FreeBSD IPsec mini-HOWTO

原创 2001年11月18日 14:44:00

FreeBSD IPsec mini-HOWTO

by Josh Tiefenbach <> and Boris Köster <>



The latest version of this tutorial can always be found at:


This document is intended to be a primer on how to get IPsec on FreeBSD up and running, interoperating both with another FreeBSD (or NetBSD or any other KAME-derived stack) machine, and a Windows 2000 machine.

IPsec is a means to secure IP layer communications between hosts, and can secure both IPv4 and IPv6 traffic. Only IPsec over IPv4 will be discussed here.

IPsec can be used to build tunnels between subnets (tunnel mode) or secure communication between two machines directly (transport mode) with the guarantee that the packets are encrypted, authenticated and anti-replay protected (by sequence-numbers) with limited traffic flow confidentiality. By design, IPsec communication is encrypted by symmetric algorithms (Blowfish, DES, 3DES). This is known as ESP (Encapsulating Security Payload) mode, in which the payload of a packet is encrypted. The headers of the packet are left untouched. If you do not want to encrypt the traffic, you can use IPsec in what's known as AH (Authenticaed Header) mode. In this mode, the payload of the packet is not encrypted, but the header fields are hashed using a secure hashing function, and an additional header containing this hash is added to the packet to allow the information in the packet to be authenticated.

This document will not describe the overall architechture of IPsec, and its component protocols. We will show only some basics here.

If we take a technical look at the tcp packet, we have the following structure now (see RFC 2406). The drawings are from this RFC for educational use:

                 BEFORE APPLYING ESP
      IPv4  |orig IP hdr  |     |      |
            |(any options)| TCP | Data |
                 AFTER APPLYING ESP
      IPv4  |orig IP hdr  | ESP |     |      |   ESP   | ESP|
            |(any options)| Hdr | TCP | Data | Trailer |Auth|
                                |<----- encrypted ---->|
                          |<------ authenticated ----->|

If we would have IPV6, the design would look like this:

                     BEFORE APPLYING ESP
      IPv6  |             | ext hdrs |     |      |
            | orig IP hdr |if present| TCP | Data |

                     AFTER APPLYING ESP
      IPv6  | orig |hop-by-hop,dest*,|   |dest|   |    | ESP   | ESP|
            |IP hdr|routing,fragment.|ESP|opt*|TCP|Data|Trailer|Auth|
                                         |<---- encrypted ---->|
                                     |<---- authenticated ---->|

            * = if present, could be before ESP, after ESP, or both

It is important to know what we are doing here to understand the mechanism how ESP works so we know what we are doing and WHY we are NOT using a SSH tunnel or similar. This is a structure of the ESP header, some of the words you may have read somewhere, and this graphic may help you to understand something more about ESP.


0                   1                   2                   3
 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6 7 8 9 0 1
+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ ----
|               Security Parameters Index (SPI)                 | ^Auth.
+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ |Cov-
|                      Sequence Number                          | |erage
+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ | ----
|                    Payload Data* (variable)                   | |   ^
~                                                               ~ |   |
|                                                               | |Conf.
+               +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ |Cov-
|               |     Padding (0-255 bytes)                     | |erage*
+-+-+-+-+-+-+-+-+               +-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ |   |
|                               |  Pad Length   | Next Header   | v   v
+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+-+ ------
|                 Authentication Data (variable)                |
~                                                               ~
|                                                               |
   * If included in the Payload field, cryptographic
          synchronization data, e.g., an Initialization Vector

If you hear somewhere words like "Padding", "Sequence Numbers", or "Payload Data"; if you are reading the docs of racoon.conf(5) or setkey(8) now you know that these bits of information are a part of the ESP header or it has something to do with IPsec.

The basic procedure for implementing IPsec is:

  • Configure kernel

  • Set security policy

  • Configure key exchange


Getting started

In order to use IPsec on a FreeBSD machine, it is highly recommended that you be running FreeBSD 4.1 or later. While the KAME IPsec code exists in versions prior to this (notably FreeBSD 3.x), it is not sufficient to be able to use the racoon IKE (Internet Key Exchange) daemon to perform automatic keying.

To add IPsec support to your kernel, add the following lines to your kernel config file

	options         IPSEC                   #IP security
	options         IPSEC_ESP               #IP security (crypto; define w/ IPSEC)
	options         IPSEC_DEBUG             #debug for IP security

Additionally, if you want to use IPsec in tunnel mode, you may will also want to add the following line to the kernel config:

	device gif 4

Recompile and install the new kernel.

Install the racoon daemon from ports:

        cd /usr/ports/security/racoon ; make all install clean

Currently the latest version of the port is racoon-20001111a. While it is possible to have 2 FreeBSD machines communicate via IPsec using only manual keying (that is, manually specifying the encryption keys), not only is it not interesting or practical, but it won't work when you try to interact with a Win2k machine.


Setting security policy

An integral part of IPsec, is letting the kernel know which packets it should be encrypting and how it should be encrypting them, whether to use AH (authentication header) mode or ESP (encapsulating security payload) mode, and what encryption and hashing algorithms to use.

These decisions are referred to as 'policy', and are stored in a table in the kernel known as the Security Policy Database (SPD). You can use the setkey(8) program to manipulate the SPD.

There is also a table in the kernel which stores the various encryption keys needed to secure communications between hosts. This table is known as the Security Association Database (SAD). If you are configuring IPsec using manual keying then the setkey(8) program is also used to configure the manual keys in the SAD. If you are using IKE to automatically exchange keys between hosts, then racoon will handle the adding and deleting of entries from the SAD.

If you have 2 FreeBSD machines, node A with an IP address of, and node B with an address of, then the following commands will add policy to the SPD to enable IPsec between the 2 nodes:

        # These commands need to be run on node A
        # The next 2 lines delete all existing entries from the SPD and SAD
        setkey -FP
        setkey -F
        # Add the policy
        setkey -c << EOF
        spdadd any -P out ipsec
        spdadd any -P in ipsec

The first spdadd command sets the policy that all outgoing packets from to will be required to be encrypted using ESP. The second spdadd command sets the same policy, but for incoming packets from to

        # These commands need to be run on node B
        # The next 2 lines delete all existing entries from the SPD and SAD
        setkey -FP
        setkey -F
        # Add the policy
        setkey -c << EOF
        spdadd any -P out ipsec
        spdadd any -P in ipsec

Examples on how to set SAD entries using setkey(8) are given in the IPsec section of the FreeBSD handbook.


AH vs ESP. Tunnel vs Transport

Given even a casual reading of the available IPsec documentation, one can get rather confused as to what mode they should be running in. Unless you are wanting to set up a VPN, then the mode that you probably want is ESP/transport.

In ESP/transport mode, each packet that is destined for a host for which IPsec is requested has its payload encrypted. In tunnel mode, the entire packet (including the encrypted payload) is encapsulated within another packet before being sent off to the remote host.

However, if your goal is to set up a VPN, that is, link 2 widely-separated networks together over the Internet, then you'll probably want to use ESP/tunnel mode. The configuration of the SPD for tunnel mode is very similar to that of transport mode. The major change that is done is the use of the gif(4) device to implement the IP-IP tunneling.

Returning to our hypothetical nodes A and B, presume the following network topology:

Internal net A <-> Node A <-----> Internet <------> Node B <-> Internal net B


node A's internal address is

external address is

node B's internal address is

external address is

then to configure policy on node A:

        # These commands need to be run on node A
        # Set up the tunnel device. This presumes you have gif(4) support
        # gif0 connects to
        gifconfig gif0
        # The 'internal' side of the tunnel connects to
        ifconfig gif0 inet netmask
        # The next 2 lines delete all existing entries from the SPD and SAD
        setkey -FP
        setkey -F
        # Add the policy
        setkey -c << EOF
        spdadd any -P out ipsec
        spdadd any -P in ipsec

Note the difference in the spdadd command. We are setting policy to have traffic from the network 10.10.10/24 to the network 10.20.20/24 be encrypted (via ESP), and routed from to, and vice versa.

And on node B:

        # These commands need to be run on node B
        # Set up the tunnel device. This presumes you have gif(4) support
        # gif0 connects to
        gifconfig gif0
        # The 'internal' side of the tunnel connects to
        ifconfig gif0 inet netmask
        # The next 2 lines delete all existing entries from the SPD and SAD
        setkey -FP
        setkey -F
        # Add the policy
        setkey -c << EOF
        spdadd any -P out ipsec
        spdadd any -P in ipsec


Automatic key exchange using racoon

Configuring racoon to the point where you can successfully exchange keys is reasonably easy. The default racoon.conf file is sufficient for a basic setup. However, we would recommend that the following items be changed.

The default log level of "debug4" is very chatty. While its handy when setting things up normally, its a bit excessive for normal usage. To reduce logging, change the line

        log "debug4";


        log "info";

In a thread on the freebsd-net mailing list, it was pointed out that the default values for the lifetime of the keys negotiated by racoon is far too short for WAN links, especially over PPPoE links. Thus, you may want to give thought to changing the 'lifetime time' and 'lifetime byte' parameters in the 'sainfo anonymous' stanza to 3600 seconds and 50000 kb respectively.

Part of the key-exchange process requires that the 2 nodes agree on some predetermined secret. This can be accomplished either by presenting X.509 certificates, or (simpler) via some pre-shared text key. To configure a pre-shared key, you must edit the /usr/local/etc/racoon/psk.txt file on both nodes.

In the psk.txt file, add the following line:

        peer_ip_address        sharedkey

If you were configuring IPsec to talk to a peer with an IP of and a shared key of 'thisisatest' then you'd add the line                thisisatest

to the psk.txt file on that machine.

Make sure that the psk.txt file is mode 600 and owned by root, else racoon will refuse to read it.

At this point, you can launch racoon on both boxes via the following command:

        /usr/local/sbin/racoon -f /usr/local/etc/racoon/racoon.conf

If you've done everything right, then pinging either host should work. There will be a brief delay while racoon exchanges keys, but then you'll see packets flow. The default location of racoon's log file is /var/log/racoon.log. By tailing the log you can see the keys being exchanged.


Interoperating with Win2k

It is possible to have a FreeBSD box use IPsec to communicate with a Win2k machine. As you cannot setup manual keying when interoperating with a Win2k machine, you must use racoon to automatically exchange keys. Also you should know that there are some limitations on a Win2k machine and it is not as secure as an encrypted FreeBSD network (fewer algorithms, fewer bits for encryption).

The very first thing you have to to if you want to create an encrypted session between your FreeBSD machine and your Win2k server is to download the latest service pack available and also the "high encryption pack for win2k". This encryption pack is neccessary for several countries to enable 128 bit 3DES encryption on your win2k box. If you do not download the pack, you will NOT be able to connect to the FreeBSD server and everything you get is a TIMEOUT. The service packs and the high encryption pack is freely available from Microsoft.

Set up the FreeBSD machine as detailed above, recompiling the kernel to include IPsec, adding the entries to the SAD using setkey(8), configuring and running racoon.

You have first to setup the basics with setkey and then you may start racoon. You should not start racoon before you have setup the basic configuration described above in this tutorial (the setkey-script).

At this point we will show you how to configure racoon specially for win2k requirements.

Have a look at this configuration file, we will call it "my-racoon.conf". we have made some modifications to it, so it is not completely the same as the original racoon.conf.

We really cannot stress enough the importance in using the latest version of racoon. Development on racoon proceeds fairly rapidly, with numerous bugs and interoperability issues fixed between releases.

A word about the option "log debug4". The first goal of this tutorial is to get the encrypted communication up and running. If it works we can go on optimizing the configuration and its options and again change the logging as noted above.

path pre_shared_key "/usr/local/etc/psk.txt" ;

log debug4;

# "padding" defines some parameter of padding. You should not touch these. padding

        maximum_length 20;      # maximum padding length.
        randomize off;          # enable randomize length.
        strict_check off;       # enable strict check.
        exclusive_tail off;     # extract last one octet.


# Specification of default various timer. timer

        # These value can be changed per remote node.
        counter 5;              # maximum trying count to send.
        interval 20 sec;        # maximum interval to resend.
        persend 1;              # the number of packets per a send.

        # timer for waiting to complete each phase.
        phase1 30 sec;
        phase2 15 sec;


remote anonymous

        #exchange_mode main,aggressive;
        exchange_mode aggressive,main;
        doi ipsec_doi;
        situation identity_only;

        #we not need an identifier, it is set automatically
        #my_identifier address;
        #my_identifier address "";
        ##peers_identifier address "";
        #certificate_type x509 "mycert" "mypriv";

        nonce_size 16;
        lifetime time 1 min;    # sec,min,hour
        lifetime byte 5 MB;     # B,KB,GB
        initial_contact on;
        support_mip6 on;
        proposal_check obey;    # obey, strict or claim

        #very important. We need 3DES for encryption and MD5 as checksum

        proposal {
                encryption_algorithm 3des;
                hash_algorithm md5;
                authentication_method pre_shared_key ;
                dh_group 2 ;


sainfo anonymous

        pfs_group 1;
        lifetime time 36000 sec;
        lifetime byte 50000 KB;
        encryption_algorithm 3des,des,cast128,blowfish ;
        authentication_algorithm hmac_sha1,hmac_md5;
        compression_algorithm deflate ;


A word about the lifetime settings. The shorter the lifetime, the better the security of your session. This is because the session keys for the symmetric encryption algorithm are changed more often. As a result, less of your communication is vulnerable to one of the session keys being cracked. But there are some limitations on the Win2k machine. You can not set up a very short lifetime with it. On the other hand, the shorter the lifetime is, the more overhead you have, as additional bandwidth and processing power is dedicated to key exchange.

As described above in this tutorial, do not forget to create a "secret file" with your pre-shared "key" (password). One of the advantages of racoon is that you do not have to make some calculations about the password-length (bits divided by 8 must fit to the password length), and you do not have to use two passwords (one for authentication, one for encryption). With Windows 2000, you cannot use two passwords. You have only one shared secret for your communication and it is not divided by seperate passes for authentication and encryption.

For debugging purposes, we start racoon with the following options:

    racoon -F -v -f my-racoon.conf

This forces racoon to run in the foreground and we have a debugging protocol on the screen for later analysis of common problems.

On the Windows machine, perform the following steps:

  • Start a command window, and launch 'mmc'. Go to Console->Add/Remove Snap in. Add the IP Security Policy Management snap-in.

  • Click on IP Security Policies in the tree listing, and then select Action->Create IP Security Policy from the menu.

  • Go through the wizard. In particular,

    • Do not activate the default response rule.

    • Edit the properties.

  • In the properties, click on the Add button to add a new rule. Go through the wizard, and ensure the following settings:

    • The rule does not specify a tunnel.

    • The rule applies to the LAN

    • Use a string to protect the key exchange. Stick in the same key as you used in the psk.txt file

    • You'll want to create a new IP filter so that only traffic to the BSD box is subjected to the security policy. Select this new filter.

    • Select 'Require Security' for the filter action.

        Make sure the used configuration for 'Require Security' is as following.
        There are several rules you might see, check for a rule with this options
        or create a new rule by yourself:

        AH is disabled
        ESP integrity is MD5
        Encryption algo is 3DES

        For our first testing purposes, the 'Session Key Settings' are disabled.
        You can change and optimize it later.
  • Restart the IPsec policy agent, via the Administrative Tools->Services selection from the Control Panel. You should restart the agent every time if you make any changes to your rulesets to ensure that the rules are promptly and properly accepted.

  • Select the new policy in the window, and click on the toggle switch icon in the menu bar to activate the policy.

  • Start the "ipsecmon" program. With this tool you can monitor the active rules on the machine.

  • Open up a command window, and ping the BSD box. The ping will 'fail' with a message 'Negotiating IP Security'. Another ping should subsequently work. As soon as you ping, you can see on the BSD box that there are a lot of debug messages.

At this point, all IP traffic between the 2 boxes has been secured.

On the windows machine, you can see the encrypted session with the ipsecmon tool. On the BSD Box you can follow the debug messages to see that everything works well.

On the BSD machine we can try to dump the data on the wire to be sure everything works as we want. A command like

   tcpdump -i ed0 -x -X -s 14400

where ed0 is your interface, will show the packets on the wire. You can see both the IKE key exchange between Win2k and racoon, and the actual encrypted packets, shown as the ESP packets.

If you are having problems with setting up IPsec, we would urge you to first direct your queries to the appropriate mailing lists; or; before contacting the authors directly.


Useful links

Kame documentation:


FreeBSD IPsec documentation:

Raccoon configuration tips:


Using certificates instead of pre-shared keys in Racoon:


NetBSD IPsec documentation:


Some RFCs:

  • RFC2709: Security Model with Tunnel-mode IPsec for NAT Domains

  • RFC2663: IP Network Address Translator (NAT) Terminology and Considerations

  • RFC2406: ESP

  • RFC2402: AH

  • RFC2409: IKE contains a comprehensive collection of the RFCs



Suggestions, hints, advice, corrections, and feedback about this document may be sent to the authors.

mpd5 l2tp

需要使用到mpd5(提供l2tp),ipsec-tools(提供ipsec) 首先需要编译内核,加入如下信息: options IPSEC #IP security options IPSEC_FI...
  • huithe
  • huithe
  • 2013年09月05日 10:27
  • 1405

freebsd ipsec 部署

A地:    内网:   外网: B地:    内网:  外网: 首先在 A 上: ...
  • huithe
  • huithe
  • 2011年09月27日 16:58
  • 741


最近一个项目用到了Remoting,据说是出于安全性的考虑。但是在开发上的效率还是比较低的,也是比较复杂的。另外还有一个安全性的问题,就是Remoting所在的机器是可以直接访问DB的,而App Se...
  • broze
  • broze
  • 2008年06月09日 17:03
  • 21000


概述 IPsec由四部分内容构成:负责密钥管理的Internet密钥交换协议(IKE,InternetKey Exchange Protocol),负责将安全服务与使用该服务的通信流相联系的安全关联(...
  • bytxl
  • bytxl
  • 2014年08月06日 10:23
  • 3620

BogoMips mini-Howto

zz:  3. The frequently asked questions about Bogo...
  • wzzushx
  • wzzushx
  • 2014年04月03日 11:21
  • 431


目  录 IPsec IPsec简介 IPsec的协议实现 IPsec基本概念 加密卡 IPsec虚拟隧道接口 使用IPsec保护IPv6路由协议 IKE IKE简介 IKE的安全...
  • tantexian
  • tantexian
  • 2015年02月03日 13:18
  • 13486


1、设置IP地址、网关 ee  /etc/rc.conf   #编辑 ifconfig_em0="inet  netmask"  #设置IP...
  • SysProgram
  • SysProgram
  • 2016年08月05日 17:29
  • 1789


命令解释程序 shell是与用户关系最密切的应用程序,用户主要通过shell使用系统。在每次登录系统之后,就启动了一个与用户交互的shell,这个shell将给出一个提示符等待用户输入,(sh为 “ ...
  • zhangdaisylove
  • zhangdaisylove
  • 2015年06月15日 11:07
  • 2061

Windows2003 IPsec

本文出自 “一颗平和的心” 博客,转载请与作者联系! 转自:
  • mergerly
  • mergerly
  • 2012年12月21日 12:34
  • 1581


session 1 ipsec知识点 IPsec(IP Security)ip安全的简称     在实施VPN时,除了实现隧道功能以外,还要实现数据安全,两者缺一不可;在隧道方面,之前所讲...
  • alone_map
  • alone_map
  • 2016年07月06日 16:10
  • 4738
您举报文章:FreeBSD IPsec mini-HOWTO