After a few days of struggling, I have successfully set up an ipsec
connection over wifi between a FreeBSD gateway and  a Windows laptop.
Since I had to search for the information I needed all over the net, I
have written a step-by-step set-up guide to help anyone else trying to
secure their wifi connection.  I hope this is useful.

Thanks for your attention.

---------Begin Guide---------

FreeBSD Wi-Fi IPsec easy-setup guide
Timothy Ham <tham (at) socrates berkeley edu>
Nov 23, 2003

Version 1.0
The latest version of this file can be found at:

0. Abstract

An IPsec tunneling connection was set up between a MS-Windows host
with wireless ethernet and a FreeBSD NAT gateway.  This setup
allowed the mobile host to have a secure and encrypted connection
over an inherently insecure wi-fi radio network.

1. Introduction

Recently I have purchased a "Wireless Bundle", consisting of a
wireless NAT router and a PCMCIA 802.11b card, for not a lot of
money (I love cheap hardware).  Being a consumer device, it was
very easy to set up and to get it working with my existing home LAN.
But difficulties arose when I tried to secure the connection, and
also when I tried to protect the rest of my LAN from any intrusion
through the wireless access point.

The choice of IPsec over WEP was for me obvious.  Besides WEP being
insecure (secret key can be recovered easily), my PCMCIA card had
a buggy firmware, which kept dropping connections when WEP was
turned on.  The problem was well documented on various web boards
and the manufacturer had no updates to fix the problem (I hate
cheap hardware). As such, I was left with a superior, but harder
to setup, choice.

There were some resources available on the web to set up IPsec
VPN, but none of them were specific enough for my case. As such,
I thought I would share my experience hoping it will be useful
for others.

2. Isolating the Wireless LAN

My existing home LAN was as follows.  I had a dual-homed FreeBSD
NAT gateway with dhcpd running to dole out private IP address to
any machine connected to the LAN.  A guest could come by and connect
their laptop to the LAN and surf the web.  A typical setup.

The first step was segregating the wireless LAN from the rest
of my home LAN.  I made this easy by installing another ethernet
card ($10) into the FreeBSD box, and giving it a separate address
space.  For example, my existing LAN was using 192.168.1.x.
The new ethernet card has With proper firewall
rules and IPsec, this segment can be isolated from the rest of my
home LAN.

Because my wireless access point is sold as a router/switch (it
was much cheaper than a stand-alone access point--go figure) its
router functions (DHPCD, NAT) had to be disabled. It had a web
interface to change its settings. I also gave the wifi net a
name. The router had 4 ethernet ports labled "LAN", and one port
labled "WAN".  Since I'm just using the wireless/switch portion,
I connected my new ethernet card ( to one of the "LAN"

The laptop was given a permanent IP of

3. Transport Mode vs Tunnel Mode

This part had confused me a great deal because the literature
out there (including the FreeBSD handbook) mentions IPsec tunnels
in terms of VPNs--that is, two gateway machines connecting two
sub-nets over a secure tunnel using a virtual interface gif.  So
at first, I thought what I wanted was a transport layer, that
encrypted packets end-to-end. But this is *not* what you want.
All packets between the laptop (host) and the gateway
(<-> were encrypted. However, any other
packets destined to the rest of the internet were not
(>  This is not what you want. What
you *do* want is a encrypted tunnel between the host and the
gateway that carries packets from the host to the rest of the

Here is what should happen:
Any outgoing packet from the host to anywhere
(> should be encrpyted and encapsulated
in another packet designated to the gateway
(>  Once the gateway receives the
packet, it is decrypted and forwarded to

A returning packet (> should be
encrypted and encapsulated by the gateway and sent to the host
(> The host will decrypt the packet and
read the contents.

The existing NAT machinery will handle the private IP address
translation at the public internet interface.

4. Setting up the Gateway

With the above in mind, here is how the gateway was set up.

A. Recompile the kernel with IPsec support by adding the following
   to the kernel config file:

        options IPSEC
        options IPSEC_ESP

   Recompile, reinstall, and reboot with the new kernel.
   Add the following to /etc/rc.conf


B. Setup the security policy.  Create /etc/ipsec.conf with the
   following.  In this example, is the laptop host
   and is the gateway interface.

        spdadd any -P in ipsec
        spdadd any -P out ipsec

   Run 'setkey -f /etc/ipsec.conf' to use the security policy.

C. Install and configure racoon.

   Racoon is found in /usr/ports/security/racoon. Make install

   Once installed, set up /usr/local/etc/racoon/psk.txt.  This lists
   the pre-shared-keys for your hosts.  For example:    SecretKey

   Try to make the secret key hard to guess.  A good resource is
   the "Passphrase FAQ" on the web.

   Now, create /usr/local/etc/racoon/racoon.conf. I copied the
   racoon.conf.dist file and changed and modified the "listen"
   directive and the "life time" values in the "remote anonymous"
   and "sainfo anonymous" directives. I set the life time to 24
   hours and 12 hours for "remote" and "sainfo" respectively,
   following suggestions from 'man racoon.conf'.

D. Start racoon

   Run 'racoon -F -v' as root to have racoon run in foreground
   and display debugging info to the standard output.

5. Setting up the Windows Machine

Windows 2000 and XP have similar but slightly different dialogs
and wizards, but the idea and the final results are the same.  I
put a summary at the end, which is the same in either version.

   - Go to the Start menu and click on Run.  Type mmc and <enter>.
   - Select Console (or File)->Add/Remove Snap In.
   - Select Add...
   - Choose IP Security Policy Mangement and click Add.
   - Select Local Computer and click Finish.
   - [In XP, also add IP Security Monitor snap-in]
   - Select Close to close the Add standalone Snap-in dialog.
   - Select OK to close Add/Remove Snap-in dialog.

You have now added the IP Security Policies snap-in. Now to setup
a wifi policy.

   - Select IP Security Policies on Local Machine and right click
     and select Create IP Security Policy.
   - Give the security policy a name (ex, wifi). Click Next.
   - Un select Activate the default response rule. Click Next.
   - Un select Edit Properties. Click Finish.

Now along with Client, Secure Server, and Server, you should
have a policy called "wifi". Now to set up filtering rules:

   - Right click on IP Security Policies leaf on Console Root and
     select Manage IP filter lists and filter actions.
   - click Add.
   - Name this filter list OutboundIPsec.  Then click on Add.
   - Follow the wizard and select My IP Address as the Source,
     Any IP Address as the destination address, and any protocol
     type.  Check the Edit Properties box.  When the edit
     properties come up, un-check "mirrored". Finish.

Now there should be one filter in the OutboundIPsec list. Select
Close.  Add a second filter list and name it InboundIPsec,
repeating the steps above.  This time, add a filter with Any IP
Address as the source and My IP Address as the destination
Be careful here. There should be two new IP filter Lists, each List
with 1 rule, not one filter List with two in/out rules. Make
sure filters are not "mirrored."
Close everything until you get back to the Console1 view.

Now to use the filters we've created in the policy:

   - Double click on the wifi policy.
   - Click Add to add new IP Security Rules.
   - Select "The tunnel endpoint is specified" radio button and
     enter in the gateway (ex, Click Next.
   - Select Local area network (LAN).  Click Next.
   - Select "Use this string to protect the key exchange", and
     enter the pre-shared-key passphrase from racoon setup above.
     Click Next.
   - Select "OutboundIPsec" IP filter list you just created. Click
   - Select Require Security. Click Next.
   - Un select edit properties. Click Next.

Repeat the above and enter the host (ex, in the
third step, and "InboundIPsec" IP filter list in step 6. Everything
else is the same.

Now that's everything. I'll summarize what you should see here
(applies to both 2000 and XP).

   - "Console root" has a branch called "IP Sec Policies on Local
   - IP Sec Polocies should have many folders, one of which is
     named "wifi".
   - Double clicking on "wifi" brings up its properties.  It
     should have two Rules, both of them checked, and with the
     following properties (which can be seen by scrolling right):

     Property           InboundIPsec            OutboundIPsec
     Filter Action      Require Security        Require Security
     Authentication     Preshared Key           Preshared Key
     Tunnel Setting  
     Connection Type    LAN                     LAN

Save the Console by selecting Console->Save As... menu.  Name it
Wifi console.

5. Testing it out

First, make sure the gateway is ready.  Run 'setkey -f
/etc/ipsec.conf' and have racoon running in the foreground in
verbous mode ('racoon -F -v').

On the Windows machine, make sure the wifi-card can see your wifi
LAN and have good signal strength.  Have the wifi console you
created open. Make sure the "wifi" policy is Unassigned.
Also have the services list open by right clicking "My Computer"
on the desktop, select Manage, and select "Services and
Applications" -> "Services".  It should give a list of all the
services running on the machine.  Have the IPSEC policy agent
selected (In XP, the name is slightly different). Also, have a
command prompt open.

(Note: Windows 2000 has a utility called ipsecmon which can be run
from the command prompt.  In WinXP this utility exists as a snap-in
which I mentioned above.)

Ping the gateway from the prompt:  "ping -t".
You should be able to ping the gateway at this point.

Go to the Wifi console, right click on the "wifi" policy, and
select "Assign". Go to the Computer Management window and right
click on IPsec Policy Agent and select "restart".

At this point, you should see lots of debugging messages from
racoon as the host tries to negotiate keys.  The ping command in
the Windows machine should show  "Negotiating IPSEC" for a few
seconds, after which pings should be returing normally.

When ping command becomes normal, run tcpdump on the gateway to
see if the packets are really encrypted by running 'tcpdump -i
ep0' or 'tcpdump -i ep0 -x -X -s 14400' for more detail. Replace
ep0 with your wifi interface, of course.

Fire up your browser and see that all the packets visible on
the wifi interface are between the gateway and host, and the
contents are encrypted.

6. Some Known Issues

- After setting up everything, the ping and tracert work fine,
  ping packets appear encrypted under tcpdump, but no sites are

  Disable the built-in "IP Firewall" in the TCP/IP setting for the
  wifi interface.  The help files say it interferes with VPN tunnels.

- The ping command returns "Negotiating IPsec" for several seconds
  then "Request timed out."

  Keep pinging with the -t flag, meanwhile, restart the IPsec
  Policy manager service.  I'm not sure what causes this, but
  it could take anywhere from a few seconds to few minutes before
  the ping command starts to work.

- When the connection is idle for a while (minutes), connectivity
  is lost.

  When an IPsec tunnel is idle for a while, it is closed.  And it
  could take several seconds to reconnect (see above).  I don't
  know of a way to force the tunnel to stay open except by keep
  sending messages through it.  I do this by having an ssh session
  open, or having a web page that reloads frequently. Any other
  workarounds (especially at the gateway end) would be welcome.

7. Conclusion

At this point you should have a secure Wifi connection between
your laptop and your gateway.  Anyone sniffing the access point
should only see packets going to and from the host and the
gateway in encrypted form.

I hope this document was helpful for you.  Any suggestions,
corrections, and tweaks are more than welcome.

(C) Timothy Ham 2003
Redistribution of this text is permitted as long as the copyright
is retained.

End of File

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