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How to Create a VPN site-to-site IPsec Tunnel Mode Connection Between an ISA 2006 Firewall and a Cisco Router

 - 1. Overview
 - 2. Configure ISA
 - 3. Configure the Cisco Router
 - 4. Test the s2s
 - 5. Monitor the s2s on ISA
 - 6. Monitor the s2s on the Cisco Router
 - 7. Configure some Basic Firewall Rules on the Cisco Router
 - 8. A Traffic Simulation Test

 1. Overview
In this article we will establish a site-to-site VPN connection between an ISA 2006 Firewall and a Cisco Router
One site is using ISA 2006 Firewall Standard Edition installed on Windows 2003 R2 Standard SP2. The network behind the ISA 2006 Firewall is
The other site is using a Cisco 3620 router. If you wonder about the IOS type and version, it’s running IP/FW/IDS PLUS IPSEC 3DES(c3620-ik9o3s-mz), version 12.2(40). OK, the version is old but it will not matter since it supports 3DES. Also since it has the IOS firewall on it we can setup it as a firewall too. If you have newer versions of  IOS, you can benefit from the enhanced firewall support. It’s all about the amount of money you have to spent(or about the router you have bought). The network behind the 3620 router is

Figure1 describes the network diagram.

The network Diagram
Figure1: The network Diagram

 2. Configure ISA
If you plan to build a quick lab, you can setup ISA 2006 in VMware(please refer to our article ISA VMware Simple Lab). Everything is identical except that the DMZ Server and the Client PC are not running. 
Before moving to configure your device please make sure you have read the following docs from VPNC(Virtual Private Network Consortium):
Documentation Profiles for IPsec Interoperability
Cisco IOS VPN Configuration
Microsoft Internet Security and Acceleration 2004 Server IPSec Interoperability Profile VPN Consortium
Also there are plenty of docs on Cisco and Microsoft sites related to IPsec tunnel mode site-to-site setup and troubleshooting.
Let’s first configure ISA 2006.

Since we already have explained some of these settings in our How to Create a VPN Site-to-Site IPsec Tunnel Mode Connection Between a Vyatta OFR and an ISA 2006 Firewall, we will not repeat them here. 
Head to “Virtual Private Network(VPN)” into the “Remote Sites” tab.
Click “Create VPN Site-to-Site Connection”. I’m going to call it Branch. Select “IP Security Protocol (IPsec) tunnel mode”. Click “Next”. Specify tunnel endpoints(see Figure2):

Tunnel Endpoints
Figure2: Tunnel Endpoints

I’m using a pre-shared key for this lab(see Figure3).

Enter the pre-shared key
Figure3: Enter the pre-shared key 

Specify the remote network address ranges(see Figure4). I also included(with ISA 2006 this is done automaticaly by the wizard) the remote endpoint IP address, so I can test connectivity from it(I will do the same on the 3620 router for ISA).

Remote network address ranges
Figure4: Remote network address ranges 

Create the network rule with a “route” relationship and the access rule allowing “All outbound traffic”. Click “Finish”.
Now double click the Branch remote site, click “Connection” tab and “IPsec settings”(seeFigure5).

Branch Properties
Figure5: Branch Properties 

Now we will configure the IKE Main Mode settings(see Figure6). IKE is defined in RFC2409, an “Internet Official Protocol Standards" (STD 1)”.

IKE Main Mode settings
Figure6:IKE Main Mode settings 

Figure6 shows the parameters used for IKE Main Mode. ISA can use 2048-bit MODP Diffie-Hellman Group 14 but the Cisco router does not(it can use 1536-bit MODP Diffie-Hellman Group 5 which is not available on ISA). The IKE SA lifetime is set to 28800s(8 hours). On the Cisco routers this is by default set to 86400 seconds(24 hours). If you are curios, we are actually using a cryptographic suite presented in RFC4308(“Internet Official Protocol Standards" (STD 1)”), Suite "VPN-A”. In this RFC it is stated that if we use IKEv1 with Suite "VPN-A" we  “must” set the IKE SA lifetime to 86400 seconds(24 hours) and the IPsec SA lifetime to 28800s(8 hours). However this is way to long if traffic it’s actually passing between the two sites. It is better suited to use by default IKE SA lifetime set to 28800s(8 hours) and IPsec SA lifetime set to 3600s(1 hour). The combination of 3DES and DH 1024 is not that strong these days(you can get some directions reading NIST Guidelines for Public-Key Sizes).
Moving to IKE Quick Mode, you can see the ones used in this lab in Figure7. The IPsec lifetime is set to 3600s(1 hour). Cisco routers by default use the 3600s(1 hour) for IPsec lifetime. PFS for keys is used meaning that keys for ESP will be obtain by running a fresh DHE exchange and not derived from the keying material obtain in Main Mode. Therefore greater resistance to cryptographic attacks is achieved. No IPsec lifetime in Kbytes is set(IPsec life type are expressed in kilobytes and/or seconds, see RFC2407). 

IKE Quick Mode parameters
Figure7: IKE Quick Mode parameters 

Click “OK” to save the changes.
Apply the new settings on ISA 2006.
So by now ISA 2006 is configured. The remote site has been created, the access and network rules defined, the IKE parameters set and the remote network address range was specified.
Note that there is an IPSec SA Idle Timer or an idle timeout for a Quick Mode SA.
On Cisco routers the IPSec SA idle timer was introduced on Cisco IOS version 12.3. So I cannot apply this in my lab since I’m using IOS version 12.2.
On Windows 2003 the IPSec SA Idle Timer can be set from registry. The default idle timeout for a Quick Mode SA is 300 seconds. You can modify it from registry(you can find the registry modification in KB 917025). If you are running ISA on a Windows 2003 SP1 this timer will apply even if there is traffic. You need to upgrade to SP2 to get rid of this issue(check this KB923339).

 3. Configure the Cisco Router
Time to configure the Cisco router. 
We need to use the exact same settings for IKE parameters on the Cisco 3620 router(called R1).
ISA 2006 Firewall is doing NAT from Internal to External. The Cisco 3620 will do the same thing. I suppose I should have used the Cisco Router and Security Device Manager (SDM), but that's the way it goes right now.
interface FastEthernet0/0
         description "External Interface"
         ip address
         ip nat outside
interface FastEthernet1/0
         description "Internal Interface"
         ip address
         ip nat inside
ip nat inside source list 111 interface FastEthernet0/0 overload
access-list 111 deny   ip
access-list 111 deny   ip host
access-list 111 permit ip any
ip route
From above, you can notice that was excluded from the NAT process(access-list 111) when accesing and host the last exclusion is used by ISA 2006 for testing connectivity from it to
A default route was also created on the Cisco 3620 router pointing to my real LAN DG so that the router and hosts behind it to have access to the Internet.
Test your configuration by trying to access a web site from a host behind the Cisco router. You should be able to do so.

Check the access-list 111 for matches(see Figure8):

sh access-list 111
Figure8: sh access-list 111 

Let’s visualize the default IKE Phase I settings(see Figure9):

IKE Phase I default settings
Figure9: IKE Phase I default settings 

They do not match our ISA settings so we will create another policy,  “isakmp policy 15”(seeFigure10).

A new isakmp policy
Figure10: A new isakmp policy 

Check what we have done. As you see(see Figure11) the settings of “isakmp policy 15” match the ones used on ISA 2006 for IKE Main Mode.

ISAKMP policy 15
Figure11: Isakmp policy 15 

Next let’s specify the pre-shared key(the same used on ISA 2006., see Figure12):

Specify the pre-shared key
Figure12: Specify the pre-shared key 

Now we need to define the Quick Mode parameters(see Figure13):

Router IKE Quick Mode parameters
Figure13: Router IKE Quick Mode parameters 

We are using with isaset “transform-set” the same settings from ISA 2006 for IKE Quick Mode, we also enabled PFS. With “access-list 101” we will specify the network address ranges for the remote site.
Let’s create the “access-list 101”(see Figure14).

Access-list 101
Figure14: Access-list 101 

First line defines the remote network can be accessed by local network The second line is used to allow connectivity testing from ISA 2006 to And finnaly, the third one permits connectivity testing from the Cisco 3620 router to  Actually you can use the ping command on Cisco IOS to specify the source interface(thus the source IP) but it’s faster to just type ping X.X.X.X.
And bind the “crypto map isavpn” to the outgoing interface “f0/0”(see Figure15).

Binding the “crypto map isavpn” to the outgoing interface “f0/0”
Figure15: Binding the “crypto map isavpn to the outgoing interface “f0/0”

Check what you have done(see Figure16):

sh crypto map int f0/0
Figure16sh crypto map int f0/0

And that’s it. No firewall settings yet on the Cisco 3620 router. The router config can be found here

 4. Test the s2s
So let’s try and bring the tunnel up. To do so, we will ping from a host behind the Cisco router, to a host behind ISA 2006 Firewall, Figure17). You can use Wireshark to capture the packets on ISA’s external interface and visualize the IKE negotiations and packets protected by IPsec ESP(see Figure18). 

ping from
Figure17: ping from 

Wireshark capture
Figure18: Wireshark capture 

And it works.

A connectivity test from the Cisco router to Figure19):

A connectivity test from the Cisco router to
Figure19: A connectivity test from the Cisco router to

You can use the ping command and by defining “extended commands” you can specify the source interface(thus the source IP address), see Figure20.

Ping extended commands
Figure20: Ping extended commands 

A connectivity test from ISA 2006 to Figure21):

A connectivity test from ISA 2006 to
Figure21: A connectivity test from ISA 2006 to 

A connectivity test from to Figure22):

A connectivity test from to
Figure22: A connectivity test from to 

 5. Monitor the s2s on ISA
Open the “IP Security Monitor” mmc on ISA and check on ISA the Main Mode and Quick Mode SAs(see Figure23 and Figure24).

IKE Main Mode SA on ISA 2006
Figure23: IKE Main Mode SA on ISA 2006 

IKE Quick Mode SA on ISA 2006
Figure24: IKE Quick Mode SAs on ISA 2006 

 6. Monitor the s2s on the Cisco Router
Moving onto the Cisco router let’s check if the access-lists have done their job(see Figure25):

Checking for matches in access-lists
Figure25: Checking for matches in access-lists

Show IKE Main Mode SA on the Cisco router(see Figure26):

Show IKE Main Mode SA on the Cisco router
Figure26: Show IKE Main Mode SA on the Cisco router

Show IKE Quick Mode SAs on Cisco router(Figure27 shows just a small part of the output):

Show IKE Quick Mode SA on the Cisco router
Figure27: Show IKE Quick Mode SAs on the Cisco router

 7. Configure some Basic Firewall Rules on the Cisco Router
Since this IOS version has firewall capabilities we can secure the external interface. The bellow configuration is just basic stuff, some quick added lines to the router configuration. As said before the IOS version is old so the protocols supported with Context-Based Access Control are limited. First thing I will do is to add and extended-access list on the external interface to allow and block traffic. I will allow IKE, IPsec ESP, returning DNS traffic, returning ICMP replies to the router and traffic from to newer IOS versions the last two lines of the access-list are not required). 
access-list 121 permit udp host eq isakmp host eq isakmp
access-list 121 permit esp host host
access-list 121 permit udp any eq domain host gt 1023
access-list 121 permit icmp any host echo-reply
access-list 121 permit ip host
access-list 121 permit ip
interface FastEthernet0/0
     ip access-group 121 in

And I want to inspect HTTP traffic from to the external world(if your IOS version has DNS support you can do the same for DNS protocol and delete the DNS line from access-list 121). For this I will use Context-based access control (CBAC).
ip inspect name test http timeout 3600
 interface FastEthernet0/0

     ip inspect test out” 

Also some extra lines on the external interface to block ICMP “Host unreachable”, “Redirect”, and “Mask Reply” messages. So in the end the configuration on the router external interface will look like:
interface FastEthernet0/0
     ip address
     ip access-group 121 in
     no ip redirects
     no ip unreachables
     ip nat outside
     ip inspect test out
     duplex auto
     speed auto
     crypto map isavpn

The “full firewall” configuration is here.

You can try now to access a HTTP web site from a host behind the router(meaning that you will alos test that DNS is working if you use FQDN). I did so from Note that with this config in place, hosts belonging to are only allowed to access external resources using DNS and HTTP protocols. Don’t go to a HTTPS web site because it will not work.

Check that the access-list 121 is working(see Figure28):

Check that access-list 121 is working
: Check that access-list 121 is working 

Actually you can for example configure the computers to use ISA’s IP address as their web proxy by creating an access rule allowing HTTP/HTTPS from Branch to External on ISA . Note that we already added the remote end-point IP addresses to the remote network address ranges on both sides. To block direct Internet access from hosts belonging to use aproppiate access-lists.

 8. A Traffic Simulation Test
I have simulated some traffic between the two sites by using a ping command for over an hour. The tunnel stayed up and not a single packets was lost(except the ones from the start of the ping command when the tunnel was not up yet). A new Quick Mode was negotiated after an hour(as configured). See Figure29Figure30Figure31Figure32.

Starting the ping marathon
Figure29: Starting the ping marathon 

Ending the ping marathon
Figure30: Ending the ping marathon 

IKE Main Mode Statistiscs from ISA
Figure31: IKE Main Mode Statistiscs from ISA 

IKE Quick Mode Statistiscs from ISA
Figure32: IKE Quick Mode Statistiscs from ISA 

 - Cisco 3620 Configuration File without Firewall Settings
 - Cisco 3620 Configuration File with Firewall Settings