24 +13,55 @@ using Xunit.Abstractions;
 
 namespace E2ETests
 {
-    public class SmokeTestsOnNanoServer : IDisposable
+    public class SmokeTestsOnNanoServerUsingStandaloneRuntime : IDisposable
     {
+        private readonly SmokeTestsOnNanoServer _smokeTestsOnNanoServer;
         private readonly XunitLogger _logger;
         private readonly RemoteDeploymentConfig _remoteDeploymentConfig;
 
-        public SmokeTestsOnNanoServer(ITestOutputHelper output)
+        public SmokeTestsOnNanoServerUsingStandaloneRuntime(ITestOutputHelper output)
         {
             _logger = new XunitLogger(output, LogLevel.Information);
+            _remoteDeploymentConfig = RemoteDeploymentConfigHelper.GetConfiguration();
+            _smokeTestsOnNanoServer = new SmokeTestsOnNanoServer(output, _remoteDeploymentConfig, _logger);
+        }
 
-            var configuration = new ConfigurationBuilder()
-                .SetBasePath(Directory.GetCurrentDirectory())
-                .AddJsonFile("remoteDeploymentConfig.json")
-                .AddUserSecrets()
-                .AddEnvironmentVariables()
-                .Build();
+        [ConditionalTheory, Trait("E2Etests", "NanoServer")]
+        [OSSkipCondition(OperatingSystems.Linux)]
+        [OSSkipCondition(OperatingSystems.MacOSX)]
+        [SkipIfEnvironmentVariableNotEnabled("RUN_TESTS_ON_NANO")]
+        [InlineData(ServerType.Kestrel, 5000, ApplicationType.Standalone)]
+        [InlineData(ServerType.WebListener, 5000, ApplicationType.Standalone)]
+        public async Task Test(ServerType serverType, int portToListen, ApplicationType applicationType)
+        {
+            var applicationBaseUrl = $"http://{_remoteDeploymentConfig.ServerName}:{portToListen}/";
+            await _smokeTestsOnNanoServer.RunTestsAsync(serverType, applicationBaseUrl, applicationType);
+        }
 
-            _remoteDeploymentConfig = new RemoteDeploymentConfig();
-            configuration.GetSection("NanoServer").Bind(_remoteDeploymentConfig);
+        public void Dispose()
+        {
+            _logger.Dispose();
+        }
+    }
+
+    // Tests here test portable app scenario, so we copy the dotnet runtime onto the
+    // target server's file share and after setting up a remote session to the server, we update the PATH environment
+    // to have the path to this copied dotnet runtime folder in the share.
+    // The dotnet runtime is copied only once for all the tests in this class.
+    public class SmokeTestsOnNanoServerUsingSharedRuntime
+        : IClassFixture<SmokeTestsOnNanoServerUsingSharedRuntime.DotnetRuntimeSetupTestFixture>, IDisposable
+    {
+        private readonly SmokeTestsOnNanoServer _smokeTestsOnNanoServer;
+        private readonly RemoteDeploymentConfig _remoteDeploymentConfig;
+        private readonly XunitLogger _logger;
+
+        public SmokeTestsOnNanoServerUsingSharedRuntime(
+            DotnetRuntimeSetupTestFixture dotnetRuntimeSetupTestFixture, ITestOutputHelper output)
+        {
+            _logger = new XunitLogger(output, LogLevel.Information);
+            _remoteDeploymentConfig = RemoteDeploymentConfigHelper.GetConfiguration();
+            _remoteDeploymentConfig.DotnetRuntimePathOnShare = dotnetRuntimeSetupTestFixture.DotnetRuntimePathOnShare;
+            _smokeTestsOnNanoServer = new SmokeTestsOnNanoServer(output, _remoteDeploymentConfig, _logger);
         }
 
         [ConditionalTheory, Trait("E2Etests", "NanoServer")]
@@ -37,21 +69,169 @@ namespace E2ETests
         [OSSkipCondition(OperatingSystems.MacOSX)]
         [SkipIfEnvironmentVariableNotEnabled("RUN_TESTS_ON_NANO")]
         [InlineData(ServerType.Kestrel, 5000, ApplicationType.Portable)]
-        [InlineData(ServerType.Kestrel, 5000, ApplicationType.Standalone)]
         [InlineData(ServerType.WebListener, 5000, ApplicationType.Portable)]
-        [InlineData(ServerType.WebListener, 5000, ApplicationType.Standalone)]
         public async Task Test(ServerType serverType, int portToListen, ApplicationType applicationType)
         {
             var applicationBaseUrl = $"http://{_remoteDeploymentConfig.ServerName}:{portToListen}/";
-            await RunTestsAsync(serverType, applicationBaseUrl, applicationType);
+            await _smokeTestsOnNanoServer.RunTestsAsync(serverType, applicationBaseUrl, applicationType);
         }
 
-        private async Task RunTestsAsync(ServerType serverType, string applicationBaseUrl, ApplicationType applicationType)
+        public void Dispose()
         {
-            using (_logger.BeginScope("SmokeTestSuite"))
+            _logger.Dispose();
+        }
+
+        // Copies dotnet runtime to the target server's file share.
+        public class DotnetRuntimeSetupTestFixture : IDisposable
+        {
+            public DotnetRuntimeSetupTestFixture()
+            {
+                RemoteDeploymentConfig = RemoteDeploymentConfigHelper.GetConfiguration();
+
+                DotnetRuntimePathOnShare = Path.Combine(RemoteDeploymentConfig.FileSharePath, "dotnet");
+
+                // Prefer copying the zip file to fileshare and extracting on file share over copying the extracted
+                // dotnet runtime folder from source to file share as the size could be significantly huge.
+                if (!string.IsNullOrEmpty(RemoteDeploymentConfig.DotnetRuntimeZipFilePath))
+                {
+                    if (!File.Exists(RemoteDeploymentConfig.DotnetRuntimeZipFilePath))
+                    {
+                        throw new InvalidOperationException(
+                           $"Expected dotnet runtime zip file at '{RemoteDeploymentConfig.DotnetRuntimeFolderPath}', but didn't find one.");
+                    }
+
+                    ZippedDotnetRuntimePathOnShare = Path.Combine(
+                        RemoteDeploymentConfig.FileSharePath,
+                        Path.GetFileName(RemoteDeploymentConfig.DotnetRuntimeZipFilePath));
+
+                    if (!File.Exists(ZippedDotnetRuntimePathOnShare))
+                    {
+                        File.Copy(RemoteDeploymentConfig.DotnetRuntimeZipFilePath, ZippedDotnetRuntimePathOnShare, overwrite: true);
+                        Console.WriteLine($"Copied the local dotnet zip folder '{RemoteDeploymentConfig.DotnetRuntimeZipFilePath}' " +
+                            $"to the file share path '{RemoteDeploymentConfig.FileSharePath}'");
+                    }
+
+                    if (Directory.Exists(DotnetRuntimePathOnShare))
+                    {
+                        Directory.Delete(DotnetRuntimePathOnShare, recursive: true);
+                    }
+
+                    ZipFile.ExtractToDirectory(ZippedDotnetRuntimePathOnShare, DotnetRuntimePathOnShare);
+                    Console.WriteLine($"Extracted dotnet runtime to folder '{DotnetRuntimePathOnShare}'");
+                }
+                else if (!string.IsNullOrEmpty(RemoteDeploymentConfig.DotnetRuntimeFolderPath))
+                {
+                    if (!Directory.Exists(RemoteDeploymentConfig.DotnetRuntimeFolderPath))
+                    {
+                        throw new InvalidOperationException(
+                            $"Expected dotnet runtime folder at '{RemoteDeploymentConfig.DotnetRuntimeFolderPath}', but didn't find one.");
+                    }
+
+                    Console.WriteLine($"Copying dotnet runtime folder from '{RemoteDeploymentConfig.DotnetRuntimeFolderPath}' to '{DotnetRuntimePathOnShare}'.");
+                    Console.WriteLine("This could take some time.");
+
+                    DirectoryCopy(RemoteDeploymentConfig.DotnetRuntimeFolderPath, DotnetRuntimePathOnShare, copySubDirs: true);
+                }
+                else
+                {
+                    throw new InvalidOperationException("Dotnet runtime is required to be copied for testing portable apps scenario. " +
+                        $"Either supply '{nameof(RemoteDeploymentConfig.DotnetRuntimeFolderPath)}' containing the unzipped dotnet runtime content or " +
+                        $"supply the dotnet runtime zip file path via '{nameof(RemoteDeploymentConfig.DotnetRuntimeZipFilePath)}'.");
+                }
+            }
+
+            public RemoteDeploymentConfig RemoteDeploymentConfig { get; }
+
+            public string ZippedDotnetRuntimePathOnShare { get; }
+
+            public string DotnetRuntimePathOnShare { get; }
+
+            private static void DirectoryCopy(string sourceDirName, string destDirName, bool copySubDirs)
+            {
+                var dir = new DirectoryInfo(sourceDirName);
+
+                if (!dir.Exists)
+                {
+                    throw new DirectoryNotFoundException(
+                        "Source directory does not exist or could not be found: "
+                        + sourceDirName);
+                }
+
+                var dirs = dir.GetDirectories();
+                if (!Directory.Exists(destDirName))
+                {
+                    Directory.CreateDirectory(destDirName);
+                }
+
+                var files = dir.GetFiles();
+                foreach (var file in files)
+                {
+                    var temppath = Path.Combine(destDirName, file.Name);
+                    file.CopyTo(temppath, false);
+                }
+
+                if (copySubDirs)
+                {
+                    foreach (var subdir in dirs)
+                    {
+                        var temppath = Path.Combine(destDirName, subdir.Name);
+                        DirectoryCopy(subdir.FullName, temppath, copySubDirs);
+                    }
+                }
+            }
+
+            public void Dispose()
+            {
+                // In case the source is provided as a folder itself, then we wouldn't have the zip file to begin with.
+                if (!string.IsNullOrEmpty(ZippedDotnetRuntimePathOnShare))
+                {
+                    try
+                    {
+                        Console.WriteLine($"Deleting the dotnet runtime zip file '{ZippedDotnetRuntimePathOnShare}'");
+                        File.Delete(ZippedDotnetRuntimePathOnShare);
+                    }
+                    catch (Exception ex)
+                    {
+                        Console.WriteLine($"Failed to delete the dotnet runtime zip file '{ZippedDotnetRuntimePathOnShare}'. Exception: "
+                            + ex.ToString());
+                    }
+                }
+
+                try
+                {
+                    Console.WriteLine($"Deleting the dotnet runtime folder '{DotnetRuntimePathOnShare}'");
+                    Directory.Delete(DotnetRuntimePathOnShare, recursive: true);
+                }
+                catch (Exception ex)
+                {
+                    Console.WriteLine($"Failed to delete the dotnet runtime folder '{DotnetRuntimePathOnShare}'. Exception: "
+                        + ex.ToString());
+                }
+            }
+        }
+    }
+
+    class SmokeTestsOnNanoServer
+    {
+        private readonly XunitLogger _logger;
+        private readonly RemoteDeploymentConfig _remoteDeploymentConfig;
+
+        public SmokeTestsOnNanoServer(ITestOutputHelper output, RemoteDeploymentConfig config, XunitLogger logger)
+        {
+            _logger = logger;
+            _remoteDeploymentConfig = config;
+        }
+
+        public async Task RunTestsAsync(
+            ServerType serverType,
+            string applicationBaseUrl,
+            ApplicationType applicationType)
+        {
+            using (_logger.BeginScope(nameof(SmokeTestsOnNanoServerUsingStandaloneRuntime)))
             {
                 var deploymentParameters = new RemoteWindowsDeploymentParameters(
                     Helpers.GetApplicationPath(applicationType),
+                    _remoteDeploymentConfig.DotnetRuntimePathOnShare,
                     serverType,
                     RuntimeFlavor.CoreClr,
                     RuntimeArchitecture.x64,
@@ -75,10 +255,28 @@ namespace E2ETests
                 }
             }
         }
+    }
 
-        public void Dispose()
+    static class RemoteDeploymentConfigHelper
+    {
+        private static RemoteDeploymentConfig _remoteDeploymentConfig;
+
+        public static RemoteDeploymentConfig GetConfiguration()
         {
-            _logger.Dispose();
+            if (_remoteDeploymentConfig == null)
+            {
+                var configuration = new ConfigurationBuilder()
+                        .SetBasePath(Directory.GetCurrentDirectory())
+                        .AddJsonFile("remoteDeploymentConfig.json")
+                        .AddUserSecrets()
+                        .AddEnvironmentVariables()
+                        .Build();
+
+                _remoteDeploymentConfig = new RemoteDeploymentConfig();
+                configuration.GetSection("NanoServer").Bind(_remoteDeploymentConfig);
+            }
+
+            return _remoteDeploymentConfig;
         }
     }
 }
diff --git a/test/E2ETests/remoteDeploymentConfig.json b/test/E2ETests/remoteDeploymentConfig.json
index 3bdc799e85..1d2a55f1d1 100644
--- a/test/E2ETests/remoteDeploymentConfig.json
+++ b/test/E2ETests/remoteDeploymentConfig.json
@@ -4,6 +4,7 @@
     "AccountName": "",
     "AccountPassword": "",
     "FileSharePath": "",
-    "ExecutableRelativePath": ""
+    "DotnetRuntimeFolderPath": "",
+    "DotnetRuntimeZipFilePath": ""
   }
 }