Racoon IPsec VPN on Debian Lenny

I’ve been wanting to set up a “pure” IPsec VPN using racoon for a while now. Part just for fun, part because I can. I spent a weekend on it once a while back, didn’t make much progress, got sick of trying to figure out cryptic racoon debug output and then gave up (more pressing stuff, you know how it is).

Anyways I ran into a situation where I NEED a VPN now. I manage a few systems that are facing the internet so they’re constantly under attack (mostly bots trying to brute force ssh all the time). Remote administration over ssh is pretty much all I need but I’d like to be able to keep a closer eye on the hardware through the “Integrated Lights-Out” system (they’re HP Proliant servers). These I don’t want facing the internet. Similarly I don’t want the configuration interfaces for my switch facing the public either.

So what I needed was a management network that I could connect to through a VPN gateway remotely (typically known as a “roadwarrior” setup). The ALIX system I’ve been blogging about in the recent past is what I’m using as the gateway / server. This post is a quick run down of the contortions I went through to get this working and why I didn’t get it working just how I want it 😦


  • racoon only, no L2TP
  • rsasig authentication
  • as little hard coded network configuration as possible on the client

I thought the above was pretty ambitious. Configuring racoon is pretty complicated but after pouring over the man page for racoon.conf I found the mode_cfg section which specifies the network configuration for the server to send out to authenticated clients. A little more digging turned up a few examples, particurlarly useful were the netbsd howto and the howto forge racoon roadwarrior configuration.

Both of these give a working example of using the hybrid_rsa authentication with mode_cfg. This isn’t exactly what I wanted but it solves 2 of my 3 requirements above so it’s a great start. Next was adding my own server and client certificates to the configuration and making sure that both the certificate and the remote identifier were being verified. I didn’t want to keep having to type in a password when connecting to the VPN so I moved on to getting rsasig authentication working. Naturally at this point all hell broke loose.

It took me forever to figure it out, but it looks like the ipsec-tools version that ships with Lenny (0.7.1) doesn’t play nice with rsasig authentication and mode_cfg. The client and server are able to negotiate phase 1 without any troubles when the client never requests the configuration data from the server. I tried all sorts of configuration combinations hoping to find something that worked with no luck. Eventually I ran across an old and unanswered post to the ipsec-tools users mailing list from a few years back describing the same problem I’m having with the 0.7.0 version of racoon. Probably safe to assume that this behavior is what I’m running into on the version 0.7.1.

At this point my options were to upgrade to a later version and hope the bug was fixed or use hybrid auth. Guess which one I chose … hybrid auth ain’t so bad 🙂 Yeah typing in a password is a PITA but both client and server can still be configured to check each others certs and asn1dns identifiers in phase 1 so very little (if any) security is compromised. 2 out of 3 requirements isn’t bad. None of the desired functionality was lost but I do have to supply a password each time I connect to the VPN. Meh.


Since the articles on howto forge and netbsd.org are so good I won’t bore you with a full description of my racoon configuration since it’s very similar. I will include them here for completeness and cover the parts where they differ.

The server.racoon.conf is very similar except for the credential verification for the client and some details in the mode_cfg. I’m using the split_network directive to send routing information to the client so we don’t have to hardcode any routes. The scripts on the client side had to be changed to accommodate this but it wasn’t that hard (I’ll get to this in a second). Also notice that I’m using all class C networks (/24 in CIDR) so no routes need to be specified on systems plugged into the management network directly.

In my client.racoon.conf the only difference is in the verification of the servers credentials (certs). I started out testing using certificates generated from my own root CA. When this was deployed I got certificates from cacert.org which is a great service.

The significant changes on the client side were in the phase one up and down networking scripts. I really didn’t like the scripts from the howto forge article (some of it didn’t seem necessary). They were a great starting place though but since I’m using the split_network I had to be able to properly handle dynamically creating and removing these routes. The final scripts can be found here: client.phaseone-up.sh and client.phaseone-down.sh

If you look closely you’ll notice that in the phaseone-down script I flush all SAs when taking down the VPN. Obviously this isn’t what we want: we want only to delete the relevant SAs. Unfortunately version 0.7.1 of the ipsec-tools package doesn’t play well with the way Linux manages SAs so the deleteall setkey function doesn’t work right. Flush is all we’re left with unless we’re gona parse the SADB output for the SPIs we need. This bug was reported on the ipsec-tools devel mailing list with a patch and it seemed well received so it’s likely in a later release. I’ll put off writing fancy bash script and just upgrade racoon soon.

Hope this is useful to everyone out there setting up a roadwarrior friendly racoon VPN. Leave me a comment if this was useful or if any of it’s unclear.

5 thoughts on “Racoon IPsec VPN on Debian Lenny

  1. Hi,
    Your links to client and server.racoon.conf are both dead.

    Can you tell me, is the $LOCAL_ADDR supposed to be that of the internet facing interface?


    1. Bad links are fixed. Thanks for pointing that out.

      As for the variable LOCAL_ADDR: this is the address of the client. In the end the client interface will have two addresses: LOCAL_ADDR which it already had before the VPN came up, and INTERNAL_ADDR4 which is the address assigned to the client by the VPN.

      Notice that LOCAL_ADDR is the client side of the IPSec tunnel created by the SA added to the SPD in the client.phaseone-up.sh script (line 65 & 66). Basically when everything is set up the encrypted tunnel exists between LOCAL_ADDR (client) and REMOTE_ADDR (VPN server).


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