diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/PSUserAgent.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/PSUserAgent.cs
index 7e23c2e5e..4408beae6 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/PSUserAgent.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/PSUserAgent.cs
@@ -4,6 +4,7 @@ Copyright (c) Microsoft Corporation.  All rights reserved.
 
 using System;
 using System.Management.Automation;
+using System.Runtime.InteropServices;
 using System.Globalization;
 
 namespace Microsoft.PowerShell.Commands
@@ -13,6 +14,9 @@ namespace Microsoft.PowerShell.Commands
     /// </summary>
     public static class PSUserAgent
     {
+
+        private static string s_windowsUserAgent;
+
         internal static string UserAgent
         {
             get
@@ -20,7 +24,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "{0} ({1}; {2}; {3}) {4}",
-                    Compatibility, Platform, OS, Culture, App);
+                    Compatibility, PlatformName, OS, Culture, App);
                 return (userAgent);
             }
         }
@@ -35,7 +39,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "{0} (compatible; MSIE 9.0; {1}; {2}; {3})",
-                    Compatibility, Platform, OS, Culture);
+                    Compatibility, PlatformName, OS, Culture);
                 return (userAgent);
             }
         }
@@ -50,7 +54,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "{0} ({1}; {2}; {3}) Gecko/20100401 Firefox/4.0",
-                    Compatibility, Platform, OS, Culture);
+                    Compatibility, PlatformName, OS, Culture);
                 return (userAgent);
             }
         }
@@ -65,7 +69,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "{0} ({1}; {2}; {3}) AppleWebKit/534.6 (KHTML, like Gecko) Chrome/7.0.500.0 Safari/534.6",
-                    Compatibility, Platform, OS, Culture);
+                    Compatibility, PlatformName, OS, Culture);
                 return (userAgent);
             }
         }
@@ -80,7 +84,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "Opera/9.70 ({0}; {1}; {2}) Presto/2.2.1",
-                    Platform, OS, Culture);
+                    PlatformName, OS, Culture);
                 return (userAgent);
             }
         }
@@ -95,7 +99,7 @@ namespace Microsoft.PowerShell.Commands
                 // format the user-agent string from the various component parts
                 string userAgent = string.Format(CultureInfo.InvariantCulture,
                     "{0} ({1}; {2}; {3}) AppleWebKit/533.16 (KHTML, like Gecko) Version/5.0 Safari/533.16",
-                    Compatibility, Platform, OS, Culture);
+                    Compatibility, PlatformName, OS, Culture);
                 return (userAgent);
             }
         }
@@ -118,11 +122,36 @@ namespace Microsoft.PowerShell.Commands
             }
         }
 
-        internal static string Platform
+        internal static string PlatformName
         {
             get
             {
-                return ("Windows NT");
+                if (Platform.IsWindows)
+                {
+                    // only generate the windows user agent once
+                    if(s_windowsUserAgent == null){
+                        // find the version in the windows operating system description
+                        string versionText = OS.Substring(OS.LastIndexOf(" ") +1);
+                        Version windowsPlatformversion = new Version(versionText);
+                        s_windowsUserAgent = $"Windows NT {windowsPlatformversion.Major}.{windowsPlatformversion.Minor}";
+                    }
+
+                    return s_windowsUserAgent;
+                }
+                else if (Platform.IsMacOS)
+                {
+                    return "Macintosh";
+                }
+                else if (Platform.IsLinux)
+                {
+                    return "Linux";
+                }
+                else
+                {
+                    // unknown/unsupported platform
+                    Diagnostics.Assert(false, "Unable to determine Operating System Platform");
+                    return String.Empty;
+                }
             }
         }
 
@@ -130,7 +159,7 @@ namespace Microsoft.PowerShell.Commands
         {
             get
             {
-                return System.Runtime.InteropServices.RuntimeInformation.OSDescription;
+                return RuntimeInformation.OSDescription.Trim();
             }
         }
 
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 6c9999586..a91875f8e 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -453,7 +453,34 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
         $response.Output.Content | Should Not Be $null
     }
 
-    It "Invoke-WebRequest returns User-Agent" {
+    #User-Agent changes on different platforms, so tests should only be run if on the correct platform
+    It "Invoke-WebRequest returns Correct User-Agent on MacOSX" -Skip:(!$IsMacOS) {
+        
+        $uri = Get-WebListenerUrl -Test 'Get'
+        $command = "Invoke-WebRequest -Uri '$uri' -TimeoutSec 5"
+
+        $result = ExecuteWebCommand -command $command
+        ValidateResponse -response $result
+
+        # Validate response content
+        $jsonContent = $result.Output.Content | ConvertFrom-Json
+        $jsonContent.headers.'User-Agent' | Should MatchExactly '.*\(Macintosh;.*\) PowerShell\/\d+\.\d+\.\d+.*'
+    }
+
+    It "Invoke-WebRequest returns Correct User-Agent on Linux" -Skip:(!$IsLinux) {
+        
+        $uri = Get-WebListenerUrl -Test 'Get'
+        $command = "Invoke-WebRequest -Uri '$uri' -TimeoutSec 5"
+
+        $result = ExecuteWebCommand -command $command
+        ValidateResponse -response $result
+
+        # Validate response content
+        $jsonContent = $result.Output.Content | ConvertFrom-Json
+        $jsonContent.headers.'User-Agent' | Should MatchExactly '.*\(Linux;.*\) PowerShell\/\d+\.\d+\.\d+.*'
+    }
+
+    It "Invoke-WebRequest returns Correct User-Agent on Windows" -Skip:(!$IsWindows) {
 
         $uri = Get-WebListenerUrl -Test 'Get'
         $command = "Invoke-WebRequest -Uri '$uri' -TimeoutSec 5"
@@ -463,7 +490,7 @@ Describe "Invoke-WebRequest tests" -Tags "Feature" {
 
         # Validate response content
         $jsonContent = $result.Output.Content | ConvertFrom-Json
-        $jsonContent.headers.'User-Agent' | Should MatchExactly '(?<!Windows)PowerShell\/\d+\.\d+\.\d+.*'
+        $jsonContent.headers.'User-Agent' | Should MatchExactly '.*\(Windows NT \d+\.\d*;.*\) PowerShell\/\d+\.\d+\.\d+.*'
     }
 
     It "Invoke-WebRequest returns headers dictionary" {
@@ -1298,7 +1325,30 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
         $response.PowerShell.Dispose()
     }
 
-    It "Invoke-RestMethod returns User-Agent" {
+    #User-Agent changes on different platforms, so tests should only be run if on the correct platform
+    It "Invoke-RestMethod returns Correct User-Agent on MacOSX" -Skip:(!$IsMacOS) {
+        
+        $uri = Get-WebListenerUrl -Test 'Get'
+        $command = "Invoke-RestMethod -Uri '$uri' -TimeoutSec 5"
+
+        $result = ExecuteWebCommand -command $command
+
+        # Validate response
+        $result.Output.headers.'User-Agent' | Should MatchExactly '.*\(Macintosh;.*\) PowerShell\/\d+\.\d+\.\d+.*'
+    }
+
+    It "Invoke-RestMethod returns Correct User-Agent on Linux" -Skip:(!$IsLinux) {
+        
+        $uri = Get-WebListenerUrl -Test 'Get'
+        $command = "Invoke-RestMethod -Uri '$uri' -TimeoutSec 5"
+
+        $result = ExecuteWebCommand -command $command
+
+        # Validate response
+        $result.Output.headers.'User-Agent' | Should MatchExactly '.*\(Linux;.*\) PowerShell\/\d+\.\d+\.\d+.*'
+    }
+
+    It "Invoke-RestMethod returns Correct User-Agent on Windows" -Skip:(!$IsWindows) {
 
         $uri = Get-WebListenerUrl -Test 'Get'
         $command = "Invoke-RestMethod -Uri '$uri' -TimeoutSec 5"
@@ -1306,7 +1356,7 @@ Describe "Invoke-RestMethod tests" -Tags "Feature" {
         $result = ExecuteWebCommand -command $command
 
         # Validate response
-        $result.Output.headers.'User-Agent' | Should MatchExactly '(?<!Windows)PowerShell\/\d+\.\d+\.\d+.*'
+        $result.Output.headers.'User-Agent' | Should MatchExactly '.*\(Windows NT \d+\.\d*;.*\) PowerShell\/\d+\.\d+\.\d+.*'
     }
 
     It "Invoke-RestMethod returns headers dictionary" {