 <p>Most likely it does not work because of your match pattern:</p> <ul> <li>the <code>{R:1}</code> will only match <code>(.*)</code> in your pattern, and will never match <code>files/123...</code></li> <li>URL in match pattern always starts with no leading slash: should be <code>files/\d+...</code> and not <code>/files/\d+...</code></li> </ul> <p>Try this one instead (works fine for me):</p> <pre><code>&lt;rule name="1" stopProcessing="true"&gt; &lt;match url="^files/\d+/.*\.html$" /&gt; &lt;action type="Redirect" url="default.aspx?url={R:0}" redirectType="Permanent" /&gt; &lt;/rule&gt; </code></pre>