diff -r 86d3a45dc928 -r 24677835f298 ui/win32/menu.c
--- a/ui/win32/menu.c	Wed Dec 31 10:06:15 2025 +0100
+++ b/ui/win32/menu.c	Wed Dec 31 10:34:29 2025 +0100
@@ -66,7 +66,7 @@
     }
 }
 
-static void menu_item_clicked(UiObject *obj, UiMenuItem *item) {
+static void menu_item_clicked(UiObject *obj, uint64_t id, UiMenuItem *item) {
     UiEvent event;
     event.obj = obj;
     event.window = obj->window;
@@ -92,8 +92,76 @@
     cxMapPut(obj->ctx->command_map, id, &cmd);
 }
 
+static void menu_stateitem_update(UiStateMenuItem *item) {
+    MENUITEMINFO mi = { 0 };
+    mi.cbSize = sizeof(mi);
+    mi.fMask = MIIM_STATE;
+    mi.fState = item->state ? MFS_CHECKED : MFS_UNCHECKED;
+    SetMenuItemInfo(item->menu, item->id, FALSE, &mi);
+}
+
+static void menu_checkitem_clicked(UiObject *obj, uint64_t id, UiStateMenuItem *item) {
+    item->state = !item->state;
+    menu_stateitem_update(item);
+
+    UiEvent event;
+    event.obj = obj;
+    event.window = obj->window;
+    event.document = obj->ctx->document;
+    event.eventdata = NULL;
+    event.eventdatatype = 0;
+    event.intval = 0;
+    event.set = 0;
+    if (item->onchange) {
+        item->onchange(&event, item->userdata);
+    }
+
+    if (item->var) {
+        UiInteger *i = item->var->value;
+        ui_notify_evt(i->observers, &event);
+    }
+}
+
 void ui_add_menu_checkitem(HMENU parent, int pos, UiMenuItemI *item, UiObject *obj) {
+    uint64_t id = ++obj->ctx->command_id_counter;
 
+    UiMenuCheckItem *i = (UiMenuCheckItem*)item;
+    AppendMenu(parent, MF_STRING, id, i->label);
+
+    // create an UiStateMenuItem with the same lifetime as the UiObject
+    UiStateMenuItem *sitem = ui_malloc(obj->ctx, sizeof(UiStateMenuItem));
+    memset(sitem, 0, sizeof(UiStateMenuItem));
+    sitem->obj = obj;
+    sitem->menu = parent;
+    sitem->id = id;
+    sitem->onchange = i->callback;
+    sitem->userdata = i->userdata;
+    sitem->var = uic_widget_var(obj->ctx, obj->ctx, NULL, i->varname, UI_VAR_INTEGER);
+    // bind to var
+    if (sitem->var) {
+        UiInteger *v = sitem->var->value;
+        sitem->state = v->value != 0;
+        v->obj = sitem;
+        v->get = ui_checkitem_get;
+        v->set = ui_checkitem_set;
+    }
+
+    // register command id
+    UiCommand cmd;
+    cmd.callback = (ui_command_func)menu_checkitem_clicked;
+    cmd.userdata = sitem;
+    cxMapPut(obj->ctx->command_map, id, &cmd);
+
+    menu_stateitem_update(sitem);
+}
+
+int64_t ui_checkitem_get(UiInteger *i) {
+    return i->value;
+}
+
+void ui_checkitem_set(UiInteger *i, int64_t value) {
+    i->value = value;
+    menu_stateitem_update(i->obj);
 }
 
 void ui_add_menu_radioitem(HMENU parent, int pos, UiMenuItemI *item, UiObject *obj) {