Kerberos authentication and Application Request Routing

By Adrian Rienzi


This walkthrough will guide you through how to configure Kerberos authentication for multiple back-end applications published by a Reverse Proxy with Application Request Routing (ARR).


To run this walkthrough, you must have the following:

  1. IIS 7 or above with ASP.NET role service enabled.
  2. URL Rewrite Module version 2.0 or above installed.
  3. Application Request Routing version 2.5 or above installed

To install ARR and all its components in the appropriate order, use the Microsoft Web Platform Installer by clicking on the link at the top of the page. Alternatively, read the following blog post for instructions on installing ARR manually: Installing ARR manually without WebPI.


By using URL Rewrite Module and Application Request Routing you can implement complex and flexible load balancing and reverse proxy configurations.

Some time ago, I had to deal with a customer’s scenario where ARR was used as a reverse proxy to make available several internal web applications to internal users.

Customer wanted internal users to browse Web applications through ARR and then it forwarded the requests to the correct Web applications for processing. Back-end applications used IIS integrated authentication. The following figure illustrates the reverse-proxy scenario:

Figure 1. Architectural diagram showing ARR configuration for using authentication

Assuming that the ARR server URL has a name as http://ARR, each web application should be accessed by using these URLs: http://ARR/sales/ and http://ARR/payroll/.

When a request is made to http://ARR/sales/default.aspx, ARR forwards these requests to an internal server using the http://APP2/sales/default.aspx URL. Similarly, requests to http://ARR/payroll/ default.aspx are forwarded to http://APP1/payroll/default.aspx.

Let’s say AD domain name is I omitted server’s suffixes for simplicity.

In addition, Internet Explorer setting has been changed to require explicit authentication for every security zone. Then detailed authentication events are recorded on client machine Security Event Log.

Accessing the Web Sites

After having publishing Web applications by following Reverse Proxy with Application Request Routing (ARR) article, when browsing for example http://ARR/payroll/default.aspx, browser asked for authentication. Typing credentials three times, the following message was displayed:

Not Authorized

HTTP Error 401. The requested resource requires user authentication.



Looking at Security Log on user machine and domain controller respectively, it could be seen a service ticket for name ARR$ was requested.

User machine:

Event 4648

Account Whose Credentials Were Used:

Account Name: adrian

Account Domain:

Target Server:

Target Server Name:

Additional Information: HTTP/

Domain controller

A Kerberos service ticket was requested.

Account Information:

Account Name:

Account Domain:

Service Information:

Service Name: ARR$


It seems a common double-hop scenario would be easy to solve just creating the following SPNs on APP1 and enabling Kerberos delegation on ARR server:

setspn –S HTTP/ARR APP1

setspn –S HTTP/ARR

For more information about Kerberos double-hop and delegation, see and

But, what would it happen with APP2? If same solution was applied, SPNs would be duplicated and authentication would fail. Duplicate SPNs result in authentication failures.

Configuring the solution

In this section you will configure the solution guarantying:

1) Kerberos authentication

2) SPNs uniqueness

To assure SPN uniqueness, I did the following:

  1. Create a DNS Host (A) record for every application. This record must point to ARR server IP address. You cannot use CNAMEs because they are resolved to the original ARR name.

For example, create a record named sales for Sales application and a record named payroll for Payroll one. So, to retrieve Sales and Payroll applications, you should browse http://payroll/payroll/default.aspx and http://sales/sales/default.aspx respectively. Although it would be possible to tune URL Rewrite rules to use a friendlier URL such as http://payroll/default.aspx or http://sales/default.aspx I won’t cover that here.


To test this record, just ping the name, for example ping payroll should retrieve:

C:\ping payroll

Pinging [] with 32 bytes of data:

Reply from bytes=32 time<1ms TTL=128

C:\ping ARR

Pinging [] with 32 bytes of data:

Reply from bytes=32 time=1ms TTL=128

  1. Register HTTP service SPNs on application servers. You must register a SPN for every name used to reach the application:

setspn -S HTTP/APP1 APP1

setspn -S HTTP/ APP1

setspn -S HTTP/payroll APP1

setspn -S HTTP/ APP1

setspn -S HTTP/APP2 APP2

setspn -S HTTP/ APP2

setspn -S HTTP/sales APP2

setspn -S HTTP/ APP2


  1. Configure Kerberos Constrained Delegation on ARR server for services:






Verifying the solution

In this section of the walkthrough, you will verify if the solution works:

  1. From a client workstation, browse for example http://payroll/payroll/default.aspx. Application should open.clip_image014
  2. To verify if Kerberos authentication is being used, as Administrator, look at Security Log on client workstation and domain controller respectively, you should see events similar to the ones below.


Client workstation:

Event 4648

Account Whose Credentials Were Used:

Account Name: adrian

Account Domain: MYDOMAIN.COM

Target Server:

Target Server Name:

Additional Information: HTTP/

Domain controller:

Event 4768

A Kerberos authentication ticket (TGT) was requested.

Account Information:

Account Name: adrian

Supplied Realm Name: MYDOMAIN

User ID: MYDOMAIN\adrian

Service Information:

Service Name: krbtgt

Service ID: MYDOMAIN\krbtgt

Network Information:

Client Address: -> Client IP address

Client Port: 49430

Event 4769

A Kerberos service ticket was requested.

Account Information:

Account Name: adrian@MYDOMAIN.COM

Account Domain: MYDOMAIN.COM

Service Information:

Service Name: APP2$


Network Information:

Client Address: -> Client IP address

Client Port: 49431

Event 4624

An account was successfully logged on.

Logon Type: 3

Impersonation Level: Impersonation

New Logon:

Security ID: MYDOMAIN\adrian

Account Name: adrian

Account Domain: MYDOMAIN

Network Information:

Workstation Name:

Source Network Address: -> ARR server IP address

Source Port: 49625

Detailed Authentication Information:

Logon Process: Kerberos

Authentication Package: Kerberos

Transited Services: -

Package Name (NTLM only): -

Key Length: 0

  1. You should be able to navigate application.


In this walkthrough you have learned how to configure Kerberos authentication for application published through a reverse proxy implemented with URL Rewrite Module and Application Request Routing.

Comments (2)
  1. Nick KNZ says:

    Hi @Adrian
    I have http://ARR for hide two App servers (APP1, APP2)

    But in your solution user must use http://payroll/payroll/default.aspx for access to Payroll App
    and http://sales/sales/default.aspx for access to Sales App

    How can I make
    working http://ARR/sales/default.aspx and http://ARR/payroll/default.aspx with kerberos?

  2. webbasan says:

    Hi @Adrian,

    I’m also searching for a practical solution to use an IIS as a reverse proxy where the backend servers use Windows integrated authentication.

    The problem with this solution is, that it ignores the intention to use a reverse proxy in the first place: in my experience, the most common use case for a reverse proxy is to use it as a “facade” in front of several different hosts.

    One technical reason might be, to avoid that the client uses CORS – some clients have issues with it, which make it impractical to use.
    This is the case, if you have for example a rich client application running in the browser, which has to access multiple backends (REST APIs). If there is only one host from the clients point of view (the reverse proxy), then there is no need for it to use CORS.

    But the backends will get requests with a Kerberos ticket with the proxy hostname and will deny to accept it. Setting a SPN with this hostname as an alias for multiple backends obviously doesn’t work…

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