Your specs look a lot like ours (we have a CMS that adds a trailing /index to every page that is part of the core navigation, and we don't want that). Here's th

Your specs look a lot like ours (we have a CMS that adds a trailing /index to every page that is part of the core navigation, and we don't want that). Here's the three primary rewrite rules we use for the issue; they don't match your spec exactly, but they might help you get started: # - Remove trailing slashes (except root /) # e.g. /foo/bar/ -> /foo/bar # ([^^] matches every character but the start of the string) rewrite [^^](.*)/$ /$1 permanent; # - Remove .html and .htm extensions # e.g. /foo/bar.htm -> /foo/bar rewrite ^(.*)\.html?$ $1 permanent; # - Remove index file URLs # e.g. /foo/bar/index -> /foo/bar/ # (the trailing slash is then removed by the first rewrite) rewrite ^(.*/)index$ $1 permanent; Edit: There's a couple extra directives that go along with the above to make it work that I neglected to include: # Try the request URI, and a potential index file in the URI (in the case of a directory). # This lets you hit the file WEBROOT/foo/bar/index with the URI /foo/bar, # and hit the file WEBROOT/foo/bar.html with the URI /foo/bar try_files $uri $uri/index $uri.html =404; # You need this (or some other way to provide the type information) # if you don't have extensions on your files. default_type text/html; Also, for error pages, you can probably just use the error_page directive: error_page 404 403 /404; # The .html in your spec will be stripped off by the above rewrite rule