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    <p>Having in mind it is easier to do with sub-domain and CNAME, I think that what you are looking for is the <a href="http://www.iis.net/download/urlrewrite" rel="nofollow noreferrer">IIS URL Rewrite module</a>. The following base rules are taken from <a href="http://forums.iis.net/t/1168364.aspx" rel="nofollow noreferrer">this IIS Forum's thread</a>, as a similar situation is described and samples rules are given. You may use them as a base:</p> <pre><code>&lt;system.webServer&gt; &lt;rewrite&gt; &lt;rules&gt; &lt;rule name="CanonicalHostNameRule"&gt; &lt;match url="(.+)/(.*)" /&gt; &lt;conditions&gt; &lt;add input="{HostToRedirect:{HTTP_HOST}/{R:1}}" pattern="(.+)" /&gt; &lt;/conditions&gt; &lt;action type="Redirect" url="http://{C:1}/{R:2}" /&gt; &lt;/rule&gt; &lt;/rules&gt; &lt;rewriteMaps&gt; &lt;rewriteMap name="HostToRedirect"&gt; &lt;add key="domain.com/mail" value="mail.domain.com" /&gt; &lt;add key="domain.net/mail" value="mail.domain.net" /&gt; &lt;/rewriteMap&gt; &lt;/rewriteMaps&gt; &lt;/rewrite&gt; &lt;/system.webServer&gt; </code></pre> <p>You may also check <a href="https://stackoverflow.com/questions/632360/how-to-redirect-subfolder-to-query-in-mod-rewrite-for-iis-7-0">this SO question</a>, as it is providing some guides on the problem you are trying to solve.</p> <p><strong>UPDATE WITH SOLUTION</strong></p> <p>This is totally achievable with <a href="http://www.iis.net/download/urlrewrite" rel="nofollow noreferrer">URL Rewrite module for IIS</a> in combination with <a href="http://www.iis.net/download/ApplicationRequestRouting" rel="nofollow noreferrer">ARR module</a>. Then you need to set a Reverse Proxy rule that will rewrite all /products requests to the corresponding web app in the cloud. Your rule will look something like that:</p> <pre><code>&lt;system.webServer&gt; &lt;rewrite&gt; &lt;rules&gt; &lt;rule name="ReverseProxyInboundRule1" patternSyntax="ECMAScript" stopProcessing="true"&gt; &lt;match url="(^products)" /&gt; &lt;conditions&gt; &lt;add input="{CACHE_URL}" pattern="^(https?)://" /&gt; &lt;/conditions&gt; &lt;action type="Rewrite" url="{C:1}://myvompany.cloudapp.net/" /&gt; &lt;/rule&gt; &lt;/rules&gt; &lt;/rewrite&gt; &lt;/system.webServer&gt; </code></pre> <p>You can tweak this later to fit your exact need, but with the above sample I just achieved what you are looking for.</p>
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    1. POa web application in the cloud as a subfolder of the main company URL
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    1. COThanks! Does this mean each and every request first comes to my server and then rewritten or is there any caching involved at the client?
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    2. COevery request will come to your server first. Then it will server as reverse proxy. You can read the ARR deocumentation on Reverse Proxy, you can cache data from cloud app to the proxy server. As for client caching - client never understands data is comming from different server. All client caching capabilities apply as normal (i.e. content caching - images/js/css) when properly configured on the server side (the application server side - cloudapp).
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