diff --git a/CHANGELOG.md b/CHANGELOG.md
index e858c19b2..b040c44d2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,8 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 
 ## [Unreleased]
+### Fixed
+- Fix song sorting with `Chronological` and `Shuffle In Order` playback orders
 
 ## [0.4.2-alpha] - 2022-02-26
 ### Fixed
diff --git a/ErsatzTV.Core/Scheduling/ChronologicalMediaComparer.cs b/ErsatzTV.Core/Scheduling/ChronologicalMediaComparer.cs
index 3c6add122..6a5c0682d 100644
--- a/ErsatzTV.Core/Scheduling/ChronologicalMediaComparer.cs
+++ b/ErsatzTV.Core/Scheduling/ChronologicalMediaComparer.cs
@@ -1,6 +1,5 @@
 using System;
 using System.Collections.Generic;
-using System.Linq;
 using ErsatzTV.Core.Domain;
 
 namespace ErsatzTV.Core.Scheduling
@@ -47,6 +46,23 @@ namespace ErsatzTV.Core.Scheduling
                 return date1.CompareTo(date2);
             }
 
+            string songDate1 = x switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Date ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+
+            string songDate2 = y switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Date ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+            
+            if (songDate1 != songDate2)
+            {
+                return string.Compare(songDate1, songDate2, StringComparison.Ordinal);
+            }
+
             int season1 = x switch
             {
                 Episode e => e.Season?.SeasonNumber ?? int.MaxValue,
@@ -85,6 +101,40 @@ namespace ErsatzTV.Core.Scheduling
                 return episode1.CompareTo(episode2);
             }
 
+            string album1 = x switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Album ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+
+            string album2 = y switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Album ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+
+            if (album1 != album2)
+            {
+                return string.Compare(album1, album2, StringComparison.Ordinal);
+            }
+
+            string track1 = x switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Track ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+
+            string track2 = y switch
+            {
+                Song s => s.SongMetadata.HeadOrNone().Match(sm => sm.Track ?? string.Empty, () => string.Empty),
+                _ => string.Empty
+            };
+
+            if (track1 != track2)
+            {
+                return string.Compare(track1, track2, StringComparison.Ordinal);
+            }
+
             return x.Id.CompareTo(y.Id);
         }
     }
diff --git a/ErsatzTV.Infrastructure/Data/Repositories/MediaCollectionRepository.cs b/ErsatzTV.Infrastructure/Data/Repositories/MediaCollectionRepository.cs
index 10d83dbb6..a0038d578 100644
--- a/ErsatzTV.Infrastructure/Data/Repositories/MediaCollectionRepository.cs
+++ b/ErsatzTV.Infrastructure/Data/Repositories/MediaCollectionRepository.cs
@@ -315,6 +315,45 @@ namespace ErsatzTV.Infrastructure.Data.Repositories
                         false));
             }
 
+            var allArtists = items.OfType<Song>()
+                .SelectMany(s => s.SongMetadata)
+                .Map(sm => sm.Artist)
+                .Distinct()
+                .ToList();
+
+            if (!allArtists.Contains(string.Empty))
+            {
+                allArtists.Add(string.Empty);
+            }
+
+            var songArtistCollections = new Dictionary<int, List<MediaItem>>();
+            foreach (Song song in items.OfType<Song>())
+            {
+                int key = allArtists.IndexOf(song.SongMetadata.HeadOrNone().Match(sm => sm.Artist, string.Empty));
+                
+                List<MediaItem> list = songArtistCollections.ContainsKey(key)
+                        ? songArtistCollections[key]
+                        : new List<MediaItem>();
+
+                if (list.All(i => i.Id != song.Id))
+                {
+                    list.Add(song);
+                }
+
+                songArtistCollections[key] = list;
+            }
+
+            foreach ((int _, List<MediaItem> list) in songArtistCollections)
+            {
+                result.Add(
+                    new CollectionWithItems(
+                        id--,
+                        list,
+                        true,
+                        PlaybackOrder.Chronological,
+                        false));
+            }
+
             result.Add(
                 new CollectionWithItems(
                     id,