Sorry for what is most likely NOT a very intelligent question, but my non-sysadmin brain is struggling to understand what is causing my problem. Basically, I wan't to enable reverse proxying on a IIS8 box. I read though this article: http://www.iis.net/learn/extensions/url-rewrite-module/reverse-proxy-with-url-rewrite-v2-and-application-request-routing And I've installed the ARR extension from here: http://www.iis.net/downloads/microsoft/application-request-routing Now, I enabled the proxying (as explained in the MS tutorial), and I felt the other setting as they where (again, as instructed in the tutorial). My rule looks like the following <rule name="Reverse Proxy to payroll" stopProcessing="true"> <match url="^mytest/(.*)" /> <action type="Rewrite" url="http://localhost:8282/{R:1}" /> </rule> But alas, it doesn't work. If I change it to a "normal" rewrite rule, as in <rule name="Reverse Proxy to payroll" stopProcessing="true"> <match url="^mytest/(.*)" /> <action type="Rewrite" url="/{R:1}" /> </rule> Then it works. So, it must differently be something with the reverse proxy. Any idea what gives?