diff --git a/Applications/PaintBrush/Tool.cpp b/Applications/PaintBrush/Tool.cpp
index 68c2270b9d..831f48c3c6 100644
--- a/Applications/PaintBrush/Tool.cpp
+++ b/Applications/PaintBrush/Tool.cpp
@@ -26,6 +26,7 @@
 
 #include "Tool.h"
 #include "ImageEditor.h"
+#include <LibGUI/Action.h>
 
 namespace PaintBrush {
 
@@ -42,4 +43,9 @@ void Tool::setup(ImageEditor& editor)
     m_editor = editor.make_weak_ptr();
 }
 
+void Tool::set_action(GUI::Action* action)
+{
+    m_action = action;
+}
+
 }
diff --git a/Applications/PaintBrush/Tool.h b/Applications/PaintBrush/Tool.h
index e76e825a84..f2061ad269 100644
--- a/Applications/PaintBrush/Tool.h
+++ b/Applications/PaintBrush/Tool.h
@@ -27,6 +27,7 @@
 #pragma once
 
 #include <LibGUI/Event.h>
+#include <LibGUI/Forward.h>
 
 namespace PaintBrush {
 
@@ -50,9 +51,13 @@ public:
     void clear() { m_editor = nullptr; }
     void setup(ImageEditor&);
 
+    GUI::Action* action() { return m_action; }
+    void set_action(GUI::Action*);
+
 protected:
     Tool();
     WeakPtr<ImageEditor> m_editor;
+    RefPtr<GUI::Action> m_action;
 };
 
 }
diff --git a/Applications/PaintBrush/ToolboxWidget.cpp b/Applications/PaintBrush/ToolboxWidget.cpp
index 124a51aa14..5eca0510ec 100644
--- a/Applications/PaintBrush/ToolboxWidget.cpp
+++ b/Applications/PaintBrush/ToolboxWidget.cpp
@@ -44,7 +44,7 @@ namespace PaintBrush {
 class ToolButton final : public GUI::Button {
     C_OBJECT(ToolButton)
 public:
-    ToolButton(ToolboxWidget& toolbox, const String& name, const GUI::Shortcut& shortcut, OwnPtr<Tool>&& tool)
+    ToolButton(ToolboxWidget& toolbox, const String& name, const GUI::Shortcut& shortcut, OwnPtr<Tool> tool)
         : m_toolbox(toolbox)
         , m_tool(move(tool))
     {
@@ -62,6 +62,7 @@ public:
                 m_toolbox.on_tool_selection(nullptr);
         });
 
+        m_tool->set_action(m_action);
         set_action(*m_action);
         m_toolbox.m_action_group.add_action(*m_action);
     }
@@ -101,6 +102,7 @@ ToolboxWidget::ToolboxWidget()
     m_action_group.set_unchecking_allowed(false);
 
     auto add_tool = [&](const StringView& name, const StringView& icon_name, const GUI::Shortcut& shortcut, NonnullOwnPtr<Tool> tool) -> ToolButton& {
+        m_tools.append(tool.ptr());
         auto& button = add<ToolButton>(*this, name, shortcut, move(tool));
         button.set_size_policy(GUI::SizePolicy::Fill, GUI::SizePolicy::Fixed);
         button.set_preferred_size(0, 32);
@@ -110,7 +112,7 @@ ToolboxWidget::ToolboxWidget()
     };
 
     add_tool("Move", "move", { 0, Key_M }, make<MoveTool>());
-    add_tool("Pen", "pen", { 0, Key_N }, make<PenTool>()).set_checked(true);
+    add_tool("Pen", "pen", { 0, Key_N }, make<PenTool>());
     add_tool("Bucket Fill", "bucket", { Mod_Shift, Key_B }, make<BucketTool>());
     add_tool("Spray", "spray", { Mod_Shift, Key_S }, make<SprayTool>());
     add_tool("Color Picker", "picker", { 0, Key_O }, make<PickerTool>());
diff --git a/Applications/PaintBrush/ToolboxWidget.h b/Applications/PaintBrush/ToolboxWidget.h
index 4f71565dc7..60a3de0c5a 100644
--- a/Applications/PaintBrush/ToolboxWidget.h
+++ b/Applications/PaintBrush/ToolboxWidget.h
@@ -40,12 +40,19 @@ public:
 
     Function<void(Tool*)> on_tool_selection;
 
+    template<typename Callback>
+    void for_each_tool(Callback callback)
+    {
+        for (auto& tool : m_tools)
+            callback(*tool);
+    }
+
 private:
     friend class ToolButton;
 
     explicit ToolboxWidget();
-
     GUI::ActionGroup m_action_group;
+    Vector<Tool*> m_tools;
 };
 
 }
diff --git a/Applications/PaintBrush/main.cpp b/Applications/PaintBrush/main.cpp
index c9bc6513fa..606bae7645 100644
--- a/Applications/PaintBrush/main.cpp
+++ b/Applications/PaintBrush/main.cpp
@@ -28,6 +28,7 @@
 #include "ImageEditor.h"
 #include "Layer.h"
 #include "PaletteWidget.h"
+#include "Tool.h"
 #include "ToolboxWidget.h"
 #include <LibGUI/AboutDialog.h>
 #include <LibGUI/Action.h>
@@ -114,6 +115,13 @@ int main(int argc, char** argv)
 
     menubar->add_menu("Edit");
 
+    auto& tool_menu = menubar->add_menu("Tool");
+    toolbox.for_each_tool([&](auto& tool) {
+        if (tool.action())
+            tool_menu.add_action(*tool.action());
+        return IterationDecision::Continue;
+    });
+
     auto& help_menu = menubar->add_menu("Help");
     help_menu.add_action(GUI::Action::create("About", [&](auto&) {
         GUI::AboutDialog::show("PaintBrush", Gfx::Bitmap::load_from_file("/res/icons/32x32/app-paintbrush.png"), window);