The End of SSL and SSH? Follow-up.


by Kurt Seifried for


The original article: The end of SSL and SSH?


December 22 2000 - Well, I certainly managed to kick over a hornet's next with my article "The End of SSL and SSH?". There were quite a few points I did not cover in the article, many I did not think of, and some I trimmed. This article will cover the reaction to SSL and SSH being "dead", as well as numerous implementation issues I did not cover. The real issue is that technology cannot solve problems completely. Anytime you put a new solution in you breed new problems. This of course assumes you installed and are maintaining the new solution correctly in the first place. Vendors ships SSL and SSH, you turn it on, it works. Unfortunately most people feel that they are then done and move on to other problems, this is far from the truth. Both SSL and SSH have numerous avenues an attacker can take, many of these rely on the end user to make the right decision or have a secure system, meaning a user can shoot themselves in the foot with incredible ease. Pretty much any cryptographic "solution" requires a degree of maintenance and continued attention.



Vendors ship server software such as SSL enabled web servers but do little to make sure that users create certificates properly or store them properly. While almost all webservers support PEM (Privacy Enhanced Mail) encoded certificates relatively few people use them since you must enter a passphrase every time you start the server, making it impractical for many such as virtual web hosting companies with dozens, hundreds or even thousands of sites. These certificates can also be retrieved from the memory of the server, this was found to be quite a bit easier then originally thought. On the client side we have web browsers with over a hundred certificates (I counted the root certificates in Internet Explorer 5.5 and it came to 120 root certificates). If any one of these certificates is compromised an attacker would be able to create and sign certificates for any name they wished to, making setup of fake sites trivial. Attackers can easily present users with a new root certificate and many users would inadvertently install, again allowing an attacker to create arbitrary certificates. You can also modify the certificate store with relative ease, since Windows 9x has no file or registry permissions and the default settings in NT are quite promiscuous this is relatively easy. The number of potential paths an attacker can take to get a root certificate into a users webbrowser are numerous and generally speaking quite weak, most depend on the user to make the right decision, or have secured their system properly, something that is relatively rare.

If an attacker manages to break into a server that uses SSL to secure services they can steal the certificate. If the certificate is PEM encoded they will need to find the passphrase, this can range from trivial to difficult in the extreme. They can then use the certificate to setup a service that looks identical to the original, with some DNS poisoning they can direct users towards it. Now a good administrator is supposed to to notice this and issue a certificate revocation. There is only one tiny problem with this scenario. I have yet to see any web browser or SSL enabled piece of software that checked for certificate revocation by default, if they have the option it is usually disabled by default. The reasons for this are many, the primary one being that a piece of client software that checks for revocation constantly will be slower and this of course will annoy users.

Darren Reed [email protected] points out that:

For Netscape there is a built-in MIME type that cannot be disabled which invokes the root CA installation code.  10:1 most people would click "ok" to install a root CA if so prompted from a random web site. Now that's without even doing anything nasty.

Even ignoring all these problems the simple fact is that SSL certificates only identify the server to the user, they do not authenticate it. This is a subtle but incredibly important difference. My online bank is at, on the other hand is owned by someone else and is still free. I know for example that is the "official" site for OpenSSL, but what about Shouldn't that be the official site for OpenSSL translated into German? Well it turns out that it isn't. Do you trust every single root certificate in your webbrowser software? Have you even heard of "IPS SERVIDORES" (, "Saunalahden Serveri CA" ( or "SERVICIOS DE CERTIFICACION - A.N.C." ( I sure as heck haven't.

Of course an attacker can simply prevent you from ever making it to the real web site, say you are shopping at, generally speaking the only part that would be SSL protected is the actual order submission, meaning an attacker can do a man in the middle attack and host a fake web site. When you hit submit to place your order they would simply direct it to either a non secure site or their own secure site.



Drop 300 and fire for effect!

Now to deal with SSH. One huge SSH problem that someone pointed out (lost your email address, sorry) is that very few people expire their SSH keys. Another friend of mine pointed out that to minimize the pain of different SSH keys on hosts the local university copies keys between servers, in a way this makes sense for ease of use, but has horrific security consequences. SSH keys can last forever if you want, and the key itself has no real binding to the host it resides on. Expiring and replacing keys is difficult as it would look exactly like a man in the middle attack to end users, "Host key has changed, blahblahblah". Implementing a PKI in SSH would negate many of the benefits SSH offers, like ease of deployment since you don't have to worry about setting up a key structure, just individual keys. However something that could improve it would be to use authentication protocols such as SRP or Kerberos that offer a number of benefits. With Kerberos for example the server authenticates itself to the client as well as the client to the server, thus making man in the middle much harder to execute. SSH also does not protect the key beyond file permissions, and has no key revocation mechanism. If an attacker were to break into a system and managed to retrieve the keys they would then be able to execute a man in the middle with extreme ease. To make matters worse the admin would have to somehow inform users (via email? memo? phone?) that the keys had been compromised, there is no way to do a key revocation. Contacting all the users for a large installation (such as a university) would be painful to say the least. Then there is the issue of protecting the known_hosts file in UNIX, often times user directories are mounted via NFS, savvy attackers could be able to modify the known_hosts file in transit (like when your local ssh client requests it) allowing them to execute a man in the middle attack successfully. This could be somewhat mitigated by populating machines with a known_hosts file in /etc however the maintenance and distribution of such a file would be non trivial.

To make matters worse here are the messages that SecureCRT ( a popular SSH client for Windows gives:

New key:

The remote host ( has not been registered.
Do you want to accept this key?
Cancel | Accept Once | Accept & Save

Changed key:

The key you received from conflicts with the previously registered key.
Do you want to accept this key?
Cancel | Accept Once | Accept & Save

No reason or explanation is given, unless the user has been educated chances are they will simply accept they new or changed key and go on with their work. Programs should flash, beep and make the user aware of potentially bad things, the error message for a changed key should be more like:

The key you received from is different then the previously registered key.
This may be due to an updated key on the server, or an attack trying to subvert your ssh connection.
You should contact your network help desk or system administrator immediately and clarify the situation.

Programs should not make it easy for a user to let an attacker execute an attack successfully. Remember, once an attacker gets on to the system with a shell chances are they can gain administrative access, meaning you will have a server to rebuild.


SRP / Kerberos and others

There are a number of protocols well suited to authentication. Kerberos allows users to authenticate themselves to a server, and vice versa based on a shared secret (usually the password). Microsoft has recently started using Kerberos (with some "enhancements"), letting you connect to Win2K servers and then use things like IPSec in a reasonably secure manner. Other ZKP (Zero Knowledge Protocols) protocols such as SRP allow you to prove your identity to a server without ever sending any sensitive data (like your password) over the network. Implementing Kerberos, SRP or other ZKP protocols into SSH would make man in the middle attacks more difficult. Unfortunately these systems do not apply to SSL much since most SSL transactions are www based and the user has no way of pre sharing a secret with the merchant.



Many people pointed out PGP and GnuPG as being potential add-on solutions. You can PGP / GnuPG sign SSH keys and distribute them, well except for the small problem that very few users have PGP or GnuPG capable mail programs and even fewer know how to use them properly. Plus they would then have to take these keys and import them into their known_hosts file (which even if done correctly doesn't guarantee security). I would not classify the use of PGP / GnuPG to "add security" to SSH or SSL as a valid solution. There are also some nasty security problems in older version of PGP and GnuPG that could allow an attacker to subvert messages and keys.



This is something I mentioned as being a potential solution. I phrased it badly, what I was aiming to get across was that the use of DNSSEC could help prevent man in the middle attacks. Currently DNS is completely insecure. DNS spoofing is a trivial matter for attackers and most clients rely heavily on DNS (how many people put the IP address of a server in the connection setting, instead using the name?). If DNSSEC were properly implemented and DNS servers were properly secured DNS spoofing would be more difficult, obviously it has a long ways to go. Widespread usage of IPSec would make man in the middle attacks harder as well, hijacking TCP sessions would be a non trivial exercise and most fail. However IPSec requires some form of authentication, this can be achieved with a PKI (such as DNSSEC) or shared secrets (such as Microsoft's Kerberos), obviously we are a long ways from widespread opportunistic IPSec usage, however in many environments IPSec can be deployed and would help. Deploying it properly and maintaining it is left as an exercise to the reader.


Social issues

Many attacks come from internal sources, the difficulty in gaining some sort of access is negated by the simple fact that the attacker already has legitimate access. Even if the technology works properly the end user must still be educated and security conscious as many attacks will ultimately end up targeting the user (often the weakest link). Security protocols and software are far from being the robust fail safe (as opposed to fail open) systems that we seem to think they are. Good security should be hard to disable or misuse, for example door locks are extremely simple to use, locking a door is a simple act and testing that it is locked is simple (I always try to turn my door handle once I have locked it when leaving the apartment). Security software should aim for this level of ease of user and safety.


Reference URL's: - Unzureichender Schutz der X.509v3-Zertifikate in Browsern - DNSSEC papers - Using certificate revocation in Apache - PAK



Last updated 8/11/2001

Copyright Kurt Seifried 2001