diff --git a/.spelling b/.spelling
index d23ed693e1..0b7489bf02 100644
--- a/.spelling
+++ b/.spelling
@@ -67,6 +67,7 @@ macOS
 Microsoft.PowerShell.Archive
 MS-PSRP
 myget
+Multipart
 New-PSSessionOption
 New-PSTransportOption
 NuGet
diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
index 750afa12c8..a730b464ee 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebRequestPSCmdlet.CoreClr.cs
@@ -389,6 +389,11 @@ namespace Microsoft.PowerShell.Commands
                     byte[] bytes = content as byte[];
                     SetRequestContent(request, bytes);
                 }
+                else if (content is MultipartFormDataContent multipartFormDataContent)
+                {
+                    WebSession.ContentHeaders.Clear();
+                    SetRequestContent(request, multipartFormDataContent);
+                }
                 else
                 {
                     SetRequestContent(request,
@@ -787,6 +792,32 @@ namespace Microsoft.PowerShell.Commands
             return streamContent.Headers.ContentLength.Value;
         }
 
+        /// <summary>
+        /// Sets the ContentLength property of the request and writes the specified content to the request's RequestStream.
+        /// </summary>
+        /// <param name="request">The WebRequest who's content is to be set</param>
+        /// <param name="multipartContent">A MultipartFormDataContent object containing multipart/form-data content.</param>
+        /// <returns>The number of bytes written to the requests RequestStream (and the new value of the request's ContentLength property</returns>
+        /// <remarks>
+        /// Because this function sets the request's ContentLength property and writes content data into the requests's stream,
+        /// it should be called one time maximum on a given request.
+        /// </remarks>
+        internal long SetRequestContent(HttpRequestMessage request, MultipartFormDataContent multipartContent)
+        {
+            if (request == null)
+            {
+                throw new ArgumentNullException("request");
+            }
+            if (multipartContent == null)
+            {
+                throw new ArgumentNullException("multipartContent");
+            }
+
+            request.Content = multipartContent;
+
+            return multipartContent.Headers.ContentLength.Value;
+        }
+
         internal long SetRequestContent(HttpRequestMessage request, IDictionary content)
         {
             if (request == null)
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 9ba437edb9..efc0007a0b 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -359,6 +359,39 @@ function ExecuteRestMethod
     return $result
 }
 
+function GetMultipartBody 
+{
+    param
+    (
+        [Switch]$String,
+        [Switch]$File
+    )
+    $multipartContent = [System.Net.Http.MultipartFormDataContent]::new()
+    if ($String.IsPresent)
+    {
+        $stringHeader = [System.Net.Http.Headers.ContentDispositionHeaderValue]::new("form-data")
+        $stringHeader.Name = "TestString"
+        $StringContent = [System.Net.Http.StringContent]::new("TestValue")
+        $StringContent.Headers.ContentDisposition = $stringHeader
+        $multipartContent.Add($stringContent)
+    }
+    if ($File.IsPresent)
+    {
+        $multipartFile = Join-Path $TestDrive 'multipart.txt'
+        "TestContent" | Set-Content $multipartFile
+        $FileStream = [System.IO.FileStream]::new($multipartFile, [System.IO.FileMode]::Open)
+        $fileHeader = [System.Net.Http.Headers.ContentDispositionHeaderValue]::new("form-data")
+        $fileHeader.Name = "TestFile"
+        $fileHeader.FileName = 'multipart.txt'
+        $fileContent = [System.Net.Http.StreamContent]::new($FileStream)
+        $fileContent.Headers.ContentDisposition = $fileHeader
+        $fileContent.Headers.ContentType = [System.Net.Http.Headers.MediaTypeHeaderValue]::Parse("text/plain")
+        $multipartContent.Add($fileContent)
+    }
+    # unary comma required to prevent $multipartContent from being unwrapped/enumerated
+    return ,$multipartContent 
+}
+
 <#
     Defines the list of redirect codes to test as well as the
     expected Method when the redirection is handled.
@@ -1200,6 +1233,41 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
         }
     }
 
+    Context "Multipart/form-data Tests" {
+        It "Verifies Invoke-WebRequest Supports Multipart String Values" {
+            $body = GetMultipartBody -String
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $response = Invoke-WebRequest -Uri $uri -Body $body -Method 'POST'
+            $result = $response.Content | ConvertFrom-Json
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Items.TestString[0] | Should Be 'TestValue'
+        }
+        It "Verifies Invoke-WebRequest Supports Multipart File Values" {
+            $body = GetMultipartBody -File
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $response = Invoke-WebRequest -Uri $uri -Body $body -Method 'POST'
+            $result = $response.Content | ConvertFrom-Json
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Files[0].FileName | Should Be 'multipart.txt'
+            $result.Files[0].ContentType | Should Be 'text/plain'
+            $result.Files[0].Content | Should Match 'TestContent'
+        }
+        It "Verifies Invoke-WebRequest Supports Mixed Multipart String and File Values" {
+            $body = GetMultipartBody -String -File
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $response = Invoke-WebRequest -Uri $uri -Body $body -Method 'POST'
+            $result = $response.Content | ConvertFrom-Json
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Items.TestString[0] | Should Be 'TestValue'
+            $result.Files[0].FileName | Should Be 'multipart.txt'
+            $result.Files[0].ContentType | Should Be 'text/plain'
+            $result.Files[0].Content | Should Match 'TestContent'
+        }
+    }
+
     BeforeEach {
         if ($env:http_proxy) {
             $savedHttpProxy = $env:http_proxy
@@ -1737,6 +1805,38 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
         }
     }
 
+    Context "Multipart/form-data Tests" {
+        It "Verifies Invoke-RestMethod Supports Multipart String Values" {
+            $body = GetMultipartBody -String
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $result = Invoke-RestMethod -Uri $uri -Body $body -Method 'POST'
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Items.TestString[0] | Should Be 'TestValue'
+        }
+        It "Verifies Invoke-RestMethod Supports Multipart File Values" {
+            $body = GetMultipartBody -File
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $result = Invoke-RestMethod -Uri $uri -Body $body -Method 'POST'
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Files[0].FileName | Should Be 'multipart.txt'
+            $result.Files[0].ContentType | Should Be 'text/plain'
+            $result.Files[0].Content | Should Match 'TestContent'
+        }
+        It "Verifies Invoke-RestMethod Supports Mixed Multipart String and File Values" {
+            $body = GetMultipartBody -String -File
+            $uri = Get-WebListenerUrl -Test 'Multipart'
+            $result = Invoke-RestMethod -Uri $uri -Body $body -Method 'POST'
+
+            $result.Headers.'Content-Type' | Should Match 'multipart/form-data'
+            $result.Items.TestString[0] | Should Be 'TestValue'
+            $result.Files[0].FileName | Should Be 'multipart.txt'
+            $result.Files[0].ContentType | Should Be 'text/plain'
+            $result.Files[0].Content | Should Match 'TestContent'
+        }
+    }
+
     #region charset encoding tests
 
     Context  "Invoke-RestMethod Encoding tests with BasicHtmlWebResponseObject response" {
diff --git a/test/tools/Modules/WebListener/WebListener.psm1 b/test/tools/Modules/WebListener/WebListener.psm1
index 09f8b6836a..9e84396235 100644
--- a/test/tools/Modules/WebListener/WebListener.psm1
+++ b/test/tools/Modules/WebListener/WebListener.psm1
@@ -116,6 +116,7 @@ function Get-WebListenerUrl {
             'Cert',
             'Get',
             'Home',
+            'Multipart',
             '/'
         )]
         [String]$Test
diff --git a/test/tools/WebListener/Controllers/MultipartController.cs b/test/tools/WebListener/Controllers/MultipartController.cs
new file mode 100644
index 0000000000..c56c6e68c9
--- /dev/null
+++ b/test/tools/WebListener/Controllers/MultipartController.cs
@@ -0,0 +1,89 @@
+using System;
+using System.Collections;
+using System.Collections.Generic;
+using System.Diagnostics;
+using System.IO;
+using System.Linq;
+using System.Threading.Tasks;
+using Microsoft.AspNetCore.Hosting;
+using Microsoft.AspNetCore.Http;
+using Microsoft.AspNetCore.Mvc;
+using Microsoft.Net.Http.Headers;
+using mvc.Models;
+
+
+namespace mvc.Controllers
+{
+    public class MultipartController : Controller
+    {
+        private IHostingEnvironment _environment;
+
+        public MultipartController(IHostingEnvironment environment)
+        {
+            _environment = environment;
+        }
+        public ActionResult Index()
+        {   
+            return View();
+        }
+
+        [HttpPost]
+        public JsonResult Index(IFormCollection collection)
+        {
+            if (!Request.HasFormContentType)
+            {
+                Response.StatusCode = 415;
+                Hashtable error = new Hashtable {{"error","Unsupported media type"}};
+                return  Json(error);
+            }
+
+            List<Hashtable> fileList = new List<Hashtable>();
+            foreach (var file in collection.Files)
+            {
+                string result = string.Empty;
+                if (file.Length > 0)
+                {
+                    using (var reader = new StreamReader(file.OpenReadStream()))
+                    {
+                        result = reader.ReadToEnd();
+                    }
+                }
+                Hashtable fileHash = new Hashtable
+                {
+                    {"ContentDisposition" , file.ContentDisposition},
+                    {"ContentType"        , file.ContentType},
+                    {"FileName"           , file.FileName},
+                    {"Length"             , file.Length},
+                    {"Name"               , file.Name},
+                    {"Content"            , result},
+                    {"Headers"            , file.Headers}
+                };
+                fileList.Add(fileHash);
+            }
+            Hashtable itemsHash = new Hashtable();
+            foreach (var key in collection.Keys)
+            {
+                itemsHash.Add(key,collection[key]);
+            }
+            MediaTypeHeaderValue mediaContentType = MediaTypeHeaderValue.Parse(Request.ContentType);
+            Hashtable headers = new Hashtable();
+            foreach (var key in Request.Headers.Keys)
+            {
+                headers.Add(key, String.Join(Constants.HeaderSeparator, Request.Headers[key]));
+            }
+            Hashtable output = new Hashtable
+            {
+                {"Files"   , fileList},
+                {"Items"   , itemsHash},
+                {"Boundary", HeaderUtilities.RemoveQuotes(mediaContentType.Boundary).Value},
+                {"Headers" , headers}
+            };
+            return Json(output);
+        }
+
+        public IActionResult Error()
+        {
+            return View(new ErrorViewModel { RequestId = Activity.Current?.Id ?? HttpContext.TraceIdentifier });
+        }
+    }
+}
diff --git a/test/tools/WebListener/README.md b/test/tools/WebListener/README.md
index 9db5f8dc07..edf9bc1872 100644
--- a/test/tools/WebListener/README.md
+++ b/test/tools/WebListener/README.md
@@ -82,3 +82,47 @@ Invoke-WebRequest -Uri 'http://localhost:8083/Get/' -Body @{TestField = 'TestVal
   "origin": "127.0.0.1"
 }
 ```
+
+## /Multipart/
+
+### GET 
+Provides an HTML form for `multipart/form-data` submission.
+
+### POST
+Accepts a `multipart/form-data` submission and returns a JSON object containing information about the submission including the items and files submitted.
+
+```json
+{
+  "Files": [
+    {
+      "ContentDisposition": "form-data; name=fileData; filename=test.txt",
+      "Headers": {
+        "Content-Disposition": [
+          "form-data; name=fileData; filename=test.txt"
+        ],
+        "Content-Type": [
+          "text/plain"
+        ]
+      },
+      "FileName": "test.txt",
+      "Length": 15,
+      "ContentType": "text/plain",
+      "Name": "fileData",
+      "Content": "Test Contents\r\n"
+    }
+  ],
+  "Items": {
+    "stringData": [
+      "TestValue"
+    ]
+  },
+  "Boundary": "83027bde-fd9b-4ea0-b1ca-a1f661d01ada",
+  "Headers": {
+    "Content-Type": "multipart/form-data; boundary=\"83027bde-fd9b-4ea0-b1ca-a1f661d01ada\"",
+    "Connection": "Keep-Alive",
+    "Content-Length": "336",
+    "Host": "localhost:8083",
+    "User-Agent": "Mozilla/5.0 (Windows NT; Microsoft Windows 10.0.15063 ; en-US) WindowsPowerShell/6.0.0"
+  }
+}
+```
diff --git a/test/tools/WebListener/Views/Home/Index.cshtml b/test/tools/WebListener/Views/Home/Index.cshtml
index 667c251276..3a13c61471 100644
--- a/test/tools/WebListener/Views/Home/Index.cshtml
+++ b/test/tools/WebListener/Views/Home/Index.cshtml
@@ -3,4 +3,5 @@
     <li><a href="/">/</a> - This page</li>
     <li><a href="/Cert/">/Cert/</a> - Client Certificate Details</li>
     <li><a href="/Get/">/Get/</a> - Emulates functionality of https://httpbin.org/get by returning GET headers, Arguments, and Request URL</li>
+    <li><a href="/Multipart/">/Multipart/</a> - Multipart/form-data submission testing</li>
 </ul>
diff --git a/test/tools/WebListener/Views/Multipart/Index.cshtml b/test/tools/WebListener/Views/Multipart/Index.cshtml
new file mode 100644
index 0000000000..01c6f69016
--- /dev/null
+++ b/test/tools/WebListener/Views/Multipart/Index.cshtml
@@ -0,0 +1,13 @@
+<form name="MultipartForm" method="post" enctype="multipart/form-data">
+    <div>
+        <label for="TextBox">TextBox text field</label>
+        <input name="TextBox" type="text" />
+    </div>
+    <div>
+        <label for="TextFile">TextFile file field</label>
+        <input name="TextFile" type="file" />
+    </div>
+    <div>
+        <input type="submit" value="Submit" />
+    </div>
+</form>