diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2675a4c8..38c41e6c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/).
 - Fix NVIDIA second-gen maxwell capabilities detection
 - Return distinct search results for episodes and other videos that have the same title
   - For example, two other videos both named `Trailer` would previously have displayed as one item in search results
+- Fix schedules that would begin to repeat the same content in the same order after a couple of days
 
 ### Added
 - Add `640x480` resolution
diff --git a/ErsatzTV.Core.Tests/ErsatzTV.Core.Tests.csproj b/ErsatzTV.Core.Tests/ErsatzTV.Core.Tests.csproj
index dd1d5d18..d7ad3ccd 100644
--- a/ErsatzTV.Core.Tests/ErsatzTV.Core.Tests.csproj
+++ b/ErsatzTV.Core.Tests/ErsatzTV.Core.Tests.csproj
@@ -31,6 +31,7 @@
 
     <ItemGroup>
       <ProjectReference Include="..\ErsatzTV.Core\ErsatzTV.Core.csproj" />
+      <ProjectReference Include="..\ErsatzTV.Infrastructure\ErsatzTV.Infrastructure.csproj" />
     </ItemGroup>
 
     <ItemGroup>
diff --git a/ErsatzTV.Core.Tests/Scheduling/PlayoutBuilderTests.cs b/ErsatzTV.Core.Tests/Scheduling/PlayoutBuilderTests.cs
index 5b0912db..e4a48c2e 100644
--- a/ErsatzTV.Core.Tests/Scheduling/PlayoutBuilderTests.cs
+++ b/ErsatzTV.Core.Tests/Scheduling/PlayoutBuilderTests.cs
@@ -2235,7 +2235,7 @@ public class PlayoutBuilderTests
             DateTimeOffset start2 = HoursAfterMidnight(0);
             DateTimeOffset finish2 = start2 + TimeSpan.FromHours(6);
 
-            Playout result2 = await builder.Build(playout, PlayoutBuildMode.Continue, start2, finish2);
+            Playout result2 = await builder.Build(result, PlayoutBuildMode.Continue, start2, finish2);
 
             int secondSeedValue = result2.ProgramScheduleAnchors.Head().EnumeratorState.Seed;
 
@@ -2244,6 +2244,57 @@ public class PlayoutBuilderTests
             result2.ProgramScheduleAnchors.Head().EnumeratorState.Index.Should().Be(0);
         }
 
+        [Test]
+        public async Task ShuffleFlood_Should_MaintainRandomSeed_MultipleDays()
+        {
+            var mediaItems = new List<MediaItem>();
+            for (int i = 1; i <= 25; i++)
+            {
+                mediaItems.Add(TestMovie(i, TimeSpan.FromMinutes(55), DateTime.Today.AddHours(i)));
+            }
+
+            (PlayoutBuilder builder, Playout playout) = TestDataFloodForItems(mediaItems, PlaybackOrder.Shuffle);
+            DateTimeOffset start = HoursAfterMidnight(0).AddSeconds(5);
+            DateTimeOffset finish = start + TimeSpan.FromDays(2);
+
+            Playout result = await builder.Build(playout, PlayoutBuildMode.Reset, start, finish);
+
+            result.Items.Count.Should().Be(53);
+            result.ProgramScheduleAnchors.Count.Should().Be(2);
+
+            result.ProgramScheduleAnchors.All(x => x.AnchorDate is not null).Should().BeTrue();
+            PlayoutProgramScheduleAnchor lastCheckpoint = result.ProgramScheduleAnchors
+                .OrderByDescending(a => a.AnchorDate ?? DateTime.MinValue)
+                .First();
+            lastCheckpoint.EnumeratorState.Seed.Should().BeGreaterThan(0);
+            lastCheckpoint.EnumeratorState.Index.Should().Be(3);
+            
+            // we need to mess up the ordering to trigger the problematic behavior
+            // this simulates the way the rows are loaded with EF
+            PlayoutProgramScheduleAnchor oldest = result.ProgramScheduleAnchors.OrderByDescending(a => a.AnchorDate).Last();
+            PlayoutProgramScheduleAnchor newest = result.ProgramScheduleAnchors.OrderByDescending(a => a.AnchorDate).First();
+
+            result.ProgramScheduleAnchors = new List<PlayoutProgramScheduleAnchor>
+            {
+                oldest,
+                newest
+            };
+
+            int firstSeedValue = lastCheckpoint.EnumeratorState.Seed;
+
+            DateTimeOffset start2 = start.AddHours(1);
+            DateTimeOffset finish2 = start2 + TimeSpan.FromDays(2);
+
+            Playout result2 = await builder.Build(result, PlayoutBuildMode.Continue, start2, finish2);
+
+            PlayoutProgramScheduleAnchor continueAnchor =
+                result2.ProgramScheduleAnchors.First(x => x.AnchorDate is null);
+            int secondSeedValue = continueAnchor.EnumeratorState.Seed;
+            
+            // the continue anchor should have the same seed as the most recent (last) checkpoint from the first run
+            firstSeedValue.Should().Be(secondSeedValue);
+        }
+
         [Test]
         public async Task FloodContent_Should_FloodWithFixedStartTime_FromAnchor()
         {
diff --git a/ErsatzTV.Core.Tests/Scheduling/ScheduleIntegrationTests.cs b/ErsatzTV.Core.Tests/Scheduling/ScheduleIntegrationTests.cs
new file mode 100644
index 00000000..a8039996
--- /dev/null
+++ b/ErsatzTV.Core.Tests/Scheduling/ScheduleIntegrationTests.cs
@@ -0,0 +1,244 @@
+using Dapper;
+using Destructurama;
+using ErsatzTV.Core.Domain;
+using ErsatzTV.Core.Interfaces.Search;
+using ErsatzTV.Core.Scheduling;
+using ErsatzTV.Infrastructure.Data;
+using ErsatzTV.Infrastructure.Data.Repositories;
+using ErsatzTV.Infrastructure.Extensions;
+using LanguageExt.UnsafeValueAccess;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Logging;
+using Moq;
+using NUnit.Framework;
+using Serilog;
+using Serilog.Events;
+using Serilog.Extensions.Logging;
+
+namespace ErsatzTV.Core.Tests.Scheduling;
+
+[TestFixture]
+[Explicit]
+public class ScheduleIntegrationTests
+{
+    public ScheduleIntegrationTests()
+    {
+        Log.Logger = new LoggerConfiguration()
+            .MinimumLevel.Information()
+            .MinimumLevel.Override("Microsoft", LogEventLevel.Warning)
+            .MinimumLevel.Override("System.Net.Http.HttpClient", LogEventLevel.Warning)
+            .WriteTo.Console()
+            .Destructure.UsingAttributes()
+            .CreateLogger();
+    }
+
+    [Test]
+    public async Task Test()
+    {
+        string dbFileName = Path.GetTempFileName() + ".sqlite3";
+
+        IServiceCollection services = new ServiceCollection()
+            .AddLogging();
+
+        var connectionString = $"Data Source={dbFileName};foreign keys=true;";
+
+        services.AddDbContext<TvContext>(
+            options => options.UseSqlite(
+                connectionString,
+                o =>
+                {
+                    o.UseQuerySplittingBehavior(QuerySplittingBehavior.SplitQuery);
+                    o.MigrationsAssembly("ErsatzTV.Infrastructure");
+                }),
+            ServiceLifetime.Scoped,
+            ServiceLifetime.Singleton);
+
+        services.AddDbContextFactory<TvContext>(
+            options => options.UseSqlite(
+                connectionString,
+                o =>
+                {
+                    o.UseQuerySplittingBehavior(QuerySplittingBehavior.SplitQuery);
+                    o.MigrationsAssembly("ErsatzTV.Infrastructure");
+                }));
+        
+        SqlMapper.AddTypeHandler(new DateTimeOffsetHandler());
+        SqlMapper.AddTypeHandler(new GuidHandler());
+        SqlMapper.AddTypeHandler(new TimeSpanHandler());
+
+        services.AddSingleton((Func<IServiceProvider, ILoggerFactory>)(_ => new SerilogLoggerFactory()));
+
+        ServiceProvider provider = services.BuildServiceProvider();
+
+        IDbContextFactory<TvContext> factory = provider.GetRequiredService<IDbContextFactory<TvContext>>();
+
+        ILogger<ScheduleIntegrationTests> logger = provider.GetRequiredService<ILogger<ScheduleIntegrationTests>>();
+        logger.LogInformation("Database is at {File}", dbFileName);
+
+        await using TvContext dbContext = await factory.CreateDbContextAsync(CancellationToken.None);
+        await dbContext.Database.MigrateAsync(CancellationToken.None);
+        await DbInitializer.Initialize(dbContext, CancellationToken.None);
+
+        var path = new LibraryPath
+        {
+            Path = "Test LibraryPath"
+        };
+        
+        var library = new LocalLibrary
+        {
+            MediaKind = LibraryMediaKind.Movies,
+            Paths = new List<LibraryPath> { path },
+            MediaSource = new LocalMediaSource()
+        };
+
+        await dbContext.Libraries.AddAsync(library);
+        await dbContext.SaveChangesAsync();
+        
+        var movies = new List<Movie>();
+        for (var i = 1; i < 25; i++)
+        {
+            var movie = new Movie
+            {
+                MediaVersions = new List<MediaVersion>
+                {
+                    new() { Duration = TimeSpan.FromMinutes(55) }
+                },
+                MovieMetadata = new List<MovieMetadata>
+                {
+                    new()
+                    {
+                        Title = $"Movie {i}",
+                        ReleaseDate = new DateTime(2000, 1, 1).AddDays(i)
+                    }
+                },
+                LibraryPath = path,
+                LibraryPathId = path.Id
+            };
+
+            movies.Add(movie);
+        }
+
+        await dbContext.Movies.AddRangeAsync(movies);
+        await dbContext.SaveChangesAsync();
+
+        var collection = new Collection
+        {
+            Name = "Test Collection",
+            MediaItems = movies.Cast<MediaItem>().ToList()
+        };
+
+        await dbContext.Collections.AddAsync(collection);
+        await dbContext.SaveChangesAsync();
+
+        var scheduleItems = new List<ProgramScheduleItem>
+        {
+            new ProgramScheduleItemDuration
+            {
+                Collection = collection,
+                CollectionId = collection.Id,
+                PlayoutDuration = TimeSpan.FromHours(1),
+                TailMode = TailMode.None, // immediately continue
+                PlaybackOrder = PlaybackOrder.Shuffle
+            }
+        };
+
+        int playoutId = await AddTestData(dbContext, scheduleItems);
+
+        DateTimeOffset start = new DateTimeOffset(2022, 7, 26, 8, 0, 5, TimeSpan.FromHours(-5));
+        DateTimeOffset finish = start.AddDays(2);
+        
+        var builder = new PlayoutBuilder(
+            new ConfigElementRepository(factory),
+            new MediaCollectionRepository(new Mock<ISearchIndex>().Object, factory),
+            new TelevisionRepository(factory),
+            new ArtistRepository(factory),
+            provider.GetRequiredService<ILogger<PlayoutBuilder>>());
+
+        for (var i = 0; i <= (24 * 4); i++)
+        {
+            await using TvContext context = await factory.CreateDbContextAsync();
+            
+            Option<Playout> maybePlayout = await GetPlayout(context, playoutId);
+            Playout playout = maybePlayout.ValueUnsafe();
+
+            await builder.Build(playout, PlayoutBuildMode.Continue, start.AddHours(i), finish.AddHours(i));
+
+            await context.SaveChangesAsync();
+        }
+    }
+
+    private static async Task<int> AddTestData(TvContext dbContext, List<ProgramScheduleItem> scheduleItems)
+    {
+        var ffmpegProfile = new FFmpegProfile
+        {
+            Name = "Test FFmpeg Profile"
+        };
+
+        await dbContext.FFmpegProfiles.AddAsync(ffmpegProfile);
+        await dbContext.SaveChangesAsync();
+        
+        var channel = new Channel(Guid.Parse("00000000-0000-0000-0000-000000000001"))
+        {
+            Name = "Test Channel",
+            FFmpegProfile = ffmpegProfile,
+            FFmpegProfileId = ffmpegProfile.Id
+        };
+
+        await dbContext.Channels.AddAsync(channel);
+        await dbContext.SaveChangesAsync();
+
+        var schedule = new ProgramSchedule
+        {
+            Name = "Test Schedule",
+            Items = scheduleItems
+        };
+
+        await dbContext.ProgramSchedules.AddAsync(schedule);
+        await dbContext.SaveChangesAsync();
+
+        var playout = new Playout
+        {
+            Channel = channel,
+            ChannelId = channel.Id,
+            ProgramSchedule = schedule,
+            ProgramScheduleId = schedule.Id
+        };
+
+        await dbContext.Playouts.AddAsync(playout);
+        await dbContext.SaveChangesAsync();
+
+        return playout.Id;
+    }
+
+    private static async Task<Option<Playout>> GetPlayout(TvContext dbContext, int playoutId)
+    {
+        return await dbContext.Playouts
+            .Include(p => p.Channel)
+            .Include(p => p.Items)
+            .Include(p => p.ProgramScheduleAnchors)
+            .ThenInclude(a => a.MediaItem)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.Collection)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.MediaItem)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.PreRollFiller)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.MidRollFiller)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.PostRollFiller)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.TailFiller)
+            .Include(p => p.ProgramSchedule)
+            .ThenInclude(ps => ps.Items)
+            .ThenInclude(psi => psi.FallbackFiller)
+            .SelectOneAsync(p => p.Id, p => p.Id == playoutId);
+    }
+}
diff --git a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
index 20b83a0b..d0bf0041 100644
--- a/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
+++ b/ErsatzTV.Core/Scheduling/PlayoutBuilder.cs
@@ -626,9 +626,7 @@ public class PlayoutBuilder : IPlayoutBuilder
                      && a.MediaItemId == collectionKey.MediaItemId
                      && a.AnchorDate is null);
 
-            var maybeEnumeratorState = collectionEnumerators.GroupBy(e => e.Key, e => e.Value.State).ToDictionary(
-                mcs => mcs.Key,
-                mcs => mcs.Head());
+            var maybeEnumeratorState = collectionEnumerators.ToDictionary(e => e.Key, e => e.Value.State);
 
             PlayoutProgramScheduleAnchor scheduleAnchor = maybeExisting.Match(
                 existing =>
@@ -658,10 +656,10 @@ public class PlayoutBuilder : IPlayoutBuilder
             result.Add(scheduleAnchor);
         }
 
-        foreach (PlayoutProgramScheduleAnchor continueAnchor in playout.ProgramScheduleAnchors.Where(
+        foreach (PlayoutProgramScheduleAnchor checkpointAnchor in playout.ProgramScheduleAnchors.Where(
                      a => a.AnchorDate is not null))
         {
-            result.Add(continueAnchor);
+            result.Add(checkpointAnchor);
         }
 
         return result;
@@ -675,7 +673,7 @@ public class PlayoutBuilder : IPlayoutBuilder
         bool randomStartPoint)
     {
         Option<PlayoutProgramScheduleAnchor> maybeAnchor = playout.ProgramScheduleAnchors
-            .OrderByDescending(a => a.AnchorDate is null)
+            .OrderByDescending(a => a.AnchorDate ?? DateTime.MaxValue)
             .FirstOrDefault(
                 a => a.ProgramScheduleId == playout.ProgramScheduleId
                      && a.CollectionType == collectionKey.CollectionType