diff --git a/Userland/Libraries/LibGUI/Toolbar.cpp b/Userland/Libraries/LibGUI/Toolbar.cpp
index daca0bd235..3e0801d9c0 100644
--- a/Userland/Libraries/LibGUI/Toolbar.cpp
+++ b/Userland/Libraries/LibGUI/Toolbar.cpp
@@ -181,13 +181,13 @@ ErrorOr<void> Toolbar::update_overflow_menu()
     Optional<size_t> marginal_index {};
     auto position { 0 };
     auto is_horizontal { m_orientation == Gfx::Orientation::Horizontal };
-    auto margin { is_horizontal ? layout()->margins().right() : layout()->margins().bottom() };
+    auto margin { is_horizontal ? layout()->margins().horizontal_total() : layout()->margins().vertical_total() };
     auto toolbar_size { is_horizontal ? width() : height() };
 
     for (size_t i = 0; i < m_items.size() - 1; ++i) {
         auto& item = m_items.at(i);
         auto item_size = is_horizontal ? item.widget->width() : item.widget->height();
-        if (position + item_size + m_button_size + margin > toolbar_size) {
+        if (position + item_size + margin > toolbar_size) {
             marginal_index = i;
             break;
         }
@@ -203,6 +203,18 @@ ErrorOr<void> Toolbar::update_overflow_menu()
         return {};
     }
 
+    if (marginal_index.value() > 0) {
+        for (size_t i = marginal_index.value() - 1; i > 0; --i) {
+            auto& item = m_items.at(i);
+            auto item_size = is_horizontal ? item.widget->width() : item.widget->height();
+            if (position + m_button_size + margin <= toolbar_size)
+                break;
+            item.widget->set_visible(false);
+            position -= item_size;
+            marginal_index = i;
+        }
+    }
+
     if (m_grouped) {
         for (size_t i = marginal_index.value(); i > 0; --i) {
             auto& item = m_items.at(i);