Convert Apache .htaccess to IIS web.config

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Convert your .htaccess to web.config with help from this post. This post describes some of the IIS URL Rewrite equivalents of commonly used Apache .htaccess settings. You may find this useful when you want to convert your .htaccess to web.config. The second part of this series outlines how to use Internet Information Services Manager to import and convert .htaccess to web.config.

Convert Apache .htaccess to IIS web.config

IIS 7.5 / 8.0 web.config equivalents for Apache’s .htaccess (modules like mod_dir, mod_headers, mod_mime mod_rewrite and mod_gzip). Most Apache .htaccess modules are supported in the IIS URL Rewrite module or as web.config configuration directive.

You just need to know where to find the correct IIS equivalent for Apache .htaccess, follow the post to find out…

Apache mod_dir to IIS web.config

http://httpd.apache.org/docs/2.2/mod/mod_dir.html
Provides for “trailing slash” redirects and serving directory index files

IIS URL Rewrite: trailing directory slash

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <rewrite>
      <rules>
        <rule name="Add trailing slash" stopProcessing="true">
          <match url="(.*[^/])$" />
          <conditions>
            <!-- if no file by that name exists -->
            <add input="{REQUEST_FILENAME}" matchType="IsFile" negate="true" />
            <!-- if a directory by that name does exist -->
            <add input="{REQUEST_FILENAME}" matchType="IsDirectory" negate="false" />
          </conditions>
          <action type="Redirect" redirectType="Permanent" url="{R:1}/" />
        </rule>
      </rules>
    </rewrite>
  </system.webServer>
</configuration>

Configure default documents in IIS, or directory index

list of resources to look for when the client requests a directory

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <defaultDocument>
      <files>
        <!-- delete all currently configured index files -->
        <clear />
        <!-- add first index file -->
        <add value="index.php" />
        <!-- add second index file -->
        <add value="index.html" />
      </files>
    </defaultDocument>
  </system.webServer>
</configuration>

IIS web.config: enable and disable directory browsing

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <!-- set to false to disable -->
    <directoryBrowse enabled="true" />
  </system.webServer>
</configuration>

Apache mod_headers

http://httpd.apache.org/docs/2.2/mod/mod_headers.html
Customization of HTTP request and response headers

Set some HTTP response headers

Example response headers:

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <httpProtocol>
      <customHeaders>
        <remove name="ETag"/>
        <!-- Set a Access-Control-Allow-Origin header -->
        <add name="Access-Control-Allow-Origin" value="*"/>
        <!-- Set a X-UA-Compatible header -->
        <add name="X-UA-Compatible" value="IE=Edge,chrome=1"/>
        <!-- remove the X-Powered-By header -->
        <remove name="X-Powered-By"/>
        <!-- Set a Cache-Control header with max-age=691200 value -->
        <add name="Cache-Control" value="max-age=691200" />
      </customHeaders>
    </httpProtocol>
  </system.webServer>
</configuration>

Apache mod_mime

http://httpd.apache.org/docs/2.2/mod/mod_mime.html
Associates the requested filename’s extensions with the file’s behavior (handlers and filters) and content (mime-type, language, character set and encoding)

Set MIME-type and charset for file extensions

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <httpProtocol>
      <staticContent>
        <remove fileExtension=".html" />
        <mimeMap fileExtension=".html" mimeType="text/html; charset=UTF-8" />
        <remove fileExtension=".htm" />
        <mimeMap fileExtension=".htm" mimeType="text/html; charset=UTF-8" />
        <!-- DON'T set UTF-8 for .css, it breaks markup in Internet Explorer -->
        <!--
          <remove fileExtension=".css" />
          <mimeMap fileExtension=".css" mimeType="text/css; charset=UTF-8" />
        -->
        <remove fileExtension=".css" />
        <mimeMap fileExtension=".css" mimeType="text/css" />
        <remove fileExtension=".js" />
        <mimeMap fileExtension=".js" mimeType="text/javascript; charset=UTF-8" />
      </staticContent>
    </httpProtocol>
  </system.webServer>
</configuration>

Apache mod_rewrite

http://httpd.apache.org/docs/2.2/mod/mod_rewrite.html
Provides a rule-based rewriting engine to rewrite requested URLs on the fly

IIS URL Rewrite equivalent (most commenly used variant)

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <rewrite>
      <rules>
        <rule name="wordpress" patternSyntax="Wildcard">
	  <match url="*" />
	    <conditions>
	      <add input="{REQUEST_FILENAME}" matchType="IsFile" negate="true" />
	      <add input="{REQUEST_FILENAME}" matchType="IsDirectory" negate="true" />
	    </conditions>
	    <action type="Rewrite" url="index.php" />
	</rule>
      </rules>
    </rewrite>
  </system.webServer>
</configuration>

Are you using WordPress? Check out my WordPress web.config!

Apache mod_deflate

http://httpd.apache.org/docs/2.2/mod/mod_deflate.html
Compress content before it is delivered to the client

Gzip compression in IIS, for both static and dynamic file types

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <!-- set minFileSizeForComp to 256 kilobytes, the minimum size to allow compression -->
    <httpCompression minFileSizeForComp="256">
      <cheme name="gzip" dll="%Windir%\system32\inetsrv\gzip.dll" />
      <dynamicTypes>
        <clear />
        <add mimeType="text/*" enabled="true" />
        <add mimeType="message/*" enabled="true" />
        <!-- text/javascript MUST BE the same as in the mimeMap -->
        <add mimeType="text/javascript" enabled="true" />
        <add mimeType="*/*" enabled="false" />
      </dynamicTypes>
      <staticTypes>
        <clear />
        <add mimeType="text/*" enabled="true" />
        <add mimeType="message/*" enabled="true" />
        <!-- text/javascript MUST BE the same as in the mimeMap -->
        <add mimeType="text/javascript" enabled="true" />
        <add mimeType="*/*" enabled="false" />
      </staticTypes>
    </httpCompression>
  </system.webServer>
</configuration>

Gzip compression is mostly configured at the web server level and may be ignored in a website’s web.config.

Freebies, IIS web.config examples

You can configure a lot of other neat stuff in your IIS web.config file. Three (3) examples.

Set Expire headers to 30 days for static content in IIS

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <httpProtocol>
      <staticContent>
        <!-- Set expire headers to 30 days for static content -->
        <clientCache cacheControlMode="UseMaxAge" cacheControlMaxAge="30.00:00:00" />
      </staticContent>
    </httpProtocol>
  </system.webServer>
</configuration>

Remove or disable unused handlers

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <handlers>
      <!-- remove Perl (.cgi, .pl) if unused -->
      <remove name="PerlPLX" />
      <!-- remove PHP3 (.php3) if unused -->
      <remove name="PHP3" />
      <!-- remove PHP4 (.php4) if unused -->
      <remove name="PHP4" />
      <!-- remove ISAPI_RewriteProxy 64-bit if unused -->
      <remove name="ISAPI_RewriteProxy-64" />
      <!-- remove ISAPI_RewriteProxy if unused -->
      <remove name="ISAPI_RewriteProxy" />
      <!-- remove PHP (.php) if unused -->
      <remove name="PHP" />
    </handlers>
  </system.webServer>
</configuration>

Remove or disable unused IIS-, .NET-modules

<?xml version="1.0" encoding="UTF-8"?>
<configuration>
  <system.webServer>
    <modules>
      <!-- remove Helicontech APE -->
      <remove name="Helicon.Ape" />
      <!-- Add Uri- File- and Token cache modules -->
      <!-- for IIS Output Cache -->
      <add name="UriCacheModule" />
      <add name="FileCacheModule" />
      <add name="TokenCacheModule" />
    </modules>
  </system.webServer>
</configuration>

IIS Manager .htaccess import

Import and convert .htaccess files with Internet Information Services (IIS) 7.0 Manager.

In the second part of this post series you can learn how to use Internet Information Services (IIS) 7.0 Manager to import and convert a .htaccess file to web.config:

IIS URL Rewrite Outbound Rules

IIS URL Rewrite also supports so called Outbound Rules. An Outbound Rule is applied to the output stream, from the web server to the client. This makes it possible to rewrite response statuses, HTTP content, and so on.
For more information on IIS Outbound Rules, see:

About the Author J. Reilink

My name is Jan. I am not a hacker, coder, developer, programmer or guru. I am merely a system administrator, doing my daily thing at Vevida in the Netherlands. With over 10 years of experience, my specialties include Windows Server, IIS, Linux (CentOS, Debian), security, PHP, websites & optimization.

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