Hands-On With the New Outlook.com

Posted on October 1, 2016 by Paul Thurrott in Outlook.com with 34 Comments

Hands-On With the New Outlook.com

As you may have heard, Microsoft is finally nearing the completion of its migration to the new Outlook.com, which brings the look and feel and some of the functionality of the commercial Office 365 offerings to consumers. Here’s a quick look at some of the key changes.

We begin, naturally enough, with the overall look and feel of the Outlook.com web experience. Depending on your experience with this service, the changes may seem a bit subtle, but those who are familiar with Office 365 will immediately recognize the new user interface as being nearly identical to Outlook on the web in Office 365.

Here’s the old Outlook.com.


And the new.


And here’s Office 365’s Outlook on the web for comparison. As you can see, the new Outlook.com more closely resembles this service than the old Outlook.com.


(The Outlook.com Calendar has likewise changed to a look and feel that more closely resembles Office 365’s calendar. You get the idea.)

The changes to Outlook.com of course go deeper than just how it looks on the web. Here are some of the functional changes that will impact your day-to-day use.

Clutter. The new Outlook.com picks up the Clutter feature from Office 365, which helps separate out low-priority email so it’s not bogging down your inbox. (This works somewhat like the Focused Inbox feature in Outlook for Android and iPhone, if you’re familiar with that app.) It’s something that improves over time, because it learns from your email habits, and you can help speed the process my manually moving emails in and out of the Clutter folder. And yes, you can turn this off if you’re not interested.


Pop-out email windows. You can now pop-out individual email messages—both new messages that you write and those you have received—into their own windows, so you can refer to other emails as you write. This is fairly sophisticated, and helps Outlook.com behave more like a client-side email application.


Add-ins. Outlook.com now supports the same add-ins that developers create for Office 365 and Outlook 2016 for Windows and Mac. Several are enabled by default, including Bing Maps, Evernote, PayPal for Outlook, Uber Ride Reminder, and others. For example, the PayPal for Outlook add-in lets you send money directly from Outlook.com without leaving the inbox.


Simple OneDrive sharing. Now, you have the option to move attached files from an email message to your OneDrive, allowing you to more easily share lots of files, or files that may exceed the limits of email.


View and edit Office attachments without leaving Outlook.com. When you receive a Word, Excel, or PowerPoint document via email, you can view and edit it right in the browser window—using Office Online—without leaving Outlook.com. And if you do edit the document, you can send it back to the person who emailed it to you without first saving it locally and re-attaching it. Nice!


Calendar search. Hold on to your hats, since even the Calendar app in Windows 10 can’t do this: You can search your calendar for events and for people associated with events!

New mobile experience. While most Outlook.com users are probably better off using Outlook for Android or iPhone, or Outlook Mail, Calendar, and People for Windows 10 Mobile, Microsoft has also refreshed the Outlook.com mobile web client for those who prefer that approach. It supports swipe gestures and, amazingly, add-ins.

There’s a whole lot more going on, of course, but these are the things that really stick out as nice improvements over the previous version of the service. For a more complete list of the changes, be sure to check out Microsoft Announces Major Changes Coming to Outlook.com.


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Comments (34)

34 responses to “Hands-On With the New Outlook.com”

  1. 442

    I still hate that Outlook no longer syncs properly with external accounts.  This is very frustrating.  I pull 2 external accounts into Outlook.  They no longer delete pulled or read messages from Outlook.com.  This requires I visit those old accounts occasionally to delete old messages.  This is tedious and frustrating.  Support has been zero help on this.

    • 430

      Why not redirect/forward from the other accounts vs pulling via POP3? 

    • 2

      So I have not tried that, but did you try removing them and re-configuring that?


  2. 3183

    Paul, now that you have the new Outlook.com can you confirm that you can add the account to a Mac (Mail, Calendar, Contacts and Outlook for Mac) as a full EAS account? On the old Outlook.com you could only add Mail as IMAP and no Contacts/Calendar support.

    • 2

      First of all, thanks for making me use a Mac. :)

      So ... No. I couldn't figure out how to connect it with the Exchange account type. On the first go, it failed with "unable to verify account name or password" and added a new User Name field. I tried an app password, I tried using the first part of my email address (before the @) and the fully-qualified name in the User Name Field, nothing worked. 

      My rough understanding here is that the issue is Mail/macOS, not Microsoft/Outlook.com. I've been able to add this account as an Exchange account type on Windows Phone for years. 

      That said, since I was going down this rabbit hole already, I tried to add this account to iOS Mail the same way. It looks similar but works a bit differently, and after parsing the account name/password, it presented that old-school EAS interface with Server, Domain, Username and Password fields. I tried this with m.outlook.com as the server name, and it failed. So I tried that with an app password ... and it worked. And I had options to enable Mail, Contacts, Calendars, Reminders, and Notes.

      Long story short, I think the issue is the Mail app in macOS, not the account.

  3. 585

    From what I understand over the next couple of months the "Clutter" feature will be going away and replaced with Focused Inbox.  I for one will welcome this change as I have loved the Focused Inbox on the iOS devices and it will be a welcome addiiton to the personal web version. 

  4. 256

    What ever happened to the Outlook Premium pilot? I have been waiting to move my own domain to Outlook (after they killed their previous program).

  5. 5519

    I also just got switched over the new outlook.com last week. 

    I noticed that a bunch of my rules for managing my mail didn't come over.  Kind of an inconvenience, but will mudlle through...

    • 5604

      In reply to Pbike908:

      Initially I also found that the rules interface was broken, making it all but impossible to successfully select from the suggestion drop-downs for senders etc..

  6. 545

    I wonder how many more accounts there are to migrate?  My wife got a note about shared calendars, so her's must be underways, while my main account still has the old interface.  I do have over 700GB of data in the OneDrive account, so I'm still in the "large accounts to get migrated later queue".  I must have gotten my secondary account migrated several months ago which has no data stored on it, just used for email.

    I would still like to see them support merging accounts, as I don't want to keep these two going on forever...nor do I want to lose my secondary email address.

  7. 5615

    In reply to Delmont:

    It's not discussed, probably because it's not new or related to the Outlook.com switchover.

  8. 5794

    Since the "upgrade" all Connected accounts (POP3) that have with personal Go Daddy custom domains, email are broken.  Stuck at "Update in Progress". Initially only offers IMAP option but these are POP only.  After days of waiting, they show POP as an option for servers.  But still dead.

    This is amazingly poor and no explanation anywhere for that.  Other than Go Daddy and MS have a too-cozy and too-obscure business relationsip.

    Moved one account to GMail and presto worked insta-magically.

    But not a solution as I use both the web outlook.com and on laptop the whatever-they-call-it-now-next Mail/Metro/blah app.

    This is very bad.  Anyone?  The Windows "help" forums are worse than bad.

    What do you know with your vast, deep contacts?

  9. 1092

    I still don't have the new outlook.com :-(

  10. 2864

    I receive emails telling me that the transition is coming. Maybe someday they will stop sending reminders and just update my account. I've waited this long so what's another few months I guess.

  11. 887

    Just a test post for Tim.

  12. 543

    I think you've buried the lead - endless scolling inbox is surely one of the main reasons one would want the update?  Certainly is for me (I still don't have the newest version).

  13. 5135

    I've yet to find that Outlook.com can deal with junk mail properly, as it requires I fish for routine email to find it in the junk, regardless of how filters or senders lists are set. As long as this is the case, any update is a matter of polishing a stinking heap, imo.

  14. 5635

    Very displeased with the new outlook.com. I've been using it via the Edge browser and it is SUPER LAGGY, like using a 1200 baud modem. If this is the responsiveness I can expect then I want to return to the old outlook.com. In fact, is there a way to roll back?

  15. 5560

    This is my new super outlook.com for at least two weeks now!

    login from ouylook.com

    • 3861

      Philip this is a "long-shot" & probably won't fix your problem, but it is worth a try. Before going to your Outlook Mail page in the web (or any other Microsoft page like Live/Microsoft Account sign-in) using your browser, first delete your browser cache. Perhaps something in your browser cache is fouling things up. Worth a try. :)

      • 5560

        In reply to Greycoat:

        Cheers Greycoat,

        I have tried everything, Edge, Firefox and chrome on my surface pro 4 and Dev machine, even win phone gives me the same response i have  even tried my wifes ipad. I have cleared the cache and tried private browsing.

        After entering my two factor code and pressing the sumit button, it appears to redirect me a few times as the url changes and the page flickers as it redraws untill i get to the error page.

        I even got i touch with Microsoft support and let them rummage around in my SP4, with no luck. I just think outlook.com dosn't like me any more.

  16. 4251

    You know you can pay them for the ad free version right?

  17. 996

    I can't find the clutter feature? Where do I enable this as it sounds fantastic.

    • 2

      When you first switch over to the new service, Clutter works in the background (supposedly) to get things going. But you can display the Clutter folder manually and just get started. To do so, go to Options and you'll see Clutter under Mail, Automatic processing. Just make sure both of the Clutter options are checked, and you will see a Clutter folder appear when you go back to the Inbox view.

  18. 5496

    Paul, test out the PayPal plugin be send $1,000. And ill let you know if it works.

    For the last 2 week, I've been getting about 20 spams a day from @(whatever).stream.com, may 1 or 2 makes it into my inbox, the rest goes into the junk folder. But even if I go and block everything in the junk folder, I still receive spams form the same address.

    I'm always getting crap from alcohol rehab(that should go to Paul), and shadow hawk(something about a flashlight). I block them, but I still get emails from them.

  19. 3494

    The new outlook.com appeared for me on Thursday. So far I like it.

  20. 2149

    Don't have the new Outlook Mail yet, but I do use it through Office 365 for Business. It's much better than Gmail's web interface in my opinion.

  21. 5662

    I am most happy about the snappier UI.  The previous one (with the old infrastructure) felt like it was connected to the data center via cups and string.  The integrations are a nice addition.  Watching the announcement of various new features was frustrating while waiting for the new experience.

  22. 4853

    I can't believe shared calendars are still broken after all this time. And the Windows "app" is even worse with zero support for ics subscriptions. Microsoft's qc is a disaster across the board lately. What's going on with them?

  23. 248

    I like the new Outlook Mail and having a single web mail platform makes so much more sense. After seeing how they plan to unite the UX across all the different experiences it gives me hope that Microsoft will be investing in this experience more and more.

  24. 906

    Alas, late to the party again. I activated Outlook.com the FIRST DAY it was available to the public. I'm still on the older version. I'd think that maybe they were rolling it out in reverse order of initial activation, but I note that Paul got his update before me -- and he had to have activated the day after they started coding the damn thing. 

    Anyway -- and, Oh Yeah, I do have a paid Office 365 account.