diff --git a/Applications/FileManager/main.cpp b/Applications/FileManager/main.cpp
index f01cefd55d..d8b0991620 100644
--- a/Applications/FileManager/main.cpp
+++ b/Applications/FileManager/main.cpp
@@ -456,6 +456,7 @@ int run_in_windowed_mode(RefPtr<Core::ConfigFile> config, String initial_locatio
             directory_view.delete_action().activate();
         refresh_tree_view();
     });
+    focus_dependent_delete_action->set_enabled(false);
 
     auto mkdir_action = GUI::Action::create("New directory...", { Mod_Ctrl | Mod_Shift, Key_N }, Gfx::Bitmap::load_from_file("/res/icons/16x16/mkdir.png"), [&](const GUI::Action&) {
         directory_view.mkdir_action().activate();
@@ -579,9 +580,10 @@ int run_in_windowed_mode(RefPtr<Core::ConfigFile> config, String initial_locatio
     };
 
     directory_view.on_selection_change = [&](GUI::AbstractView& view) {
-        // FIXME: Figure out how we can enable/disable the paste action, based on clipboard contents.
         auto& selection = view.selection();
         copy_action->set_enabled(!selection.is_empty());
+        focus_dependent_delete_action->set_enabled((!tree_view.selection().is_empty() && tree_view.is_focused())
+            || !directory_view.current_view().selection().is_empty());
     };
 
     directory_context_menu->add_action(copy_action);
@@ -681,6 +683,9 @@ int run_in_windowed_mode(RefPtr<Core::ConfigFile> config, String initial_locatio
     };
 
     tree_view.on_selection_change = [&] {
+        focus_dependent_delete_action->set_enabled((!tree_view.selection().is_empty() && tree_view.is_focused())
+            || !directory_view.current_view().selection().is_empty());
+
         if (tree_view.selection().is_empty())
             return;
         auto path = directories_model->full_path(tree_view.selection().first());
@@ -692,6 +697,11 @@ int run_in_windowed_mode(RefPtr<Core::ConfigFile> config, String initial_locatio
         directory_view.delete_action().set_enabled(!tree_view.selection().is_empty());
     };
 
+    tree_view.on_focus_change = [&]([[ maybe_unused ]] const bool has_focus, [[ maybe_unused ]] const GUI::FocusSource source) {
+        focus_dependent_delete_action->set_enabled((!tree_view.selection().is_empty() && has_focus)
+                                                   || !directory_view.current_view().selection().is_empty());
+    };
+
     tree_view.on_context_menu_request = [&](const GUI::ModelIndex& index, const GUI::ContextMenuEvent& event) {
         if (index.is_valid()) {
             tree_view_directory_context_menu->popup(event.screen_position());
diff --git a/Libraries/LibGUI/Widget.h b/Libraries/LibGUI/Widget.h
index 10d3366cfc..ec8e5b5f7c 100644
--- a/Libraries/LibGUI/Widget.h
+++ b/Libraries/LibGUI/Widget.h
@@ -165,6 +165,8 @@ public:
     bool is_focused() const;
     void set_focus(bool, FocusSource = FocusSource::Programmatic);
 
+    Function<void(const bool, const FocusSource)> on_focus_change;
+
     // Returns true if this widget or one of its descendants is focused.
     bool has_focus_within() const;
 
diff --git a/Libraries/LibGUI/Window.cpp b/Libraries/LibGUI/Window.cpp
index 6faaa5a08a..7389b1d350 100644
--- a/Libraries/LibGUI/Window.cpp
+++ b/Libraries/LibGUI/Window.cpp
@@ -558,14 +558,21 @@ void Window::set_focused_widget(Widget* widget, FocusSource source)
 {
     if (m_focused_widget == widget)
         return;
-    if (m_focused_widget) {
-        Core::EventLoop::current().post_event(*m_focused_widget, make<FocusEvent>(Event::FocusOut, source));
-        m_focused_widget->update();
-    }
+
+    WeakPtr<Widget> previously_focused_widget = m_focused_widget;
     m_focused_widget = widget;
+
+    if (previously_focused_widget) {
+        Core::EventLoop::current().post_event(*previously_focused_widget, make<FocusEvent>(Event::FocusOut, source));
+        previously_focused_widget->update();
+        if (previously_focused_widget && previously_focused_widget->on_focus_change)
+            previously_focused_widget->on_focus_change(previously_focused_widget->is_focused(), source);
+    }
     if (m_focused_widget) {
         Core::EventLoop::current().post_event(*m_focused_widget, make<FocusEvent>(Event::FocusIn, source));
         m_focused_widget->update();
+        if (m_focused_widget && m_focused_widget->on_focus_change)
+            m_focused_widget->on_focus_change(m_focused_widget->is_focused(), source);
     }
 }