Battling Graymail With Hotmail (And My Quest To Tame My Inbox)

Disclaimer: This is a sponsored post that I was approached to write by Microsoft and Technorati Media, and I am receiving compensation for authoring it.

While Hotmail generally has a pretty bad reputation amongst the tech-savvy crowd, I’ve happily used a Hotmail account over the past three years without issue (on top of several Gmail accounts and my iCloud account.) And, throughout my time with email, I’ve never been one to bother with any organization whatsoever. I never took advantage of the labels, features, and stars that tickles the fancy of Gmail users, nor did I use some of the new features and improvements that have been added to Hotmail over the last year of two, some of which I’ve blogged about in the past.

As part of penning this sponsored post, I had to immerse myself in learning about these features in Hotmail, particularly those which help people control what they refer to as graymail. Basically, graymail occupies that “gray” area that lies between spam and legitimate emails; it’s stuff like newsletters, daily deals, social updates, notifications, and other things that you’ve signed up for, but lost control of over the past few years. As part of Hotmail’s campaign against graymail, they estimate that the average inbox in 2012 will receive around 14,600 emails, and, thanks to graymail, this figure will rise to 15,330 by 2015.

My own email inbox can also attest to this; with around 6,500 unread emails at the time of writing, and likely far more read emails, I’ve noticed that the bulk of it is what would be considered graymail. While spam rarely makes its way into my inbox, I’ve been the cause of its demise with the barrage of emails from Groupon, Gilt Group,, Twitter, Amazon, Barnes and Noble, ZDNet, and other miscellaneous newsletters that I don’t remember signing up for. With that in mind, I’m going to walk you through the numerous features that Hotmail put in place to solve this problem while I regain control of my own Hotmail inbox in the process.

Before I begin, here’s a list of the features that I will be using for this mission:

  • Sweep: Allows you to delete or move all the emails you’ve received from a specific sender – past, present and future.
  • Categories: Hotmail automatically categorizes newsletters, social updates and photos to within 95% accuracy. You can also create your own custom categories to tag your mail with.
  • Alias: Allows you to create full, disposable email addresses to use for signing up to sites and notifications. Email sent to these addresses will arrive in your inbox, but senders will never know your actual email address.
  • Schedule Cleanup: Just like Sweep, but with the added factor of automatically running rules like based on time intervals. So you can keep only the latest mail from a sender, or have Hotmail delete or move files that are older than 3, 10, 30, or 60 days.

First, I began automating content that I may like to scan over (such as certain daily deals).

Next, I went about trimming my entire inbox using the Sweep > Delete All function. Pretty much every newsletter subscription I ever had was exiled, and configured to never set foot in my inbox again. Interestingly enough, the automatic “newsletter” Hotmail category only discovered and appropriately categorized some of the newsletters I had, so I had to randomly go looking about for them. It wasn’t that big of a deal, but it would be nice if it could have gathered a more significant portion so I could axe them all more easily.

I took a break from exiling newsletters to get a grip on my social updates. As I did with the content I wanted, I automated what happens to them through Schedule Cleanup.

There isn’t much to write about here because the process was quite quick. Above is a photo of the end result of 20 minutes of work; I think there are a few stray emails that may have survived the pruning, so I’ll go ahead and seek them out now. But I’m quite happy! As you can tell by the trash can, quite a lot of emails were deleted. Now, one annoyance is when newsletter providers use different email addresses and alternate between them, but there isn’t really much Hotmail can do about that.

I’m just glad that I won’t be receiving even more emails from the addresses that I did manage to exile today. Also happy that the content which is either important to somewhat important will be purged when it is no longer relevant.

If you want to take back your Hotmail inbox, you can as well (and easily, too.) Click here to learn about smart tools from Hotmail to manage your inbox automatically and conquer graymail.

Published by

Paul Paliath

Paul Paliath is a designer. You should follow me on Twitter here.

  • I liked this, and I had not even known about this. I like the Sweep option the best.

  • I personally use hotmail for my site since google apps only allows 10 free email. I like it. Gmail is better but for normal emailing stuff, it offers same productivity.

  • Dave

    I like Hotmail (much more than Gmail), but one thing has always concerned me: its apparent lack of concern for better preventative account security. E.g. just about all other email accounts I have (Hushmail, myopera, to name two, as well as Gmail) allow for looooong passwords: 35+ characters. Hotmail inexplicably limits password length to 16 characters, which some security-minded people think is the *least* amount an email account password should be!!

    Also, Gmail’s two-step authentication (not as password recovery only but also for login security), if implemented by Hotmail, would make the latter’s accounts much more hack-proof, no?

    IOW, Gmail seems to provide more in the way of *preventative* security for its account holders, as opposed to Hotmail, which is more strictly about after-the-fact measures — measures which themselves aren’t always successful and can lead to *many* frustrated users who are locked out of accounts with little help from the Windows Help personnel. Perhaps if those users had better proactive security options from Hotmail. ???