Google is known for releasing lots of helpful tools that, well, help make our lives easier on a day to day basis. The Gmail team has come up with a few ideas in the past that are more often hit than miss. We get the feeling Mail Goggles will be one of the rarer ideas that’s falls just short of the mark.

Mail Goggles is geared towards the kind of people who are likely to send a late night email to someone they shouldn’t; an ex-girlfriend, a current girlfriend, a co-worker. Yes, unfortunately there are all too many familiar with the accidental send of a drunk-draft. The Gmail team aims to help put a stop to that morning-after-the-night-before feeling by asking to break out your middle school math skills to make sure you’re really dedicated to sending that email.

So, how does it work? You’re out partying on a Saturday night (or in getting pie-eyed, alone), and you decide there’s no better time than 3 a.m. to email your best friend’s sister. You hit send and you’re stonewalled by a series of questions (difficulty determined by you, which is probably determined by how good you are at 3rd grade math when inebriated) and only 60 seconds to answer. Mail Goggles is, by default, only activated during times when you’re more likely to send an email you might regret, i.e. late night on the weekends.

We adjusted these settings to try out Mail Goggles. Gmail now thinks I shouldn’t send mail between 3 p.m. and 5 p.m. on a Tuesday and gives me five simple math questions (the addition and subtraction of double-digit whole numbers). We had one problem (aside from the fact that Google was second guessing our judgment): Goggles only asks questions for the first email. Any subsequent emails are sent as normal, so no continuous assessment. This is something that’s likely to catch out those leaving late for the office Christmas party. Send off the spreadsheets a little later than usual and you’ll likely have a red face Monday morning. It also seems to send fine from Google Mobile.

Mail Goggles was developed by Gmail engineer, Jon Perlow and is, of course, optional. To activate Goggles hit the “Labs” tab in your Gmail settings.