diff --git a/osu.Game/Database/LegacyImportManager.cs b/osu.Game/Database/LegacyImportManager.cs
index 20738f859e..7e1641d16f 100644
--- a/osu.Game/Database/LegacyImportManager.cs
+++ b/osu.Game/Database/LegacyImportManager.cs
@@ -3,6 +3,9 @@
 
 using System;
 using System.Collections.Generic;
+using System.Diagnostics.CodeAnalysis;
+using System.IO;
+using System.Linq;
 using System.Threading;
 using System.Threading.Tasks;
 using osu.Framework;
@@ -54,6 +57,49 @@ namespace osu.Game.Database
 
         public void UpdateStorage(string stablePath) => cachedStorage = new StableStorage(stablePath, gameHost as DesktopGameHost);
 
+        /// <summary>
+        /// Checks whether a valid location to run a stable import from can be determined starting from the supplied <paramref name="directory"/>.
+        /// </summary>
+        /// <param name="directory">The directory to check for stable import eligibility.</param>
+        /// <param name="stableRoot">
+        /// If the return value is <see langword="true"/>,
+        /// this parameter will contain the <see cref="DirectoryInfo"/> to use as the root directory for importing.
+        /// </param>
+        public bool IsUsableForStableImport(DirectoryInfo? directory, [NotNullWhen(true)] out DirectoryInfo? stableRoot)
+        {
+            if (directory == null)
+            {
+                stableRoot = null;
+                return false;
+            }
+
+            // A full stable installation will have a configuration file present.
+            // This is the best case scenario, as it may contain a custom beatmap directory we need to traverse to.
+            if (directory.GetFiles(@"osu!.*.cfg").Any())
+            {
+                stableRoot = directory;
+                return true;
+            }
+
+            // The user may only have their songs or skins folders left.
+            // We still want to allow them to import based on this.
+            if (directory.GetDirectories(@"Songs").Any() || directory.GetDirectories(@"Skins").Any())
+            {
+                stableRoot = directory;
+                return true;
+            }
+
+            // The user may have traversed *inside* their songs or skins folders.
+            if (directory.Parent != null && (directory.Name == @"Songs" || directory.Name == @"Skins"))
+            {
+                stableRoot = directory.Parent;
+                return true;
+            }
+
+            stableRoot = null;
+            return false;
+        }
+
         public bool CheckSongsFolderHardLinkAvailability()
         {
             var stableStorage = GetCurrentStableStorage();
diff --git a/osu.Game/Overlays/FirstRunSetup/ScreenImportFromStable.cs b/osu.Game/Overlays/FirstRunSetup/ScreenImportFromStable.cs
index 23f3b3e1af..24ac5e72e8 100644
--- a/osu.Game/Overlays/FirstRunSetup/ScreenImportFromStable.cs
+++ b/osu.Game/Overlays/FirstRunSetup/ScreenImportFromStable.cs
@@ -244,6 +244,8 @@ namespace osu.Game.Overlays.FirstRunSetup
             [Resolved(canBeNull: true)] // Can't really be null but required to handle potential of disposal before DI completes.
             private OsuGameBase? game { get; set; }
 
+            private bool changingDirectory;
+
             protected override void LoadComplete()
             {
                 base.LoadComplete();
@@ -259,24 +261,37 @@ namespace osu.Game.Overlays.FirstRunSetup
 
             private void onDirectorySelected(ValueChangedEvent<DirectoryInfo?> directory)
             {
-                if (directory.NewValue == null)
-                {
-                    Current.Value = string.Empty;
+                if (changingDirectory)
                     return;
+
+                try
+                {
+                    changingDirectory = true;
+
+                    if (directory.NewValue == null)
+                    {
+                        Current.Value = string.Empty;
+                        return;
+                    }
+
+                    // DirectorySelectors can trigger a noop value changed, but `DirectoryInfo` equality doesn't catch this.
+                    if (directory.OldValue?.FullName == directory.NewValue.FullName)
+                        return;
+
+                    if (legacyImportManager.IsUsableForStableImport(directory.NewValue, out var stableRoot))
+                    {
+                        this.HidePopover();
+
+                        string path = stableRoot.FullName;
+
+                        legacyImportManager.UpdateStorage(path);
+                        Current.Value = path;
+                        currentDirectory.Value = stableRoot;
+                    }
                 }
-
-                // DirectorySelectors can trigger a noop value changed, but `DirectoryInfo` equality doesn't catch this.
-                if (directory.OldValue?.FullName == directory.NewValue.FullName)
-                    return;
-
-                if (directory.NewValue?.GetFiles(@"osu!.*.cfg").Any() ?? false)
+                finally
                 {
-                    this.HidePopover();
-
-                    string path = directory.NewValue.FullName;
-
-                    legacyImportManager.UpdateStorage(path);
-                    Current.Value = path;
+                    changingDirectory = false;
                 }
             }
 
diff --git a/osu.Game/Overlays/Settings/Sections/Maintenance/StableDirectorySelectScreen.cs b/osu.Game/Overlays/Settings/Sections/Maintenance/StableDirectorySelectScreen.cs
index 1b935b0cec..3f12b9c0df 100644
--- a/osu.Game/Overlays/Settings/Sections/Maintenance/StableDirectorySelectScreen.cs
+++ b/osu.Game/Overlays/Settings/Sections/Maintenance/StableDirectorySelectScreen.cs
@@ -1,11 +1,13 @@
 // 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.Tasks;
+using osu.Framework.Allocation;
 using osu.Framework.Localisation;
 using osu.Framework.Screens;
+using osu.Game.Database;
 
 namespace osu.Game.Overlays.Settings.Sections.Maintenance
 {
@@ -13,9 +15,12 @@ namespace osu.Game.Overlays.Settings.Sections.Maintenance
     {
         private readonly TaskCompletionSource<string> taskCompletionSource;
 
+        [Resolved]
+        private LegacyImportManager legacyImportManager { get; set; } = null!;
+
         protected override OverlayActivation InitialOverlayActivationMode => OverlayActivation.Disabled;
 
-        protected override bool IsValidDirectory(DirectoryInfo? info) => info?.GetFiles("osu!.*.cfg").Any() ?? false;
+        protected override bool IsValidDirectory(DirectoryInfo? info) => legacyImportManager.IsUsableForStableImport(info, out _);
 
         public override LocalisableString HeaderText => "Please select your osu!stable install location";
 
@@ -26,7 +31,10 @@ namespace osu.Game.Overlays.Settings.Sections.Maintenance
 
         protected override void OnSelection(DirectoryInfo directory)
         {
-            taskCompletionSource.TrySetResult(directory.FullName);
+            if (!legacyImportManager.IsUsableForStableImport(directory, out var stableRoot))
+                throw new InvalidOperationException($@"{nameof(OnSelection)} was called on an invalid directory. This should never happen.");
+
+            taskCompletionSource.TrySetResult(stableRoot.FullName);
             this.Exit();
         }