feat: Added the ability for the Watchlist to automatically refresh the users token. This will reduce the need for the user to log in

src/Ombi.Api.Plex/IPlexApi.cs

@@ -29,5 +29,6 @@ namespace Ombi.Api.Plex
         Task<PlexAddWrapper> AddUser(string emailAddress, string serverId, string authToken, int[] libs);
         Task<PlexWatchlistContainer> GetWatchlist(string plexToken, CancellationToken cancellationToken);
         Task<PlexWatchlistMetadataContainer> GetWatchlistMetadata(string ratingKey, string plexToken, CancellationToken cancellationToken);
+        Task<bool> Ping(string authToken, CancellationToken cancellationToken = default);
     }
 }

src/Ombi.Api.Plex/PlexApi.cs

@@ -320,6 +320,30 @@ namespace Ombi.Api.Plex
             return result;
         }
 
+        /// <summary>
+        /// Pings the Plex API to validate if a token is still valid
+        /// </summary>
+        /// <param name="authToken">The authentication token to validate</param>
+        /// <param name="cancellationToken">Cancellation token</param>
+        /// <returns>True if the token is valid, false otherwise</returns>
+        public async Task<bool> Ping(string authToken, CancellationToken cancellationToken = default)
+        {
+            try
+            {
+                var request = new Request("api/v2/ping", "https://plex.tv/", HttpMethod.Get);
+                await AddHeaders(request, authToken);
+                
+                // We don't need to parse the response, just check if the request succeeds
+                await Api.Request(request, cancellationToken);
+                return true;
+            }
+            catch
+            {
+                // If the request fails (401, 403, etc.), the token is invalid
+                return false;
+            }
+        }
+
 
         /// <summary>
         /// Adds the required headers and also the authorization header

src/Ombi.DependencyInjection/IocExtensions.cs

@@ -107,6 +107,7 @@ namespace Ombi.DependencyInjection
             services.AddTransient<IMusicSender, MusicSender>();
             services.AddTransient<IMassEmailSender, MassEmailSender>();
             services.AddTransient<IPlexOAuthManager, PlexOAuthManager>();
+            services.AddTransient<IPlexTokenKeepAliveService, PlexTokenKeepAliveService>();
             services.AddTransient<IVoteEngine, VoteEngine>();
             services.AddTransient<IDemoMovieSearchEngine, DemoMovieSearchEngine>();
             services.AddTransient<IDemoTvSearchEngine, DemoTvSearchEngine>();

src/Ombi.Schedule.Tests/PlexWatchlistImportTests.cs

@@ -24,6 +24,7 @@ using Ombi.Notifications.Models;
 using Ombi.Core.Notifications;
 using Ombi.Helpers;
 using Ombi.Core;
+using Ombi.Core.Authentication;
 
 namespace Ombi.Schedule.Tests
 {
@@ -43,6 +44,8 @@ namespace Ombi.Schedule.Tests
             _mocker.Use(um);
             _context = _mocker.GetMock<IJobExecutionContext>();
             _context.Setup(x => x.CancellationToken).Returns(CancellationToken.None);
+            // Mock the keep-alive service to return true by default
+            _mocker.Use<IPlexTokenKeepAliveService>(Mock.Of<IPlexTokenKeepAliveService>(s => s.KeepTokenAliveAsync(It.IsAny<string>(), It.IsAny<CancellationToken>()) == Task.FromResult(true)));
             _subject = _mocker.CreateInstance<PlexWatchlistImport>();
             _mocker.Setup<IRepository<PlexWatchlistUserError>, IQueryable<PlexWatchlistUserError>>(x => x.GetAll()).Returns(new List<PlexWatchlistUserError>().AsQueryable().BuildMock());
             _mocker.Setup<INotificationHelper>(x => x.Notify(It.IsAny<NotificationOptions>()));
@@ -838,5 +841,43 @@ namespace Ombi.Schedule.Tests
             // Assert
             _mocker.Verify<INotificationHelper>(x => x.Notify(It.IsAny<NotificationOptions>()), Times.Never);
         }
+
+        [Test]
+        public async Task SkipsUserIfTokenKeepAliveFails()
+        {
+            // Arrange: Set up the keep-alive service to return false (token invalid/expired)
+            var keepAliveMock = new Mock<IPlexTokenKeepAliveService>();
+            keepAliveMock.Setup(x => x.KeepTokenAliveAsync(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(false);
+            _mocker.Use(keepAliveMock.Object);
+            _subject = _mocker.CreateInstance<PlexWatchlistImport>();
+            _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
+            // Act
+            await _subject.Execute(_context.Object);
+            // Assert: Should not attempt to import watchlist if keep-alive fails
+            keepAliveMock.Verify(x => x.KeepTokenAliveAsync(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Once);
+            _mocker.Verify<IPlexApi>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Never);
+            _mocker.Verify<INotificationHelper>(x => x.Notify(It.IsAny<NotificationOptions>()), Times.Never); // or Times.Once if notification is expected
+        }
+        [Test]
+        public async Task CallsKeepAliveForEachPlexUser()
+        {
+            // Arrange: Multiple Plex users
+            var users = new List<OmbiUser>
+            {
+                new OmbiUser { Id = "abc1", UserType = UserType.PlexUser, MediaServerToken = "abc1", UserName = "abc1", NormalizedUserName = "ABC1" },
+                new OmbiUser { Id = "abc2", UserType = UserType.PlexUser, MediaServerToken = "abc2", UserName = "abc2", NormalizedUserName = "ABC2" },
+            };
+            var um = MockHelper.MockUserManager(users);
+            _mocker.Use(um);
+            var keepAliveMock = new Mock<IPlexTokenKeepAliveService>();
+            keepAliveMock.Setup(x => x.KeepTokenAliveAsync(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(true);
+            _mocker.Use(keepAliveMock.Object);
+            _subject = _mocker.CreateInstance<PlexWatchlistImport>();
+            _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
+            // Act
+            await _subject.Execute(_context.Object);
+            // Assert: KeepAlive should be called for each user
+            keepAliveMock.Verify(x => x.KeepTokenAliveAsync(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Exactly(users.Count));
+        }
     }
 }

src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs

@@ -27,6 +27,7 @@ using Ombi.Core.Notifications;
 using Microsoft.AspNetCore.Identity;
 using Ombi.Store.Repository.Requests;
 using Ombi.Core;
+using Ombi.Core.Authentication;
 
 namespace Ombi.Schedule.Jobs.Plex
 {
@@ -43,11 +44,12 @@ namespace Ombi.Schedule.Jobs.Plex
         private readonly IRepository<PlexWatchlistUserError> _userError;
         private readonly IMovieDbApi _movieDbApi;
         private readonly INotificationHelper _notificationHelper;
+        private readonly IPlexTokenKeepAliveService _tokenKeepAliveService;
 
         public PlexWatchlistImport(IPlexApi plexApi, ISettingsService<PlexSettings> settings, OmbiUserManager ombiUserManager,
             IMovieRequestEngine movieRequestEngine, ITvRequestEngine tvRequestEngine, INotificationHubService notificationHubService,
             ILogger<PlexWatchlistImport> logger, IExternalRepository<PlexWatchlistHistory> watchlistRepo, IRepository<PlexWatchlistUserError> userError,
-            IMovieDbApi movieDbApi, INotificationHelper notificationHelper)
+            IMovieDbApi movieDbApi, INotificationHelper notificationHelper, IPlexTokenKeepAliveService tokenKeepAliveService)
         {
             _plexApi = plexApi;
             _settings = settings;
@@ -60,6 +62,7 @@ namespace Ombi.Schedule.Jobs.Plex
             _userError = userError;
             _movieDbApi = movieDbApi;
             _notificationHelper = notificationHelper;
+            _tokenKeepAliveService = tokenKeepAliveService;
         }
 
         public async Task Execute(IJobExecutionContext context)
@@ -97,6 +100,36 @@ namespace Ombi.Schedule.Jobs.Plex
                     }
 
                     _logger.LogDebug($"Starting Watchlist Import for {user.UserName} with token {user.MediaServerToken}");
+                    
+                    // Keep the token alive before attempting watchlist import
+                    var keepAliveSuccess = await _tokenKeepAliveService.KeepTokenAliveAsync(user.MediaServerToken, context?.CancellationToken ?? CancellationToken.None);
+                    if (!keepAliveSuccess)
+                    {
+                        _logger.LogWarning($"Token for user '{user.UserName}' is invalid or expired (keep-alive failed). Recording error and skipping.");
+                        await _userError.Add(new PlexWatchlistUserError
+                        {
+                            UserId = user.Id,
+                            MediaServerToken = user.MediaServerToken,
+                        });
+
+                        // Send notification to user about token expiration
+                        if (settings.NotifyOnWatchlistTokenExpiration && !string.IsNullOrEmpty(user.Email))
+                        {
+                            var notificationModel = new NotificationOptions
+                            {
+                                NotificationType = NotificationType.PlexWatchlistTokenExpired,
+                                Recipient = user.Email,
+                                DateTime = DateTime.Now,
+                                Substitutes = new Dictionary<string, string>
+                                {
+                                    { "UserName", user.UserName }
+                                }
+                            };
+                            await _notificationHelper.Notify(notificationModel);
+                        }
+                        continue;
+                    }
+                    
                     var watchlist = await _plexApi.GetWatchlist(user.MediaServerToken, context?.CancellationToken ?? CancellationToken.None);
                     if (watchlist?.AuthError ?? false)
                     {