So, my co-worker and I spent a full day trying to figure out how to
enable CakePHP-IIS-ISAPI Rewrite and after struggling a little, we
demystified how to enable ISAPI Rewrite on IIS and I figure I'd share
it here since everyone here has helped me out tremendously. :)

For the longer version, you can read about it here:
http://blog.localkinegrinds.com/2006/07/28/cakephp-and-iis-solved/

For the shorter version:

Step 1. Setup define('IIS_SERVER', true);
Step 2. Download ISAPI Rewrite
Step 3. Setup virtual directory in IIS to point to
CAKE_INSTALL/app/webroot
Step 4. Change httpd.ini file (the second rule) to the following:

RewriteRule ^/virtual_directory_name_here/(.*)/
/virtual_directory_name_here/index.php?url=/$1

Step 5. If you're using $html->link, make sure that all your links end
with slashes.  You can read more about it on the blog posting I made,
but I didn't know how to get the equivalent of RewriteCond
%{REQUEST_FILENAME} !-f with the ISAPI Rewrite dll. The end slash
matches files not served up by webroot directory.

Step 6. To enable the virtual_directory in the subsequent link names,
make sure to define('WEBROOT_DIR', 'virtual_directory_name') in
the app/webroot/index.php and voila...

ISAPI Rewrite should be working. :)

If you have any questions, or if you can think up a better RewriteRule,
feel free to contact me, I only had a day to look at it, so we just
wanted something quick and dirty to work. Btw, keep on baking. :)


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