diff --git a/BeefLibs/Beefy2D/src/sys/SysMenu.bf b/BeefLibs/Beefy2D/src/sys/SysMenu.bf
index a125a554..98ab168f 100644
--- a/BeefLibs/Beefy2D/src/sys/SysMenu.bf
+++ b/BeefLibs/Beefy2D/src/sys/SysMenu.bf
@@ -3,6 +3,7 @@ using System.Collections;
 using System.Text;
 using Beefy.widgets;
 using Beefy;
+using System.Diagnostics;
 
 namespace Beefy.sys
 {    
@@ -22,10 +23,6 @@ namespace Beefy.sys
         public Event<MenuItemUpdateHandler> mOnMenuItemUpdate ~ _.Dispose();
         public List<SysMenu> mChildren ~ DeleteContainerAndItems!(_);
 
-        public this()
-        {
-        }
-
 		public int ChildCount
 		{
 			get
@@ -135,6 +132,8 @@ namespace Beefy.sys
         {
             mWindow.mSysMenuMap.Remove((int)mNativeBFMenu);
             mWindow.DeleteMenuItem(mNativeBFMenu);
+			if (mParent != null)
+				mParent.mChildren.Remove(this);
         }
 
 		public void UpdateChildItems()
diff --git a/BeefySysLib/platform/win/WinBFApp.cpp b/BeefySysLib/platform/win/WinBFApp.cpp
index de5938cb..33aaea1f 100644
--- a/BeefySysLib/platform/win/WinBFApp.cpp
+++ b/BeefySysLib/platform/win/WinBFApp.cpp
@@ -2131,8 +2131,9 @@ void WinBFWindow::RemoveMenuItem(BFMenu* item)
 	WinBFMenu* aMenu = (WinBFMenu*) item;
 	WinBFMenu* parentMenu = (WinBFMenu*) item->mParent;
 
-	//auto itr = mMenuIDMap.find(aMenu->mMenuId);
-	//mMenuIDMap.erase(itr);
+	if (parentMenu != NULL)
+		parentMenu->mBFMenuList.Remove(item);
+	
 	mMenuIDMap.Remove(aMenu->mMenuId);
 
 	::RemoveMenu(parentMenu->mMenu, aMenu->mMenuId, MF_BYCOMMAND);
diff --git a/IDE/src/IDEApp.bf b/IDE/src/IDEApp.bf
index 77cdb203..519b93ed 100644
--- a/IDE/src/IDEApp.bf
+++ b/IDE/src/IDEApp.bf
@@ -5189,13 +5189,16 @@ namespace IDE
 		[IDECommand]
 		public void ReloadSettings()
 		{
-			delete mSettings;
-			mSettings = new .();
+			var prevSettings = mSettings;
+			defer delete prevSettings;
+			mSettings = new .(prevSettings);
 
 			DeleteAndNullify!(mKeyChordState);
 
 		    mSettings.Load();
 			mSettings.Apply();
+			UpdateRecentFileMenuItems();
+			UpdateRecentDisplayedFilesMenuItems();
 		}
 
 		public void CheckReloadSettings()
diff --git a/IDE/src/Settings.bf b/IDE/src/Settings.bf
index 1bd1d217..ec6d2d69 100644
--- a/IDE/src/Settings.bf
+++ b/IDE/src/Settings.bf
@@ -1106,12 +1106,24 @@ namespace IDE
 		public bool mEnableDevMode;
 		public TutorialsFinished mTutorialsFinished = .();
 
-
 		public this()
 		{
 			SetDefaults();
 		}
 
+		public this(Settings prevSettings)
+		{
+			Swap!(mRecentFiles, prevSettings.mRecentFiles);
+
+			for (var recent in mRecentFiles.mRecents)
+			{
+				recent.mList.ClearAndDeleteItems();
+				for (var item in recent.mMenuItems)
+					item.Dispose();
+				recent.mMenuItems.ClearAndDeleteItems();
+			}
+		}
+
 		public void SetDefaults()
 		{
 			mVSSettings.SetDefaults();
@@ -1192,6 +1204,9 @@ namespace IDE
 
 		public bool WantsReload()
 		{
+			if (mSettingFileDateTime == default)
+				return false;
+
 			String path = scope .();
 			GetSettingsPath(path);