diff --git a/Jellyfin.Plugin.SmartNotify/Notifiers/SmartNotifyBackgroundService.cs b/Jellyfin.Plugin.SmartNotify/Notifiers/SmartNotifyBackgroundService.cs
index d3c4c4d..6bb1077 100644
--- a/Jellyfin.Plugin.SmartNotify/Notifiers/SmartNotifyBackgroundService.cs
+++ b/Jellyfin.Plugin.SmartNotify/Notifiers/SmartNotifyBackgroundService.cs
@@ -254,7 +254,12 @@ public class SmartNotifyBackgroundService : IHostedService, IDisposable
                 return;
             }
 
-            _logger.LogDebug("Processing {Count} pending notifications", pendingNotifications.Count);
+            _logger.LogInformation(
+                "Processing {Count} pending notifications (delay={Delay}min, grouping={Grouping}min, cutoff={Cutoff})",
+                pendingNotifications.Count,
+                delayMinutes,
+                groupingWindowMinutes,
+                cutoff);
 
             // Group episodes by series
             var episodesBySeries = pendingNotifications
@@ -262,6 +267,17 @@ public class SmartNotifyBackgroundService : IHostedService, IDisposable
                 .GroupBy(n => n.SeriesId!)
                 .ToList();
 
+            // Log unmatched notifications (neither episode with series nor movie)
+            var unmatchedCount = pendingNotifications.Count
+                - pendingNotifications.Count(n => n.ItemType == "Episode" && !string.IsNullOrEmpty(n.SeriesId))
+                - pendingNotifications.Count(n => n.ItemType == "Movie");
+            if (unmatchedCount > 0)
+            {
+                _logger.LogWarning(
+                    "{Count} notifications are neither episodes (with SeriesId) nor movies and will be skipped",
+                    unmatchedCount);
+            }
+
             // Process each series group
             foreach (var seriesGroup in episodesBySeries)
             {
@@ -271,19 +287,34 @@ public class SmartNotifyBackgroundService : IHostedService, IDisposable
                 // Only process if the oldest notification is outside the grouping window
                 if (oldestInGroup > groupingCutoff)
                 {
-                    _logger.LogDebug(
-                        "Waiting for grouping window for series {SeriesId}, oldest: {Oldest}",
+                    _logger.LogInformation(
+                        "Waiting for grouping window for series {SeriesName} ({SeriesId}), oldest queued: {Oldest}, grouping cutoff: {Cutoff}",
+                        seriesGroup.First().SeriesName,
                         seriesGroup.Key,
-                        oldestInGroup);
+                        oldestInGroup,
+                        groupingCutoff);
                     continue;
                 }
 
-                await _discordService.SendGroupedEpisodeNotificationAsync(
+                _logger.LogInformation(
+                    "Sending grouped notification for {SeriesName}: {Count} episodes",
+                    seriesGroup.First().SeriesName,
+                    seriesGroup.Count());
+
+                var success = await _discordService.SendGroupedEpisodeNotificationAsync(
                     seriesGroup,
                     CancellationToken.None);
 
-                var idsToRemove = seriesGroup.Select(n => n.Id).ToList();
-                _historyService.RemoveNotifications(idsToRemove);
+                if (success)
+                {
+                    var idsToRemove = seriesGroup.Select(n => n.Id).ToList();
+                    _historyService.RemoveNotifications(idsToRemove);
+                    _logger.LogInformation("Removed {Count} processed episode notifications from queue", idsToRemove.Count);
+                }
+                else
+                {
+                    _logger.LogWarning("Discord send failed for {SeriesName}, keeping notifications in queue for retry", seriesGroup.First().SeriesName);
+                }
             }
 
             // Process movies
@@ -293,8 +324,19 @@ public class SmartNotifyBackgroundService : IHostedService, IDisposable
 
             foreach (var movie in movies)
             {
-                await _discordService.SendMovieNotificationAsync(movie, CancellationToken.None);
-                _historyService.RemoveNotifications(new[] { movie.Id });
+                _logger.LogInformation("Sending movie notification for: {Name}", movie.Name);
+
+                var success = await _discordService.SendMovieNotificationAsync(movie, CancellationToken.None);
+
+                if (success)
+                {
+                    _historyService.RemoveNotifications(new[] { movie.Id });
+                    _logger.LogInformation("Removed processed movie notification from queue: {Name}", movie.Name);
+                }
+                else
+                {
+                    _logger.LogWarning("Discord send failed for movie {Name}, keeping in queue for retry", movie.Name);
+                }
             }
         }
         catch (Exception ex)
diff --git a/Jellyfin.Plugin.SmartNotify/Services/DiscordNotificationService.cs b/Jellyfin.Plugin.SmartNotify/Services/DiscordNotificationService.cs
index a8be990..5eaf34d 100644
--- a/Jellyfin.Plugin.SmartNotify/Services/DiscordNotificationService.cs
+++ b/Jellyfin.Plugin.SmartNotify/Services/DiscordNotificationService.cs
@@ -38,8 +38,8 @@ public class DiscordNotificationService
     /// </summary>
     /// <param name="notifications">The notifications to group and send.</param>
     /// <param name="cancellationToken">The cancellation token.</param>
-    /// <returns>A task representing the async operation.</returns>
-    public async Task SendGroupedEpisodeNotificationAsync(
+    /// <returns>True if the notification was sent successfully.</returns>
+    public async Task<bool> SendGroupedEpisodeNotificationAsync(
         IEnumerable<PendingNotification> notifications,
         CancellationToken cancellationToken)
     {
@@ -47,13 +47,13 @@ public class DiscordNotificationService
         if (config == null || string.IsNullOrEmpty(config.DiscordWebhookUrl))
         {
             _logger.LogWarning("Discord webhook URL not configured");
-            return;
+            return false;
         }
 
         var notificationList = notifications.ToList();
         if (notificationList.Count == 0)
         {
-            return;
+            return false;
         }
 
         var first = notificationList.First();
@@ -70,7 +70,7 @@ public class DiscordNotificationService
         var title = $"📺 {seriesName}";
         var description = $"Neue Episoden hinzugefügt:\n{episodeDescription}";
 
-        await SendDiscordWebhookAsync(
+        return await SendDiscordWebhookAsync(
             config,
             title,
             description,
@@ -153,7 +153,8 @@ public class DiscordNotificationService
     /// </summary>
     /// <param name="notification">The notification.</param>
     /// <param name="cancellationToken">The cancellation token.</param>
-    public async Task SendMovieNotificationAsync(
+    /// <returns>True if the notification was sent successfully.</returns>
+    public async Task<bool> SendMovieNotificationAsync(
         PendingNotification notification,
         CancellationToken cancellationToken)
     {
@@ -161,7 +162,7 @@ public class DiscordNotificationService
         if (config == null || string.IsNullOrEmpty(config.DiscordWebhookUrl))
         {
             _logger.LogWarning("Discord webhook URL not configured");
-            return;
+            return false;
         }
 
         var title = $"🎬 {notification.Name}";
@@ -176,7 +177,7 @@ public class DiscordNotificationService
             description = description.Substring(0, 297) + "...";
         }
 
-        await SendDiscordWebhookAsync(
+        return await SendDiscordWebhookAsync(
             config,
             title,
             description,
@@ -236,7 +237,8 @@ public class DiscordNotificationService
     /// <summary>
     /// Sends the actual Discord webhook request, with optional image attachment.
     /// </summary>
-    private async Task SendDiscordWebhookAsync(
+    /// <returns>True if the webhook was sent successfully.</returns>
+    private async Task<bool> SendDiscordWebhookAsync(
         PluginConfiguration config,
         string title,
         string description,
@@ -260,7 +262,16 @@ public class DiscordNotificationService
 
         if (!string.IsNullOrEmpty(externalLinks))
         {
-            embed["footer"] = new Dictionary<string, string> { ["text"] = externalLinks };
+            var fields = new List<Dictionary<string, object>>
+            {
+                new Dictionary<string, object>
+                {
+                    ["name"] = "Links",
+                    ["value"] = externalLinks,
+                    ["inline"] = false
+                }
+            };
+            embed["fields"] = fields;
         }
 
         embed["timestamp"] = DateTime.UtcNow.ToString("o");
@@ -272,7 +283,7 @@ public class DiscordNotificationService
         };
 
         var json = JsonSerializer.Serialize(payload);
-        _logger.LogDebug("Sending Discord webhook: {Json}", json);
+        _logger.LogInformation("Sending Discord webhook for: {Title}", title);
 
         try
         {
@@ -281,6 +292,7 @@ public class DiscordNotificationService
 
             if (hasImage)
             {
+                _logger.LogInformation("Attaching image from: {Path}", imagePath);
                 // Send as multipart/form-data with image attachment
                 using var form = new MultipartFormDataContent();
                 form.Add(new StringContent(json, Encoding.UTF8, "application/json"), "payload_json");
@@ -306,15 +318,16 @@ public class DiscordNotificationService
                     "Discord webhook failed with status {Status}: {Body}",
                     response.StatusCode,
                     responseBody);
+                return false;
             }
-            else
-            {
-                _logger.LogInformation("Discord notification sent successfully: {Title}", title);
-            }
+
+            _logger.LogInformation("Discord notification sent successfully: {Title}", title);
+            return true;
         }
         catch (Exception ex)
         {
             _logger.LogError(ex, "Failed to send Discord webhook");
+            return false;
         }
     }
 }