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chromium/third_party/blink/web_tests/fast/multicol/outline/outline-inline-continuation-across-columns.html 

<!DOCTYPE html>
<style>
.columns {
  column-fill: auto;
  column-width: 10ch;
  orphans: 1;
  widows: 1;
  font-size: 20px;
  line-height: 22px;
  height: 90px;
  margin-bottom: 1em;
}
.loose {
  line-height: 24px;
  height: 100px;
}
</style>
<body>
  <div class="columns">
    123456789
    12345
    <span style="outline: auto">
      789
      123456789
      <div>
        123456789
        123456789
        123456789
        123456789
        123456789
        123456789
      </div>
      123456789
      123</span>
    56789
    123456789
  </div>

  <div class="columns loose">
    123456789
    12345
    <span style="outline: auto">
      789
      123456789
      <div>
        123456789
        123456789
        123456789
        123456789
        123456789
        123456789
      </div>
      123456789
      123</span>
    56789
    123456789
  </div>

  <div class="columns">
    123456789
    12345
    <span style="outline: 5px solid blue">
      789
      123456789
      <div>
        123456789
        123456789
        123456789
        123456789
        123456789
        123456789
      </div>
      123456789
      123</span>
    56789
    123456789
  </div>
</body>