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The Risks of SSL Inspection

Posted on March 13, 2015 by Will Dormann in Vulnerability Analysis

Recently, SuperFish and PrivDog have received some attention because of the risks that they both introduced to customers because of implementation flaws. Looking closer into these types of applications with my trusty CERT Tapioca VM at hand, I've come to realize a few things.

In this blog post, I will explain

  1. The capabilities of SSL and TLS are not well understood by many.
  2. SSL inspection is much more widespread than I suspected.
  3. Many applications that perform SSL inspection have flaws that put users at increased risk.
  4. Even if SSL inspection were performed at least as well as the browsers do, the risk introduced to users is not zero.

SSL and TLS are used for two primary purposes:

  1. Authentication of the server that a client is communicating with.
  2. Encrypting data sent between the client and the server.

Some folks may assume that SSL or TLS attempt to achieve the above goals on an end-to-end basis. This is an invalid assumption. SSL and TLS can practically achieve secure authentication and encryption only on a point-to-point basis, not an end-to-end basis. What is the difference, you may ask. Let's first look at the case where the point-to-point communication is also end-to-end:

The client has the ability to verify secure communications only with the next point that it is communicating with. In the above case, the client establishes an SSL or TLS connection directly with the target system. The client software verifies that the system that it is connected to has been verified by one of the potentially hundreds of root CA certificates that may be present on the system. Whether or not the system that is being communicated with is what the user expects is another story.

When a user loads a website in his/her browser that should be protected with HTTPS (and subsequently SSL or TLS), that browser is actually only confirming that the system it is communicating with is providing a certificate that is issued by one of the root CAs that the browser trusts. You are implicitly trusting that each root CA has done its due diligence to verify the identity of the server that you are connecting to. Sometimes root CAs get tricked. You are also trusting that each root CA has taken the appropriate steps to protect its own systems. Sometimes root CAs get compromised. See Moxie Marlinspike's blog post, SSL And The Future Of Authenticity. for more details about these problems.

Consider the case of the recent SuperFish and PrivDog vulnerabilities. Those applications install a new trusted root CA certificate. Note the specific use of the term "trusted" here. We're not talking about anything along the lines of the web of trust used by the PGP and GPG applications, where the user explicitly indicates a level of trust with individual keys. A "trusted root CA certificate" is simply one that can be used by client software without generating warnings. It has nothing to do with the "trust" that is the confidence a user has in something.

Luckily for the end user, both SuperFish and PrivDog install trusted root CA certificates that have clear indications that they are from SuperFish and Privdog, respectively. However, there is absolutely nothing preventing an application from installing a certificate with a more deceptive name, such as "VeriSign."

Now, consider the case where a user with PrivDog or Superfish installed is visiting a site over HTTPS because he/she is providing sensitive information, such as a username and password. If his/her browser does not complain about the certificate, at best that means that whatever system he/she is talking to was issued by one of the trusted root CAs, including SuperFish or Privdog.

If somebody wants to verify that a certificate is issued by a "real" certificate authority, for example by checking the issuer's thumbprint, the steps required to do so can vary from browser to browser. Some browsers, such as Microsoft Internet Explorer, don't even allow viewing a certificate until after you have accepted it, which can make it tricky for even a security professional to determine if he/she is connected to the machine that he/she thinks.

Host-level software like Superfish or Privdog is just the beginning, though. As it turns out, there are plenty of network-level applications, devices, and appliances that do SSL inspection. Secure web gateways, firewalls, data loss prevention (DLP) products, and other applications all seem to have jumped on the SSL inspection bandwagon. Sure, there may be reasons why a network administrator may want to look into traffic that should be protected by SSL or TLS, but what people may not realize are the security impacts of deploying software that does not do SSL inspection at least as well as the browsers do. Consider the following diagram:

In the above scenario, the client can verify only that it is communicating with the SSL-inspecting software. The client is unaware of what technique the SSL-inspecting software is using for

validating SSL certificates. And perhaps more importantly, whether there are additional points between the SSL-inspecting software and the target system is impossible for the client to determine. Is there an attacker between the SSL-inspecting software and the target server? The client has no way of knowing. Because of this lack of transparency, the client must assume that the SSL inspecting software is doing everything perfectly. Unfortunately, SSL-inspecting software does not do everything perfectly.

In our analysis of software that performs SSL inspection, we have observed SSL inspection software make a variety of mistakes:

1) Incomplete validation of upstream certificate validity

Some SSL-inspecting software fails to validate the certificates of systems that it connects to. In some cases, the software may attempt to perform some validation of the certificate, but the validation may be insufficient.

Risks. Clients cannot know if they are connected to a legitimate site or not.

2) Not conveying validation of upstream certificate to the client

In some cases, the SSL inspection software does perform validation of upstream certificates, but it does not relay the results of the validation to the client.

Risks. Clients cannot know if they are connected to a legitimate site or not.

3) Overloading of certificate Canonical Name (CN) field

Some SSL inspecting software attempts to relay the validity of the upstream certificate to the client by way of the CN field of the certificate. For example, Komodia SSL Digestor changes the CN to begin with "verify_fail" if the server-provided certificate is invalid for any reason. There are a number of issues with this technique. The most obvious mistake being that the actual error conveyed to the user usually has nothing to do with why it failed.

Risks. Users of client systems may not know why certificate validation failed, or even if it failed. An attacker may be able to specify a Subject Alternative Name field to specify any domain that the certificate specifies it is valid for, which results in a browser that does not display a certificate warning.

4) Use of the application layer to convey certificate validity

To relay the validity of the certificate to the client, some SSL inspectors provide web content (e.g. HTML) to the client, describing what is wrong with the certificate. The normal mechanisms through which client software ascertains and displays certificate validity may still indicate that the certificate is fine.

Risks. Not everything that accesses data using HTTPS is a human using a web browser. For example, the client may be an application that communicates with a server using JSON data. This flaw also causes inconsistent use of SSL validity indicators (e.g. "Where do I look for the padlock again?").

5) Use of a User-Agent HTTP header to determine when to validate a certificate

Some software will selectively decide when to validate upstream certificates based on the User-Agent HTTP header provided by the client. This technique is likely used in conjunction with the technique described above where certificate validity is conveyed in the application layer.

Risks: Not every web client may receive certificate validation. Various web browser versions and non-browser software may be exempt from validation.

6) Communication before warning

Upon detecting a certificate error, some SSL inspection applications will send the client's request to the server prior to presenting a warning to the user.

Risks. An attacker still may be able to view or modify sensitive data.

7) Same root CA certificate

Some SSL inspection applications use and install the same trusted root CA certificate for each installation of the application.

Risks. An attacker may be able to extract the private key from the software and sign all visited sites with the universally-trusted root CA certificate.

Consider the case where an SSL inspection application performs flawlessly. That is, it has none of the above seven flaws, or flaws similar to them. It validates the identity of the upstream server based on its own trusted root CA certificate store. However, the client has no visibility into what root CAs the SSL inspection software trusts, in particular if it's a separate device on the network. The use of SSL inspection software reduces or completely prevents clients from successfully validating the identity of the servers that they are communicating with.

Given the architecture of SSL and TLS, users have a difficult enough time making a security decision based on the information provided to them. Once the concept of SSL inspection is thrown into the mix, it only makes the decision more difficult.

Potentially Affected Software

By performing a web search for "ssl inspection ," we were able to construct a list of applications that may be affected by a number of the above-outlined vulnerabilities. However, due to time and resource constraints, we have not been able to acquire or test a number of these applications, so we are soliciting feedback from the community to ascertain their status. Just because a product is listed, does not necessarily mean that it contains any of the seven vulnerabilities above. The list of applications possibly affected includes the following:

Category: Insurance

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