diff --git a/Userland/Services/WindowServer/Button.cpp b/Userland/Services/WindowServer/Button.cpp
index 7265494b31..e428260b1b 100644
--- a/Userland/Services/WindowServer/Button.cpp
+++ b/Userland/Services/WindowServer/Button.cpp
@@ -62,22 +62,36 @@ void Button::on_mouse_event(const MouseEvent& event)
 {
     auto& wm = WindowManager::the();
 
-    if (event.type() == Event::MouseDown && event.button() == MouseButton::Left) {
+    if (event.type() == Event::MouseDown && (event.button() == MouseButton::Left || event.button() == MouseButton::Right || event.button() == MouseButton::Middle)) {
         m_pressed = true;
         wm.set_cursor_tracking_button(this);
         m_frame.invalidate(m_relative_rect);
         return;
     }
 
-    if (event.type() == Event::MouseUp && event.button() == MouseButton::Left) {
+    if (event.type() == Event::MouseUp && (event.button() == MouseButton::Left || event.button() == MouseButton::Right || event.button() == MouseButton::Middle)) {
         if (wm.cursor_tracking_button() != this)
             return;
         wm.set_cursor_tracking_button(nullptr);
         bool old_pressed = m_pressed;
         m_pressed = false;
         if (rect().contains(event.position())) {
-            if (on_click)
-                on_click(*this);
+            switch (event.button()) {
+            case MouseButton::Left:
+                if (on_click)
+                    on_click(*this);
+                break;
+
+            case MouseButton::Right:
+                if (on_right_click)
+                    on_right_click(*this);
+                break;
+
+            default:
+                if (on_middle_click)
+                    on_middle_click(*this);
+                break;
+            }
         }
         if (old_pressed != m_pressed) {
             // Would like to compute:
diff --git a/Userland/Services/WindowServer/Button.h b/Userland/Services/WindowServer/Button.h
index e6c0433025..29de9488c4 100644
--- a/Userland/Services/WindowServer/Button.h
+++ b/Userland/Services/WindowServer/Button.h
@@ -53,6 +53,8 @@ public:
     void on_mouse_event(const MouseEvent&);
 
     Function<void(Button&)> on_click;
+    Function<void(Button&)> on_right_click;
+    Function<void(Button&)> on_middle_click;
 
     bool is_visible() const { return m_visible; }
 
diff --git a/Userland/Services/WindowServer/Window.cpp b/Userland/Services/WindowServer/Window.cpp
index 2d8889c7ea..04095761a3 100644
--- a/Userland/Services/WindowServer/Window.cpp
+++ b/Userland/Services/WindowServer/Window.cpp
@@ -360,7 +360,21 @@ void Window::set_maximized(bool maximized, Optional<Gfx::IntPoint> fixed_point)
     Core::EventLoop::current().post_event(*this, make<ResizeEvent>(m_rect));
     set_default_positioned(false);
 }
+void Window::set_vertically_maximized()
+{
+    if (m_maximized)
+        return;
+    if (!is_resizable() || resize_aspect_ratio().has_value())
+        return;
 
+    auto max_rect = WindowManager::the().maximized_window_rect(*this);
+
+    auto new_rect = Gfx::IntRect(
+        Gfx::IntPoint(rect().x(), max_rect.y()),
+        Gfx::IntSize(rect().width(), max_rect.height()));
+    set_rect(new_rect);
+    Core::EventLoop::current().post_event(*this, make<ResizeEvent>(new_rect));
+}
 void Window::set_resizable(bool resizable)
 {
     if (m_resizable == resizable)
diff --git a/Userland/Services/WindowServer/Window.h b/Userland/Services/WindowServer/Window.h
index 3e8e2b18b3..9debf465b3 100644
--- a/Userland/Services/WindowServer/Window.h
+++ b/Userland/Services/WindowServer/Window.h
@@ -106,6 +106,8 @@ public:
     bool is_maximized() const { return m_maximized; }
     void set_maximized(bool, Optional<Gfx::IntPoint> fixed_point = {});
 
+    void set_vertically_maximized();
+
     bool is_fullscreen() const { return m_fullscreen; }
     void set_fullscreen(bool);
 
diff --git a/Userland/Services/WindowServer/WindowFrame.cpp b/Userland/Services/WindowServer/WindowFrame.cpp
index 49fd3b2cd8..85b13b554d 100644
--- a/Userland/Services/WindowServer/WindowFrame.cpp
+++ b/Userland/Services/WindowServer/WindowFrame.cpp
@@ -83,6 +83,9 @@ WindowFrame::WindowFrame(Window& window)
         auto button = make<Button>(*this, [this](auto&) {
             WindowManager::the().maximize_windows(m_window, !m_window.is_maximized());
         });
+        button->on_middle_click = [&](auto&) {
+            m_window.set_vertically_maximized();
+        };
         m_maximize_button = button.ptr();
         m_buttons.append(move(button));
     }
diff --git a/Userland/Services/WindowServer/WindowManager.cpp b/Userland/Services/WindowServer/WindowManager.cpp
index 602b3e8e3b..134715eac1 100644
--- a/Userland/Services/WindowServer/WindowManager.cpp
+++ b/Userland/Services/WindowServer/WindowManager.cpp
@@ -579,6 +579,15 @@ bool WindowManager::process_ongoing_window_resize(const MouseEvent& event, Windo
     if (event.type() == Event::MouseUp && event.button() == m_resizing_mouse_button) {
         dbgln_if(RESIZE_DEBUG, "[WM] Finish resizing Window({})", m_resize_window);
 
+        auto max_rect = maximized_window_rect(*m_resize_window);
+        if (event.y() > max_rect.bottom()) {
+            dbgln<RESIZE_DEBUG>("Should Maximize vertically");
+            m_resize_window->set_vertically_maximized();
+            m_resize_window = nullptr;
+            m_resizing_mouse_button = MouseButton::None;
+            return true;
+        }
+
         Core::EventLoop::current().post_event(*m_resize_window, make<ResizeEvent>(m_resize_window->rect()));
         m_resize_window->invalidate();
         if (m_resize_window->rect().contains(event.position()))