Skip to main content

Flaw in email security means signed mails cannot be encrypted

I was at a company the other day that uses a well-known email encryption solution as they have some very sensitive information that they need to send both internally and externally. As is common for these solutions, it is possible to automatically sign the email by putting a keyword in the subject line, such as 'signemail'. Similarly, the mail will be encrypted automatically if the confidential flag is set or a keyword, such as 'encryptemail' is added to the subject.

So far, so good. There are no messy button presses or extra steps for the user. However, there is a flaw with the solution. (I should point out that at this moment it is unclear if it is a product problem or a configuration problem, hence my not mentioning the product.)

The issue is that signing the message appears to take precedence over encryption. So, if you add both keywords to the subject then the message will only be signed and not encrypted. Now the encryption solution does also sign the message, so if you want it encrypted then you don't need to specifically sign it as well.

So is this really a problem or am I just making a fuss? Well, I can envisage several situations when it would be a problem. The most likely is probably replying to a signed message with confidential data. Let's say that Alice puts in a request for sensitive information from Bob via a signed email - only certain people can have access to the information so it is reasonable to expect Alice to digitally sign the request, but the request is not sensitive in itself.

Now, if Bob replies to that request with the sensitive information attached he will follow policy and mark it as confidential and add the encryption keyword, 'encryptemail', to the subject line. He will now assume that the information will automatically be encrypted. However, if he doesn't remove Alice's 'signemail' keyword it will just be signed and not encrypted. This then violates the policy and sends confidential information in plaintext while the user believes that it has been encrypted.

It also highlights that you shouldn't use a keyword that might be used as part of everyday language. For example, don't use the keyword 'sign' as someone could send a sensitive document with a subject something like 'Contract for you to sign'.

I suggest that everyone using this type of solution should test it to see if this happens on their system. If it does, you will, at the least, need to publish an advisory warning to your users.
Labels:

Comments

  1. public key infrastructure21 November 2011 at 02:18

    I really enjoyed the article. It proved to be Very helpful to me and I am sure to all the commentters here!Keep writing.Thanks.

    pki certificate.

    ReplyDelete

Post a Comment

Popular Posts

Coventry Building Society Grid Card

Coventry Building Society have recently introduced the Grid Card as a simple form of 2-factor authentication. It replaces memorable words in the login process. Now the idea is that you require something you know (i.e. your password) and something you have (i.e. the Grid Card) to log in - 2 things = 2 factors. For more about authentication see this post . How does it work? Very simply is the answer. During the log in process, you will be asked to enter the digits at 3 co-ordinates. For example: c3, d2 and j5 would mean that you enter 5, 6 and 3 (this is the example Coventry give). Is this better than a secret word? Yes, is the short answer. How many people will choose a memorable word that someone close to them could guess? Remember, that this isn't a password as such, it is expected to be a word and a word that means something to the user. The problem is that users cannot remember lots of passwords, so remembering two would be difficult. Also, having two passwords isn't real
Post a Comment
Read more

How Reliable is RAID?

We all know that when we want a highly available and reliable server we install a RAID solution, but how reliable actually is that? Well, obviously, you can work it out quite simply as we will see below, but before you do, you have to know what sort of RAID are you talking about, as some can be less reliable than a single disk. The most common types are RAID 0, 1 and 5. We will look at the reliability of each using real disks for the calculations, but before we do, let's recap on what the most common RAID types are. Common Types of RAID RAID 0 is the Stripe set, which consists of 2 or more disks with data written in equal sized blocks to each of the disks. This is a fast way of reading and writing data to disk, but it gives you no redundancy at all. In fact, RAID 0 is actually less reliable than a single disk, as all the disks are in series from a reliability point of view. If you lose one disk in the array, you've lost the whole thing. RAID 0 is used purely to speed up dis
Post a Comment
Read more

Telephone Systems a Hackable Backdoor?

I have been talking to a company that provides telephone exchanges and services to companies this week on behalf of a client and it has highlighted a worrying backdoor. It turns out that many of these companies have a way to remotely connect to their exchange for support purposes - they can remotely control, configure and troubleshoot your system to get you back up and running. Exchanges often have additional modems in them to allow for remote connections. This is all very well and good from a managed service point of view, but what about the rest of your network? Can this be exploited to gain entry to your network? Quite possibly in some cases - it certainly needs to be included in your security audit and perimeter testing. Talking about a specific company now, they supply the software to monitor and bill phone calls through the exchange. They remotely install, monitor and manage this software. How do they do that? Well, it turns out that they install LogMeIn on your machine. Now t
1 comment
Read more