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chromium/third_party/blink/web_tests/external/wpt/infrastructure/testdriver/actions/actionsWithKeyPressed.html 

<!DOCTYPE html>
<meta charset="utf-8">
<title>TestDriver actions: actions with key pressed</title>
<script src="/resources/testharness.js"></script>
<script src="/resources/testharnessreport.js"></script>
<script src="/resources/testdriver.js"></script>
<script src="/resources/testdriver-actions.js"></script>
<script src="/resources/testdriver-vendor.js"></script>

<style>
div#test1, div#test2 {
  position: fixed;
  top: 0;
  left: 0;
  width: 100px;
  height: 100px;
  background-color: blue;
}

div#test2 {
  position: fixed;
  top: 100px;
  left: 0;
  width: 100px;
  height: 100px;
  background-color: green;
}
</style>

<div id="test1">
</div>

<div id="test2">
</div>

<script>
let keys = [];

promise_test(async t => {
  let test1 = document.getElementById("test1");
  let test2 = document.getElementById("test2");
  document.getElementById("test1").addEventListener("click",
    e => {keys.push(e.getModifierState("Shift"))});
  document.getElementById("test2").addEventListener("click",
    e => {keys.push(e.getModifierState("Shift"))});

  let actions = new test_driver.Actions()
    .keyDown("\uE008")
    .addTick()
    .pointerMove(0, 0, {origin: test1})
    .pointerDown()
    .pointerUp()
    .pointerMove(0, 0, {origin: test2})
    .pointerDown()
    .pointerUp()
    .addTick()
    .keyUp("\uE008")
    .addTick()
    .pointerMove(0, 0, {origin: test1})
    .pointerDown()
    .pointerUp();

  await actions.send();
  assert_array_equals(keys, [true, true, false]);
});
</script>