diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/MainActivity.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/MainActivity.java
index 46302965b5..f55486d51d 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/MainActivity.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/MainActivity.java
@@ -72,7 +72,7 @@ public final class MainActivity extends AppCompatActivity
     if (savedInstanceState == null)
       StartupHandler.HandleInit(this);
 
-    if (PermissionsHandler.hasWriteAccess(this))
+    if (!DirectoryInitialization.isWaitingForWriteAccess(this))
     {
       new AfterDirectoryInitializationRunner()
               .run(this, false, this::setPlatformTabsAndStartGameFileCacheService);
@@ -249,16 +249,14 @@ public final class MainActivity extends AppCompatActivity
 
     if (requestCode == PermissionsHandler.REQUEST_CODE_WRITE_PERMISSION)
     {
-      if (grantResults[0] == PackageManager.PERMISSION_GRANTED)
+      if (grantResults[0] == PackageManager.PERMISSION_DENIED)
       {
-        DirectoryInitialization.start(this);
-        new AfterDirectoryInitializationRunner()
-                .run(this, false, this::setPlatformTabsAndStartGameFileCacheService);
-      }
-      else
-      {
-        Toast.makeText(this, R.string.write_permission_needed, Toast.LENGTH_LONG).show();
+        PermissionsHandler.setWritePermissionDenied();
       }
+
+      DirectoryInitialization.start(this);
+      new AfterDirectoryInitializationRunner()
+              .run(this, false, this::setPlatformTabsAndStartGameFileCacheService);
     }
   }
 
diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/TvMainActivity.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/TvMainActivity.java
index ac846d4c24..38b8fed094 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/TvMainActivity.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/ui/main/TvMainActivity.java
@@ -30,6 +30,7 @@ import org.dolphinemu.dolphinemu.model.GameFile;
 import org.dolphinemu.dolphinemu.model.TvSettingsItem;
 import org.dolphinemu.dolphinemu.services.GameFileCacheService;
 import org.dolphinemu.dolphinemu.ui.platform.Platform;
+import org.dolphinemu.dolphinemu.utils.AfterDirectoryInitializationRunner;
 import org.dolphinemu.dolphinemu.utils.DirectoryInitialization;
 import org.dolphinemu.dolphinemu.utils.FileBrowserHelper;
 import org.dolphinemu.dolphinemu.utils.PermissionsHandler;
@@ -287,15 +288,13 @@ public final class TvMainActivity extends FragmentActivity
 
     if (requestCode == PermissionsHandler.REQUEST_CODE_WRITE_PERMISSION)
     {
-      if (grantResults[0] == PackageManager.PERMISSION_GRANTED)
+      if (grantResults[0] == PackageManager.PERMISSION_DENIED)
       {
-        DirectoryInitialization.start(this);
-        GameFileCacheService.startLoad(this);
-      }
-      else
-      {
-        Toast.makeText(this, R.string.write_permission_needed, Toast.LENGTH_LONG).show();
+        PermissionsHandler.setWritePermissionDenied();
       }
+
+      DirectoryInitialization.start(this);
+      GameFileCacheService.startLoad(this);
     }
   }
 
@@ -314,7 +313,7 @@ public final class TvMainActivity extends FragmentActivity
     ArrayObjectAdapter rowsAdapter = new ArrayObjectAdapter(new ListRowPresenter());
     mGameRows.clear();
 
-    if (PermissionsHandler.hasWriteAccess(this))
+    if (!DirectoryInitialization.isWaitingForWriteAccess(this))
     {
       GameFileCacheService.startLoad(this);
     }
diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/AfterDirectoryInitializationRunner.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/AfterDirectoryInitializationRunner.java
index 5a7f33f42a..4b07636a64 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/AfterDirectoryInitializationRunner.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/AfterDirectoryInitializationRunner.java
@@ -62,7 +62,7 @@ public class AfterDirectoryInitializationRunner
       runnable.run();
     }
     else if (abortOnFailure &&
-            showErrorMessage(context, DirectoryInitialization.getDolphinDirectoriesState(context)))
+            showErrorMessage(context, DirectoryInitialization.getDolphinDirectoriesState()))
     {
       runFinishedCallback();
     }
@@ -115,10 +115,6 @@ public class AfterDirectoryInitializationRunner
   {
     switch (state)
     {
-      case EXTERNAL_STORAGE_PERMISSION_NEEDED:
-        Toast.makeText(context, R.string.write_permission_needed, Toast.LENGTH_LONG).show();
-        return true;
-
       case CANT_FIND_EXTERNAL_STORAGE:
         Toast.makeText(context, R.string.external_storage_not_mounted, Toast.LENGTH_LONG).show();
         return true;
diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/DirectoryInitialization.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/DirectoryInitialization.java
index 0dc5432c54..c2f6d638df 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/DirectoryInitialization.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/DirectoryInitialization.java
@@ -13,6 +13,7 @@ import android.os.Environment;
 import android.preference.PreferenceManager;
 
 import androidx.annotation.NonNull;
+import androidx.annotation.Nullable;
 import androidx.localbroadcastmanager.content.LocalBroadcastManager;
 
 import org.dolphinemu.dolphinemu.NativeLibrary;
@@ -47,7 +48,6 @@ public final class DirectoryInitialization
   {
     NOT_YET_INITIALIZED,
     DOLPHIN_DIRECTORIES_INITIALIZED,
-    EXTERNAL_STORAGE_PERMISSION_NEEDED,
     CANT_FIND_EXTERNAL_STORAGE
   }
 
@@ -65,34 +65,27 @@ public final class DirectoryInitialization
   {
     if (directoryState != DirectoryInitializationState.DOLPHIN_DIRECTORIES_INITIALIZED)
     {
-      if (PermissionsHandler.hasWriteAccess(context))
+      if (setDolphinUserDirectory(context))
       {
-        if (setDolphinUserDirectory(context))
+        initializeInternalStorage(context);
+        boolean wiimoteIniWritten = initializeExternalStorage(context);
+        NativeLibrary.Initialize();
+        NativeLibrary.ReportStartToAnalytics();
+
+        areDirectoriesAvailable = true;
+
+        if (wiimoteIniWritten)
         {
-          initializeInternalStorage(context);
-          boolean wiimoteIniWritten = initializeExternalStorage(context);
-          NativeLibrary.Initialize();
-          NativeLibrary.ReportStartToAnalytics();
-
-          areDirectoriesAvailable = true;
-
-          if (wiimoteIniWritten)
-          {
-            // This has to be done after calling NativeLibrary.Initialize(),
-            // as it relies on the config system
-            EmulationActivity.updateWiimoteNewIniPreferences(context);
-          }
-
-          directoryState = DirectoryInitializationState.DOLPHIN_DIRECTORIES_INITIALIZED;
-        }
-        else
-        {
-          directoryState = DirectoryInitializationState.CANT_FIND_EXTERNAL_STORAGE;
+          // This has to be done after calling NativeLibrary.Initialize(),
+          // as it relies on the config system
+          EmulationActivity.updateWiimoteNewIniPreferences(context);
         }
+
+        directoryState = DirectoryInitializationState.DOLPHIN_DIRECTORIES_INITIALIZED;
       }
       else
       {
-        directoryState = DirectoryInitializationState.EXTERNAL_STORAGE_PERMISSION_NEEDED;
+        directoryState = DirectoryInitializationState.CANT_FIND_EXTERNAL_STORAGE;
       }
     }
 
@@ -100,16 +93,29 @@ public final class DirectoryInitialization
     sendBroadcastState(directoryState, context);
   }
 
+  @Nullable
+  private static File getLegacyUserDirectoryPath()
+  {
+    File externalPath = Environment.getExternalStorageDirectory();
+    if (externalPath == null)
+      return null;
+
+    return new File(externalPath, "dolphin-emu");
+  }
+
   private static boolean setDolphinUserDirectory(Context context)
   {
     if (!Environment.MEDIA_MOUNTED.equals(Environment.getExternalStorageState()))
       return false;
 
-    File externalPath = Environment.getExternalStorageDirectory();
-    if (externalPath == null)
+    File path = preferLegacyUserDirectory(context) && PermissionsHandler.hasWriteAccess(context) ?
+            getLegacyUserDirectoryPath() : context.getExternalFilesDir(null);
+
+    if (path == null)
       return false;
 
-    userPath = externalPath.getAbsolutePath() + "/dolphin-emu";
+    userPath = path.getAbsolutePath();
+
     Log.debug("[DirectoryInitialization] User Dir: " + userPath);
     NativeLibrary.SetUserDirectory(userPath);
 
@@ -207,7 +213,8 @@ public final class DirectoryInitialization
   public static boolean shouldStart(Context context)
   {
     return !isDolphinDirectoryInitializationRunning.get() &&
-            getDolphinDirectoriesState(context) == DirectoryInitializationState.NOT_YET_INITIALIZED;
+            getDolphinDirectoriesState() == DirectoryInitializationState.NOT_YET_INITIALIZED &&
+            !isWaitingForWriteAccess(context);
   }
 
   public static boolean areDolphinDirectoriesReady()
@@ -215,17 +222,9 @@ public final class DirectoryInitialization
     return directoryState == DirectoryInitializationState.DOLPHIN_DIRECTORIES_INITIALIZED;
   }
 
-  public static DirectoryInitializationState getDolphinDirectoriesState(Context context)
+  public static DirectoryInitializationState getDolphinDirectoriesState()
   {
-    if (directoryState == DirectoryInitializationState.NOT_YET_INITIALIZED &&
-            !PermissionsHandler.hasWriteAccess(context))
-    {
-      return DirectoryInitializationState.EXTERNAL_STORAGE_PERMISSION_NEEDED;
-    }
-    else
-    {
-      return directoryState;
-    }
+    return directoryState;
   }
 
   public static String getUserDirectory()
@@ -335,11 +334,6 @@ public final class DirectoryInitialization
     }
   }
 
-  public static boolean isExternalStorageLegacy()
-  {
-    return Build.VERSION.SDK_INT < Build.VERSION_CODES.Q || Environment.isExternalStorageLegacy();
-  }
-
   public static boolean preferOldFolderPicker(Context context)
   {
     // As of January 2021, ACTION_OPEN_DOCUMENT_TREE seems to be broken on the Nvidia Shield TV
@@ -347,16 +341,60 @@ public final class DirectoryInitialization
     // for the time being - Android 11 hasn't been released for this device. We have an explicit
     // check for Android 11 below in hopes that Nvidia will fix this before releasing Android 11.
     //
-    // No Android TV device other than the Nvidia Shield TV is known to have an implementation
-    // of ACTION_OPEN_DOCUMENT or ACTION_OPEN_DOCUMENT_TREE that even launches, but "fortunately"
-    // for us, the Nvidia Shield TV is the only Android TV device in existence so far that can
-    // run Dolphin at all (due to the 64-bit requirement), so we can ignore this problem.
+    // No Android TV device other than the Nvidia Shield TV is known to have an implementation of
+    // ACTION_OPEN_DOCUMENT or ACTION_OPEN_DOCUMENT_TREE that even launches, but "fortunately", no
+    // Android TV device other than the Shield TV is known to be able to run Dolphin (either due to
+    // the 64-bit requirement or due to the GLES 3.0 requirement), so we can ignore this problem.
     //
     // All phones which are running a compatible version of Android support ACTION_OPEN_DOCUMENT and
-    // ACTION_OPEN_DOCUMENT_TREE, as this is required by the Android CTS (unlike with Android TV).
+    // ACTION_OPEN_DOCUMENT_TREE, as this is required by the mobile Android CTS (unlike Android TV).
 
-    return Build.VERSION.SDK_INT < Build.VERSION_CODES.R && isExternalStorageLegacy() &&
-            TvUtil.isLeanback(context);
+    return Build.VERSION.SDK_INT < Build.VERSION_CODES.R &&
+            PermissionsHandler.isExternalStorageLegacy() && TvUtil.isLeanback(context);
+  }
+
+  private static boolean isExternalFilesDirEmpty(Context context)
+  {
+    File dir = context.getExternalFilesDir(null);
+    if (dir == null)
+      return false;  // External storage not available
+
+    File[] contents = dir.listFiles();
+    return contents == null || contents.length == 0;
+  }
+
+  private static boolean legacyUserDirectoryExists()
+  {
+    try
+    {
+      return getLegacyUserDirectoryPath().exists();
+    }
+    catch (SecurityException e)
+    {
+      // Most likely we don't have permission to read external storage.
+      // Return true so that external storage permissions will be requested.
+      //
+      // Strangely, we don't seem to trigger this case in practice, even with no permissions...
+      // But this only makes things more convenient for users, so no harm done.
+
+      return true;
+    }
+  }
+
+  private static boolean preferLegacyUserDirectory(Context context)
+  {
+    return PermissionsHandler.isExternalStorageLegacy() &&
+            !PermissionsHandler.isWritePermissionDenied() &&
+            isExternalFilesDirEmpty(context) && legacyUserDirectoryExists();
+  }
+
+  public static boolean isWaitingForWriteAccess(Context context)
+  {
+    // This first check is only for performance, not correctness
+    if (getDolphinDirectoriesState() != DirectoryInitializationState.NOT_YET_INITIALIZED)
+      return false;
+
+    return preferLegacyUserDirectory(context) && !PermissionsHandler.hasWriteAccess(context);
   }
 
   private static native void CreateUserDirectories();
diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/PermissionsHandler.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/PermissionsHandler.java
index 63a70870bf..a4c69281f2 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/PermissionsHandler.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/PermissionsHandler.java
@@ -2,10 +2,10 @@
 
 package org.dolphinemu.dolphinemu.utils;
 
-import android.annotation.TargetApi;
 import android.content.Context;
 import android.content.pm.PackageManager;
 import android.os.Build;
+import android.os.Environment;
 
 import androidx.core.content.ContextCompat;
 import androidx.fragment.app.FragmentActivity;
@@ -15,38 +15,41 @@ import static android.Manifest.permission.WRITE_EXTERNAL_STORAGE;
 public class PermissionsHandler
 {
   public static final int REQUEST_CODE_WRITE_PERMISSION = 500;
+  private static boolean sWritePermissionDenied = false;
 
-  @TargetApi(Build.VERSION_CODES.M)
-  public static boolean checkWritePermission(final FragmentActivity activity)
+  public static void requestWritePermission(final FragmentActivity activity)
   {
     if (android.os.Build.VERSION.SDK_INT < Build.VERSION_CODES.M)
-    {
-      return true;
-    }
+      return;
 
-    int hasWritePermission = ContextCompat.checkSelfPermission(activity, WRITE_EXTERNAL_STORAGE);
-
-    if (hasWritePermission != PackageManager.PERMISSION_GRANTED)
-    {
-      // We only care about displaying the "Don't ask again" check and can ignore the result.
-      // Previous toasts already explained the rationale.
-      activity.shouldShowRequestPermissionRationale(WRITE_EXTERNAL_STORAGE);
-      activity.requestPermissions(new String[]{WRITE_EXTERNAL_STORAGE},
-              REQUEST_CODE_WRITE_PERMISSION);
-      return false;
-    }
-
-    return true;
+    activity.requestPermissions(new String[]{WRITE_EXTERNAL_STORAGE},
+            REQUEST_CODE_WRITE_PERMISSION);
   }
 
   public static boolean hasWriteAccess(Context context)
   {
-    if (android.os.Build.VERSION.SDK_INT >= Build.VERSION_CODES.M)
-    {
-      int hasWritePermission = ContextCompat.checkSelfPermission(context, WRITE_EXTERNAL_STORAGE);
-      return hasWritePermission == PackageManager.PERMISSION_GRANTED;
-    }
+    if (android.os.Build.VERSION.SDK_INT < Build.VERSION_CODES.M)
+      return true;
 
-    return true;
+    if (!isExternalStorageLegacy())
+      return false;
+
+    int hasWritePermission = ContextCompat.checkSelfPermission(context, WRITE_EXTERNAL_STORAGE);
+    return hasWritePermission == PackageManager.PERMISSION_GRANTED;
+  }
+
+  public static boolean isExternalStorageLegacy()
+  {
+    return Build.VERSION.SDK_INT < Build.VERSION_CODES.Q || Environment.isExternalStorageLegacy();
+  }
+
+  public static void setWritePermissionDenied()
+  {
+    sWritePermissionDenied = true;
+  }
+
+  public static boolean isWritePermissionDenied()
+  {
+    return sWritePermissionDenied;
   }
 }
diff --git a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/StartupHandler.java b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/StartupHandler.java
index a3ce3d2802..547d6934d1 100644
--- a/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/StartupHandler.java
+++ b/Source/Android/app/src/main/java/org/dolphinemu/dolphinemu/utils/StartupHandler.java
@@ -22,8 +22,9 @@ public final class StartupHandler
 
   public static void HandleInit(FragmentActivity parent)
   {
-    // Ask the user to grant write permission if it's not already granted
-    PermissionsHandler.checkWritePermission(parent);
+    // Ask the user to grant write permission if relevant and not already granted
+    if (DirectoryInitialization.isWaitingForWriteAccess(parent))
+      PermissionsHandler.requestWritePermission(parent);
 
     // Ask the user if he wants to enable analytics if we haven't yet.
     Analytics.checkAnalyticsInit(parent);
diff --git a/Source/Android/app/src/main/res/values/strings.xml b/Source/Android/app/src/main/res/values/strings.xml
index 2cb4b45643..897aa639e5 100644
--- a/Source/Android/app/src/main/res/values/strings.xml
+++ b/Source/Android/app/src/main/res/values/strings.xml
@@ -481,7 +481,6 @@ It can efficiently compress both junk data and encrypted Wii data.
     <!-- Rumble -->
     <string name="rumble_not_found">Device rumble not found</string>
 
-    <string name="write_permission_needed">You need to allow write access to external storage for the emulator to work</string>
     <string name="load_settings">Loading Settings...</string>
     <string name="setting_not_runtime_editable">This setting can\'t be changed while a game is running.</string>
     <string name="setting_clear_info">Long press a setting to clear it.</string>