diff --git a/Userland/Libraries/LibWeb/Layout/Box.cpp b/Userland/Libraries/LibWeb/Layout/Box.cpp
index 523bad3dae..d3cd09e1fc 100644
--- a/Userland/Libraries/LibWeb/Layout/Box.cpp
+++ b/Userland/Libraries/LibWeb/Layout/Box.cpp
@@ -42,8 +42,6 @@ void Box::paint(PaintContext& context, PaintPhase phase)
         Painting::paint_border(context, Painting::BorderEdge::Bottom, bordered_rect, computed_values());
     }
 
-    Layout::NodeWithStyleAndBoxModelMetrics::paint(context, phase);
-
     if (phase == PaintPhase::Overlay && dom_node() && document().inspected_node() == dom_node()) {
         auto content_rect = absolute_rect();
 
@@ -179,23 +177,6 @@ StackingContext* Box::enclosing_stacking_context()
     VERIFY_NOT_REACHED();
 }
 
-bool Box::establishes_stacking_context() const
-{
-    if (!has_style())
-        return false;
-    if (dom_node() == document().root())
-        return true;
-    auto position = computed_values().position();
-    auto z_index = computed_values().z_index();
-    if (position == CSS::Position::Absolute || position == CSS::Position::Relative) {
-        if (z_index.has_value())
-            return true;
-    }
-    if (position == CSS::Position::Fixed || position == CSS::Position::Sticky)
-        return true;
-    return false;
-}
-
 LineBox& Box::ensure_last_line_box()
 {
     if (m_line_boxes.is_empty())
diff --git a/Userland/Libraries/LibWeb/Layout/Box.h b/Userland/Libraries/LibWeb/Layout/Box.h
index a86f34d57f..08a6620241 100644
--- a/Userland/Libraries/LibWeb/Layout/Box.h
+++ b/Userland/Libraries/LibWeb/Layout/Box.h
@@ -104,7 +104,6 @@ public:
 
     void set_containing_line_box_fragment(LineBoxFragment&);
 
-    bool establishes_stacking_context() const;
     StackingContext* stacking_context() { return m_stacking_context; }
     const StackingContext* stacking_context() const { return m_stacking_context; }
     void set_stacking_context(NonnullOwnPtr<StackingContext> context) { m_stacking_context = move(context); }
diff --git a/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.cpp b/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.cpp
index ea86059d97..0b71a20cfa 100644
--- a/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.cpp
+++ b/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.cpp
@@ -56,18 +56,7 @@ void InitialContainingBlockBox::paint_document_background(PaintContext& context)
 void InitialContainingBlockBox::paint_all_phases(PaintContext& context)
 {
     paint_document_background(context);
-
-    paint(context, PaintPhase::Background);
-    paint(context, PaintPhase::Border);
-    paint(context, PaintPhase::Foreground);
-    if (context.has_focus())
-        paint(context, PaintPhase::FocusOutline);
-    paint(context, PaintPhase::Overlay);
-}
-
-void InitialContainingBlockBox::paint(PaintContext& context, PaintPhase phase)
-{
-    stacking_context()->paint(context, phase);
+    stacking_context()->paint(context);
 }
 
 HitTestResult InitialContainingBlockBox::hit_test(const Gfx::IntPoint& position, HitTestType type) const
diff --git a/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.h b/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.h
index 7334f9bcde..1466b4bbc0 100644
--- a/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.h
+++ b/Userland/Libraries/LibWeb/Layout/InitialContainingBlockBox.h
@@ -19,7 +19,6 @@ public:
     const DOM::Document& dom_node() const { return static_cast<const DOM::Document&>(*Node::dom_node()); }
 
     void paint_all_phases(PaintContext&);
-    virtual void paint(PaintContext&, PaintPhase) override;
 
     void paint_document_background(PaintContext&);
 
diff --git a/Userland/Libraries/LibWeb/Layout/Node.cpp b/Userland/Libraries/LibWeb/Layout/Node.cpp
index c51945b225..1c5e2a0dab 100644
--- a/Userland/Libraries/LibWeb/Layout/Node.cpp
+++ b/Userland/Libraries/LibWeb/Layout/Node.cpp
@@ -67,6 +67,18 @@ const BlockBox* Node::containing_block() const
     return nearest_block_ancestor();
 }
 
+bool Node::establishes_stacking_context() const
+{
+    if (!has_style())
+        return false;
+    if (dom_node() == document().root())
+        return true;
+    auto position = computed_values().position();
+    if (position == CSS::Position::Absolute || position == CSS::Position::Relative || position == CSS::Position::Fixed || position == CSS::Position::Sticky)
+        return true;
+    return false;
+}
+
 void Node::paint(PaintContext& context, PaintPhase phase)
 {
     if (!is_visible())
diff --git a/Userland/Libraries/LibWeb/Layout/Node.h b/Userland/Libraries/LibWeb/Layout/Node.h
index a68e2a6a55..770339732c 100644
--- a/Userland/Libraries/LibWeb/Layout/Node.h
+++ b/Userland/Libraries/LibWeb/Layout/Node.h
@@ -112,6 +112,8 @@ public:
     const BlockBox* containing_block() const;
     BlockBox* containing_block() { return const_cast<BlockBox*>(const_cast<const Node*>(this)->containing_block()); }
 
+    bool establishes_stacking_context() const;
+
     bool can_contain_boxes_with_position_absolute() const;
 
     const Gfx::Font& font() const;
diff --git a/Userland/Libraries/LibWeb/Painting/StackingContext.cpp b/Userland/Libraries/LibWeb/Painting/StackingContext.cpp
index 1d3565065d..bbd9e8ae76 100644
--- a/Userland/Libraries/LibWeb/Painting/StackingContext.cpp
+++ b/Userland/Libraries/LibWeb/Painting/StackingContext.cpp
@@ -22,24 +22,80 @@ StackingContext::StackingContext(Box& box, StackingContext* parent)
         m_parent->m_children.append(this);
 
         // FIXME: Don't sort on every append..
+        // FIXME: Apparently this also breaks tree order inside layers
         quick_sort(m_parent->m_children, [](auto& a, auto& b) {
             return a->m_box.computed_values().z_index().value_or(0) < b->m_box.computed_values().z_index().value_or(0);
         });
     }
 }
 
-void StackingContext::paint(PaintContext& context, PaintPhase phase)
+void StackingContext::paint_descendants(PaintContext& context, Node& box, StackingContextPaintPhase phase)
 {
-    if (!is<InitialContainingBlockBox>(m_box)) {
-        m_box.paint(context, phase);
-    } else {
-        // NOTE: InitialContainingBlockBox::paint() merely calls StackingContext::paint()
-        //       so we call its base class instead.
-        downcast<InitialContainingBlockBox>(m_box).BlockBox::paint(context, phase);
-    }
+    box.for_each_child([&](auto& child) {
+        switch (phase) {
+        case StackingContextPaintPhase::BackgroundAndBorders:
+            if (!child.is_floating() && !child.is_positioned()) {
+                child.paint(context, PaintPhase::Background);
+                child.paint(context, PaintPhase::Border);
+                paint_descendants(context, child, phase);
+            }
+            break;
+        case StackingContextPaintPhase::Floats:
+            if (!child.is_positioned()) {
+                if (child.is_floating()) {
+                    child.paint(context, PaintPhase::Background);
+                    child.paint(context, PaintPhase::Border);
+                    paint_descendants(context, child, StackingContextPaintPhase::BackgroundAndBorders);
+                }
+                paint_descendants(context, child, phase);
+            }
+            break;
+        case StackingContextPaintPhase::Foreground:
+            if (!child.is_positioned()) {
+                child.paint(context, PaintPhase::Foreground);
+                child.before_children_paint(context, PaintPhase::Foreground);
+                paint_descendants(context, child, phase);
+                child.after_children_paint(context, PaintPhase::Foreground);
+            }
+            break;
+        case StackingContextPaintPhase::FocusAndOverlay:
+            if (context.has_focus()) {
+                child.paint(context, PaintPhase::FocusOutline);
+            }
+            child.paint(context, PaintPhase::Overlay);
+            paint_descendants(context, child, phase);
+            break;
+        }
+    });
+}
+
+void StackingContext::paint(PaintContext& context)
+{
+    // For a more elaborate description of the algorithm, see CSS 2.1 Appendix E
+    // Draw the background and borders for the context root (steps 1, 2)
+    m_box.paint(context, PaintPhase::Background);
+    m_box.paint(context, PaintPhase::Border);
+    // Draw positioned descendants with negative z-indices (step 3)
     for (auto* child : m_children) {
-        child->paint(context, phase);
+        if (child->m_box.computed_values().z_index().has_value() && child->m_box.computed_values().z_index().value() < 0)
+            child->paint(context);
     }
+    // Draw the background and borders for block-level children (step 4)
+    paint_descendants(context, m_box, StackingContextPaintPhase::BackgroundAndBorders);
+    // Draw the non-positioned floats (step 5)
+    paint_descendants(context, m_box, StackingContextPaintPhase::Floats);
+    // Draw inline content, replaced content, etc. (steps 6, 7)
+    paint_descendants(context, m_box, StackingContextPaintPhase::Foreground);
+    // Draw other positioned descendants (steps 8, 9)
+    for (auto* child : m_children) {
+        if (child->m_box.computed_values().z_index().has_value() && child->m_box.computed_values().z_index().value() < 0)
+            continue;
+        child->paint(context);
+    }
+
+    m_box.paint(context, PaintPhase::FocusOutline);
+    m_box.paint(context, PaintPhase::Overlay);
+    paint_descendants(context, m_box, StackingContextPaintPhase::FocusAndOverlay);
 }
 
 HitTestResult StackingContext::hit_test(const Gfx::IntPoint& position, HitTestType type) const
diff --git a/Userland/Libraries/LibWeb/Painting/StackingContext.h b/Userland/Libraries/LibWeb/Painting/StackingContext.h
index 7dccd290d4..687e887b49 100644
--- a/Userland/Libraries/LibWeb/Painting/StackingContext.h
+++ b/Userland/Libraries/LibWeb/Painting/StackingContext.h
@@ -18,7 +18,15 @@ public:
     StackingContext* parent() { return m_parent; }
     const StackingContext* parent() const { return m_parent; }
 
-    void paint(PaintContext&, PaintPhase);
+    enum class StackingContextPaintPhase {
+        BackgroundAndBorders,
+        Floats,
+        Foreground,
+        FocusAndOverlay,
+    };
+
+    void paint_descendants(PaintContext&, Node&, StackingContextPaintPhase);
+    void paint(PaintContext&);
     HitTestResult hit_test(const Gfx::IntPoint&, HitTestType) const;
 
     void dump(int indent = 0) const;