diff --git a/scripts/map.lic b/scripts/map.lic
index 3da543abc..8d1a54b36 100644
--- a/scripts/map.lic
+++ b/scripts/map.lic
@@ -694,7 +694,10 @@ Gtk.queue {
 
   menu_borderless = Gtk::CheckMenuItem.new(:label => 'borderless')
   menu_borderless.active = setting_borderless
-  menu_borderless.signal_connect('toggled') { |owner| window.set_decorated(!setting_borderless = owner.active?) }
+  menu_borderless.signal_connect('toggled') { |owner|
+    setting_borderless = owner.active?
+    window.set_decorated(!setting_borderless)
+  }
 
   menu_hide_scrollbars = Gtk::CheckMenuItem.new(:label => 'hide scrollbars')
   menu_hide_scrollbars.active = setting_hide_scrollbars
@@ -1124,6 +1127,10 @@ before_dying {
   }
   sleep 0.01 while window_height.nil?
   Gtk.queue {
+    # Hide image widgets before destroying the window to prevent
+    # a GTK3/macOS Quartz segfault in Cairo surface teardown
+    image.hide
+    circle_image.hide
     menu.destroy
     window.destroy
   }
diff --git a/spec/map/map_gtk_bugs_spec.rb b/spec/map/map_gtk_bugs_spec.rb
new file mode 100644
index 000000000..e0e20234f
--- /dev/null
+++ b/spec/map/map_gtk_bugs_spec.rb
@@ -0,0 +1,194 @@
+# frozen_string_literal: true
+
+# Tests for GTK3 bugfixes in scripts/map.lic
+#
+# These tests verify the behavioral contracts of two fixes:
+#   1. Borderless toggle: compound expression split to avoid
+#      gobject-introspection invoke crash
+#   2. before_dying cleanup: image widgets hidden before window
+#      destruction to prevent macOS Quartz segfault
+
+# Minimal GTK doubles — no GTK3 gem required to run these specs
+module Gtk
+  class Window
+    attr_reader :decorated, :calls
+
+    def initialize
+      @decorated = true
+      @calls = []
+    end
+
+    def set_decorated(val)
+      @calls << [:set_decorated, val]
+      @decorated = val
+    end
+
+    def destroy
+      @calls << [:destroy]
+    end
+  end
+
+  class Image
+    attr_reader :calls, :visible
+
+    def initialize
+      @calls = []
+      @visible = true
+    end
+
+    def hide
+      @calls << [:hide]
+      @visible = false
+    end
+
+    def destroy
+      @calls << [:destroy]
+    end
+  end
+
+  class Menu
+    attr_reader :calls
+
+    def initialize
+      @calls = []
+    end
+
+    def destroy
+      @calls << [:destroy]
+    end
+  end
+
+  class CheckMenuItem
+    attr_accessor :active
+
+    def initialize(active: false)
+      @active = active
+    end
+  end
+end
+
+describe "map.lic GTK bugfixes" do
+  describe "borderless toggle (Bug 1)" do
+    # The fix splits:
+    #   window.set_decorated(!setting_borderless = owner.active?)
+    # into:
+    #   setting_borderless = owner.active?
+    #   window.set_decorated(!setting_borderless)
+
+    let(:window) { Gtk::Window.new }
+
+    def apply_borderless_toggle(window, owner_active)
+      # This is the fixed handler logic from map.lic line 697-700
+      setting_borderless = owner_active
+      window.set_decorated(!setting_borderless)
+      setting_borderless
+    end
+
+    it "sets decorated to false when toggled on" do
+      setting_borderless = apply_borderless_toggle(window, true)
+      expect(window.decorated).to eq(false)
+      expect(setting_borderless).to eq(true)
+    end
+
+    it "sets decorated to true when toggled off" do
+      setting_borderless = apply_borderless_toggle(window, false)
+      expect(window.decorated).to eq(true)
+      expect(setting_borderless).to eq(false)
+    end
+
+    it "calls set_decorated with a plain boolean, not a compound expression" do
+      apply_borderless_toggle(window, true)
+      expect(window.calls.size).to eq(1)
+
+      call_name, call_arg = window.calls.first
+      expect(call_name).to eq(:set_decorated)
+      # The argument must be a simple boolean — not the result of an inline
+      # assignment, which is what crashed gobject-introspection's invoke.
+      expect(call_arg).to eq(false)
+      expect([true, false]).to include(call_arg)
+    end
+
+    it "correctly round-trips through multiple toggles" do
+      # Toggle on
+      setting_borderless = apply_borderless_toggle(window, true)
+      expect(setting_borderless).to eq(true)
+      expect(window.decorated).to eq(false)
+
+      # Toggle off
+      setting_borderless = apply_borderless_toggle(window, false)
+      expect(setting_borderless).to eq(false)
+      expect(window.decorated).to eq(true)
+    end
+  end
+
+  describe "before_dying cleanup order (Bug 2)" do
+    # The fix adds image.hide and circle_image.hide before
+    # menu.destroy and window.destroy to prevent a macOS Quartz
+    # segfault in _gdk_quartz_unref_cairo_surface.
+
+    let(:window) { Gtk::Window.new }
+    let(:image) { Gtk::Image.new }
+    let(:circle_image) { Gtk::Image.new }
+    let(:menu) { Gtk::Menu.new }
+
+    def run_cleanup(image, circle_image, menu, window)
+      # This is the fixed cleanup logic from map.lic lines 1129-1136
+      image.hide
+      circle_image.hide
+      menu.destroy
+      window.destroy
+    end
+
+    it "hides image before destroying window" do
+      run_cleanup(image, circle_image, menu, window)
+      expect(image.visible).to eq(false)
+      expect(image.calls.first).to eq([:hide])
+    end
+
+    it "hides circle_image before destroying window" do
+      run_cleanup(image, circle_image, menu, window)
+      expect(circle_image.visible).to eq(false)
+      expect(circle_image.calls.first).to eq([:hide])
+    end
+
+    it "destroys menu before window" do
+      run_cleanup(image, circle_image, menu, window)
+      expect(menu.calls).to eq([[:destroy]])
+      expect(window.calls).to eq([[:destroy]])
+    end
+
+    it "executes operations in the correct order" do
+      call_log = []
+
+      allow(image).to receive(:hide) { call_log << :image_hide }
+      allow(circle_image).to receive(:hide) { call_log << :circle_hide }
+      allow(menu).to receive(:destroy) { call_log << :menu_destroy }
+      allow(window).to receive(:destroy) { call_log << :window_destroy }
+
+      run_cleanup(image, circle_image, menu, window)
+
+      expect(call_log).to eq([
+                               :image_hide,
+                               :circle_hide,
+                               :menu_destroy,
+                               :window_destroy
+                             ])
+    end
+
+    it "hides all images before any destroy call" do
+      call_log = []
+
+      allow(image).to receive(:hide) { call_log << [:hide, :image] }
+      allow(circle_image).to receive(:hide) { call_log << [:hide, :circle_image] }
+      allow(menu).to receive(:destroy) { call_log << [:destroy, :menu] }
+      allow(window).to receive(:destroy) { call_log << [:destroy, :window] }
+
+      run_cleanup(image, circle_image, menu, window)
+
+      hide_indices = call_log.each_index.select { |i| call_log[i][0] == :hide }
+      destroy_indices = call_log.each_index.select { |i| call_log[i][0] == :destroy }
+
+      expect(hide_indices.max).to be < destroy_indices.min
+    end
+  end
+end