diff --git a/src/PowderCoating.Web/Controllers/InvoicesController.cs b/src/PowderCoating.Web/Controllers/InvoicesController.cs
index b43ae8b..0d4abef 100644
--- a/src/PowderCoating.Web/Controllers/InvoicesController.cs
+++ b/src/PowderCoating.Web/Controllers/InvoicesController.cs
@@ -917,7 +917,7 @@ public class InvoicesController : Controller
 
             TempData["Success"] = $"Invoice {invoice.InvoiceNumber} marked as sent.";
             if (!pdfAndNotifSucceeded)
-                TempData["Warning"] = "The invoice is marked as sent, but PDF generation or the customer email failed. Check the notification logs or your email configuration.";
+                TempData["WarningPermanent"] = "The invoice is marked as sent, but PDF generation or the customer email failed. Check the notification logs or your email configuration.";
             return RedirectToAction(nameof(Details), new { id });
         }
         catch (Exception ex)
@@ -1302,8 +1302,8 @@ public class InvoicesController : Controller
         }
         catch (Exception ex)
         {
-            _logger.LogError(ex, "Error generating PDF for invoice {Id}", id);
-            TempData["Error"] = "An error occurred while generating the PDF.";
+            _logger.LogError(ex, "Error generating PDF for invoice {Id}. Inner: {Inner}", id, ex.InnerException?.Message ?? ex.Message);
+            TempData["ErrorPermanent"] = $"PDF generation failed: {ex.Message}";
             return RedirectToAction(nameof(Details), new { id });
         }
     }
diff --git a/src/PowderCoating.Web/Helpers/ToastHelper.cs b/src/PowderCoating.Web/Helpers/ToastHelper.cs
index 9d479a3..22ff16b 100644
--- a/src/PowderCoating.Web/Helpers/ToastHelper.cs
+++ b/src/PowderCoating.Web/Helpers/ToastHelper.cs
@@ -31,6 +31,9 @@ namespace PowderCoating.Web.Helpers
         /// <summary>TempData key read by the layout to render a yellow warning toast.</summary>
         private const string WarningKey = "Warning";
 
+        /// <summary>TempData key read by the layout to render a yellow warning toast that does not auto-dismiss.</summary>
+        private const string WarningPermanentKey = "WarningPermanent";
+
         /// <summary>TempData key read by the layout to render a blue info toast.</summary>
         private const string InfoKey = "Info";
 
@@ -67,6 +70,15 @@ namespace PowderCoating.Web.Helpers
             tempData[WarningKey] = message;
         }
 
+        /// <summary>
+        /// Stores a warning (yellow) toast that requires manual dismissal (no auto-timeout).
+        /// Use for critical warnings the user must not miss, such as email delivery failures.
+        /// </summary>
+        public static void WarningPermanent(this ITempDataDictionary tempData, string message)
+        {
+            tempData[WarningPermanentKey] = message;
+        }
+
         /// <summary>
         /// Stores an informational (blue) toast message in TempData for display on
         /// the next page render after a redirect.
@@ -123,6 +135,15 @@ namespace PowderCoating.Web.Helpers
             controller.TempData.Warning(message);
         }
 
+        /// <summary>
+        /// Stores a permanent warning (yellow, no auto-dismiss) in the controller's TempData.
+        /// Use for failures the user must not miss — email delivery errors, PDF generation failures.
+        /// </summary>
+        public static void ToastWarningPermanent(this Controller controller, string message)
+        {
+            controller.TempData.WarningPermanent(message);
+        }
+
         /// <summary>
         /// Stores an informational (blue) toast in the controller's TempData.
         /// Convenience wrapper around <see cref="ToastHelper.Info"/>.
@@ -165,7 +186,7 @@ namespace PowderCoating.Web.Helpers
                         : $"{channel} notification was skipped.");
                     break;
                 case NotificationStatus.Failed:
-                    controller.ToastWarning(!string.IsNullOrEmpty(log.ErrorMessage)
+                    controller.ToastWarningPermanent(!string.IsNullOrEmpty(log.ErrorMessage)
                         ? $"{channel} delivery failed: {log.ErrorMessage}"
                         : $"{channel} notification failed.");
                     break;
diff --git a/src/PowderCoating.Web/Views/Shared/_Layout.cshtml b/src/PowderCoating.Web/Views/Shared/_Layout.cshtml
index 449d017..fc9a0e2 100644
--- a/src/PowderCoating.Web/Views/Shared/_Layout.cshtml
+++ b/src/PowderCoating.Web/Views/Shared/_Layout.cshtml
@@ -890,6 +890,10 @@
     {
         <div id="tempdata-warning-message" style="display:none;">@TempData["Warning"]</div>
     }
+    @if (TempData["WarningPermanent"] != null)
+    {
+        <div id="tempdata-warning-permanent-message" style="display:none;">@TempData["WarningPermanent"]</div>
+    }
     @if (TempData["Info"] != null)
     {
         <div id="tempdata-info-message" style="display:none;">@TempData["Info"]</div>
diff --git a/src/PowderCoating.Web/wwwroot/js/toast-notifications.js b/src/PowderCoating.Web/wwwroot/js/toast-notifications.js
index 06087c6..bf85dae 100644
--- a/src/PowderCoating.Web/wwwroot/js/toast-notifications.js
+++ b/src/PowderCoating.Web/wwwroot/js/toast-notifications.js
@@ -118,6 +118,12 @@ function displayTempDataMessages() {
         showWarning(warningMsg.textContent.trim());
     }
 
+    // Permanent warning — no auto-dismiss
+    const warningPerm = document.getElementById('tempdata-warning-permanent-message');
+    if (warningPerm && warningPerm.textContent.trim()) {
+        toastr.warning(warningPerm.textContent.trim(), 'Warning', { timeOut: 0, extendedTimeOut: 0 });
+    }
+
     // Info message
     const infoMsg = document.getElementById('tempdata-info-message');
     if (infoMsg && infoMsg.textContent.trim()) {