h2g2 The Hitchhiker's Guide to the Galaxy: Earth Edition

A few of you may be familiar with the Guardian newspaper column "You Are The Ref". It describes in cartoon form an on-field situation in a football match which poses a dilemma for the referee, then asks what the correct decision should be. Here's a link: http://www.theguardian.com/football/2014/jan/16/you-are-the-ref-paul-trevillion

Anyway, when you've had some fun with that, I want to start a new column called "You Are The Tech". I describe a tricky problem reported to the IT service desk, and you have to work out what caused it and how to fix it.

You can ask me some yes-or-no questions about it if you like, and I'll do my best to answer them. The winner is the first person to post the correct cause and fix.

So, here goes for the first episode:

You Are The Tech

A user rings the help desk and says that when she sends an encrypted e-mail, it arrives at the other end unencrypted.

What has happened?

Using which email system?

Yes

*sulks*

Is she emailing from a crypt to the outside, then?

No, she isn't.

Ti, it's a well-known cloud-based e-mail service she's using (which shall remain nameless)

Tools/Settings?

Not knowing which email system she's using is a bit frustrating...

OK, silly question - why would the receiver prefer to receive the encrypted e-mail encrypted rather than be able to read it straight away?

1. Is the problem between the chair and the keyboard?

2. Or is it an actual IT problem?

Or maybe the problem is Icy himself? *stares at him in an unnerving way*

She's sending commercially sensitive information.

She's doing everything correctly.

Just to ask stupidly obvious question. The recipient hasn't the other side of the encryption software? That would open the email automatically?

To be honest, I haven't a clue.

Isn't an encrypted email supposed to be encrypted only between the 2 computers, or something?
Otherwise, what good would it be to receive an email you can't read?

Presumably the person at the other end is *supposed* to be able to read it: it's encrypted to protect the information in transit. (Reminder: e-mail is not secure.) So I'm going with Lanzababy's guess: the message is being decrypted automatically at the far end, and this process is transparent to the end-user.

I'm going to add to Lanzababy's guess. Here's my guess:

Perhaps it used to be difficult to decrypt e-mails, and then the software was updated to improve usability, but actually ended up unnerving people, because they were used to a complicated workflow for encrypted messages, and when that workflow disappeared, they were worried that the messages weren't encrypted.

TRiG.

I wish that, when I was doing IT support, ~I~ was allowed to only say yes or no.

Is the caller using a mobile phone to send the encrypted message?

The user, isn't encrypting it, they just think they are... user non-technical, error code 1...

My guess is that the encrypted email has been decrypted on arrival at the recipient's machine. Which is precisely what is supposed to happen.

So, there isn't actually any problem at all. Everything is working as it should.

It's just that the sender doesn't quite understand how the process works.


Geggs

Sadly I don't have more technical details (sorry, this exercise was a little ill-thought out), other than it was sent with the expectation that it was encrypted but detected on arrival as being unencrypted.

If it helps, it took our experts a couple of days to ponder before they came up with a very simple and unforeseen reason for it.

So far then:

Icy says that the sender is doing everything right.
Icy says the email is leaving the sender encrypted.

The email arrives unencrypted.

So, the main point to focus on is where the email is being unencrypted.
Either it's being unencrypted in transit, which is unlikely.
Or it's being unencrypted at the receiver's machine.

My initial guess that the email is being unencrypted at the receiver's machine, and that their tech people set it up for the receiver without her realising.

You've made a small mistake in your analysis there, Pastey, and you may not discover it if you continue on the basis you mentioned.