Republished with permission from WatchGuard Technologies, Inc.

WatchGuard LiveSecurity


Deploying Mobile User (IPsec) VPN 

by David Piscitello, Core Competence, Inc.

Communication has always been the most important application for the Internet. The ideal is to be connected, any time, over any distance; and moreover, connected securely and privately. This ideal is largely achievable using Mobile User Virtual Private Networking (MUVPN). But the process of implementing MUVPN requires diligence. This article explains the steps required to get IPsec MUVPN going with your WatchGuard Firebox, including: 

  • Planning your MUVPN implementation

  • Documenting your constituency and configuration

  • Managing client software and its distribution

  • Using the Firebox logs to monitor remote access connections.

Below, I'll detail what happens when things go well. In next week's article, "Debugging Mobile User VPN," I'll show you how to troubleshoot failed MUVPN connections. 

Planning Eliminates Surprises
As with site-to-site IPsec VPNs, secure remote access requires careful planning. It also demands a good understanding of your IP addressing, the IPsec capabilities of your Firebox, and the IPsec client software that you license for use. If you saw my column, Incorporating a Firebox into a Multi-vendor VPN, you’ll recall I stressed the importance of documenting your site-to-site VPN before you attempt to build it. Planning is no less important when you connect remote users. Before you start increasing outside connections past your network defenses, I recommend you:

  • Determine how the addition of remote users affects the topology of the network, and the configuration of your Firebox, DNS, and routes to servers. 

  • Create a topology map to illustrate all the (IP) networks that users will be permitted to access using VPN tunnels. 

  • Identify the networks by domain name, IP address, and subnet mask.

This investment of time will save you from a lot of frustrating and inefficient experimentation later.

Document Your Constituency and Configuration
Try to view remote user management as a painstaking rather than painful process. Document as you go. For a remote access deployment of up to several hundred users, an Excel spreadsheet or text file works well as a database of users, identities, and the pre-shared secrets that are used for authentication. If your number of users is greater than that, you really need to consider using a public key infrastructure (PKI) rather than pre-shared secrets. In addition to the obvious user and credentialing information, you may find it worthwhile documenting equipment, adapter cards, and Windows OS versions. Review this information to ascertain whether your user’s client environment can support MUVPN.

For each user, you must enter a unique identifier (typically, an e-mail address) and passphrase; the phrase is the pre-shared secret key for tunnel encryption. You’ll also configure ESP tunnel protection. I recommend you choose the strongest protection available, currently SHA1-HMAC and 3DES-CBC, for all users. Remote users are generally bandwidth constrained and they won’t see a performance hit when you use stronger encryption.

The Firebox implementation of remote access IPsec requires that you specify an unused IP address for each remote user (the Virtual IP). This address is needed to route protected traffic back to the user, through the tunnel. This static assignment is simple to deploy for small numbers of users, but can become challenging should your mobile and teleworker population grow. You may wish to create a separate Secondary Network on your Trusted Interface solely for the purpose of addressing remote users.

Finally, consider your firewall policy configuration. You must add an ANY service and permit the ipsec_users group Incoming and Outgoing access through this service. Enable logging for Incoming and Outgoing allowed and denied packets to assist in debugging. You may further restrict access through additional IPsec tunnel and service policies, but these are additive: you must allow IPsec traffic through the firewall. If you added a Secondary Network for remote users, consider whether your existing firewall rules must be revised to accommodate users numbered from this new IP address space.

Manage Client Software and Configuration Distribution
With routing and addressing considerations under your belt, you'll then want to figure out how you can securely and conveniently deliver the MUVPN client software that the configuration (<username>.EXP) file generated when you added remote users, and plan how you'll deliver “installation and use” instructions to mobile users. Explain to those users the importance of maintaining the integrity of the .EXP file -- any unauthorized changes a user makes may cause problems. Spend some time explaining where to find the log files generated by the MUVPN client and how to e-mail logs to support staff; as I’ll show later, a log file can save you and your users time and aggravation by keeping them connected and productive.

Common methods for delivering this content include using a secure Web server, push (secure) e-mail, or removable medium (CD-ROM or floppy), hand delivered and signed upon receipt (or sent registered mail). To prevent theft, you also need a separate process for informing users of their remote access user ID and password. A FAQ page and a short list of how to troubleshoot and resolve commonly encountered problems is well worth the time, even if it saves only one helpdesk call.

You can avoid “one-off” problems resulting from permutations and combi- nations of Windows OS, third party software, adapter cards, and device drivers by utilizing a standardized client environment (e.g., everyone uses Windows 98), and using hardware and adapters demonstrated to work with MUVPN. If you haven’t implemented standardized desktops, prepare for helpdesk calls.

Use Firebox Logging to Understand Mobile User (IPsec) VPN
You’re now armed and ready to manage the onslaught of remote access. At this point, make use of your firewall logs to understand how IPsec is implemented for MUVPN.

IKE and MUVPN -- a breed apart
The Internet Key Exchange (IKE) provides key and security session management between MUVPN clients and your Firebox. IKE has two phases of operation. During Phase I, the Firebox and MUVPN client employ Aggressive Mode to identify and authenticate each other, and agree on the parameters of the IKE security association (SA). Aggressive Mode is different from Main Mode used in Branch Office VPN in two important ways:

  1. The process of establishing IKE SA’s takes three messages rather than six, and

  2. Identity information exchanged between a remote user and the Firebox is not encrypted. Aggressive Mode configurations that use dynamic addressing sacrifice identity protection.

Let’s look at a successful Phase 1 exchange in a Firebox log to appreciate the Aggressive Mode. In this example, a remote user, lisa, attempts to connect to the Trusted Network ( from an address ( somewhere on the Internet. My Firebox’s External Interface is

   77888 06/12/01 15:47:02 iked[90] 
          ISA_NONCE ISA_ID

   77898 06/12/01 15:47:02 iked[90] 

   77908 06/12/01 15:47:02 iked[90] 
          CRYPTO ACTIVE after delay

   77918 06/12/01 15:47:03 iked[90] 

   77928 06/12/01 15:47:03 iked[90] 
          Phase 1 completed as responder

   77938 06/12/01 15:47:03 iked[90] 
          Updated lisa000 channel for lisa rgw

   77958 06/12/01 15:47:03 iked[90] 
          User "lisa" at logged in

   77968 06/12/01 15:47:03 iked[90] 
          Add Host 8 ipsec_users lisa

   77978 06/12/01 15:47:03 iked[90] 
          lisa bound to

Log entries 77888, 77898 and 77918 show the three messages that comprise an Aggressive Mode Phase 1 exchange initiated by a remote client at to a Firebox. The first two messages (77888, 77898) use the following information to negotiate the security policy for the IKE SA:

  • Security Association proposal (ISA_SA). The IKE security policy for MUVPN is the same as Branch Office VPNs, so the ISA_SA specifies 
    - authentication method is pre-shared keys 
    - encryption algorithm is DES-CBC
    - message hash algorithm is MD5-HMAC
    - Diffie-Hellman group is 1
    - SA lifetime is 3600 seconds
  • Diffie-Hellman public values, or key exchange material (ISA_KE) 
  • A one-time random value called a nonce, which protects against replay attacks (ISA_NONCE) 
  • The Identity (ISA_ID), which for MUVPN is the User Fully Qualified Domain Name assigned when we created this remote user. By convention, this is typically an e-mail address of the form; in our examples, however, we’ll simply use “lisa.”

The second and fourth messages (77898, 77918) also authenticate the responder and initiator using a keyed hash (ISA-HASH). Log entries 77928-77978 confirm IKE Phase 1 related actions (success!). The Firebox has assigned a remote user “lisa” the Virtual IP address from the Trusted Network and is connecting from outside the Firebox at a public IP address of

IPsec and MUVPN  -- more of the same…
IKE SAs created between the Firebox and MUVPN client provide a secure control channel for creating Phase II IPsec SAs. Here, parameters are negotiated for IPsec security associations that permit data transfer. These parameters, discussed earlier, are selected when you create a remote user.

Phase II begins at log entry 81848. The security policies selected for MUVPN IPsec Security Associations are negotiated using Quick Mode (log entries 81848, 81868). These messages are encrypted with DES (note the *), and a keyed message hash and nonce are included for message integrity and protection against replay, respectively.

   81848 06/12/01 15:57:48 iked[90] 
          FROM QM-HDR*-7E36F121 

   81858 06/12/01 15:57:48 iked[90] 
          Getting IPSEC preferences as Responder
          propnum=1, mode=(Tunnel), laddr=,

   81868 06/12/01 15:57:48 iked[90] 
          TO QM-HDR*-7E36F121 

   81878 06/12/01 15:57:49 iked[90] 
          FROM QM-HDR*-7E36F121 ISA_HASH

   81888 06/12/01 15:57:49 iked[90] 
          Load outbound ESP SA,
          Life=3600sec/0KB SPI=6985177e

   81898 06/12/01 15:57:49 iked[90] 

   81908 06/12/01 15:57:49 iked[90] 
          Load inbound ESP SA,
          Life=3600sec/0KB SPI=0004a135

   81918 06/12/01 15:57:49 iked[90] 

   81928 06/12/01 15:57:49 iked[90] 
          Committing SAs for channel=0 established
          with QM message_id=7e36f121

   81938 06/12/01 15:57:49 kernel ipsec: 
          make bundle for channel 0, 1 in SA's, 
          1 out SA's

   81978 06/12/01 15:57:51 firewalld[74] 
          allow in ipsec0 64 tcp 20 128
 1532 21 syn (Any)

Log entries 81888 and 81898 show the security policies selected for the two IPsec SA's between my Firebox and the MUVPN client used by lisa. There are two IDs (note them at the end of 81868) because IKE shows one apiece for the local networks at each end of the tunnel. 

Log entry 81978 shows an incoming TCP connect request (SYN packet) allowed in from lisa’s host ( to an FTP server (port 21) on the Trusted Network ( Success! The  Firebox blocks incoming FTP requests over eth0 but allows encrypted FTP sessions from authenticated remote users through the virtual interface ipsec0.

Now you've seen what a successful MUVPN connection looks like. But not everyone achieves a successful MUVPN tunnel on the first attempt. In next week's column, we'll troubleshoot unsuccessful remote access connections. See you then! ##

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