diff --git a/src/Ombi.Api.Plex/IPlexApi.cs b/src/Ombi.Api.Plex/IPlexApi.cs
index c79ec50c9..a4597765e 100644
--- a/src/Ombi.Api.Plex/IPlexApi.cs
+++ b/src/Ombi.Api.Plex/IPlexApi.cs
@@ -23,7 +23,7 @@ namespace Ombi.Api.Plex
         Task<PlexFriends> GetUsers(string authToken);
         Task<PlexAccount> GetAccount(string authToken);
         Task<PlexMetadata> GetRecentlyAdded(string authToken, string uri, string sectionId);
-        Task<OAuthPin> GetPin(int pinId);
+        Task<OAuthContainer> GetPin(int pinId);
         Task<Uri> GetOAuthUrl(string code, string applicationUrl);
         Task<PlexAddWrapper> AddUser(string emailAddress, string serverId, string authToken, int[] libs);
     }
diff --git a/src/Ombi.Api.Plex/Models/OAuth/OAuthPin.cs b/src/Ombi.Api.Plex/Models/OAuth/OAuthPin.cs
index e65cd91d4..3ab857ed3 100644
--- a/src/Ombi.Api.Plex/Models/OAuth/OAuthPin.cs
+++ b/src/Ombi.Api.Plex/Models/OAuth/OAuthPin.cs
@@ -1,7 +1,14 @@
 using System;
+using System.Collections.Generic;
 
 namespace Ombi.Api.Plex.Models.OAuth
 {
+    public class OAuthContainer
+    {
+        public OAuthPin Result { get; set; }
+        public OAuthErrorsContainer Errors { get; set; }
+    }
+
     public class OAuthPin
     {
         public int id { get; set; }
@@ -24,4 +31,15 @@ namespace Ombi.Api.Plex.Models.OAuth
         public string coordinates { get; set; }
     }
 
+    public class OAuthErrorsContainer
+    {
+        public List<OAuthErrors> errors { get; set; }
+    }
+
+    public class OAuthErrors
+    {
+        public int code { get; set; }
+        public string message { 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 0d6356457..b80534bb9 100644
--- a/src/Ombi.Api.Plex/PlexApi.cs
+++ b/src/Ombi.Api.Plex/PlexApi.cs
@@ -1,7 +1,7 @@
 using System;
 using System.Net.Http;
-using System.Reflection;
 using System.Threading.Tasks;
+using Newtonsoft.Json;
 using Ombi.Api.Plex.Models;
 using Ombi.Api.Plex.Models.Friends;
 using Ombi.Api.Plex.Models.OAuth;
@@ -208,12 +208,28 @@ namespace Ombi.Api.Plex
             return await Api.Request<PlexMetadata>(request);
         }
 
-        public async Task<OAuthPin> GetPin(int pinId)
+        public async Task<OAuthContainer> GetPin(int pinId)
         {
             var request = new Request($"api/v2/pins/{pinId}", "https://plex.tv/", HttpMethod.Get);
             await AddHeaders(request);
 
-            return await Api.Request<OAuthPin>(request);
+            var response = await Api.RequestContent(request);
+
+            if (response.Contains("errors"))
+            {
+                var errors = JsonConvert.DeserializeObject<OAuthErrorsContainer>(response, Ombi.Api.Api.Settings);
+                return new OAuthContainer
+                {
+                    Errors = errors
+                };
+            }
+
+            var pinResult = JsonConvert.DeserializeObject<OAuthPin>(response, Ombi.Api.Api.Settings);
+
+            return new OAuthContainer
+            {
+                Result = pinResult
+            };
         }
 
         public async Task<Uri> GetOAuthUrl(string code, string applicationUrl)
diff --git a/src/Ombi.Api/Api.cs b/src/Ombi.Api/Api.cs
index 7a8e7678b..66dec8b0b 100644
--- a/src/Ombi.Api/Api.cs
+++ b/src/Ombi.Api/Api.cs
@@ -73,7 +73,7 @@ namespace Ombi.Api
                 }
 
                 // do something with the response
-                var receivedString = await httpResponseMessage.Content.ReadAsStringAsync();
+                var receivedString = await httpResponseMessage.Content.ReadAsStringAsync(cancellationToken);
                 LogDebugContent(receivedString);
                 if (request.ContentType == ContentType.Json)
                 {
diff --git a/src/Ombi.Core/Authentication/PlexOAuthManager.cs b/src/Ombi.Core/Authentication/PlexOAuthManager.cs
index 76b1b5d97..78f33cee8 100644
--- a/src/Ombi.Core/Authentication/PlexOAuthManager.cs
+++ b/src/Ombi.Core/Authentication/PlexOAuthManager.cs
@@ -1,5 +1,7 @@
 using System;
+using System.Collections.Generic;
 using System.Threading.Tasks;
+using Microsoft.Extensions.Logging;
 using Ombi.Api.Plex;
 using Ombi.Api.Plex.Models;
 using Ombi.Api.Plex.Models.OAuth;
@@ -11,24 +13,37 @@ namespace Ombi.Core.Authentication
 {
     public class PlexOAuthManager : IPlexOAuthManager
     {
-        public PlexOAuthManager(IPlexApi api, ISettingsService<CustomizationSettings> settings)
+        public PlexOAuthManager(IPlexApi api, ISettingsService<CustomizationSettings> settings, ILogger<PlexOAuthManager> logger)
         {
             _api = api;
             _customizationSettingsService = settings;
+            _logger = logger;
         }
 
         private readonly IPlexApi _api;
         private readonly ISettingsService<CustomizationSettings> _customizationSettingsService;
+        private readonly ILogger _logger;
 
         public async Task<string> GetAccessTokenFromPin(int pinId)
         {
             var pin = await _api.GetPin(pinId);
-            if (pin.expiresAt < DateTime.UtcNow)
+            if (pin.Errors != null)
             {
+                foreach (var err in pin.Errors?.errors ?? new List<OAuthErrors>())
+                { 
+                    _logger.LogError($"Code: '{err.code}' : '{err.message}'");
+                }
+
+                return string.Empty;
+            }
+
+            if (pin.Result.expiresIn <= 0)
+            {
+                _logger.LogError("Pin has expired");
                 return string.Empty;
             }
 
-            return pin.authToken;
+            return pin.Result.authToken;
         }
 
         public async Task<PlexAccount> GetAccount(string accessToken)
diff --git a/src/Ombi/ClientApp/src/app/services/applications/plextv.service.ts b/src/Ombi/ClientApp/src/app/services/applications/plextv.service.ts
index f214ac291..3ce0e0a8b 100644
--- a/src/Ombi/ClientApp/src/app/services/applications/plextv.service.ts
+++ b/src/Ombi/ClientApp/src/app/services/applications/plextv.service.ts
@@ -20,6 +20,7 @@ export class PlexTvService {
         "X-Plex-Device": "Ombi (Web)",
         "X-Plex-Platform": "Web",
         "Accept": "application/json",
+        'X-Plex-Model': 'Plex OAuth',
     });
         return this.http.post<IPlexPin>("https://plex.tv/api/v2/pins?strong=true", null,  {headers});
     }