diff --git a/Jellyfin.Server.Implementations/Item/BaseItemRepository.cs b/Jellyfin.Server.Implementations/Item/BaseItemRepository.cs
index 2a8c0535..122b3f15 100644
--- a/Jellyfin.Server.Implementations/Item/BaseItemRepository.cs
+++ b/Jellyfin.Server.Implementations/Item/BaseItemRepository.cs
@@ -63,6 +63,9 @@ public sealed class BaseItemRepository
     /// </summary>
     public static readonly Guid PlaceholderId = Guid.Parse("00000000-0000-0000-0000-000000000001");
 
+    private const string PlaceholderType = "PLACEHOLDER";
+    private const string PlaceholderName = "This is a placeholder item for UserData that has been detacted from its original item";
+
     /// <summary>
     /// This holds all the types in the running assemblies
     /// so that we can de-serialize properly when we don't have strong types.
@@ -129,6 +132,8 @@ public sealed class BaseItemRepository
                 {
                     var date = (DateTime?)DateTime.UtcNow;
 
+                    await EnsurePlaceholderItemAsync(context, cancellationToken).ConfigureAwait(false);
+
                     var relatedItems = ids.SelectMany(f => TraverseHirachyDown(f, context)).ToArray();
 
                     // Remove any UserData entries for the placeholder item that would conflict with the UserData
@@ -196,6 +201,38 @@ public sealed class BaseItemRepository
         }
     }
 
+    private async Task EnsurePlaceholderItemAsync(JellyfinDbContext context, CancellationToken cancellationToken)
+    {
+        if (await context.BaseItems.AnyAsync(e => e.Id == PlaceholderId, cancellationToken).ConfigureAwait(false))
+        {
+            return;
+        }
+
+        var placeholder = new BaseItemEntity
+        {
+            Id = PlaceholderId,
+            Type = PlaceholderType,
+            Name = PlaceholderName
+        };
+
+        await context.BaseItems.AddAsync(placeholder, cancellationToken).ConfigureAwait(false);
+
+        try
+        {
+            await context.SaveChangesAsync(cancellationToken).ConfigureAwait(false);
+            _logger.LogWarning("The detached UserData placeholder item was missing and has been recreated.");
+        }
+        catch (DbUpdateException)
+        {
+            context.Entry(placeholder).State = EntityState.Detached;
+
+            if (!await context.BaseItems.AnyAsync(e => e.Id == PlaceholderId, cancellationToken).ConfigureAwait(false))
+            {
+                throw;
+            }
+        }
+    }
+
     /// <inheritdoc />
     public void UpdateInheritedValues()
     {
diff --git a/tests/Jellyfin.Server.Implementations.Tests/Item/BaseItemRepositoryTests.cs b/tests/Jellyfin.Server.Implementations.Tests/Item/BaseItemRepositoryTests.cs
index ed6a9ec3..74c60aec 100644
--- a/tests/Jellyfin.Server.Implementations.Tests/Item/BaseItemRepositoryTests.cs
+++ b/tests/Jellyfin.Server.Implementations.Tests/Item/BaseItemRepositoryTests.cs
@@ -5,9 +5,17 @@
 namespace Jellyfin.Server.Implementations.Tests.Item;
 
 using System;
+using System.Threading;
+using System.Threading.Tasks;
+using Jellyfin.Database.Implementations;
 using Jellyfin.Database.Implementations.Entities;
+using Jellyfin.Database.Implementations.Locking;
 using Jellyfin.Server.Implementations.Item;
 using MediaBrowser.Controller;
+using MediaBrowser.Controller.Configuration;
+using MediaBrowser.Controller.Persistence;
+using Microsoft.Data.Sqlite;
+using Microsoft.EntityFrameworkCore;
 using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
@@ -73,4 +81,112 @@ public class BaseItemRepositoryTests
         // Assert
         Assert.NotNull(result);
     }
+
+    [Fact]
+    public async Task DeleteItemAsync_RecreatesMissingPlaceholderBeforeDetachingUserData()
+    {
+        await using var dbFactory = new TestDbContextFactory();
+
+        Guid itemId;
+        await using (var context = await dbFactory.CreateDbContextAsync(CancellationToken.None))
+        {
+            await context.Database.EnsureCreatedAsync();
+
+            var user = new User("test-user", "Default", "Default");
+            var item = new BaseItemEntity
+            {
+                Id = Guid.NewGuid(),
+                Type = "TestItem",
+                Name = "Delete me"
+            };
+
+            context.Users.Add(user);
+            context.BaseItems.Add(item);
+            context.UserData.Add(new UserData
+            {
+                CustomDataKey = "userdata-key",
+                ItemId = item.Id,
+                Item = item,
+                UserId = user.Id,
+                User = user,
+                Played = true,
+                PlayCount = 1
+            });
+
+            await context.SaveChangesAsync();
+
+            var placeholder = await context.BaseItems.SingleAsync(e => e.Id == BaseItemRepository.PlaceholderId);
+            context.BaseItems.Remove(placeholder);
+            await context.SaveChangesAsync();
+
+            itemId = item.Id;
+        }
+
+        var repository = new BaseItemRepository(
+            dbFactory,
+            Mock.Of<IServerApplicationHost>(),
+            Mock.Of<IItemTypeLookup>(),
+            Mock.Of<IServerConfigurationManager>(),
+            NullLogger<BaseItemRepository>.Instance);
+
+        await repository.DeleteItemAsync([itemId], CancellationToken.None);
+
+        await using var verificationContext = await dbFactory.CreateDbContextAsync(CancellationToken.None);
+        var recreatedPlaceholder = await verificationContext.BaseItems.SingleOrDefaultAsync(e => e.Id == BaseItemRepository.PlaceholderId);
+        var detachedUserData = await verificationContext.UserData.SingleAsync();
+
+        Assert.NotNull(recreatedPlaceholder);
+        Assert.Null(await verificationContext.BaseItems.SingleOrDefaultAsync(e => e.Id == itemId));
+        Assert.Equal(BaseItemRepository.PlaceholderId, detachedUserData.ItemId);
+        Assert.NotNull(detachedUserData.RetentionDate);
+    }
+
+    private sealed class TestDbContextFactory : IDbContextFactory<JellyfinDbContext>, IAsyncDisposable
+    {
+        private readonly SqliteConnection _connection;
+        private readonly DbContextOptions<JellyfinDbContext> _options;
+        private readonly Mock<IJellyfinDatabaseProvider> _databaseProviderMock;
+        private readonly Mock<IEntityFrameworkCoreLockingBehavior> _lockingBehaviorMock;
+
+        public TestDbContextFactory()
+        {
+            _connection = new SqliteConnection("Data Source=:memory:");
+            _connection.Open();
+
+            _options = new DbContextOptionsBuilder<JellyfinDbContext>()
+                .UseSqlite(_connection)
+                .Options;
+
+            _databaseProviderMock = new Mock<IJellyfinDatabaseProvider>();
+            _databaseProviderMock.Setup(m => m.OnModelCreating(It.IsAny<ModelBuilder>()));
+            _databaseProviderMock.Setup(m => m.ConfigureConventions(It.IsAny<ModelConfigurationBuilder>()));
+
+            _lockingBehaviorMock = new Mock<IEntityFrameworkCoreLockingBehavior>();
+            _lockingBehaviorMock
+                .Setup(m => m.OnSaveChanges(It.IsAny<JellyfinDbContext>(), It.IsAny<Action>()))
+                .Callback<JellyfinDbContext, Action>((_, saveChanges) => saveChanges());
+            _lockingBehaviorMock
+                .Setup(m => m.OnSaveChangesAsync(It.IsAny<JellyfinDbContext>(), It.IsAny<Func<Task>>()))
+                .Returns<JellyfinDbContext, Func<Task>>((_, saveChanges) => saveChanges());
+        }
+
+        public JellyfinDbContext CreateDbContext()
+        {
+            return new JellyfinDbContext(
+                _options,
+                NullLogger<JellyfinDbContext>.Instance,
+                _databaseProviderMock.Object,
+                _lockingBehaviorMock.Object);
+        }
+
+        public ValueTask<JellyfinDbContext> CreateDbContextAsync(CancellationToken cancellationToken = default)
+        {
+            return ValueTask.FromResult(CreateDbContext());
+        }
+
+        public async ValueTask DisposeAsync()
+        {
+            await _connection.DisposeAsync();
+        }
+    }
 }