diff --git a/pcsx2/gui/App.h b/pcsx2/gui/App.h
index 6b03938381..a080dd369e 100644
--- a/pcsx2/gui/App.h
+++ b/pcsx2/gui/App.h
@@ -86,6 +86,7 @@ enum MenuIdentifiers
 	MenuId_Boot_Iso,			// Opens submenu with Iso browser, and recent isos.
 	MenuId_RecentIsos_reservedStart,
 	MenuId_IsoBrowse = MenuId_RecentIsos_reservedStart + 100,			// Open dialog, runs selected iso.
+	MenuId_Ask_On_Booting,
 	MenuId_Boot_CDVD,
 	MenuId_Boot_CDVD2,
 	MenuId_Boot_ELF,
diff --git a/pcsx2/gui/AppConfig.cpp b/pcsx2/gui/AppConfig.cpp
index 1a1a4e88ee..d0ff02de7a 100644
--- a/pcsx2/gui/AppConfig.cpp
+++ b/pcsx2/gui/AppConfig.cpp
@@ -670,6 +670,7 @@ void AppConfig::LoadSaveRootItems( IniInterface& ini )
 
 	IniEntry( EnablePresets );
 	IniEntry( PresetIndex );
+	IniEntry( AskOnBoot );
 	
 	#ifdef __WXMSW__
 	IniEntry( McdCompressNTFS );
diff --git a/pcsx2/gui/AppConfig.h b/pcsx2/gui/AppConfig.h
index 89b2dd9a62..cf9682cadf 100644
--- a/pcsx2/gui/AppConfig.h
+++ b/pcsx2/gui/AppConfig.h
@@ -315,6 +315,8 @@ public:
 	bool		EnablePresets;
 	int			PresetIndex;
 
+	bool		AskOnBoot;
+
 	wxString				CurrentIso;
 	wxString				CurrentELF;
 	wxString				CurrentIRX;
diff --git a/pcsx2/gui/AppRes.cpp b/pcsx2/gui/AppRes.cpp
index 250c912dfd..42d426511a 100644
--- a/pcsx2/gui/AppRes.cpp
+++ b/pcsx2/gui/AppRes.cpp
@@ -63,7 +63,10 @@ const wxImage& LoadImageAny(
 RecentIsoList::RecentIsoList(int firstIdForMenuItems_or_wxID_ANY)
 {
 	Menu = std::unique_ptr<wxMenu>(new wxMenu());
-	Menu->Append( MenuId_IsoBrowse, _("Browse..."), _("Browse for an ISO that is not in your recent history.") );
+	Menu->AppendCheckItem( MenuId_Ask_On_Booting, _("Always ask when booting"), _("Manually select an ISO upon boot ignoring the selection from recent ISO list.") );
+	Menu->AppendSeparator();
+	Menu->Append( MenuId_IsoBrowse, _("Browse..."), _("Browse for an ISO that is not in your recent history."))->Enable(!g_Conf->AskOnBoot);
+	Menu->Check( MenuId_Ask_On_Booting, g_Conf->AskOnBoot );
 	Manager = std::unique_ptr<RecentIsoManager>(new RecentIsoManager( Menu.get(), firstIdForMenuItems_or_wxID_ANY ));
 }
 
diff --git a/pcsx2/gui/MainFrame.cpp b/pcsx2/gui/MainFrame.cpp
index 2c91c0a100..ecd498e822 100644
--- a/pcsx2/gui/MainFrame.cpp
+++ b/pcsx2/gui/MainFrame.cpp
@@ -209,6 +209,7 @@ void MainEmuFrame::ConnectMenus()
 	Bind(wxEVT_MENU, &MainEmuFrame::Menu_CdvdSource_Click, this, MenuId_Src_Iso);
 	Bind(wxEVT_MENU, &MainEmuFrame::Menu_CdvdSource_Click, this, MenuId_Src_Plugin);
 	Bind(wxEVT_MENU, &MainEmuFrame::Menu_CdvdSource_Click, this, MenuId_Src_NoDisc);
+	Bind(wxEVT_MENU, &MainEmuFrame::Menu_Ask_On_Boot_Click, this, MenuId_Ask_On_Booting);
 	Bind(wxEVT_MENU, &MainEmuFrame::Menu_Debug_CreateBlockdump_Click, this, MenuId_Debug_CreateBlockdump);
 
 	// Config
diff --git a/pcsx2/gui/MainFrame.h b/pcsx2/gui/MainFrame.h
index 16a061c19a..ef730faa2b 100644
--- a/pcsx2/gui/MainFrame.h
+++ b/pcsx2/gui/MainFrame.h
@@ -195,6 +195,7 @@ protected:
 	void Menu_Debug_MemoryDump_Click(wxCommandEvent &event);
 	void Menu_Debug_Logging_Click(wxCommandEvent &event);
 	void Menu_Debug_CreateBlockdump_Click(wxCommandEvent &event);
+	void Menu_Ask_On_Boot_Click(wxCommandEvent &event);
 
 	void Menu_ShowConsole(wxCommandEvent &event);
 	void Menu_ChangeLang(wxCommandEvent &event);
diff --git a/pcsx2/gui/MainMenuClicks.cpp b/pcsx2/gui/MainMenuClicks.cpp
index 6e891054d5..c2798db9b8 100644
--- a/pcsx2/gui/MainMenuClicks.cpp
+++ b/pcsx2/gui/MainMenuClicks.cpp
@@ -331,7 +331,7 @@ void MainEmuFrame::_DoBootCdvd()
 			selector = true;
 		}
 
-		if( selector )
+		if( selector || g_Conf->AskOnBoot)
 		{
 			wxString result;
 			if( !_DoSelectIsoBrowser( result ) )
@@ -412,6 +412,17 @@ void MainEmuFrame::Menu_IsoBrowse_Click( wxCommandEvent &event )
 	AppSaveSettings();		// save the new iso selection; update menus!
 }
 
+void MainEmuFrame::Menu_Ask_On_Boot_Click(wxCommandEvent &event)
+{
+	g_Conf->AskOnBoot = event.IsChecked();
+
+	if (SysHasValidState())
+		return;
+
+	wxGetApp().GetRecentIsoManager().EnableItems(!event.IsChecked());
+	FindItemInMenuBar(MenuId_IsoBrowse)->Enable(!event.IsChecked());
+}
+
 void MainEmuFrame::Menu_Debug_CreateBlockdump_Click(wxCommandEvent &event)
 {
 	g_Conf->EmuOptions.CdvdDumpBlocks = event.IsChecked();
diff --git a/pcsx2/gui/RecentIsoList.cpp b/pcsx2/gui/RecentIsoList.cpp
index aede377a90..42fee63606 100644
--- a/pcsx2/gui/RecentIsoList.cpp
+++ b/pcsx2/gui/RecentIsoList.cpp
@@ -171,13 +171,16 @@ void RecentIsoManager::InsertIntoMenu( int id )
 		wxid = this->m_firstIdForMenuItems_or_wxID_ANY + id;
 
 	curitem.ItemPtr = m_Menu->AppendRadioItem( wxid, Path::GetFilename(curitem.Filename), curitem.Filename );
-	bool exists = wxFileExists( curitem.Filename );
+	curitem.ItemPtr->Enable(wxFileExists(curitem.Filename) && !g_Conf->AskOnBoot);
+}
 
-	if( m_cursel == id && exists )
-		curitem.ItemPtr->Check();
-
-	if ( !exists )
-		curitem.ItemPtr->Enable( false );
+void RecentIsoManager::EnableItems(bool display)
+{
+	for (const auto& list : m_Items)
+	{
+		// Files which don't exist still need to be grayed out.
+		list.ItemPtr->Enable(display && wxFileExists(list.Filename));
+	}
 }
 
 void RecentIsoManager::LoadListFrom( IniInterface& ini )
diff --git a/pcsx2/gui/RecentIsoList.h b/pcsx2/gui/RecentIsoList.h
index 8c2f077b84..da65d312fb 100644
--- a/pcsx2/gui/RecentIsoList.h
+++ b/pcsx2/gui/RecentIsoList.h
@@ -53,6 +53,7 @@ public:
 	virtual ~RecentIsoManager();
 
 	void RemoveAllFromMenu();
+	void EnableItems(bool display);
 	void Repopulate();
 	void Clear();
 	void Add( const wxString& src );
diff --git a/pcsx2/gui/UpdateUI.cpp b/pcsx2/gui/UpdateUI.cpp
index 11566d5265..5397e2a96b 100644
--- a/pcsx2/gui/UpdateUI.cpp
+++ b/pcsx2/gui/UpdateUI.cpp
@@ -55,6 +55,8 @@ void UI_DisableSysShutdown()
 	if( wxGetApp().Rpc_TryInvokeAsync( &UI_DisableSysShutdown ) ) return;
 
 	sMainFrame.EnableMenuItem( MenuId_Sys_Shutdown, false );
+	sMainFrame.EnableMenuItem(MenuId_IsoBrowse, !g_Conf->AskOnBoot);
+	wxGetApp().GetRecentIsoManager().EnableItems(!g_Conf->AskOnBoot);
 }
 
 void UI_EnableSysShutdown()
@@ -79,6 +81,8 @@ void UI_EnableSysActions()
 	if( wxGetApp().Rpc_TryInvokeAsync( &UI_EnableSysActions ) ) return;
 
 	sMainFrame.EnableMenuItem( MenuId_Sys_Shutdown, true );
+	sMainFrame.EnableMenuItem(MenuId_IsoBrowse, true);
+	wxGetApp().GetRecentIsoManager().EnableItems(true);
 	
 	_SaveLoadStuff( true );
 }