diff --git a/Userland/Applications/PixelPaint/GuideTool.cpp b/Userland/Applications/PixelPaint/GuideTool.cpp
index d9a1bb0787..9633b47f91 100644
--- a/Userland/Applications/PixelPaint/GuideTool.cpp
+++ b/Userland/Applications/PixelPaint/GuideTool.cpp
@@ -57,6 +57,8 @@ void GuideTool::on_mousedown(Layer&, GUI::MouseEvent& mouse_event, GUI::MouseEve
     if (mouse_event.button() != GUI::MouseButton::Left)
         return;
 
+    m_editor->set_guide_visibility(true);
+
     RefPtr<Guide> new_guide;
     if (image_event.position().x() < 0 || image_event.position().x() > editor()->image().size().width()) {
         new_guide = Guide::construct(Guide::Orientation::Vertical, image_event.position().x());
@@ -129,6 +131,11 @@ void GuideTool::on_mousemove(Layer&, GUI::MouseEvent&, GUI::MouseEvent& image_ev
 
 void GuideTool::on_context_menu(Layer&, GUI::ContextMenuEvent& event)
 {
+    if (!m_editor)
+        return;
+
+    m_editor->set_guide_visibility(true);
+
     if (!m_context_menu) {
         m_context_menu = GUI::Menu::construct();
         m_context_menu->add_action(GUI::Action::create(
@@ -148,6 +155,12 @@ void GuideTool::on_context_menu(Layer&, GUI::ContextMenuEvent& event)
     m_context_menu->popup(event.screen_position());
 }
 
+void GuideTool::on_tool_activation()
+{
+    if (m_editor)
+        m_editor->set_guide_visibility(true);
+}
+
 GUI::Widget* GuideTool::get_properties_widget()
 {
     if (!m_properties_widget) {
diff --git a/Userland/Applications/PixelPaint/GuideTool.h b/Userland/Applications/PixelPaint/GuideTool.h
index 6999acf1a8..58c93673e1 100644
--- a/Userland/Applications/PixelPaint/GuideTool.h
+++ b/Userland/Applications/PixelPaint/GuideTool.h
@@ -23,6 +23,8 @@ public:
     virtual void on_mouseup(Layer&, GUI::MouseEvent& layer_event, GUI::MouseEvent& image_event) override;
     virtual void on_context_menu(Layer&, GUI::ContextMenuEvent&) override;
 
+    virtual void on_tool_activation() override;
+
     virtual GUI::Widget* get_properties_widget() override;
     virtual Gfx::StandardCursor cursor() override { return Gfx::StandardCursor::Crosshair; }
 
diff --git a/Userland/Applications/PixelPaint/ImageEditor.cpp b/Userland/Applications/PixelPaint/ImageEditor.cpp
index f180b5e110..248f37a611 100644
--- a/Userland/Applications/PixelPaint/ImageEditor.cpp
+++ b/Userland/Applications/PixelPaint/ImageEditor.cpp
@@ -316,10 +316,24 @@ void ImageEditor::set_active_tool(Tool* tool)
 
     if (m_active_tool) {
         m_active_tool->setup(*this);
+        m_active_tool->on_tool_activation();
         m_active_cursor = m_active_tool->cursor();
     }
 }
 
+void ImageEditor::set_guide_visibility(bool show_guides)
+{
+    if (m_show_guides == show_guides)
+        return;
+
+    m_show_guides = show_guides;
+
+    if (on_set_guide_visibility)
+        on_set_guide_visibility(m_show_guides);
+
+    update();
+}
+
 void ImageEditor::layers_did_change()
 {
     update();
diff --git a/Userland/Applications/PixelPaint/ImageEditor.h b/Userland/Applications/PixelPaint/ImageEditor.h
index 122892699f..9e2de93e09 100644
--- a/Userland/Applications/PixelPaint/ImageEditor.h
+++ b/Userland/Applications/PixelPaint/ImageEditor.h
@@ -85,7 +85,9 @@ public:
     Gfx::FloatPoint editor_position_to_image_position(Gfx::IntPoint const&) const;
 
     NonnullRefPtrVector<Guide> const& guides() const { return m_guides; }
-    void toggle_guide_visibility() { m_show_guides = !m_show_guides; }
+    bool guide_visibility() { return m_show_guides; }
+    void set_guide_visibility(bool show_guides);
+    Function<void(bool)> on_set_guide_visibility;
 
 private:
     explicit ImageEditor(NonnullRefPtr<Image>);
diff --git a/Userland/Applications/PixelPaint/Tool.h b/Userland/Applications/PixelPaint/Tool.h
index 2cb115481b..67b5251029 100644
--- a/Userland/Applications/PixelPaint/Tool.h
+++ b/Userland/Applications/PixelPaint/Tool.h
@@ -27,6 +27,7 @@ public:
     virtual void on_second_paint(Layer const&, GUI::PaintEvent&) { }
     virtual void on_keydown(GUI::KeyEvent&) { }
     virtual void on_keyup(GUI::KeyEvent&) { }
+    virtual void on_tool_activation() { }
     virtual GUI::Widget* get_properties_widget() { return nullptr; }
     virtual Gfx::StandardCursor cursor() { return Gfx::StandardCursor::None; }
 
diff --git a/Userland/Applications/PixelPaint/main.cpp b/Userland/Applications/PixelPaint/main.cpp
index f6f95526e5..dfa3a1ca25 100644
--- a/Userland/Applications/PixelPaint/main.cpp
+++ b/Userland/Applications/PixelPaint/main.cpp
@@ -399,9 +399,9 @@ int main(int argc, char** argv)
         window);
 
     auto show_guides_action = GUI::Action::create_checkable(
-        "Show Guides", [&](auto&) {
+        "Show Guides", [&](auto& action) {
             if (auto* editor = current_image_editor()) {
-                editor->toggle_guide_visibility();
+                editor->set_guide_visibility(action.is_checked());
             }
         },
         window);
@@ -706,6 +706,10 @@ int main(int argc, char** argv)
             statusbar.set_override_text({});
         };
 
+        image_editor.on_set_guide_visibility = [&](bool show_guides) {
+            show_guides_action->set_checked(show_guides);
+        };
+
         // NOTE: We invoke the above hook directly here to make sure the tab title is set up.
         image_editor.on_image_title_change(image->title());
 
@@ -742,6 +746,7 @@ int main(int argc, char** argv)
                 image_editor.set_active_tool(&tool);
             }
         });
+        show_guides_action->set_checked(image_editor.guide_visibility());
     };
 
     if (Core::File::exists(file_to_edit_full_path)) {