What is a wildcard certificate and why are they a bad idea?

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Wildcard certificates are SSL/TLS server certificates that unlike their traditional counterparts bind a entire domain (or sub-domain) to a single private key, for information on the kind of wildcards one can specify see: http://support.microsoft.com/kb/258858.

Why would someone want to have a certificate like this? Well in my experience the decision is most often made on cost factors (acquisition, management, and politics), in other words I would rather buy onecertificate for my entire server farm instead of one for each server.

What makes the use of these certificates a bad idea? Well there are several reasons:

First, SSL/TLS typically provides two key properties; authentication of the server and confidentiality of the session; the core value of that pair is the authentication of the server as you should not even consider submitting data if you don’t know who its going to and if you never submit data you don’t need to worry about if the session is encrypted (most of the time).

Lets explore why we care about “who” were talking to and why that need to specific, certification authorities only issue certificates to entities that agree to something commonly referred to as a subscriber agreement; this agreement obliges the subscriber to have certain practices, the most basic of which might be not to publish the associated private key on the web or to not host malicious content.

With a wildcard certificate you may or may not know if the site content your experiencing agreed to such an agreement, more over you have a pretty high probability that the private key associatedwith the certificate exists in multiple locations, this also increases the likely hood that the private key is in software and not hardware making it a practical possibility a remote exploit could expose the private key to an attacker.

Then there is the question of who your talking to, many sites use sub-domains (for example WordPress), this becoming more and more common with the exhaustion of easy to remember domains and new community sites that what remember-able URLs for their members, each of these “subs-sites” typically have control over their own content and knowing who their hosting provider is doesn’t tell you anything about them in particular.

Now I am not suggesting that having a certificate tells you that the content being served from that host is somehow more trustworthy but knowing who you are talking to went to the trouble to prove who they are to you is useful when making a trust decision.

Secondly there is the practical issue of key management, as I mentioned earlier you know that the key has (very likely) been shared amongst multiple hosts, and keys that have been spread out like the dogs breakfast are much less trustworthy than ones that have never been shared.

If these things are so bad why did they get developed? Well there are a few reasons, certainly cost was one of the but I actually believe it was done in the hope to enable intermediary SSL/TLS accelerators too to service multiple sites; the thing is that these devices have always been able to handle different certificates for each of the hosts they secure so this would have just been a excuse.

In my opinion all browsers should have a setting that allows users to disable the wildcard behavior, in-fact I would go so far to say that this should be the default.

There is another similar case to the wildcard certificate, it is possible to bind multiple identities to a single key pair, one can put in multiple Subject Alternate Names, in other words I can create a certificatethat binds 100 host names into a single certificate; this still has many of the problems of a wildcard certificate and I would argue that this case should also be covered by any setting that disabled ambiguously bound certificates.

Alun Jones has a good blog post from a while ago on this topic that is worth a read too.

ASKING THE DRUNK IF THEY ARE DRUNK

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For a over decade there has been a slow move towards building networks where only authenticated users can get on (wireless networks are a great example of this), this later moved towards building networks where onlyauthenticated users on managed machines get on, the most recent change to this trend has been to add checks that also require these machines meet a base-line configuration that gives the network administrators some idea of what kind of risks they are exposed to by letting these machines on their networks.

This all makes sense, after all machines that do not have up-to-date antivirus or the latest patches certainly represent more risk to the network than those that do.  A great example of this is actually SQL Slammer, even today five years after the patch for this vulnerability it is still negatively effecting customer environments.

Analysts have given solutions in this space the label of Network Admissions Control (NAC), these systems rely on two basic models one where the behavior of the host is externally monitored and its access is limited if it behaviors out of norm with the networks policy and another where the host makes claims about its configuration that is then evaluated to decide of the host is conformant with the networks policy to see if access should be limited.

Both of these models are examples of what I call “asking the drunk if he is drunk”,  I say this because in both cases the client can control if it displays a behavior (I used to work with a security consultant who would always say “give me your rules and I will comply with them”, this is a example of just that – warning pdf link) or produces a claim that will result in access being given or restricted. The core difference between the two approaches is how rich is the information that is available to make policy decisions on.

The problem with this is if we are to deploy solutions like this we must also accept that it is possible for malware (like root kits or other malicious host software) to change the behavior of the host so that it isn’t “caught” by these checks.

If thats really the case do these systems still have value? I would argue they do, you see they give systems administrators get something they have never really had before, insight into their networks risk profile (how many people on my network do not have this patch, are not running antivirus or have out of date signatures, etc.).

There are other values too, in general users actually “want to do the right thing™” but they don’t necessarily know what that means and these systems help them do just that, in addition these systems often implement concepts of “automatic remediation” so that you can remove the obligation of the user to do anything and instead you just fix it for the user without their interaction.

These reasons underscore why even in computing it’s important to “pull the drunk over and ask him to walk the line”, but does this mean we should accept the status quo? I would say no, although it will never be possible for a running system to evaluate its own state in without potentially being fooled there are lots of things we can do to make the host itself more trustworthy.

As a example many of the technologies in VISTA do just that (and I thinkSymantec would agree), some of the technologies in VISTA that help here today include:

  • Bitlocker – Protects the host from offline attacks of trusted software components and cryptographic keys.
  • Secure Startup – Increases the trustworthiness of the OS by checking to see that core components are authentic as part of the startup sequence.
  • Code Integrity – Increases the trustworthiness of the running state of the OS by checking to see if they are authentic before being loaded.
  • UAC – Reduces the negative impact that can be caused by careless users and/or malware by giving these processes a restricted token.
  • ASLR – Makes it more difficult for malware to attack running code by randomizing where code is running in memory.
  • DEP – Makes it more difficult for malicious code to get and keep running.

This represents just the beginning through, future versions of these conditional network access solutions will also leverage hardware that runs before the operating system (TPM) to verify that the components that implement the above are not tampered with before the operating system even is invoked.

Later systems will even be able to use virtual machines to add even more protection from these sorts of attacks, again that’s not to say that when we get here we will have made these systems fool proof; it’s just not possible(my friend Cem always has great analogies, one of my favorites is “Security is often a exercise of re-arranging deck chairs on a sinking ship” this problem is a example of just that) but that doesn’t mean there is not value in raising the bar and I think the industry is well on its way to do just that.

As a side note, we have deployed the Microsoft solution in this space (Network Access Protection) to over 75,000 hosts over the last few months pretty cool if you ask me.

Understanding Server Gated Cryptography

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Chris Baily and I wrote this paper back in 2004 and for various reasons we never got around to publishing it, while looking through my un-published articles I saw this and though that it might still have some value so I am publishing it here.

Introduction
If you have ever looked into purchasing a certificate to secure your Web site, you’ve probably heard of Server Gated Cryptography (SGC). If you have ever wondered what it is and how it affects your Web site, this is the article for you.

Let’s begin with why we even bother with SSL and TLS. Now, most people know that SSL and TLS are the technologies that enable the “lock” icon in browsers. This icon signifies that the session is “secure” to users, but what does this really mean?

Name Authenticity – The client can rely on the fact that it is communicating with the server represented in the host name in the Web address.

Confidentiality – The information being sent from both the client and your SSL and TLS enabled server has been encrypted. These are all great characteristics, but there’s more to them than may be apparent on the surface.

Let’s explore each of them what makes them factual.

Name Authenticity
The SSL and TLS protocols are based on the premise that each server or cluster of servers that represent a particular host name has a secret called a private key. The operative word here is private. If the secrecy of this key is compromised, an attacker could spoof the server’s identity or even decrypt the data being sent to the server.

Having a private key isn’t enough—you also need the corresponding public key. That key, along with the name of the server, is wrapped up or bound together into a certificate. A certificate asserts the name of the server in a way that is provable. Why is having a certificate important?

Consider the HTTP protocol and the use of the Domain Name System (DNS) resolution protocol to resolve the IP address of the server being communicated with. Because DNS is a protocol that was designed without a security subsystem, DNS can suffer from a number of network-based attacks. For example, in DNS there is simple man-in-the-middle attack where an attacker intercepts a request for the IP address that is associated with a server. The attacker then returns the IP address for their server instead of the one originally requested. When that server hosts a web site the attacker can then duplicates the look and feel of the Web site in question and leverages the user’s trust of that Web site to gather confidential information from that user.

Without the SSL and TLS, protocols, the user wouldn’t have known that this attack had taken place. By using SSL and TLS in the HTTP protocol, however, we can detect these types of attacks and prevent connections to fraudulent servers. SSL and TLS use certificates to enable this. The client and the server use a negotiation process to prove that the server has the private key associated with the certificate presented by the server, that the server certificate was issued by a certificate authority trusted by the client, and that the server certificate is associated with the same server that they are communicating with.

What is a certificate authority? A certificate authority is a third party that verifies the identities of individuals and their affiliations with the organizations that they claim to represent. They do this by having strong authentication and operational practices for themselves and their subscribers.

Confidentiality
The confidentiality offered by SSL and TLS are primarily the result of two assumptions in the protocol—the secrecy of the private key possessed by the Web server, and the strength of the cryptographic algorithms and keys that are used to protect data as it passes between the client and the server.
Although the identity of the server is authenticated using its private key and associated certificate, the data that is passed between the client and the server are encrypted using secret keys (symmetric keys) that are exchanged as part of the SSL and TLS protocol.
A number of cryptographic algorithms are based on secret keys. The strength of these types of algorithms is measured in part by the length of the secret keys that they can use to encrypt data. These algorithms provide varying levels of security. The accepted standard is that algorithms that can encrypt data with keys that are 128-bit or longer are strong while anything protected with keys of lengths less than that are considered weak. This is where SGC has an important role.

What is Server Gated Cryptography?

SGC is a (software) technology from Microsoft that allows U.S. vendors to ship software outside of the U.S. to companies that need strong cryptography for session protection—not for the encryption of the data to be persisted. This technology requires digital certificates.

The U.S. government at one time restricted U.S. vendors from offering strong cryptography to countries outside North America. In fact, strong cryptography was considered to be munitions by what is now known as the Bureau of Industry and Security (Department of Commerce, U.S. Government). Despite this, we still had in a global economy. The need for secure communications with parties outside the U.S. still existed. This is why SGC was developed.

To satisfy the requirement for security, the software vendors who supported cryptography had to ship two different versions of their software—export and nonexport.

To get permission to export this software outside of the U.S., these vendors had to implement constraints to prevent entities considered to be hostile from getting these more secure sessions. In the case of SSL/TLS, this was done by requiring that the authorities that issued certificates signed contracts agreeing to issue only certificates capable of SGC to authorized users such as financial institutions. Without a certificate from one of these SGC-enabled certificate authorities, clients without direct support for strong cryptography were only protected by 40- or 56-bit security, which during software export restrictions was considered weak.

Microsoft and other software vendors stopped shipping nonexport or weak encryption versions of their software shortly after the U.S. lifted its export restrictions in early 2000.

The Waning Need for Server Gated Cryptography

Today, almost all Web software by default supports strong (128-bit or greater) SSL without the use of SGC. The primary value of SGC–to ensure a strong encryption SSL session to clients supporting only weak cryptography–has waned. The importance of having a strongly encrypted SSL session has not. Advances in computing power along with more sophisticated attacks have made the adoption of 128-bit security more important than ever. RSA Laboratories estimates that an arbitrary 56-bit symmetric key can be broken by an attacker in less than 5 minutes. Additionally, the recent improvements in specialized factoring hardware has changed the landscape when it comes to the security offered by small RSA keys as well.

As of January 2004, an estimated 85% of browsers in use were shipped with strong encryption by default [IE 5.5, IE 6.0, Mozilla 1, Opera 7.0, and Safari]. Additionally, conservative figures would suggest that 10% of the platforms that didn’t support strong cryptography have been upgraded, and the remaining 5% are rapidly being upgraded as well.

This data shows that only the browsers released before the export restrictions were lifted (2000) don’t support strong cryptography out of the box. These browsers also have known security issues. For example, Internet Explorer 5.01, released in 1998, was the last browser released by Microsoft that didn’t by default support strong cryptography. This version of the browser had sixteen critical updates and each one of these updates may have fixed several issues. Security issues are not limited to Internet Explorer. For example Netscape Navigator also has had numerous critical issues fixed since it was originally released. These older browsers don’t support the newer revisions of the SSL and TLS protocol that were developed to address security vulnerabilities in these protocols. This alone may be adequate justification for requiring older clients update their browsers.

Although clients play a significant role in the establishment of secure communications with servers, administrators can take small steps to help enable secure communications with their customers. Specifically, to significantly reduce the risks of downgrade attacks, their can configure their servers to use only strong cryptographic suites and the latest versions of SSL (TLS).

SGC can help strengthen the security of the SSL session. SGC does this by increasing the strength of the encryption used for clients running on old browsers. This object is defeated if a potential attacker can exploit a security weakness in the browser or the protocol that is not related to encryption strength. Users who want stronger security must keep their software up to date, and if possible, upgrade to the latest browser versions (see sidebar) so as to benefit from the security improvements offered in these more recent versions.

Summary
Encouraging clients to migrate to more recent browsers that are capable of supporting the more modern security protocols and strong cryptography will also address known security vulnerabilities in these clients. As a result, users will have a more secure and reliable Web experience. Continuing to depend solely on SGC provides only a feeling of security rather than a more secure environment if these other issues are not also addressed.