Skip to main content

Microsoft Clutter Misses the Target

By November 17, 2014October 21st, 2021Blog

Microsoft Clutter misses the target. It’s a new email filtering tool that Microsoft will begin including in the Outlook Web App (OWA), OWA for devices, the standalone Office 365 Outlook App, and Exchange-connected devices. Harsh as this may sound there are good reasons to quickly judge this solution. There are two fundamental reasons to take issue with the claims proposed by Microsoft that Clutter will unjunk your inbox.

Most of your email is unwanted.

First, Clutter comes from a perspective that most of your email is wanted mail. (Accept this statement for now. I’ll come back to it.) Therefore Clutter will only have to remove the egregious mail from your inbox.

But let’s consider the basics of how Clutter will identify unwanted mail.  If your habits are to never open emails…

  • From certain senders,
  • That have specific words in the subject line,
  • That have attachments,
  • Or are CC’s

then an email with similar attributes is something Clutter may potentially purge.

On the surface this sounds ok.  After all, spam filters have been doing this exact same thing for years. In the case of spam filters they don’t use your habits, but instead use input from security analysts.

Here’s the problem: You’re not a security analyst. You open email when the mood strikes you. Sometimes you open the advert for a discounted weekend trip.  You may open the daily inventory report every 3rd day. You always open your boss’ email regardless of whether you or not you are just CCed.

The point is that your habits change based on your mood so it’s hard for a computer algorithm to get a firm understanding of what’s important to you. Since there are only two choices for Clutter— either keep or remove an email— most of your email will be kept in your inbox. This is because the evidence to remove will only be strong enough in a few consistent cases, leaving Clutter to assume that you want most of your email.  (Actually fully 85% of the email in your inbox does not require your immediate attention (reference: Sendio verification chart 2014))

Now this is just a simplified explanation. The wonderful thing about artificial intelligence (AI) engines is that they can compute a lot of different variables.  My few examples are trivial. However, AI is not smart.  When data conflicts, the AI needs a whole lot more data to figure out what to do with the emails. That means it needs to review a lot of your email decisions to arrive at a relevant yes or no decision. Do you open emails containing vacation discounts only during the week prior a holiday weekend? It will take several holiday weekends to determine this. Did you not open a vacation discount email prior to a holiday weekend, BUT you also had twice as many meetings on your calendar that week and had no TIME to open? This is the rabbit hole most AI engines go down when there are only two choices it can make.

The engine will make mistakes

The second fundamental problem: The engine will make mistakes. It is absolutely guaranteed to make mistakes because it is required to do so in order to learn. When Microsoft says in their YouTube video that all you have to do is pull the junked email out of the folder and drag it to the inbox, it means you need to do so in order to teach Clutter what is relevant. Now here’s what 12 years in the email security industry has taught me: When a good email is mistaken for a junk email, it is almost always a very important email. If a mistake is made, it’s not the email from a friend inviting you to lunch; that would be too easy.  Instead it’s something like an email from your best customer telling you that he’s leaving for his holiday vacation in an hour and, while it is short notice, if he doesn’t have the contract before he leaves it will have to wait until next fiscal year.

As a result you are on the hook to review frequently the mail that most likely you didn’t want in the first place. It’s always an issue with a filter looking at the content instead of the sender. Indeed it doesn’t matter too much if the parameters were set by your habits or by the security analyst. The ability to determine the validity of an email sent by those who are paid to make sure that email gets to your inbox is a losing proposition.

The funny thing is that there is an easy way to achieve the desired results.  Just ask the sender….