diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
index de26f49c75..acf8135f73 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/Common/WebRequestPSCmdlet.Common.cs
@@ -88,7 +88,7 @@ namespace Microsoft.PowerShell.Commands
     /// <summary>
     /// Base class for Invoke-RestMethod and Invoke-WebRequest commands.
     /// </summary>
-    public abstract class WebRequestPSCmdlet : PSCmdlet
+    public abstract class WebRequestPSCmdlet : PSCmdlet, IDisposable
     {
         #region Fields
 
@@ -132,6 +132,11 @@ namespace Microsoft.PowerShell.Commands
         /// </summary>
         private bool _resumeSuccess = false;
 
+        /// <summary>
+        /// True if the Dispose() method has already been called to cleanup Disposable fields.
+        /// </summary>
+        private bool _disposed = false;
+
         #endregion Fields
 
         #region Virtual Properties
@@ -522,7 +527,7 @@ namespace Microsoft.PowerShell.Commands
 
                 bool handleRedirect = keepAuthorizationOnRedirect || AllowInsecureRedirect || PreserveHttpMethodOnRedirect;
 
-                using HttpClient client = GetHttpClient(handleRedirect);
+                HttpClient client = GetHttpClient(handleRedirect);
 
                 int followedRelLink = 0;
                 Uri uri = Uri;
@@ -639,7 +644,7 @@ namespace Microsoft.PowerShell.Commands
                             // Errors with redirection counts of greater than 0 are handled automatically by .NET, but are
                             // impossible to detect programmatically when we hit this limit. By handling this ourselves
                             // (and still writing out the result), users can debug actual HTTP redirect problems.
-                            if (WebSession.MaximumRedirection == 0 && IsRedirectCode(response.StatusCode))
+                            if (_maximumRedirection == 0 && IsRedirectCode(response.StatusCode))
                             {
                                 ErrorRecord er = new(new InvalidOperationException(), "MaximumRedirectExceeded", ErrorCategory.InvalidOperation, request);
                                 er.ErrorDetails = new ErrorDetails(WebCmdletStrings.MaximumRedirectionCountExceeded);
@@ -688,6 +693,33 @@ namespace Microsoft.PowerShell.Commands
         /// </summary>
         protected override void StopProcessing() => _cancelToken?.Cancel();
 
+        /// <summary>
+        /// Disposes the associated WebSession if it is not being used as part of a persistent session.
+        /// </summary> 
+        /// <param name="disposing">True when called from Dispose() and false when called from finalizer.</param>
+        protected virtual void Dispose(bool disposing)
+        {
+            if (!_disposed)
+            {
+                if (disposing && !IsPersistentSession())
+                {
+                    WebSession?.Dispose();
+                    WebSession = null;
+                }
+
+                _disposed = true;
+            }
+        }
+
+        /// <summary>
+        /// Disposes the associated WebSession if it is not being used as part of a persistent session.
+        /// </summary> 
+        public void Dispose()
+        {
+            Dispose(disposing: true);
+            GC.SuppressFinalize(this);
+        }
+
         #endregion Overrides
 
         #region Virtual Methods
@@ -900,20 +932,41 @@ namespace Microsoft.PowerShell.Commands
                 WebSession.UserAgent = UserAgent;
             }
 
-            if (Proxy is not null)
+            // Proxy and NoProxy parameters are mutually exclusive.
+            // If NoProxy is provided, WebSession will turn off the proxy
+            // and if Proxy is provided NoProxy will be turned off.
+            if (NoProxy.IsPresent)
             {
-                WebProxy webProxy = new(Proxy);
-                webProxy.BypassProxyOnLocal = false;
-                if (ProxyCredential is not null)
+                WebSession.NoProxy = true;
+            }
+            else
+            {
+                if (Proxy is not null)
                 {
-                    webProxy.Credentials = ProxyCredential.GetNetworkCredential();
-                }
-                else
-                {
-                    webProxy.UseDefaultCredentials = ProxyUseDefaultCredentials;
-                }
+                    WebProxy webProxy = new(Proxy);
+                    webProxy.BypassProxyOnLocal = false;
+                    if (ProxyCredential is not null)
+                    {
+                        webProxy.Credentials = ProxyCredential.GetNetworkCredential();
+                    }
+                    else
+                    {
+                        webProxy.UseDefaultCredentials =  ProxyUseDefaultCredentials;
+                    }
 
-                WebSession.Proxy = webProxy;
+                    // We don't want to update the WebSession unless the proxies are different
+                    // as that will require us to create a new HttpClientHandler and lose connection
+                    // persistence.
+                    if (!webProxy.Equals(WebSession.Proxy))
+                    {
+                        WebSession.Proxy = webProxy;
+                    }
+                }
+            }
+
+            if (MyInvocation.BoundParameters.ContainsKey(nameof(SslProtocol)))
+            {
+                WebSession.SslProtocol = SslProtocol;
             }
 
             if (MaximumRedirection > -1)
@@ -921,6 +974,8 @@ namespace Microsoft.PowerShell.Commands
                 WebSession.MaximumRedirection = MaximumRedirection;
             }
 
+            WebSession.SkipCertificateCheck = SkipCertificateCheck.IsPresent;
+
             // Store the other supplied headers
             if (Headers is not null)
             {
@@ -945,63 +1000,20 @@ namespace Microsoft.PowerShell.Commands
                 // Only set retry interval if retry count is set.
                 WebSession.RetryIntervalInSeconds = RetryIntervalSec;
             }
+
+            WebSession.TimeoutSec = TimeoutSec;
         }
 
         internal virtual HttpClient GetHttpClient(bool handleRedirect)
         {
-            HttpClientHandler handler = new();
-            handler.CookieContainer = WebSession.Cookies;
-            handler.AutomaticDecompression = DecompressionMethods.All;
+            HttpClient client = WebSession.GetHttpClient(handleRedirect, out bool clientWasReset);
 
-            // Set the credentials used by this request
-            if (WebSession.UseDefaultCredentials)
+            if (clientWasReset)
             {
-                // The UseDefaultCredentials flag overrides other supplied credentials
-                handler.UseDefaultCredentials = true;
-            }
-            else if (WebSession.Credentials is not null)
-            {
-                handler.Credentials = WebSession.Credentials;
+                WriteVerbose(WebCmdletStrings.WebSessionConnectionRecreated);
             }
 
-            if (NoProxy)
-            {
-                handler.UseProxy = false;
-            }
-            else if (WebSession.Proxy is not null)
-            {
-                handler.Proxy = WebSession.Proxy;
-            }
-
-            if (WebSession.Certificates is not null)
-            {
-                handler.ClientCertificates.AddRange(WebSession.Certificates);
-            }
-
-            if (SkipCertificateCheck)
-            {
-                handler.ServerCertificateCustomValidationCallback = HttpClientHandler.DangerousAcceptAnyServerCertificateValidator;
-                handler.ClientCertificateOptions = ClientCertificateOption.Manual;
-            }
-
-            // This indicates GetResponse will handle redirects.
-            if (handleRedirect || WebSession.MaximumRedirection == 0)
-            {
-                handler.AllowAutoRedirect = false;
-            }
-            else if (WebSession.MaximumRedirection > 0)
-            {
-                handler.MaxAutomaticRedirections = WebSession.MaximumRedirection;
-            }
-
-            handler.SslProtocols = (SslProtocols)SslProtocol;
-
-            HttpClient httpClient = new(handler);
-
-            // Check timeout setting (in seconds instead of milliseconds as in HttpWebRequest)
-            httpClient.Timeout = TimeoutSec is 0 ? TimeSpan.FromMilliseconds(Timeout.Infinite) : new TimeSpan(0, 0, TimeoutSec);
-
-            return httpClient;
+            return client;
         }
 
         internal virtual HttpRequestMessage GetRequest(Uri uri)
@@ -1459,6 +1471,8 @@ namespace Microsoft.PowerShell.Commands
             }
         }
 
+        private bool IsPersistentSession() => MyInvocation.BoundParameters.ContainsKey(nameof(WebSession)) || MyInvocation.BoundParameters.ContainsKey(nameof(SessionVariable));
+
         /// <summary>
         /// Sets the ContentLength property of the request and writes the specified content to the request's RequestStream.
         /// </summary>
@@ -1686,7 +1700,7 @@ namespace Microsoft.PowerShell.Commands
         private static StringContent GetMultipartStringContent(object fieldName, object fieldValue)
         {
             ContentDispositionHeaderValue contentDisposition = new("form-data");
-            
+
             // .NET does not enclose field names in quotes, however, modern browsers and curl do.
             contentDisposition.Name = "\"" + LanguagePrimitives.ConvertTo<string>(fieldName) + "\"";
 
@@ -1773,7 +1787,7 @@ namespace Microsoft.PowerShell.Commands
             {
                 // Ignore errors
             }
-            
+
             if (string.IsNullOrEmpty(formattedError))
             {
                 // Remove HTML tags making it easier to read
diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
index 0f46827bd6..6890599b51 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/CoreCLR/WebProxy.cs
@@ -6,7 +6,7 @@ using System.Net;
 
 namespace Microsoft.PowerShell.Commands
 {
-    internal class WebProxy : IWebProxy
+    internal class WebProxy : IWebProxy, IEquatable<WebProxy>
     {
         private ICredentials _credentials;
         private readonly Uri _proxyAddress;
@@ -18,6 +18,23 @@ namespace Microsoft.PowerShell.Commands
             _proxyAddress = address;
         }
 
+        public override bool Equals(object obj) => Equals(obj as WebProxy);
+
+        public override int GetHashCode() => HashCode.Combine(_proxyAddress, _credentials, BypassProxyOnLocal);
+
+        public bool Equals(WebProxy other)
+        {
+            if (other is null)
+            {
+                return false;
+            }
+
+            // _proxyAddress cannot be null as it is set in the constructor            
+            return other._credentials == _credentials
+                && _proxyAddress.Equals(other._proxyAddress)
+                && BypassProxyOnLocal == other.BypassProxyOnLocal;
+        }
+
         public ICredentials Credentials
         {
             get => _credentials;
diff --git a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/WebRequestSession.cs b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/WebRequestSession.cs
index c100f345a7..4e58503659 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/WebRequestSession.cs
+++ b/src/Microsoft.PowerShell.Commands.Utility/commands/utility/WebCmdlet/WebRequestSession.cs
@@ -4,15 +4,37 @@
 using System;
 using System.Collections.Generic;
 using System.Net;
+using System.Net.Http;
+using System.Security.Authentication;
 using System.Security.Cryptography.X509Certificates;
+using System.Threading;
 
 namespace Microsoft.PowerShell.Commands
 {
     /// <summary>
     /// WebRequestSession for holding session infos.
     /// </summary>
-    public class WebRequestSession
+    public class WebRequestSession : IDisposable
     {
+        private HttpClient _client;
+        private CookieContainer _cookies;
+        private bool _useDefaultCredentials;
+        private ICredentials _credentials;
+        private X509CertificateCollection _certificates;
+        private IWebProxy _proxy;
+        private int _maximumRedirection;
+        private WebSslProtocol _sslProtocol;
+        private bool _allowAutoRedirect;
+        private bool _skipCertificateCheck;
+        private bool _noProxy;
+        private bool _disposed;
+        private int _timeoutSec;
+
+        /// <summary>
+        /// Contains true if an existing HttpClient had to be disposed and recreated since the WebSession was last used.
+        /// </summary>
+        private bool _disposedClient;
+
         /// <summary>
         /// Gets or sets the Header property.
         /// </summary>
@@ -27,25 +49,25 @@ namespace Microsoft.PowerShell.Commands
         /// <summary>
         /// Gets or sets the Cookies property.
         /// </summary>
-        public CookieContainer Cookies { get; set; }
+        public CookieContainer Cookies { get => _cookies; set => SetClassVar(ref _cookies, value); }
 
         #region Credentials
 
         /// <summary>
         /// Gets or sets the UseDefaultCredentials property.
         /// </summary>
-        public bool UseDefaultCredentials { get; set; }
+        public bool UseDefaultCredentials { get => _useDefaultCredentials; set => SetStructVar(ref _useDefaultCredentials, value); }
 
         /// <summary>
         /// Gets or sets the Credentials property.
         /// </summary>
-        public ICredentials Credentials { get; set; }
+        public ICredentials Credentials { get => _credentials; set => SetClassVar(ref _credentials, value); }
 
         /// <summary>
         /// Gets or sets the Certificates property.
         /// </summary>
         [System.Diagnostics.CodeAnalysis.SuppressMessage("Microsoft.Usage", "CA2227:CollectionPropertiesShouldBeReadOnly")]
-        public X509CertificateCollection Certificates { get; set; }
+        public X509CertificateCollection Certificates { get => _certificates; set => SetClassVar(ref _certificates, value); }
 
         #endregion
 
@@ -57,12 +79,23 @@ namespace Microsoft.PowerShell.Commands
         /// <summary>
         /// Gets or sets the Proxy property.
         /// </summary>
-        public IWebProxy Proxy { get; set; }
+        public IWebProxy Proxy
+        {
+            get => _proxy;
+            set
+            {
+                SetClassVar(ref _proxy, value);
+                if (_proxy is not null)
+                {
+                    NoProxy = false;
+                }
+            }
+        }
 
         /// <summary>
-        /// Gets or sets the RedirectMax property.
+        /// Gets or sets the MaximumRedirection property.
         /// </summary>
-        public int MaximumRedirection { get; set; }
+        public int MaximumRedirection { get => _maximumRedirection; set => SetStructVar(ref _maximumRedirection, value); }
 
         /// <summary>
         /// Gets or sets the count of retries for request failures.
@@ -79,23 +112,42 @@ namespace Microsoft.PowerShell.Commands
         /// </summary>
         public WebRequestSession()
         {
-            // build the headers collection
+            // Build the headers collection
             Headers = new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
             ContentHeaders = new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
 
-            // build the cookie jar
-            Cookies = new CookieContainer();
+            // Build the cookie jar
+            _cookies = new CookieContainer();
 
-            // initialize the credential and certificate caches
-            UseDefaultCredentials = false;
-            Credentials = null;
-            Certificates = null;
+            // Initialize the credential and certificate caches
+            _useDefaultCredentials = false;
+            _credentials = null;
+            _certificates = null;
 
-            // setup the default UserAgent
+            // Setup the default UserAgent
             UserAgent = PSUserAgent.UserAgent;
 
-            Proxy = null;
-            MaximumRedirection = -1;
+            _proxy = null;
+            _maximumRedirection = -1;
+            _allowAutoRedirect = true;
+        }
+
+        internal WebSslProtocol SslProtocol { set => SetStructVar(ref _sslProtocol, value); }
+
+        internal bool SkipCertificateCheck { set => SetStructVar(ref _skipCertificateCheck, value); }
+
+        internal int TimeoutSec { set => SetStructVar(ref _timeoutSec, value); }
+
+        internal bool NoProxy
+        {
+            set
+            {
+                SetStructVar(ref _noProxy, value);
+                if (_noProxy)
+                {
+                    Proxy = null;
+                }
+            }
         }
 
         /// <summary>
@@ -105,8 +157,139 @@ namespace Microsoft.PowerShell.Commands
         internal void AddCertificate(X509Certificate certificate)
         {
             Certificates ??= new X509CertificateCollection();
+            if (!Certificates.Contains(certificate))
+            {
+                ResetClient();
+                Certificates.Add(certificate);
+            }
+        }
 
-            Certificates.Add(certificate);
+        /// <summary>
+        /// Gets an existing or creates a new HttpClient for this WebRequest session if none currently exists (either because it was never
+        /// created, or because changes to the WebSession properties required the existing HttpClient to be disposed).
+        /// </summary>
+        /// <param name="suppressHttpClientRedirects">True if the caller does not want the HttpClient to ever handle redirections automatically.</param>
+        /// <param name="clientWasReset">Contains true if an existing HttpClient had to be disposed and recreated since the WebSession was last used.</param>
+        /// <returns>The HttpClient cached in the WebSession, based on all current settings.</returns>
+        internal HttpClient GetHttpClient(bool suppressHttpClientRedirects, out bool clientWasReset)
+        {
+            // Do not auto redirect if the the caller does not want it, or maximum redirections is 0
+            SetStructVar(ref _allowAutoRedirect, !(suppressHttpClientRedirects || MaximumRedirection == 0));
+
+            clientWasReset = _disposedClient;
+
+            if (_client is null)
+            {
+                _client = CreateHttpClient();
+                _disposedClient = false;
+            }
+
+            return _client;
+        }
+
+        private HttpClient CreateHttpClient()
+        {
+            HttpClientHandler handler = new();
+
+            handler.CookieContainer = Cookies;
+            handler.AutomaticDecompression = DecompressionMethods.All;
+
+            if (Credentials is not null)
+            {
+                handler.Credentials = Credentials;
+            }
+            else
+            {
+                handler.UseDefaultCredentials = UseDefaultCredentials;
+            }
+
+            if (_noProxy)
+            {
+                handler.UseProxy = false;
+            }
+            else if (Proxy is not null)
+            {
+                handler.Proxy = Proxy;
+            }
+
+            if (Certificates is not null)
+            {
+                handler.ClientCertificates.AddRange(Certificates);
+            }
+
+            if (_skipCertificateCheck)
+            {
+                handler.ServerCertificateCustomValidationCallback = HttpClientHandler.DangerousAcceptAnyServerCertificateValidator;
+                handler.ClientCertificateOptions = ClientCertificateOption.Manual;
+            }
+
+            handler.AllowAutoRedirect = _allowAutoRedirect;
+            if (_allowAutoRedirect && MaximumRedirection > 0)
+            {
+                handler.MaxAutomaticRedirections = MaximumRedirection;
+            }
+
+            handler.SslProtocols = (SslProtocols)_sslProtocol;
+
+            // Check timeout setting (in seconds instead of milliseconds as in HttpWebRequest)
+            return new HttpClient(handler)
+            {
+                Timeout = _timeoutSec is 0 ? TimeSpan.FromMilliseconds(Timeout.Infinite) : TimeSpan.FromSeconds(_timeoutSec)
+            };
+        }
+
+        private void SetClassVar<T>(ref T oldValue, T newValue) where T : class
+        {
+            if (oldValue != newValue)
+            {
+                ResetClient();
+                oldValue = newValue;
+            }
+        }
+
+        private void SetStructVar<T>(ref T oldValue, T newValue) where T : struct
+        {
+            if (!oldValue.Equals(newValue))
+            {
+                ResetClient();
+                oldValue = newValue;
+            }
+        }
+
+        private void ResetClient()
+        {
+            if (_client is not null)
+            {
+                _disposedClient = true;
+                _client.Dispose();
+                _client = null;
+            }
+        }
+
+        /// <summary>
+        /// Dispose the WebRequestSession.
+        /// </summary>
+        /// <param name="disposing">True when called from Dispose() and false when called from finalizer.</param>
+        protected virtual void Dispose(bool disposing)
+        {
+            if (!_disposed)
+            {
+                if (disposing)
+                {
+                    _client?.Dispose();
+                }
+
+                _disposed = true;
+            }
+        }
+
+        /// <summary>
+        /// Dispose the WebRequestSession.
+        /// </summary>
+        public void Dispose()
+        {
+            Dispose(disposing: true);
+            GC.SuppressFinalize(this);
         }
     }
 }
diff --git a/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx b/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
index 99a1d0ef7c..5b1b33eae6 100644
--- a/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
+++ b/src/Microsoft.PowerShell.Commands.Utility/resources/WebCmdletStrings.resx
@@ -249,4 +249,7 @@
   <data name="JsonMaxDepthReached" xml:space="preserve">
     <value>Resulting JSON is truncated as serialization has exceeded the set depth of {0}.</value>
   </data>
+  <data name="WebSessionConnectionRecreated" xml:space="preserve">
+    <value>The WebSession properties were changed between requests forcing all HTTP connections in the session to be recreated.</value>
+  </data>
 </root>
diff --git a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1 b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
index 2109fc1fed..fe6db03a2a 100644
--- a/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
+++ b/test/powershell/Modules/Microsoft.PowerShell.Utility/WebCmdlets.Tests.ps1
@@ -2250,6 +2250,148 @@ Describe "Invoke-WebRequest tests" -Tags "Feature", "RequireAdminOnWindows" {
             $pathologicalRatio | Should -BeGreaterThan 5
         }
     }
+
+    Context 'Invoke-WebSession: Connection persistence in a WebSession' {
+        # Match verbose message from resource name WebSessionConnectionRecreated with message:
+        # The WebSession properties were changed between requests forcing all HTTP connections in the session to be recreated.
+        $matchConnRecreatedMessage = [regex]::new('WebSession.+HTTP')
+
+        function RunCheckingPersistence {
+            param(
+                [uri]$Uri,
+                [string]$Command,
+                [object]$Session,
+                [switch]$ExpectConnectionRecreated,
+                [switch]$CaptureSession
+            )
+
+            $pwsh = [PowerShell]::Create()
+            $pwsh.Runspace.SessionStateProxy.SetVariable('uri', $Uri)
+            if ($Session) {
+                $pwsh.Runspace.SessionStateProxy.SetVariable('Session', $Session)
+                $command = "$command -WebSession `$Session"
+            }
+            if ($CaptureSession) {
+                $command = "$command -SessionVariable Session"
+            }
+            $script = "`$null = $command -Verbose"
+            $pwsh.AddScript($script).Invoke()
+            $session = $pwsh.Runspace.SessionStateProxy.GetVariable('Session')
+
+            $expectedConnRecreatedCount = if ($ExpectConnectionRecreated) { 1 } else { 0 }
+            ($pwsh.Streams.Verbose | Where-Object { $matchConnRecreatedMessage.Matches($_.Message) }).Count | Should -Be $expectedConnRecreatedCount
+
+            $pwsh.Dispose()
+
+            return $session
+        }
+
+        It 'Connection persistence maintained' {
+            $uri = Get-WebListenerUrl
+            $Session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            1 .. 3 | ForEach-Object {
+                RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri' -Session $Session
+            }
+        }
+
+        It 'Connection persistence impacted by changing SkipCertificateCheck' {
+            $uri = Get-WebListenerUrl -Https
+            # This first request will throw because the certificate is invalid
+            $session = $null
+            $session = RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            # No change in setting
+            $session = RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri -SkipCertificateCheck:$false' -Session $session
+            # Skipping cert check changes persistence
+            $session = RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri -SkipCertificateCheck' -Session $session -ExpectConnectionRecreated
+            # Same settings won't lose persistence
+            $session = RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri -SkipCertificateCheck' -Session $session
+            # Lose persistence due to changing cert check - this will also throw
+            $session = RunCheckingPersistence -Uri $uri  -Command 'Invoke-WebRequest -Uri $uri -SkipCertificateCheck:$false' -Session $session -ExpectConnectionRecreated
+        }
+
+        It 'Connection persistence is not impacted by changing request headers' {
+            $uri = Get-WebListenerUrl
+            $session = $null
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -Headers @{ A = "B" }' -Session $session
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -Headers @{}' -Session $session
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -Headers @{ A = "C"; B = "D"}' -Session $session
+        }
+
+        It 'Connection persistence is impacted by changing the session cookie jar' {
+            $uri = Get-WebListenerUrl
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            $session.Cookies = New-Object System.Net.CookieContainer
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session -ExpectConnectionRecreated
+
+            # Adding a cookie to the container does not lose persistence
+            $Session.Cookies.Add('http://localhost', [system.net.cookie]::new('cookie', 'value'))
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+        }
+
+        It 'Connection persistence is not impacted by changing the user agent' {
+            $uri = Get-WebListenerUrl
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -UserAgent Powershell' -CaptureSession
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -UserAgent "PowerShell Core"' -Session $session
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -UserAgent "PowerShell Core with HttpClient"' -Session $session
+            # Ensure persistence is lost when we change a different setting
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -NoProxy -UserAgent "PowerShell Core"' -Session $session -ExpectConnectionRecreated
+        }
+
+        It 'Connection persistence is not impacted when NoProxy parameter is not supplied' {
+            $uri = Get-WebListenerUrl
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            # Explicitly prevent proxy - connection lost
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -NoProxy' -Session $session -ExpectConnectionRecreated
+            # Provide explicit switch value - connection maintained
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -NoProxy:$true' -Session $session
+            # No spec for proxy - connection maintained
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+            # Two follow up calls without altering anything do not lose connection
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+        }
+
+        It 'Connection persistence is not impacted when SslProtocol parameter is not supplied' {
+            $uri = Get-WebListenerUrl
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -SslProtocol Tls12' -CaptureSession
+            # No SslProtocol provided - keeps last value - connection retained
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+            # Explicit default - loses connection
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -SslProtocol Default' -Session $session -ExpectConnectionRecreated
+            # No SslProtocol provided - keeps last value - connection retained
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -Session $session
+            # Explicitly set to same value as last time it was set - connection retained
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri -SslProtocol Default' -Session $session
+        }
+
+        It 'Connection persistence is not impacted by Proxy and NoProxy unless changed parameters are used between invocations' {
+            $uri = Get-WebListenerUrl
+            $session = RunCheckingPersistence -Uri $uri -Command 'Invoke-WebRequest -Uri $uri' -CaptureSession
+            $proxy = 'http://127.0.0.1:8080'
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri -proxy $proxy" -Session $session -ExpectConnectionRecreated
+            # same proxy - do not lose persistence
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri -proxy $proxy" -Session $session
+            # No proxy at all - use previous setting and don't lose connection
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri" -Session $session
+
+            # NoProxy toggles proxy off - loses connection
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri -NoProxy" -Session $session -ExpectConnectionRecreated
+            # No setting at all - retains NoProxy setting
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri" -Session $session
+
+            # Use proxy again - lose connection
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri -proxy $proxy" -Session $session -ExpectConnectionRecreated
+            # No proxy specified - connection retained
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri" -Session $session
+
+            # Proxy changed - lose connection
+            $proxy = 'http://localhost:8080'
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri -proxy $proxy" -Session $session -ExpectConnectionRecreated
+            # No proxy specified - connection retained
+            $session = RunCheckingPersistence -Uri $uri -Command "Invoke-WebRequest -Uri $uri" -Session $session
+        }
+    }
 }
 
 Describe "Invoke-RestMethod tests" -Tags "Feature", "RequireAdminOnWindows" {