diff --git a/src/modules/cmdpal/Microsoft.CmdPal.Common/Helpers/DiagnosticsHelper.cs b/src/modules/cmdpal/Microsoft.CmdPal.Common/Helpers/DiagnosticsHelper.cs
new file mode 100644
index 0000000000..d2e9ddbcb3
--- /dev/null
+++ b/src/modules/cmdpal/Microsoft.CmdPal.Common/Helpers/DiagnosticsHelper.cs
@@ -0,0 +1,66 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using System;
+using System.Runtime.InteropServices;
+
+namespace Microsoft.CmdPal.Common.Helpers;
+
+/// <summary>
+/// Provides utility methods for building diagnostic and error messages.
+/// </summary>
+public static class DiagnosticsHelper
+{
+    /// <summary>
+    /// Builds a comprehensive exception message with timestamp and detailed diagnostic information.
+    /// </summary>
+    /// <param name="exception">The exception that occurred.</param>
+    /// <param name="extensionHint">A hint about which extension caused the exception to help with debugging.</param>
+    /// <returns>A string containing the exception details, timestamp, and source information for diagnostic purposes.</returns>
+    public static string BuildExceptionMessage(Exception exception, string? extensionHint)
+    {
+        var locationHint = string.IsNullOrWhiteSpace(extensionHint) ? "application" : $"'{extensionHint}' extension";
+
+        // let's try to get a message from the exception or inferred it from the HRESULT
+        // to show at least something
+        var message = exception.Message;
+        if (string.IsNullOrWhiteSpace(message))
+        {
+            var temp = Marshal.GetExceptionForHR(exception.HResult)?.Message;
+            if (!string.IsNullOrWhiteSpace(temp))
+            {
+                message = temp + $" (inferred from HRESULT 0x{exception.HResult:X8})";
+            }
+        }
+
+        if (string.IsNullOrWhiteSpace(message))
+        {
+            message = "[No message available]";
+        }
+
+        // note: keep date time kind and format consistent with the log
+        return $"""
+                ============================================================
+                😢 An unexpected error occurred in the {locationHint}.
+
+                Summary:
+                  Message:    {message}
+                  Type:       {exception.GetType().FullName}
+                  Source:     {exception.Source ?? "N/A"}
+                  Time:       {DateTimeOffset.Now:yyyy-MM-dd HH:mm:ss.fffffff}
+                  HRESULT:    0x{exception.HResult:X8} ({exception.HResult})
+
+                Stack Trace:
+                {exception.StackTrace ?? "[No stack trace available]"}
+
+                ------------------ Full Exception Details ------------------
+                {exception}
+
+                ℹ️ If you need further assistance, please include this information in your support request.
+                ℹ️ Before sending, take a quick look to make sure it doesn't contain any personal or sensitive information.
+                ============================================================
+
+                """;
+    }
+}
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs b/src/modules/cmdpal/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
index 7a301c89b0..046c9fae93 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.Core.ViewModels/PageViewModel.cs
@@ -5,6 +5,7 @@
 using System.Collections.ObjectModel;
 using CommunityToolkit.Mvvm.ComponentModel;
 using CommunityToolkit.Mvvm.Input;
+using Microsoft.CmdPal.Common.Helpers;
 using Microsoft.CmdPal.Core.ViewModels.Models;
 using Microsoft.CommandPalette.Extensions;
 
@@ -223,9 +224,10 @@ public partial class PageViewModel : ExtensionObjectViewModel, IPageContext
         extensionHint ??= ExtensionHost.GetExtensionDisplayName() ?? Title;
         Task.Factory.StartNew(
             () =>
-        {
-            ErrorMessage += $"A bug occurred in {$"the \"{extensionHint}\"" ?? "an unknown's"} extension's code:\n{ex.Message}\n{ex.Source}\n{ex.StackTrace}\n\n";
-        },
+            {
+                var message = DiagnosticsHelper.BuildExceptionMessage(ex, extensionHint);
+                ErrorMessage += message;
+            },
             CancellationToken.None,
             TaskCreationOptions.None,
             Scheduler);
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/TopLevelCommandManager.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/TopLevelCommandManager.cs
index 3bd2d8cedf..f55a322792 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/TopLevelCommandManager.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/TopLevelCommandManager.cs
@@ -410,8 +410,8 @@ public partial class TopLevelCommandManager : ObservableObject,
 
     void IPageContext.ShowException(Exception ex, string? extensionHint)
     {
-        var errorMessage = $"A bug occurred in {$"the \"{extensionHint}\"" ?? "an unknown's"} extension's code:\n{ex.Message}\n{ex.Source}\n{ex.StackTrace}\n\n";
-        CommandPaletteHost.Instance.Log(errorMessage);
+        var message = DiagnosticsHelper.BuildExceptionMessage(ex, extensionHint ?? "TopLevelCommandManager");
+        CommandPaletteHost.Instance.Log(message);
     }
 
     internal bool IsProviderActive(string id)