In the interests of showing the world that I am not perfect, I just had to Blog about this incident.
I sent an email with an attachment out to the wrong person. Its the classic case autocomplete messing up - typing some letters and recognising the person's first name. Click send and then realise your mistake when the wrong Jason (it wasn't Jason in this case...) sends back an email asking "huh?!"
Its one type of "oops" that DLP is supposed to prevent.
The interesting part of it all was that the email went out (of all the people in the world) to the sales rep I've been dealing with who has been trying to sell me DLP...
I guess this just makes it more difficult to say "no".