diff --git a/CONTRIBUTORS.md b/CONTRIBUTORS.md
index 9b1ac0673a..7a763a46c1 100644
--- a/CONTRIBUTORS.md
+++ b/CONTRIBUTORS.md
@@ -106,6 +106,7 @@
  - [shemanaev](https://github.com/shemanaev)
  - [skaro13](https://github.com/skaro13)
  - [sl1288](https://github.com/sl1288)
+ - [Smith00101010](https://github.com/Smith00101010)
  - [sorinyo2004](https://github.com/sorinyo2004)
  - [sparky8251](https://github.com/sparky8251)
  - [spookbits](https://github.com/spookbits)
diff --git a/Emby.Server.Implementations/Sorting/AiredEpisodeOrderComparer.cs b/Emby.Server.Implementations/Sorting/AiredEpisodeOrderComparer.cs
index 1f68a9c810..60698e803d 100644
--- a/Emby.Server.Implementations/Sorting/AiredEpisodeOrderComparer.cs
+++ b/Emby.Server.Implementations/Sorting/AiredEpisodeOrderComparer.cs
@@ -131,11 +131,11 @@ namespace Emby.Server.Implementations.Sorting
             return GetSpecialCompareValue(x).CompareTo(GetSpecialCompareValue(y));
         }
 
-        private static int GetSpecialCompareValue(Episode item)
+        private static long GetSpecialCompareValue(Episode item)
         {
             // First sort by season number
             // Since there are three sort orders, pad with 9 digits (3 for each, figure 1000 episode buffer should be enough)
-            var val = (item.AirsAfterSeasonNumber ?? item.AirsBeforeSeasonNumber ?? 0) * 1000000000;
+            var val = (item.AirsAfterSeasonNumber ?? item.AirsBeforeSeasonNumber ?? 0) * 1000000000L;
 
             // Second sort order is if it airs after the season
             if (item.AirsAfterSeasonNumber.HasValue)
diff --git a/Emby.Server.Implementations/TV/TVSeriesManager.cs b/Emby.Server.Implementations/TV/TVSeriesManager.cs
index 839b62448b..d3f6fa34d8 100644
--- a/Emby.Server.Implementations/TV/TVSeriesManager.cs
+++ b/Emby.Server.Implementations/TV/TVSeriesManager.cs
@@ -2,7 +2,6 @@
 
 using System;
 using System.Collections.Generic;
-using System.Globalization;
 using System.Linq;
 using Jellyfin.Data.Entities;
 using Jellyfin.Data.Enums;
@@ -11,7 +10,6 @@ using MediaBrowser.Controller.Dto;
 using MediaBrowser.Controller.Entities;
 using MediaBrowser.Controller.Library;
 using MediaBrowser.Controller.TV;
-using MediaBrowser.Model.Entities;
 using MediaBrowser.Model.Querying;
 using Episode = MediaBrowser.Controller.Entities.TV.Episode;
 using Series = MediaBrowser.Controller.Entities.TV.Series;
@@ -23,12 +21,14 @@ namespace Emby.Server.Implementations.TV
         private readonly IUserManager _userManager;
         private readonly IUserDataManager _userDataManager;
         private readonly ILibraryManager _libraryManager;
+        private readonly IServerConfigurationManager _configurationManager;
 
-        public TVSeriesManager(IUserManager userManager, IUserDataManager userDataManager, ILibraryManager libraryManager)
+        public TVSeriesManager(IUserManager userManager, IUserDataManager userDataManager, ILibraryManager libraryManager, IServerConfigurationManager configurationManager)
         {
             _userManager = userManager;
             _userDataManager = userDataManager;
             _libraryManager = libraryManager;
+            _configurationManager = configurationManager;
         }
 
         public QueryResult<BaseItem> GetNextUp(NextUpQuery request, DtoOptions dtoOptions)
@@ -200,13 +200,10 @@ namespace Emby.Server.Implementations.TV
                 ParentIndexNumberNotEquals = 0,
                 DtoOptions = new DtoOptions
                 {
-                    Fields = new ItemFields[]
-                    {
-                        ItemFields.SortName
-                    },
+                    Fields = new[] { ItemFields.SortName },
                     EnableImages = false
                 }
-            }).FirstOrDefault();
+            }).Cast<Episode>().FirstOrDefault();
 
             Func<Episode> getEpisode = () =>
             {
@@ -224,6 +221,43 @@ namespace Emby.Server.Implementations.TV
                     DtoOptions = dtoOptions
                 }).Cast<Episode>().FirstOrDefault();
 
+                if (_configurationManager.Configuration.DisplaySpecialsWithinSeasons)
+                {
+                    var consideredEpisodes = _libraryManager.GetItemList(new InternalItemsQuery(user)
+                    {
+                        AncestorWithPresentationUniqueKey = null,
+                        SeriesPresentationUniqueKey = seriesKey,
+                        ParentIndexNumber = 0,
+                        IncludeItemTypes = new[] { nameof(Episode) },
+                        IsPlayed = false,
+                        IsVirtualItem = false,
+                        DtoOptions = dtoOptions
+                    })
+                    .Cast<Episode>()
+                    .Where(episode => episode.AirsBeforeSeasonNumber != null || episode.AirsAfterSeasonNumber != null)
+                    .ToList();
+
+                    if (lastWatchedEpisode != null)
+                    {
+                        // Last watched episode is added, because there could be specials that aired before the last watched episode
+                        consideredEpisodes.Add(lastWatchedEpisode);
+                    }
+
+                    if (nextEpisode != null)
+                    {
+                        consideredEpisodes.Add(nextEpisode);
+                    }
+
+                    var sortedConsideredEpisodes = _libraryManager.Sort(consideredEpisodes, user, new[] { (ItemSortBy.AiredEpisodeOrder, SortOrder.Ascending) })
+                        .Cast<Episode>();
+                    if (lastWatchedEpisode != null)
+                    {
+                        sortedConsideredEpisodes = sortedConsideredEpisodes.SkipWhile(episode => episode.Id != lastWatchedEpisode.Id).Skip(1);
+                    }
+
+                    nextEpisode = sortedConsideredEpisodes.FirstOrDefault();
+                }
+
                 if (nextEpisode != null)
                 {
                     var userData = _userDataManager.GetUserData(user, nextEpisode);