diff --git a/osu.Game.Tournament.Tests/NonVisual/CustomTourneyDirectoryTest.cs b/osu.Game.Tournament.Tests/NonVisual/CustomTourneyDirectoryTest.cs
new file mode 100644
index 0000000000..757465d4ad
--- /dev/null
+++ b/osu.Game.Tournament.Tests/NonVisual/CustomTourneyDirectoryTest.cs
@@ -0,0 +1,157 @@
+// Copyright (c) ppy Pty Ltd <contact@ppy.sh>. Licensed under the MIT Licence.
+// See the LICENCE file in the repository root for full licence text.
+
+using System;
+using System.IO;
+using System.Linq;
+using System.Threading;
+using System.Threading.Tasks;
+using NUnit.Framework;
+using osu.Framework;
+using osu.Framework.Allocation;
+using osu.Framework.Platform;
+using osu.Game.Tournament.Configuration;
+using osu.Game.Tournament.IO;
+using osu.Game.Tests;
+
+namespace osu.Game.Tournament.Tests.NonVisual
+{
+    [TestFixture]
+    public class CustomTourneyDirectoryTest
+    {
+        [SetUp]
+        public void SetUp()
+        {
+        }
+
+        [Test]
+        public void TestDefaultDirectory()
+        {
+            using (HeadlessGameHost host = new CleanRunHeadlessGameHost(nameof(TestDefaultDirectory)))
+            {
+                try
+                {
+                    var osu = loadOsu(host);
+                    var storage = osu.Dependencies.Get<TournamentStorage>();
+                    var defaultStorage = Path.Combine(RuntimeInfo.StartupDirectory, "headless", nameof(TestDefaultDirectory), "tournaments", "default");
+                    Assert.That(storage.GetFullPath("."), Is.EqualTo(defaultStorage));
+                }
+                finally
+                {
+                    host.Exit();
+                }
+            }
+        }
+
+        [Test]
+        public void TestCustomDirectory()
+        {
+            using (HeadlessGameHost host = new HeadlessGameHost(nameof(TestCustomDirectory)))
+            {
+                string osuDesktopStorage = Path.Combine(RuntimeInfo.StartupDirectory, "headless", nameof(TestCustomDirectory));
+                const string custom_tournament = "custom";
+
+                // need access before the game has constructed its own storage yet.
+                Storage storage = new DesktopStorage(osuDesktopStorage, host);
+                // manual cleaning so we can prepare a config file.
+                storage.DeleteDirectory(string.Empty);
+
+                using (var storageConfig = new TournamentStorageManager(storage))
+                    storageConfig.Set(StorageConfig.CurrentTournament, custom_tournament);
+
+                try
+                {
+                    var osu = loadOsu(host);
+
+                    storage = osu.Dependencies.Get<TournamentStorage>();
+
+                    Assert.That(storage.GetFullPath("."), Is.EqualTo(Path.Combine(tournamentBasePath(nameof(TestCustomDirectory)), "custom")));
+                }
+                finally
+                {
+                    host.Exit();
+                }
+            }
+        }
+
+        [Test]
+        public void TestMigration()
+        {
+            using (HeadlessGameHost host = new HeadlessGameHost(nameof(TestMigration)))
+            {
+                string basePath = Path.Combine(RuntimeInfo.StartupDirectory, "headless", nameof(TestMigration), "tournament");
+
+                string videosPath = Path.Combine(basePath, "videos");
+                string modsPath = Path.Combine(basePath, "mods");
+                string flagsPath = Path.Combine(basePath, "flags");
+
+                Directory.CreateDirectory(videosPath);
+                Directory.CreateDirectory(modsPath);
+                Directory.CreateDirectory(flagsPath);
+
+                string bracketFile = Path.Combine(RuntimeInfo.StartupDirectory, "headless", nameof(TestMigration), "bracket.json");
+                string videoFile = Path.Combine(videosPath, "video.mp4");
+                string modFile = Path.Combine(modsPath, "mod.png");
+                string flagFile = Path.Combine(flagsPath, "flag.png");
+
+                File.WriteAllText(bracketFile, "{}");
+
+                File.WriteAllText(videoFile, "test");
+                File.WriteAllText(modFile, "test");
+                File.WriteAllText(flagFile, "test");
+
+                try
+                {
+                    var osu = loadOsu(host);
+
+                    var storage = osu.Dependencies.Get<TournamentStorage>();
+
+                    var migratedPath = Path.Combine(RuntimeInfo.StartupDirectory, "headless", nameof(TestMigration), "tournaments", "default");
+
+                    videosPath = Path.Combine(migratedPath, "videos");
+                    modsPath = Path.Combine(migratedPath, "mods");
+                    flagsPath = Path.Combine(migratedPath, "flags");
+
+                    videoFile = Path.Combine(videosPath, "video.mp4");
+                    modFile = Path.Combine(modsPath, "mod.png");
+                    flagFile = Path.Combine(flagsPath, "flag.png");
+
+                    Assert.That(storage.GetFullPath("."), Is.EqualTo(migratedPath));
+                    Assert.That(storage.GetFiles(".", "bracket.json").Single(), Is.EqualTo("bracket.json"));
+                    Assert.True(storage.Exists(videoFile));
+                    Assert.True(storage.Exists(modFile));
+                    Assert.True(storage.Exists(flagFile));
+                }
+                finally
+                {
+                    // Cleaning up after ourselves.
+                    host.Storage.Delete("tournament.ini");
+                    host.Storage.DeleteDirectory("tournaments");
+
+                    host.Exit();
+                }
+            }
+        }
+
+        private TournamentGameBase loadOsu(GameHost host)
+        {
+            var osu = new TournamentGameBase();
+            Task.Run(() => host.Run(osu));
+            waitForOrAssert(() => osu.IsLoaded, @"osu! failed to start in a reasonable amount of time");
+            return osu;
+        }
+
+        private static void waitForOrAssert(Func<bool> result, string failureMessage, int timeout = 90000)
+        {
+            Task task = Task.Run(() =>
+            {
+                while (!result()) Thread.Sleep(200);
+            });
+
+            Assert.IsTrue(task.Wait(timeout), failureMessage);
+        }
+
+        private string oldPath => Path.Combine(RuntimeInfo.StartupDirectory, "tournament");
+        private string tournamentBasePath(string testInstance) => Path.Combine(RuntimeInfo.StartupDirectory, "headless", testInstance, "tournaments");
+    }
+}
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