Watchgautd Site-to-site VPN Problem

Posted on 2010-09-19
Last Modified: 2012-05-10
Hi There,

i give you a brife explnation on what do i want to achive with ipsec tunnel, i want to conect two site through Internet , Site A has watchgaurs (managed by me) as Internet gateway and the Site B has Cisco ASA as internet gateway which is managed by ISP.
I communicate with ISP and wemanaged to setup ipsec/BOVPN successfully, phase1 and phase 2 can establish. but i cannot any PC's behand firewalls.

Watchgaurd model is
site A ip subnet is default gateway (watchgaurd)
Site B ip subnet is default gateway (Cisco ASA)
Note: From a PC at site B, i can ping watchgaurs ( Internal ip address but not any other machine behind it.

Also from a PC at site A, i cannot ping any ip address at site B.

so i think that routing/natting should working fine at Cisco ASA because site B can ping my watchggautd Internal IP.

i think there should be a routing/NAt issue at watchgaurd which cannot route packet to inside or from inside route to

I addedd watchgaurd and Cisco ASA configs, the red lin shows the new configs on ASA

your assist on this is much appreciate.

 watchgaurd.docx Cisco.doc
Question by:rafatifard
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 3
  • 3
  • 2
  • +1

Expert Comment

ID: 33714489
From what I can see of the ASA config, is not one of its interfaces, although it could be an internal router.  I don't know much about Watchguards, but if you have to add a route back to, then you might try using their outside IP ( as the gateway.
LVL 11

Expert Comment

ID: 33715124
apart from the previous comment you can allow all port open between the vpn channel

Author Comment

ID: 33715162
you right, is internal switch. where should i add route back, on watchgard ?

Microsoft Certification Exam 74-409

Veeam® is happy to provide the Microsoft community with a study guide prepared by MVP and MCT, Orin Thomas. This guide will take you through each of the exam objectives, helping you to prepare for and pass the examination.


Author Comment

ID: 33715182
as far as i know all porrs (any) are open between trustes-external and the VPN tunnel, or if there is not the case, where should i add the policy, on whatcguard or ASA ? if yes can you send me an example.

Also, i can ping from a PC at site B to (the internal watchgaurd IP address) but not get through any server/pc behind it. and from a PC at site A i cannot ping anything beyond the tunnel.

Author Comment

ID: 33721471
Hi There,

Any comment on this, i need an assist on this to fix the routing quickly

Mant thanks

Expert Comment

ID: 33721525
 Does the Watchguard have any sort of monitoring of the VPN tunnel statistics, like number of packets encrpted/decrypted?  If so, then try starting a continuous ping from site B to the Watchguard.  If everything is working like we think it is, the number of encrypt/decrypt packets should increase steadily.  Once that is confirmed, try pinging a known live IP in your network.  If both counters increase, then the problem is probably not on your side.  If however, you only see the decrypt counter increase, then that means the Watchguard isn't sending traffic back through the tunnel for some reason.  You may also want to trace route from both sites and see if there are any abnormal results, like public IPs showing up, indicating the traffic is going out the public interface rather than the tunnel.

  Right now, there are some devices on the other side that you don't have control of and we don't know the details of, like the managed switch at  Since it's managed, is it also a layer 3 switch?  If so, there might be other routing issues that we're unaware of, but first we have to verify that traffic is indeed being encrypted on your side and being forwarded to the ASA.

Expert Comment

ID: 33756277
it looks like both ends of the routes are missing. I would also make sure your tunnel is part of a ANY ANY rule if you are allowing everything through.

Expert Comment

ID: 33756581
Site B wouldn't be able to ping the Watchguard if that were the case.  We need to see some trace route and encrypt/decrypt stats to get a better idea of exactly where packets are getting lost.

Accepted Solution

LBACIS earned 500 total points
ID: 33783632
Ok kuoh I have been doing this for 20 years, sorry for being a little off. If he can ping one way but not the other the single round would have the failed or non configured routes. The tunnel would not create if the dynamic VPN policies did not match. I would also look at that to make sure the policy was written for 2 way. Double check the dynamic NAT on the advanced tab of the VPN policy and make sure you have it checked. Or if you want to attach the policy here and I will look at it.

Featured Post

Free Tool: SSL Checker

Scans your site and returns information about your SSL implementation and certificate. Helpful for debugging and validating your SSL configuration.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Suggested Solutions

Title # Comments Views Activity
Telepresence on backup 3 79
Moving vSAN traffic to a new network 4 105
IPSec firewall rules 1 37
Cisco ASA 5510 Question 2 28
Envision that you are chipping away at another e-business site with a team of pundit developers and designers. Everything seems, by all accounts, to be going easily.
I recently attended Cisco Live! in Las Vegas, a conference that boasted over 28,000 techies in attendance, and a week of hands-on learning hosted by a solid partner with which Concerto goes to market.  Every year, Cisco displays cutting-edge technol…
After creating this article (, I decided to make a video (no audio) to show you how to configure the routers and run some trace routes and pings between the 7 sites…
Both in life and business – not all partnerships are created equal. As the demand for cloud services increases, so do the number of self-proclaimed cloud partners. Asking the right questions up front in the partnership, will enable both parties …

739 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question