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chromium/third_party/blink/web_tests/external/wpt/css/css-shapes/shape-outside/shape-image/shape-image-029.html 

<!DOCTYPE html>
<link rel="help" href="https://drafts.csswg.org/css-shapes-2/#shapes-from-image"/>
<link rel="help" href="https://drafts.csswg.org/css-shapes-2/#shape-outside-property"/>
<meta name="flags" content="ahem"/>
<meta name="assert"
  content="WebKit and Blink had a bug that a negative margin was applied
           incorrectly if float's writing-mode was different from the
           container's writing-mode. This test verifies a browser has no
           such bug."/>
<link rel="match" href="reference/shape-image-000-ref.html"/>
<link rel="stylesheet" href="/fonts/ahem.css" />
<style>
.container {
  width: 100px;
  font: 10px/1 Ahem;
  background-color: red;
  color: rgb(0, 100, 0);
  overflow: hidden;
}
#f {
  display: inline-block;
  width: 100px;
  height: 100px;
  background: url(support/left-half-rectangle.png);
  shape-outside: url(support/left-half-rectangle.png);
  float: left;
  margin-left: -10px;
  writing-mode: vertical-lr;
}
</style>
<p>The test passes if you see a solid green square. There should be no red.</p>

<div class="container"><span id="f"></span>
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</div>