diff --git a/src/PowerShellEditorServices/Services/PowerShell/Handlers/GetVersionHandler.cs b/src/PowerShellEditorServices/Services/PowerShell/Handlers/GetVersionHandler.cs
index f8a6d5521..afe0b8e20 100644
--- a/src/PowerShellEditorServices/Services/PowerShell/Handlers/GetVersionHandler.cs
+++ b/src/PowerShellEditorServices/Services/PowerShell/Handlers/GetVersionHandler.cs
@@ -19,8 +19,6 @@ namespace Microsoft.PowerShell.EditorServices.Handlers
 {
     internal class GetVersionHandler : IGetVersionHandler
     {
-        private static readonly Version s_desiredPackageManagementVersion = new Version(1, 4, 6);
-
         private readonly ILogger<GetVersionHandler> _logger;
         private IRunspaceContext _runspaceContext;
         private readonly IInternalPowerShellExecutionService _executionService;
@@ -58,11 +56,6 @@ public async Task<PowerShellVersion> Handle(GetVersionParams request, Cancellati
                 }
             }
 
-            if (VersionUtils.IsPS5 && _configurationService.CurrentSettings.PromptToUpdatePackageManagement)
-            {
-                await CheckPackageManagement().ConfigureAwait(false);
-            }
-
             return new PowerShellVersion
             {
                 Version = VersionUtils.PSVersionString,
@@ -78,80 +71,5 @@ private enum PowerShellProcessArchitecture
             X86,
             X64
         }
-
-        private async Task CheckPackageManagement()
-        {
-            PSCommand getModule = new PSCommand().AddCommand("Get-Module").AddParameter("ListAvailable").AddParameter("Name", "PackageManagement");
-            foreach (PSModuleInfo module in await _executionService.ExecutePSCommandAsync<PSModuleInfo>(getModule, CancellationToken.None).ConfigureAwait(false))
-            {
-                // The user has a good enough version of PackageManagement
-                if (module.Version >= s_desiredPackageManagementVersion)
-                {
-                    break;
-                }
-
-                _logger.LogDebug("Old version of PackageManagement detected.");
-
-                if (_runspaceContext.CurrentRunspace.Runspace.SessionStateProxy.LanguageMode != PSLanguageMode.FullLanguage)
-                {
-                    _languageServer.Window.ShowWarning("You have an older version of PackageManagement known to cause issues with the PowerShell extension. Please run the following command in a new Windows PowerShell session and then restart the PowerShell extension: `Install-Module PackageManagement -Force -AllowClobber -MinimumVersion 1.4.6`");
-                    return;
-                }
-
-                var takeActionText = "Yes";
-                MessageActionItem messageAction = await _languageServer.Window.ShowMessageRequest(new ShowMessageRequestParams
-                {
-                    Message = "You have an older version of PackageManagement known to cause issues with the PowerShell extension. Would you like to update PackageManagement (You will need to restart the PowerShell extension after)?",
-                    Type = MessageType.Warning,
-                    Actions = new[]
-                    {
-                        new MessageActionItem
-                        {
-                            Title = takeActionText
-                        },
-                        new MessageActionItem
-                        {
-                            Title = "Not now"
-                        }
-                    }
-                })
-                .ConfigureAwait(false);
-
-                // If the user chose "Not now" ignore it for the rest of the session.
-                if (messageAction?.Title == takeActionText)
-                {
-                    var command = new PSCommand().AddScript("powershell.exe -NoLogo -NoProfile -Command 'Install-Module -Name PackageManagement -Force -MinimumVersion 1.4.6 -Scope CurrentUser -AllowClobber'");
-
-                    await _executionService.ExecutePSCommandAsync(
-                        command,
-                        CancellationToken.None,
-                        new PowerShellExecutionOptions { WriteInputToHost = true, WriteOutputToHost = true, AddToHistory = true, ThrowOnError = false }).ConfigureAwait(false);
-
-                    // TODO: Error handling here
-
-                    /*
-                    if (errors.Length == 0)
-                    {
-                        _logger.LogDebug("PackageManagement is updated.");
-                        _languageServer.Window.ShowMessage(new ShowMessageParams
-                        {
-                            Type = MessageType.Info,
-                            Message = "PackageManagement updated, If you already had PackageManagement loaded in your session, please restart the PowerShell extension."
-                        });
-                    }
-                    else
-                    {
-                        // There were errors installing PackageManagement.
-                        _logger.LogError($"PackageManagement installation had errors: {errors.ToString()}");
-                        _languageServer.Window.ShowMessage(new ShowMessageParams
-                        {
-                            Type = MessageType.Error,
-                            Message = "PackageManagement update failed. This might be due to PowerShell Gallery using TLS 1.2. More info can be found at https://aka.ms/psgallerytls"
-                        });
-                    }
-                    */
-                }
-            }
-        }
     }
 }
diff --git a/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs b/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
index 73e4fb229..d6974db2c 100644
--- a/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
+++ b/src/PowerShellEditorServices/Services/Workspace/Handlers/ConfigurationHandler.cs
@@ -203,13 +203,6 @@ private void SendFeatureChangesTelemetry(LanguageServerSettingsWrapper incomingS
                 configChanges["CodeFolding"] = incomingSettings.Powershell.CodeFolding.Enable;
             }
 
-            // Send telemetry if the user opted-out of the prompt to update PackageManagement
-            if (!incomingSettings.Powershell.PromptToUpdatePackageManagement &&
-                _configurationService.CurrentSettings.PromptToUpdatePackageManagement != incomingSettings.Powershell.PromptToUpdatePackageManagement)
-            {
-                configChanges["PromptToUpdatePackageManagement"] = incomingSettings.Powershell.PromptToUpdatePackageManagement;
-            }
-
             // Send telemetry if the user opted-out of Profile loading
             if (!incomingSettings.Powershell.EnableProfileLoading &&
                 _configurationService.CurrentSettings.EnableProfileLoading != incomingSettings.Powershell.EnableProfileLoading)
diff --git a/src/PowerShellEditorServices/Services/Workspace/LanguageServerSettings.cs b/src/PowerShellEditorServices/Services/Workspace/LanguageServerSettings.cs
index f538f7575..8e597e621 100644
--- a/src/PowerShellEditorServices/Services/Workspace/LanguageServerSettings.cs
+++ b/src/PowerShellEditorServices/Services/Workspace/LanguageServerSettings.cs
@@ -17,7 +17,6 @@ internal class LanguageServerSettings
     {
         private readonly object updateLock = new();
         public bool EnableProfileLoading { get; set; }
-        public bool PromptToUpdatePackageManagement { get; set; } = true;
         public ScriptAnalysisSettings ScriptAnalysis { get; set; }
         public CodeFormattingSettings CodeFormatting { get; set; }
         public CodeFoldingSettings CodeFolding { get; set; }
@@ -42,7 +41,6 @@ public void Update(
                 lock (updateLock)
                 {
                     EnableProfileLoading = settings.EnableProfileLoading;
-                    PromptToUpdatePackageManagement = settings.PromptToUpdatePackageManagement;
                     ScriptAnalysis.Update(settings.ScriptAnalysis, workspaceRootPath, logger);
                     CodeFormatting = new CodeFormattingSettings(settings.CodeFormatting);
                     CodeFolding.Update(settings.CodeFolding, logger);