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I'm configuring IIS to work as a proxy in front of several java web servers. I know that static compression cannot be enabled when using rewrite rules because the outbound rule won't work. There are several post concerning this issues and some blog post offer the solution i.e. http://codeblog.shawson.co.uk/iis7-urlrewrite-outbound-links-with-compression-enabled/ I have applied this with success on IIS 7.5 but this doesn't seem to work anymore with ARR 3.0 and IIS 8.5 on windows server 2012. Anyone has some experience with this and could help me solve this issue

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I did not really solve the core of this issue, but there are 2 ways to solve this

  • disable the gzip compression on tomcat. This is a dirty solution, because it impacts your performance, but the site is accesible
  • use tomcat 8. Tomcat 8 works out the box when using IIS redirecting
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