Существует mod_ntlm и mod_auth_sspi. Вы могли попробовать любое из этого.
PS: Ваш старый вопрос в stackoverflow не был удален. его перемещенный здесь.
Когда вы вводите URL без порта, подразумевается порт 80.
Ни один из известных мне браузеров не может изменить это поведение; если вы хотите использовать порт 3333, он вам понадобится в URL.
You can use Reverse Proxy to silently redirect all HTTP requests to another port. Obviously, there still should be a site bound to TCP port 80 (that is the port which is used when no specific port is specified), which you will configure to make such redirect to another port.
It is possible with IIS 7 + URL Rewrite module + Application Request Routing (or IIS 7 + Helicon Ape if you prefer Apache-style configuration).
Question is -- if you can bind a site to port 80, why would you need to run it on port 3333 then?
When you assign an IIS site to a TCP port, the IIS process actually binds to the TCP port. This means that any connection (less filtering at the stack level, example: software firewall) incoming on that TCP port is serviced by this IIS site instance.
What you could do is:
For instance, a user hits: http://redmine
All the user did was hit http://redmine
This obviously allows you to host multiple sites on a single box. "Virtual host" if you will.