I’ve been having a problem lately. It’s not an enormous issue, but it bothers me. As you have likely already gleaned, I am receiving junk mail in my Outlook.com account which is already flagged, like so:


An example of a pre-flagged spam message.

I don’t think most people have noticed it for a couple reasons:

  • I don’t think a lot of users flag their emails unless they are using the desktop version.
  • Flagging is a visual cue that has only recently started to become a component of organization tools, i.e., Microsoft To Do.

Outlook.com, however, is an interesting beast; at once the best damned email client on the planet while being rather terrible at handling spam… sorta. I’ll get to the best part in a sec, but Google’s Gmail is far better at filtering spam.

The online version of Outlook was originally designed to not only replace HoTMaiL (if you’ve never noticed, the capitalization is deliberate), but to compete with the growing number of players in the nascent Webmail arena. Microsoft had fumbled in the early days of the internet had to catch up to the growth of services like Google’s Gmail, Yahoo!’s RocketMail, and offerings from AOL (“You’ve Got Mail!”) and Compuserve.

In 2012, Microsoft replaced Microsoft Live Hotmail with Outlook.com, and offered the Beta version to the general public to try. I joined that beta, and added an Outlook.com address to my seldom-used Hotmail account. I was immediately impressed with the new interface, and have mostly enjoyed using it over Gmail for years now. The current version of Outlook.com is extremely complete, and I can understand why casual users might find it confusing. If, however, you are experienced with using the Outlook desktop application, you won’t have too steep a learning curve.

But it’s generally never about the features that work when I post. In this case, it’s about spam getting flagged automatically. This is a real problem now, and I’ll explain why, but let’s first take a look at what another Windows user posted to Microsoft’s community support forums:

This is one of the only posts I could find about this issue and the answers were… unhelpful?

As you likely noted in the image at the top of this post, I’ve been having the same problem. Some emails will come set to Urgent and Flagged. Flagging a message in any version of Outlook is a visual indicator that you, as the user, add to show importance or act as a reminder. As I mentioned before, the Flag has traditionally been a user-only function.

That changed after Microsoft acquired Wunderlist from German developer 6Wunderkinder GmbH.

That’s not to suggest that Redmond’s acquisition had a lot to do with the issues I and other(s?) face, but it’s how I discovered the issue in the first place. I used Wunderlist as an all around replacement for Evernote and a checklist app. It was very good at that, but MS decided they needed an app like that, so they bought the company and finally phased out Wunderlist on May 6th of this year. Now we have To Do, a fine app that leans even more into the task management space.

Unfortunately, one of its neat little productivity features is that it has an auto-generated listicle with all of your Flagged messages. This would really be great if it worked as intended, showing the items you flagged so you can be reminded to handle them. Instead, upon initial inspection I was treated to a cavalcade of Coronavirus cures, manhood pills, offers of millions of dollars from some dead prince in Idaho or Saskatchewan or Kazakhstan.

So, that’s about it. There’s no real solution that I’ve sussed out just yet, nor have I seen very many questions posted about it. Like I said, I don’t think a lot of people are going to experience what I believe is an edge case. This just doesn’t yet happen to many users.

We’ll see where things go from here.

PS: This is a repost from my blog, which I’ve been having issues with. I’m now in the process of making a decision about where my bloggings will reside. My options are to restore WordPress on my most atrocious host, go back to PostHaven (which I adore but has posting and formatting limitations), or devote my efforts to Medium (which has an in-built audience.) I have yet to choose.

PPS: Part of the problem, and it’s a large part, is the depression I’ve been “managing” over the years. The pandemic hasn’t helped, as you can well imagine, and the current political climate on Earth is… er, suboptimal, to say the least. Shit like this makes the future unclear for the billions of regular peeps around the world who just want to live a life. And the leadership necessary to guide us out of this dark place we’ve allowed ourselves to get lost in seems to be down at the pub doing lines of coke and kicking hobos for fun, so few peeps have hope for a brighter, less self-destructive future.

PPPS: You don’t have to love everyone, just don’t go around killing them. They randomly appeared on Earth just like everyone else. We don’t get to choose who we are or where or to whom we are born, whether it is the chaotic, unintelligent course of events of a vast unknown cosmos or the will of some god(s). Is it not, then, logical to presume, until evidence to the contrary of course, that none of us are inherently superior to anyone else? Life, for now, is just the luck of the draw, and maybe 3% of peeps win the lottery. The name of the game has always been extraction…

PPPPS: Listen to Dylan, then extrapolate from then until now and what’s happening. Its ugly and we’re in deep, deep trouble if we don’t do something fast. What those fixes are, I have no idea.