diff --git a/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs b/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
index 10e34bf20..d1217c8b5 100644
--- a/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
+++ b/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
@@ -1,4 +1,5 @@
-using Microsoft.Extensions.Logging;
+using Microsoft.AspNetCore.SignalR;
+using Microsoft.Extensions.Logging;
 using Ombi.Api.Plex;
 using Ombi.Api.Plex.Models;
 using Ombi.Core.Authentication;
@@ -8,9 +9,11 @@ using Ombi.Core.Models.Requests;
 using Ombi.Core.Settings;
 using Ombi.Core.Settings.Models.External;
 using Ombi.Helpers;
+using Ombi.Hubs;
 using Ombi.Store.Entities;
 using Ombi.Store.Entities.Requests;
 using Quartz;
+using System;
 using System.Collections.Generic;
 using System.Linq;
 using System.Threading;
@@ -25,10 +28,11 @@ namespace Ombi.Schedule.Jobs.Plex
         private readonly OmbiUserManager _ombiUserManager;
         private readonly IMovieRequestEngine _movieRequestEngine;
         private readonly ITvRequestEngine _tvRequestEngine;
+        private readonly IHubContext<NotificationHub> _hub;
         private readonly ILogger _logger;
 
         public PlexWatchlistImport(IPlexApi plexApi, ISettingsService<PlexSettings> settings, OmbiUserManager ombiUserManager,
-            IMovieRequestEngine movieRequestEngine, ITvRequestEngine tvRequestEngine,
+            IMovieRequestEngine movieRequestEngine, ITvRequestEngine tvRequestEngine, IHubContext<NotificationHub> hub,
             ILogger<PlexWatchlistImport> logger)
         {
             _plexApi = plexApi;
@@ -36,6 +40,7 @@ namespace Ombi.Schedule.Jobs.Plex
             _ombiUserManager = ombiUserManager;
             _movieRequestEngine = movieRequestEngine;
             _tvRequestEngine = tvRequestEngine;
+            _hub = hub;
             _logger = logger;
         }
 
@@ -44,48 +49,69 @@ namespace Ombi.Schedule.Jobs.Plex
             var settings = await _settings.GetSettingsAsync();
             if (!settings.Enable || !settings.EnableWatchlistImport)
             {
+                _logger.LogDebug($"Not enabled. Plex Enabled: {settings.Enable}, Watchlist Enabled: {settings.EnableWatchlistImport}");
                 return;
             }
 
             var plexUsersWithTokens = _ombiUserManager.Users.Where(x => x.UserType == UserType.PlexUser && x.MediaServerToken != null).ToList();
+            _logger.LogInformation($"Found {plexUsersWithTokens.Count} users with tokens");
+            await NotifyClient("Starting Watchlist Import");
+
             foreach (var user in plexUsersWithTokens)
             {
-                var watchlist = await _plexApi.GetWatchlist(user.MediaServerToken, context?.CancellationToken ?? CancellationToken.None);
-                if (watchlist == null || !(watchlist.MediaContainer?.Metadata?.Any() ?? false))
+                try
                 {
-                    return;
-                }
 
-                var items = watchlist.MediaContainer.Metadata;
-                foreach (var item in items)
-                {
-                    var providerIds = await GetProviderIds(user.MediaServerToken, item, context?.CancellationToken ?? CancellationToken.None);
-                    if (!providerIds.TheMovieDb.HasValue())
+                    _logger.LogDebug($"Starting Watchlist Import for {user.UserName} with token {user.MediaServerToken}");
+                    var watchlist = await _plexApi.GetWatchlist(user.MediaServerToken, context?.CancellationToken ?? CancellationToken.None);
+                    if (watchlist == null || !(watchlist.MediaContainer?.Metadata?.Any() ?? false))
                     {
-                        // We need a MovieDbId to support this;
+                        _logger.LogDebug($"No watchlist found for {user.UserName}");
                         return;
                     }
-                    switch (item.type)
+
+                    var items = watchlist.MediaContainer.Metadata;
+                    _logger.LogDebug($"Items found in watchlist: {watchlist.MediaContainer.totalSize}");
+                    foreach (var item in items)
                     {
-                        case "show":
-                            await ProcessShow(int.Parse(providerIds.TheMovieDb), user, context?.CancellationToken ?? CancellationToken.None);
-                            break;
-                        case "movie":
-                            await ProcessMovie(int.Parse(providerIds.TheMovieDb), user, context?.CancellationToken ?? CancellationToken.None);
-                            break;
+                        _logger.LogDebug($"Processing {item.title} {item.type}");
+                        var providerIds = await GetProviderIds(user.MediaServerToken, item, context?.CancellationToken ?? CancellationToken.None);
+                        if (!providerIds.TheMovieDb.HasValue())
+                        {
+                            _logger.LogWarning($"No TheMovieDb Id found for {item.title}, could not import via Plex WatchList");
+                            // We need a MovieDbId to support this;
+                            return;
+                        }
+                        switch (item.type)
+                        {
+                            case "show":
+                                await ProcessShow(int.Parse(providerIds.TheMovieDb), user);
+                                break;
+                            case "movie":
+                                await ProcessMovie(int.Parse(providerIds.TheMovieDb), user);
+                                break;
+                        }
                     }
                 }
+                catch (Exception ex)
+                {
+                    _logger.LogError(ex, $"Exception thrown when importing watchlist for user {user.UserName}");
+                    continue;
+                }
             }
+
+            await NotifyClient("Finished Watchlist Import");
         }
 
-        private async Task ProcessMovie(int theMovieDbId, OmbiUser user, CancellationToken cancellationToken)
+        private async Task ProcessMovie(int theMovieDbId, OmbiUser user)
         {
             _movieRequestEngine.SetUser(user);
-            var response = await _movieRequestEngine.RequestMovie(new() { TheMovieDbId = theMovieDbId, Source = RequestSource.PlexWatchlist});
+            var response = await _movieRequestEngine.RequestMovie(new() { TheMovieDbId = theMovieDbId, Source = RequestSource.PlexWatchlist });
             if (response.IsError)
             {
                 if (response.ErrorCode == ErrorCode.AlreadyRequested)
                 {
+                    _logger.LogDebug($"Movie already requested for user '{user.UserName}'");
                     return;
                 }
                 _logger.LogInformation($"Error adding title from PlexWatchlist for user '{user.UserName}'. Message: '{response.ErrorMessage}'");
@@ -97,7 +123,7 @@ namespace Ombi.Schedule.Jobs.Plex
         }
 
 
-        private async Task ProcessShow(int theMovieDbId, OmbiUser user, CancellationToken cancellationToken)
+        private async Task ProcessShow(int theMovieDbId, OmbiUser user)
         {
             _tvRequestEngine.SetUser(user);
             var response = await _tvRequestEngine.RequestTvShow(new TvRequestViewModelV2 { RequestAll = true, TheMovieDbId = theMovieDbId, Source = RequestSource.PlexWatchlist });
@@ -105,6 +131,7 @@ namespace Ombi.Schedule.Jobs.Plex
             {
                 if (response.ErrorCode == ErrorCode.AlreadyRequested)
                 {
+                    _logger.LogDebug($"Show already requested for user '{user.UserName}'");
                     return;
                 }
                 _logger.LogInformation($"Error adding title from PlexWatchlist for user '{user.UserName}'. Message: '{response.ErrorMessage}'");
@@ -144,6 +171,15 @@ namespace Ombi.Schedule.Jobs.Plex
             return providerIds;
         }
 
+        private async Task NotifyClient(string message)
+        {
+            if (_hub?.Clients == null)
+            {
+                return;
+            }
+            await _hub?.Clients?.Clients(NotificationHub.AdminConnectionIds)?
+                .SendAsync(NotificationHub.NotificationEvent, $"Plex Watchlist Import - {message}");
+        }
         public void Dispose() { }
     }
 }