Jakob Ƙstergaard Hegelund

Tech stuff of all kinds

The rocket science of VPN


The phasing out of older systems and introduction of new ones landed me in a situation where I needed to configure a VPN service for myself and a group of colleagues.

Requirements were something like:

You'd think this was pretty basic stuff right? After all, VPNs have been around for decades - the newest technologies mentioned here are iOS and Android, none of those are exactly experimental untried platforms either.

Well it turns out, this sort of technology is completely unheard of, unrealistic to implement and I am apparently decades ahead of my time, thinking something like this would be nice to have

Goodbye: most protocols

No single protocol, that I want to use, is supported natively (built-in) across all the devices and systems I need.


I specifically do not want Layer-2 tunneling and therefore I will disregard L2TP/IPSec. This pretty much leaves me with IKEv2 as the only choice - it may require an app on Android devices, but I think we will survive that.

An alternative approach would be to accept that no built-in protocol is "good enough" and then go full third-party; OpenVPN or some other solution. I dislike this approach because I don't like to force installs of special software for basic networking functionality onto all clients - I don't have any hard evidence saying this would not work or this would be bad for some specific reason, I just don't like it. And since I'm the one tasked with this, what I like and don't like matters.

I'm going to set up an IKEv2 provider using StrongSwan running on Ubuntu, and that's that

Goodbye: Kerberos

Windows, in the old days before Kerberos (or "Active Directory" as the marketing term is for Kerberos and LDAP on Windows), invented various more or less safe password exchange schemes so that a client could authenticate against a server without transmitting too much information about the password onto the network for an attacker to be able to derive the password. One such protocol is MSCHAPv2. The MSCHAPv2 protocol requires that the server has a specially hashed version of the user's password on file, or simply the full plain text password.

After Windows adopted Kerberos in 1999 and released it with Windows 2000, there has not been a need for protocols like MSCHAPv2 since the Kerberos protocol not only solves the same problem as MSCHAPv2 better, but also provides functionality such as actual Single-Sign-On which is completely out of the scope of MSCHAPv2.

You might think, then, that 17 years after that, it would be possible to have a Windows VPN client authenticate against a Kerberos infrastructure - well if you thought so you'd be wrong. Windows servers only support MSCHAPv2 as user/password authentication protocol for IKEv2. And, to be consistent, OSX does exactly the same.

If you run your VPN server on Windows, your VPN clients can validate up against their "AD" passwords, because the AD will keep the necessary extra password material on file - this is not Kerberos authentication, it is not single-sign-on, it is a crude hack that allows the use of arcane authentication protocols against what could have been a modern authentication system. Well, I don't run my VPN servers on Windows, so this is not directly an option.

Goodbye: Workaround with KCRAP

The MIT Kerberos KDC actually supports the same hash function as is necessary for the MSCHAPv2 exchange; you could actually configure your KDC to store these hashes alongside the other information it stores.

On top of that, you would need the KCRAP service which allows the extraction of these hashes from your KDC database.

On top of that, you would need a FreeRADIUS server, which could support an MSCHAPv2 exchange using the KCRAP service as its back-end

And finally you would need the StrongSwan VPN provider to talk to FreeRADIUS which can talk to KCRAP and then all should work in theory...

This is too much. There is an excellent description of how to configure this here, but it is too much for me. Too many moving parts. Too much highly experimental software. Too many things that I will need to support entirely on my own, patch with every upgrade of other components, etc.

If StrongSwan had a KCRAP module and if the KCRAP server was an integrated part of the KDC, I might go this route. But with the current state of things, this is not something I want to bother with in a production setup - I have a job to do besides this.

Goodbye: Text files with user passwords in the clear

The simple way to get this working, is to set up every user with their clear text password in the /etc/ipsec.secrets file. Most guides on the interwebs describe this (you could use a database or other store, but it would still basically be plain text passwords on file) - and I got it working. But hang on... This won't fly for several reasons:

I need to find a way to keep user credentials on the server that does not involve storing them in clear text and requiring me to manage them manually.

Goodbye: TOTP and 2FA

One option I considered was using one-time passwords. If I can't use my Kerberos infrastructure, at least I could set up a TOTP infrastructure and the users would then have either a HW token or an app on their smartphone which could provide them with a password.

The obvious benefit here is that the server would always know the current clear text password (it is easy to generate), so MSCHAPv2 could work against this. And the OATH framework has been around for ages, so there must be good support for this, right? Yeah well you'd think that, but then you'd be wrong. Again.

First of all; in a TOTP setup it's nice to allow a little bit of slack so that the user can use an OTP that just expired - for usability and to account for user's device's clocks being a little off - this is completely incompatible with MSCHAPv2 since the hash of the "only correct" password is used in the challenge the server sends to the client. It just can't work.

Second, what I really wanted was proper two-factor authentication - I would like the user to log on with a TOTP, and then provide their username and password (or the other way around, I'm flexible). While IKEv2 does support multiple rounds of authentication, the Windows client does not. Well I guess we won't be going down this route either then.

Hello: Certificates

Left with the prospect of using "large machine-generated passwords" as the best authentication for my users, it suddenly becomes relevant to consider simple Certificate based authentication.

Passwords alone are bad because they get leaked or even guessed if they're really poor; large machine generated passwords don't have the problem of being guessed. But if they are large, they will certainly be written down (anyone saying "we have a policy that says users shouldn't do that" has completely lost the connection to the real world in my not so humble opinion) - so they will be leaked. This is a compromise.

Certificates is really a way of dealing with this: A certificate holds a key that is so large it will not be guessed, and the certificate file is the accepted method of transportation of this key. Therefore, while it may be copied around, it will not get written down or left on a sticky-note on someone's desk. Certificates also have a lifetime built right into them.

The only downside I really see with certificates is that I need to maintain a Certificate Revocation List (CRL) for certificates that have been used on devices that are lost. If we used passwords or pre-shared keys, it would be simple to delete the key from the VPN server. But really, mechanisms for this are established and - almost to my surprise at this point - well integrated.

So actually - at the start of this process, messing with certificates was the last thing I wanted to do - but as each desirable option proved unworkable, certificates started looking less unattractive. At this point, maintaining our own public key infrastructure does not seem all that unreasonable after all.

The PKI setup

Losely based on the guidelines at the excellent StrongSwan wiki, we set up a self-signed Certificate Authority certificate. From here on, it was pretty simple to create certificates for the VPN servers and individual certificates for all the users.

The StrongSwan server needs no reconfiguration as users are added - any user who can present a (non-revoked) certificate signed by our CA is allowed access.

Users receive a PKCS12 file containing their user specific certificate and the private key for that certificate. A machine generated password is set on the file (not stored with the file) and given to the user to use for certificate import.

Users then simply need to install our CA certificate and their own personal certificate - with these bits our VPN gateway can authenticate the user and the user can authenticate the VPN gateway.


Clearly, if a certificate is leaked, just like when a password is leaked, access is granted to people you did not intend to grant access to. Certificates are no different from passwords in this regard.

The only real solution to this problem, as it stands today, seems to be two-factor authentication. While IKEv2 does support multiple authentication rounds, the Windows IKEv2 client does not support this part of the standard. There appears to be no way to implement 2FA on IKEv2, if it is a requirement to use the built-in VPN clients, at least on Windows today (and I simply didn't investigate the other platforms so Windows may not be alone in lacking this support for an otherwise standard feature in IKEv2).

To mitigate this, we use a relatively short (less than one year) lifetime on the certificates. While this is not much use if a device is stolen and abused right away, it will at least mitigate the problem with certificates on old or unused office computers that are later recycled internally or even discarded without being wipe.

A note on certificate file formats

While there are heaps of helpful pages on the interwebs detailing how to convert your DER format certificates to PEM or PFX or PKCS12, there is very little easily digestable information about why these formats exist and what they are all good for.

The one major pitfall to be aware of, is, that some of these files are "container" formats that are used to ship chains of certificates or even certificates along with private keys. Other formats will just hold your certificate.

While I may not want to admit this actually happened to me during the early experiments with the certificate infrastructure, imagine what happens when you convert your CA certificate into a PFX file (to make it easier to import on a Windows machine) and then just because the conversion example you found on the net told you to, you also provide the private key of the certificate... Well now you have a PFX file holding your CA Certificate and the private key for the certificate... Ouch! Not something you would want to distribute to your clients (as anyone with the private key of the CA can generate new certificates in your name).

A short rundown of the formats I encountered and their uses:

PEMCertificate or key; text format
PKCS12Certificate(s) and private key(s) - a bundle for distributing a user certificate and its key to a user, for example
DERCertificate or key; binary format
PFXCertificate and optionally a key - also a bundle format

We use PEM format on the VPN server and distribute PKCS12 files to the users. The PKCS12 files have the extra little benefit of being able to require a password for import - so you can distribute the PKCS12 file by one mechanism and give the user the import password through another mechanism.

Just as you thought you were done...

So I have a Windows workstation, my Macbook and my iPhone connecting via VPN and it is all good! Except... nothing really works. DNS doesn't resolve any of the internal hosts.

While IKEv2 does indeed support split tunnelling, split horizon DNS was not part of the standard... It is being worked on, and it is an IETF draft as of this writing, but it is not in IKEv2. In an older IPSec setup (which could not be brought to work with Windows unfortunately) we used an internal DNS for the internal domains and the client would use "whatever other" DNS it was using for everything else. That is simply not a possibility with IKEv2 today.

Well, the quick solution to that is to use our internal DNS for everything - it can handle the load no worries, and it will forward requests to external DNS just fine. So that solves it right? Well you might think so, but if you thought so you'd be wrong, yet again.

It turns out that OSX and iOS both ignore the DNS information pushed from the IKEv2 server, if split networking is used. However, if you simply don't use split networking, your OSX and iOS devices will happily use the IKEv2 server provided DNS. Well, I suppose our gateways can forward traffic to the outside as well then...

Split DNS on iOS

When I say split DNS isn't possible on iOS it's not entirely true. Apple has a tool dubbed "Configurator 2" which can configure "Policies" for your iOS devices. If you generate such a policy, include your user certificate, define the IKEv2 VPN setup in the policy and then store the policy, this tool will generate a rather nasty looking XML file for you

What you do next, is edit this profile XML document and insert some extra DNS entries that you cannot insert using the Configurator tool. Now when you import this profile on your iOS device, it will import the certificate, set up the VPN, and supposedly correctly apply split DNS configuration as desired

This, of course, is completely unmanageable for me - all I need is VPN access - I don't want to have to hire a full time employee to configure our iOS devices in all eternity. I don't know how Windows worked with DNS and split tunnelling; it doesn't matter since iOS and OSX dictate that we won't be doing split tunnelling any time soon.

Debian and Ubuntu client support

Finally, as we got OSX, Windows and iOS users connecting, setting this up on Linux proved to be the next obstacle. Frankly I had delayed testing this because the servers run StrongSwan on Linux and I "knew" this would just work. Well, at least you would think so right, but then you would be... yes, wrong.

While it is of course possible to manually edit the config files and make StrongSwan connect as client up against the VPN servers, the graphical "Network Manager" tool that modern day Linux users have come to expect, simply doesn't work for configuring an IKEv2 VPN

On Debian 8, there's just no support. It simply isn't there. On Ubuntu 16.04LTS, it is there but it doesn't work. There is a bug in the network manager plugin version that is on Ubuntu 16.04 (Xenial) which is fixed in a later Ubuntu (Zesty) - but it appears it is not getting fixed in 16.04LTS. One can only hope for a fixed plugin in the next .minor release on the LTS.

In conclusion

I am absolutely amazed at how little integration there is in the products that make up a VPN, authentication and authorization infrastructure. While I was of course expecting a challenge or two, I am absolutely flabbergasted at how close to "impossible" something as simple as a relatively secure VPN could be to set up so that it works out of the box on a selection of common modern clients.

That we, 17 years after MSCHAPv2 ceased to be relevant, are still forced to base a mostly non-Windows infrastructure around it, is shocking.

Anyway I am moderately happy with having finally gotten a reasonably secure VPN going to take over from an older much less secure VPN which was not supporting the clients we needed. I would have liked 2FA and Kerberos, but that is apparently not realistic today and maybe never will be (if no-one has gotten it in the past 17 years, I am not holding my breath for the next 17).

Onwards, to glory! Back to real work. With some basic infrastructure in place, chances are we can now focus on real work.