diff --git a/src/Ombi.Api.Plex/Models/PlexWatchlistContainer.cs b/src/Ombi.Api.Plex/Models/PlexWatchlistContainer.cs
index b208c189f..2eab1d255 100644
--- a/src/Ombi.Api.Plex/Models/PlexWatchlistContainer.cs
+++ b/src/Ombi.Api.Plex/Models/PlexWatchlistContainer.cs
@@ -1,9 +1,12 @@
 using System.Collections.Generic;
+using System.Text.Json.Serialization;
 
 namespace Ombi.Api.Plex.Models
 {
     public class PlexWatchlistContainer
     {
         public PlexWatchlist MediaContainer { get; set; }
+        [JsonIgnore]
+        public bool AuthError { get; set; }
     }
 }
\ No newline at end of file
diff --git a/src/Ombi.Api.Plex/PlexApi.cs b/src/Ombi.Api.Plex/PlexApi.cs
index 9f91c540c..fae4a78b9 100644
--- a/src/Ombi.Api.Plex/PlexApi.cs
+++ b/src/Ombi.Api.Plex/PlexApi.cs
@@ -1,4 +1,5 @@
 using System;
+using System.Net;
 using System.Net.Http;
 using System.Threading;
 using System.Threading.Tasks;
@@ -295,9 +296,18 @@ namespace Ombi.Api.Plex
             var request = new Request("library/sections/watchlist/all", WatchlistUri, HttpMethod.Get);
             await AddHeaders(request, plexToken);
 
-            var result = await Api.Request<PlexWatchlistContainer>(request, cancellationToken);
+            var result = await Api.Request(request, cancellationToken);
 
-            return result;
+            if (result.StatusCode.Equals(HttpStatusCode.Unauthorized))
+            {
+                return new PlexWatchlistContainer
+                {
+                    AuthError = true
+                };
+            }
+
+            var receivedString = await result.Content.ReadAsStringAsync(cancellationToken);
+            return JsonConvert.DeserializeObject<PlexWatchlistContainer>(receivedString);
         }
         
         public async Task<PlexWatchlistMetadataContainer> GetWatchlistMetadata(string ratingKey, string plexToken, CancellationToken cancellationToken)
diff --git a/src/Ombi.Schedule.Tests/PlexWatchlistImportTests.cs b/src/Ombi.Schedule.Tests/PlexWatchlistImportTests.cs
index 950f6f431..b11a3d48b 100644
--- a/src/Ombi.Schedule.Tests/PlexWatchlistImportTests.cs
+++ b/src/Ombi.Schedule.Tests/PlexWatchlistImportTests.cs
@@ -1,4 +1,5 @@
-using Moq;
+using MockQueryable.Moq;
+using Moq;
 using Moq.AutoMock;
 using NUnit.Framework;
 using Ombi.Api.Plex;
@@ -8,6 +9,7 @@ using Ombi.Core.Engine.Interfaces;
 using Ombi.Core.Models.Requests;
 using Ombi.Core.Settings;
 using Ombi.Core.Settings.Models.External;
+using Ombi.Core.Tests;
 using Ombi.Schedule.Jobs.Plex;
 using Ombi.Store.Entities;
 using Ombi.Store.Repository;
@@ -32,11 +34,12 @@ namespace Ombi.Schedule.Tests
         public void Setup()
         {
             _mocker = new AutoMocker();
-            var um = MockHelper.MockUserManager(new List<OmbiUser> { new OmbiUser { Id = "abc", UserType = UserType.PlexUser, MediaServerToken = "abc", UserName = "abc", NormalizedUserName = "ABC" } });
+            var um = MockHelper.MockUserManager(new List<OmbiUser> { new OmbiUser { Id = "abc", UserType = UserType.PlexUser, MediaServerToken = "token1", UserName = "abc", NormalizedUserName = "ABC" } });
             _mocker.Use(um);
             _context = _mocker.GetMock<IJobExecutionContext>();
             _context.Setup(x => x.CancellationToken).Returns(CancellationToken.None);
             _subject = _mocker.CreateInstance<PlexWatchlistImport>();
+            _mocker.Setup<IExternalRepository<PlexWatchlistUserError>, IQueryable<PlexWatchlistUserError>>(x => x.GetAll()).Returns(new List<PlexWatchlistUserError>().AsQueryable().BuildMock().Object);
         }
 
         [Test]
@@ -53,6 +56,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task TerminatesWhenWatchlistIsNotEnabled()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = false });
             await _subject.Execute(null);
             _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
@@ -75,9 +79,74 @@ namespace Ombi.Schedule.Tests
             _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.Add(It.IsAny<PlexWatchlistHistory>()), Times.Never);
         }
 
+        [Test]
+        public async Task AuthenticationError()
+        {
+
+            _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
+            _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer { AuthError = true });
+            await _subject.Execute(_context.Object);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IPlexApi>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Once);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.GetAll(), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.Add(It.IsAny<PlexWatchlistHistory>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistUserError>>(x => x.Add(It.Is<PlexWatchlistUserError>(x => x.UserId == "abc")), Times.Once);
+        }
+
+        [Test]
+        public async Task FailedWatchListUser_NewToken_ShouldBeRemoved()
+        {
+            _mocker.Setup<IExternalRepository<PlexWatchlistUserError>, IQueryable<PlexWatchlistUserError>>(x => x.GetAll()).Returns(new List<PlexWatchlistUserError>
+            {
+                new PlexWatchlistUserError
+                {
+                    UserId = "abc",
+                    MediaServerToken = "dead"
+                }
+            }.AsQueryable().BuildMock().Object);
+
+            _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
+            _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer { AuthError = false });
+            await _subject.Execute(_context.Object);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IPlexApi>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Once);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.GetAll(), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.Add(It.IsAny<PlexWatchlistHistory>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistUserError>>(x => x.Add(It.Is<PlexWatchlistUserError>(x => x.UserId == "abc")), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistUserError>>(x => x.Delete(It.Is<PlexWatchlistUserError>(x => x.UserId == "abc")), Times.Once);
+        }
+
+        [Test]
+        public async Task FailedWatchListUser_OldToken_ShouldSkip()
+        {
+            _mocker.Setup<IExternalRepository<PlexWatchlistUserError>, IQueryable<PlexWatchlistUserError>>(x => x.GetAll()).Returns(new List<PlexWatchlistUserError>
+            {
+                new PlexWatchlistUserError
+                {
+                    UserId = "abc",
+                    MediaServerToken = "token1"
+                }
+            }.AsQueryable().BuildMock().Object);
+
+            _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
+            _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer { AuthError = false });
+            await _subject.Execute(_context.Object);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IPlexApi>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>()), Times.Never);
+            _mocker.Verify<IMovieRequestEngine>(x => x.RequestMovie(It.IsAny<MovieRequestViewModel>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.GetAll(), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistHistory>>(x => x.Add(It.IsAny<PlexWatchlistHistory>()), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistUserError>>(x => x.Add(It.Is<PlexWatchlistUserError>(x => x.UserId == "abc")), Times.Never);
+            _mocker.Verify<IExternalRepository<PlexWatchlistUserError>>(x => x.Delete(It.Is<PlexWatchlistUserError>(x => x.UserId == "abc")), Times.Never);
+        }
+
+
         [Test]
         public async Task NoPlexUsersWithToken()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             var um = MockHelper.MockUserManager(new List<OmbiUser>
             {
@@ -102,6 +171,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task MultipleUsers()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             var um = MockHelper.MockUserManager(new List<OmbiUser>
             {
@@ -125,6 +195,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task MovieRequestFromWatchList_NoGuid()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -175,6 +246,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task TvRequestFromWatchList_NoGuid()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -224,6 +296,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task MovieRequestFromWatchList_AlreadyRequested()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -273,6 +346,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task TvRequestFromWatchList_AlreadyRequested()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -322,6 +396,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task MovieRequestFromWatchList_NoTmdbGuid()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -371,6 +446,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task TvRequestFromWatchList_NoTmdbGuid()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
@@ -420,6 +496,7 @@ namespace Ombi.Schedule.Tests
         [Test]
         public async Task MovieRequestFromWatchList_AlreadyImported()
         {
+            
             _mocker.Setup<ISettingsService<PlexSettings>, Task<PlexSettings>>(x => x.GetSettingsAsync()).ReturnsAsync(new PlexSettings { Enable = true, EnableWatchlistImport = true });
             _mocker.Setup<IPlexApi, Task<PlexWatchlistContainer>>(x => x.GetWatchlist(It.IsAny<string>(), It.IsAny<CancellationToken>())).ReturnsAsync(new PlexWatchlistContainer
             {
diff --git a/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs b/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
index 8e6b443ef..69b42213b 100644
--- a/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
+++ b/src/Ombi.Schedule/Jobs/Plex/PlexWatchlistImport.cs
@@ -1,4 +1,5 @@
 using Microsoft.AspNetCore.SignalR;
+using Microsoft.EntityFrameworkCore;
 using Microsoft.Extensions.Logging;
 using Ombi.Api.Plex;
 using Ombi.Api.Plex.Models;
@@ -32,10 +33,11 @@ namespace Ombi.Schedule.Jobs.Plex
         private readonly IHubContext<NotificationHub> _hub;
         private readonly ILogger _logger;
         private readonly IExternalRepository<PlexWatchlistHistory> _watchlistRepo;
+        private readonly IExternalRepository<PlexWatchlistUserError> _userError;
 
         public PlexWatchlistImport(IPlexApi plexApi, ISettingsService<PlexSettings> settings, OmbiUserManager ombiUserManager,
             IMovieRequestEngine movieRequestEngine, ITvRequestEngine tvRequestEngine, IHubContext<NotificationHub> hub,
-            ILogger<PlexWatchlistImport> logger, IExternalRepository<PlexWatchlistHistory> watchlistRepo)
+            ILogger<PlexWatchlistImport> logger, IExternalRepository<PlexWatchlistHistory> watchlistRepo, IExternalRepository<PlexWatchlistUserError> userError)
         {
             _plexApi = plexApi;
             _settings = settings;
@@ -45,6 +47,7 @@ namespace Ombi.Schedule.Jobs.Plex
             _hub = hub;
             _logger = logger;
             _watchlistRepo = watchlistRepo;
+            _userError = userError;
         }
 
         public async Task Execute(IJobExecutionContext context)
@@ -64,9 +67,35 @@ namespace Ombi.Schedule.Jobs.Plex
             {
                 try
                 {
+                    // Check if the user has errors and the token is the same (not refreshed)
+                    var failedUser = await _userError.GetAll().Where(x => x.UserId == user.Id).FirstOrDefaultAsync();
+                    if (failedUser != null)
+                    {
+                        if (failedUser.MediaServerToken.Equals(user.MediaServerToken))
+                        {
+                            _logger.LogInformation($"Skipping Plex Watchlist Import for user '{user.UserName}' as they failed previously and the token has not yet been refreshed");
+                            continue;
+                        }
+                        else
+                        {
+                            // remove that guy
+                            await _userError.Delete(failedUser);
+                            failedUser = null;
+                        }
+                    }
 
                     _logger.LogDebug($"Starting Watchlist Import for {user.UserName} with token {user.MediaServerToken}");
                     var watchlist = await _plexApi.GetWatchlist(user.MediaServerToken, context?.CancellationToken ?? CancellationToken.None);
+                    if (watchlist?.AuthError ?? false)
+                    {
+                        _logger.LogError($"Auth failed for user '{user.UserName}'. Need to re-authenticate with Ombi.");
+                        await _userError.Add(new PlexWatchlistUserError
+                        {
+                            UserId = user.Id,
+                            MediaServerToken = user.MediaServerToken,
+                        });
+                        continue;
+                    }
                     if (watchlist == null || !(watchlist.MediaContainer?.Metadata?.Any() ?? false))
                     {
                         _logger.LogDebug($"No watchlist found for {user.UserName}");
diff --git a/src/Ombi.Store/Context/ExternalContext.cs b/src/Ombi.Store/Context/ExternalContext.cs
index f13c1e74f..5926aae9d 100644
--- a/src/Ombi.Store/Context/ExternalContext.cs
+++ b/src/Ombi.Store/Context/ExternalContext.cs
@@ -28,6 +28,7 @@ namespace Ombi.Store.Context
         public DbSet<PlexSeasonsContent> PlexSeasonsContent { get; set; }
         public DbSet<PlexEpisode> PlexEpisode { get; set; }
         public DbSet<PlexWatchlistHistory> PlexWatchlistHistory { get; set; }
+        public DbSet<PlexWatchlistUserError> PlexWatchListUserError { get; set; }
         public DbSet<RadarrCache> RadarrCache { get; set; }
         public DbSet<CouchPotatoCache> CouchPotatoCache { get; set; }
         public DbSet<EmbyContent> EmbyContent { get; set; }
diff --git a/src/Ombi.Store/Entities/PlexWatchlistUserError.cs b/src/Ombi.Store/Entities/PlexWatchlistUserError.cs
new file mode 100644
index 000000000..6a94c226f
--- /dev/null
+++ b/src/Ombi.Store/Entities/PlexWatchlistUserError.cs
@@ -0,0 +1,14 @@
+using System.ComponentModel.DataAnnotations.Schema;
+
+namespace Ombi.Store.Entities
+{
+    [Table(nameof(PlexWatchlistUserError))]
+    public class PlexWatchlistUserError : Entity
+    {
+        public string UserId { get; set; }
+        public string MediaServerToken { get; set; }
+
+        [ForeignKey(nameof(UserId))]
+        public OmbiUser User { get; set; }
+    }
+}
diff --git a/src/Ombi.Core.Tests/DbHelper.cs b/src/Ombi.Test.Common/DbHelper.cs
similarity index 100%
rename from src/Ombi.Core.Tests/DbHelper.cs
rename to src/Ombi.Test.Common/DbHelper.cs