Thanks Andre for the help,

We are routing the request from IIS 7.5 to Apache using reverse Proxy. It seems 
like Apache is not allowing the authentication nor its accepting the username 
and password passed from IIS.

--  The AJP connector details in Server to XML were uncommented as shown in 
below, we added tomcatAuthentication="false" and still it was failing with 
empty username and password error.
        
     <Connector port="8010" tomcatAuthentication="false" protocol="AJP/1.3" 
redirectPort="8443" />

-- We are currently on Apache Tomcat 8.0.22, this is installation was part of 
our Siebel application suite, thus could not have all the necessary connector 
setting installed in it. Is there a way we can check and install AJP connector 
on the top of Apache Tomcat we got as a part of Siebel Application.

-- Also with IIS we were using [UserSpecSource = Server] and [UserSpec = 
REMOTE_USER], are they the correct value for Tomcat webserver as well.

Thanks & Regards,
Suraj Agrawal


-----Original Message-----
From: André Warnier (tomcat) [mailto:a...@ice-sa.com] 
Sent: Thursday, January 4, 2018 9:07 AM
To: users@tomcat.apache.org
Subject: Re: WELCOME to users@tomcat.apache.org

Hi.

On 03.01.2018 18:31, Agrawal, Suraj (CORP) wrote:
> Hi Team,
>
> We are currently working on "Apache Tomcat Version 8.0.22". We are 
> using Apache to host javacontainer for Rest calls for our Siebel 
> application. The javacontainer is listening to Port 9001 as below-
>
> <Connector port="9001" redirectPort="8443" connectionTimeout="20000" 
> protocol="HTTP/1.1"/>
>
> We are trying to setup Windows Authentication in Apache by using Reverse 
> Proxy with IIS, and have followed the below steps as per the Apache 
> documentation.
>
> ---Steps followed :
> There are three steps to configuring IIS to provide Windows authentication. 
> They are:
> 1. Configure IIS as a reverse proxy for Tomcat (see the  IIS Web Server 
> How-To).
> ---- This is done and working as expected

There is a bit of confusing information in the page 
http://tomcat.apache.org/connectors-doc/webserver_howto/iis.html
in that it talks (in the title and elsewhere) of the "ISAPI redirector", but 
then later it mentions "The mod_jk module uses the AJP protocol to send 
requests to the Tomcat containers".  In fact, "mod_jk" and "ISAPI redirector" 
are functionaly the same thing (and probably much the same code), but
- mod_jk is the plugin proxy module to use with an Apache httpd webserver 
front-end (under Linux and/or Windows)
- isapi_redirector is the plugin proxy module to use with an IIS webserver 
front-end (Windows only)

But /both/ use the same protocol to talk with the back-end Tomcat, and that 
protocol is AJP, not HTTP.
So in both cases, what they are "talking to" is the AJP Connector in Tomcat, 
and not the HTTP Connector.

The AJP protocol is somewhat different from HTTP :
- both essentially carry the same information (requests and responses) but
- HTTP carries all its information back and forth in a text form as per HTTP RFC
- AJP encodes some of this information in a binary form (a bit more efficient)
- one of the "binary" parameters which the AJP protocol does transmit from the 
front-end to the back-end, is the authenticated user-id on the front-end, if 
any.
(HTTP does not normally do this in any standard way).

At the Tomcat level (the AJP Connector), the attribute "tomcatAuthentication" 
(true/false) serves to tell Tomcat to either "believe" (false) the user-id that 
it receives from the front-end through AJP, or to ignore it (true) and do its 
own authentication anyway.

At the Tomcat level, this "tomcatAuthentication" attribute only makes sense 
with the AJP Connector (and protocol).
See : http://tomcat.apache.org/tomcat-8.5-doc/config/ajp.html#Common_Attributes
(tomcatAuthentication AND tomcatAuthorization)

while here : 
http://tomcat.apache.org/tomcat-8.5-doc/config/http.html#Common_Attributes
this attribute is not mentioned (so if you add it, it will simply be ignored).

>
> 2. Configure IIS to use Windows authentication
> ---- This is done and working as expected
>
> 3. Configure Tomcat to use the authentication user information from IIS by 
> setting the tomcatAuthentication attribute on the  AJP connector to false. 
> Alternatively, set the tomcatAuthorization attribute to true to allow IIS to 
> authenticate, while Tomcat performs the authorization.
>

Right. But on which Tomcat connector did you set this ? (HTTP or AJP ?)

> Q1 ----  We were able to configure the reverse proxy with Anon user but the 
> Windows authentication is failing at Apache level with below error :-
> Thread[http-nio-9001-exec-15,5,main]  [2017-12-27 13:17:12.637] [null] Error 
> while login : The username cannot be empty. Please select a username.
>

Your problem may be there, with this "anonymous" authentication at the IIS 
level.  Maybe the isapi_redirector interprets this as "no user", and transmits 
an empty user-id to Tomcat.  Have you tried with a real Windows-level user-id ?


> Q2 ----  Our configuration is using "HTTP" protocol, do we need to change the 
> server.xml entry for 9001 to use AJP protocol and then add entry " 
> tomcatAuthentication=False"
>

Yes, probably.

> Q3 ---- Do we need to install AJP connector on top of Tomcat or its installed 
> by default, or we do not need it for Windows Authentication.
>

You do need it.
It is provided by default, but you may need to uncomment the corresponding 
lines in the server.xml file.
Considering your previous statements above, make sure that the HTTP Connector 
(if any) and the AJP Connector (if any) use different ports.
And on the IIS/ISAPI redirector side, make sure that the settings specify the 
correct
(AJP) port.

This is all quite logical, but a bit convoluted, due to the many ways in which 
you can use a front-end with Tomcat, and the many ways in which one can do 
authentication/authorization in the WWW.

I have found that it often helps to draw a schema in advance, such as

browser <--(1)--> front-end (2) <-----(4)---> tomcat (5)
                  + proxy module (3)          + Connector(6)

where :
(1) is the protocol used between the browser and the front-end http server 
(HTTP or HTTPS)
(2) is the front-end webserver (Apache httpd or IIS (or others)), which can be 
doing its own authentication/authorization or not
(3) is the proxy module add-on to (2).  There are a number of possibilities 
here, depending on (2) and (4)
(4) is the protocol used between the front-end webserver and Tomcat (HTTP, 
HTTPS or AJP)
(5) is Tomcat, which can be doing its own authentication/authorization or not
(6) is the Tomcat Connector, which depends on (3) and (4)

Depending on the circumstances and on what you want to achieve in the end, the 
variable elements above allow for a lot of combinations.  And that of course 
makes it rather difficult to provide a fully comprehensive, all-in-one-place 
documentation.


>
> Thanks & Regards,
> Suraj Agrawal
>
>
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