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.