diff --git a/osu.Game.Tests/NonVisual/CustomDataDirectoryTest.cs b/osu.Game.Tests/NonVisual/CustomDataDirectoryTest.cs
index ef2b20de64..743c924bbd 100644
--- a/osu.Game.Tests/NonVisual/CustomDataDirectoryTest.cs
+++ b/osu.Game.Tests/NonVisual/CustomDataDirectoryTest.cs
@@ -211,7 +211,61 @@ namespace osu.Game.Tests.NonVisual
                     var osu = loadOsu(host);
 
                     Assert.DoesNotThrow(() => osu.Migrate(customPath));
-                    Assert.Throws<InvalidOperationException>(() => osu.Migrate(customPath));
+                    Assert.Throws<ArgumentException>(() => osu.Migrate(customPath));
+                }
+                finally
+                {
+                    host.Exit();
+                }
+            }
+        }
+
+        [Test]
+        public void TestMigrationToNestedTargetFails()
+        {
+            using (HeadlessGameHost host = new CleanRunHeadlessGameHost(nameof(TestMigrationToNestedTargetFails)))
+            {
+                try
+                {
+                    var osu = loadOsu(host);
+
+                    Assert.DoesNotThrow(() => osu.Migrate(customPath));
+
+                    string subFolder = Path.Combine(customPath, "sub");
+
+                    if (Directory.Exists(subFolder))
+                        Directory.Delete(subFolder, true);
+
+                    Directory.CreateDirectory(subFolder);
+
+                    Assert.Throws<ArgumentException>(() => osu.Migrate(subFolder));
+                }
+                finally
+                {
+                    host.Exit();
+                }
+            }
+        }
+
+        [Test]
+        public void TestMigrationToSeeminglyNestedTarget()
+        {
+            using (HeadlessGameHost host = new CleanRunHeadlessGameHost(nameof(TestMigrationToSeeminglyNestedTarget)))
+            {
+                try
+                {
+                    var osu = loadOsu(host);
+
+                    Assert.DoesNotThrow(() => osu.Migrate(customPath));
+
+                    string seeminglySubFolder = customPath + "sub";
+
+                    if (Directory.Exists(seeminglySubFolder))
+                        Directory.Delete(seeminglySubFolder, true);
+
+                    Directory.CreateDirectory(seeminglySubFolder);
+
+                    osu.Migrate(seeminglySubFolder);
                 }
                 finally
                 {
diff --git a/osu.Game/IO/OsuStorage.cs b/osu.Game/IO/OsuStorage.cs
index 71b01ce479..ac28a05375 100644
--- a/osu.Game/IO/OsuStorage.cs
+++ b/osu.Game/IO/OsuStorage.cs
@@ -48,11 +48,21 @@ namespace osu.Game.IO
             var source = new DirectoryInfo(GetFullPath("."));
             var destination = new DirectoryInfo(newLocation);
 
+            // using Uri is the easiest way to check equality and contains (https://stackoverflow.com/a/7710620)
+            var sourceUri = new Uri(source.FullName + Path.DirectorySeparatorChar);
+            var destinationUri = new Uri(destination.FullName + Path.DirectorySeparatorChar);
+
+            if (sourceUri == destinationUri)
+                throw new ArgumentException("Destination provided is already the current location", nameof(newLocation));
+
+            if (sourceUri.IsBaseOf(destinationUri))
+                throw new ArgumentException("Destination provided is inside the source", nameof(newLocation));
+
             // ensure the new location has no files present, else hard abort
             if (destination.Exists)
             {
                 if (destination.GetFiles().Length > 0 || destination.GetDirectories().Length > 0)
-                    throw new InvalidOperationException("Migration destination already has files present");
+                    throw new ArgumentException("Destination provided already has files or directories present", nameof(newLocation));
 
                 deleteRecursive(destination);
             }