Hi all, we are going to sign off now. 947 questions, impressive. Thank you for all your questions and feedback. We'll see you back here for sure at some point, maybe less than a year from now even. Follow @outlook on Twitter for updates.

Hi Reddit! We are the engineers and product managers behind Outlook.com. It's been just over a year since we launched Outlook.com in preview and since our last AMA. We'd love to hear from you (and figured it was about time).

We'll be here from 10 am to 11 am PDT. Ask us anything!

Update: Yo! My name is Dick Craddock, and I run the program management team for Outlook.com. Yes, I have a Reddit account, and, No, I won’t tell you what it is. Anyway, I’m here with some folks from the Outlook.com team. We launched Outlook.com about a year ago, and did an AMA shortly after launch. We’ve had an action-packed year since then, upgrading about a zillion people to Outlook.com, fixing a bunch of stuff you told us about, and doing a few new features. So, we’re back. Ask us anything.

Update 2: Thanks for all the awesome questions. We are going to keep answering for about another 10 min. Get them in while you can!

Comments: 2539 • Responses: 46  • Date: 

Lord-Tywin_Lannister1803 karma

Why should I adopt this 'email' when a raven can adequately carry a message to the other side of the Seven Kingdoms within a week?

OutlookOnReddit2102 karma

You don't have to worry about arrows with email.


OutlookOnReddit178 karma


CaptinKnightMayor1345 karma

Will my emails be read by the NSA if I use Outlook.com or more importantly will you let them? edit: spelling

OutlookOnReddit1631 karma

Hey, this is John from the Outlook.com team.

Outlook.com provides customer data only when we receive a legally binding order or subpoena to do so. We do not provide any government with direct access to emails or instant messages. Full stop. In addition, we only ever comply with orders for requests about specific accounts or identifiers, not on an aggregate basis. You can find more details on our blog entry from July 16

siiiiiip708 karma

How many requests have you gotten from law enforcements, and have you ever denied them from accessing clients' emails?

OutlookOnReddit2461 karma

John again - In 2012, Microsoft (including Skype) received a total of 75,378 law enforcement requests. Those requests covered a total of 137,424 accounts. ~18% of those requests resulted in no data being supplied. ~80% resulted in non-content (meta-data) information. ~2 % resulted in disclosure of actual customer content. You can get all the details, including actual numbers and our 2012 law enforcement requests report from this blog post

You could always ask Marissa Mayer

falconer729 karma

When will Outlook.com support IMAP? It stands out as the only major missing feature vs. Gmail, Yahoo! Mail, and iCloud Mail. http://www.microsoft.com/en-us/outlook-com/compare/

OutlookOnReddit1558 karma

Hey, this is Steve from the Outlook.com team.

It wouldn't be an AMA session without an IMAP question :) I’m excited to announce that starting right now we DO support IMAP, and we wanted you folks to be the first to know. Go check it out.


o Incoming IMAP mail server: imap-mail.outlook.com

o Incoming IMAP mail server port: 993

o Encryption: SSL


o Outgoing SMTP mail server: smtp-mail.outlook.com

o Outgoing SMTP mail server port: 587

o Encryption: TLS

We’re also supporting OAuth so that all sorts of 3rd party apps and services can easily and safely integrate with Outlook.com. We’ll have a blog post up soon with more details, including a description of some partners who are launching support today: TripIt, Sift, Slice, motley*bunch, Unroll.me, OtherInbox, and Context.IO.

And remember, you heard it here first!

UnrollmeTeam597 karma

Unroll.me is proud to announce full Outlook support! https://unroll.me/outlook

OutlookOnReddit400 karma

Thanks a ton for your partnership. Go team!

OutlookOnReddit350 karma

(this is Dick)

By the way, Steve worked on IMAP and he's here in the room with several other engineers that got this done. So, if you want to give mad props, they go to Steve, Ashu, Ben, John, Leela, Anu, Saad, Pooja, Chris, Levey, Mohammed, Michael, and a bunch of other folks. (edit: fixed typo in team member name. awkward)

Nebulaeus184 karma

Sweet hot diggity! thanks Outlook peeps!

OutlookOnReddit162 karma

Hey Nebulaeus! This is Saad from the Outlook.com Imap dev team. Glad you like it! Let us know if you run in to any issues!

Hoooooooar166 karma




OutlookOnReddit125 karma

They're definitely aware of the request.


falconer84 karma

That's awesome! What a way to announce it, too! I'm excited that my question got this long-awaited answer. Thank you, thank you, thank you.

OutlookOnReddit77 karma

Thanks for staying a cool user of our products. Well, your question gave us the opportunity to announce IMAP availability. We would like to send you some pizza :)

-Ashu from Outlook.com team

Nebulaeus37 karma

Does this include CardDAV or CalDAV perchance?

OutlookOnReddit71 karma

No CardDAV or CalDAV right now, but we're tracking demand for it and will decide if we want to add it just as we did with IMAP. - David

FrancoGag15 karma

It's not working on my android phone Am I missing something? Does it work on hotmail accounts?

EDIT: After some help from the Outlook team and changing the SMPT Encryption to: STARTTLS and Outgoing SMTP mail server to: smtp-mail.outlook.com, it was fixed and now it is working totally fine.

OutlookOnReddit16 karma

Which app, and what settings are you using? What errors are you seeing?

Edit: On the stock Android email app, when configuring SMTP settings, make sure to choose "STARTTLS" as the Security Type.

[deleted]5 karma


Nebulaeus6 karma

That would be a very cool way to announce this feature. Hope they remember CalDAV and CardDAV too though... :-)

OutlookOnReddit14 karma

With EAS (Exchange ActiveSync), you can sync mail, contacts and calendars across a wide variety of devices. We listen closely to our customers’ feedback, and, just as we have done with IMAP, we will continue to evaluate how best to ensure our customers have access to all their data wherever they are.

bravo_zulu362 karma

Why can my password only be 16 characters or less?

OutlookOnReddit347 karma

Please note our research has shown uniqueness is more important than length and (like all major account systems) we see criminals attempt to victimize our customers in various ways; however, while we agree that in general longer is better, we’ve found the vast majority of attacks are through phishing, malware infected machines and the reuse of passwords on third-party sites – none of which are helped by very long passwords.

Sixteen characters has been the limit for years now. We will always prioritize the protection needs of users’ accounts and we will continue to monitor the new ways hijackers and spammers attempt to compromise accounts, and we design innovative features based on this. At this time, we encourage customers to frequently reset their Microsoft account passwords and use unique passwords that are different from other services. More information is available here: http://aka.ms/cantsignin.


[edit] Adding on: We are working on increasing the password length. Unfortunately, for historical reasons, the password validation logic is decentralized across different products, so it's a bigger change than it should be and takes longer to get to market. It's also worth noting that the vast majority of compromised accounts are through malware and phishing. The small fraction of brute force is primarily common passwords like "123456" not due to a lack of complexity.

espen_f355 karma

When can we get a button that removes all FWD: THIS IS SO FUNNY mails that is sent from our mom/aunt/grandma?

OutlookOnReddit397 karma

Sweet idea. I'll add it to our feature suggestion list! - David.

OutlookOnReddit466 karma

BTW: You could create a rule that does that automatically. No button needed! - David

nietAlessandro301 karma


OutlookOnReddit402 karma

That is a good feature request. We will consider that.

  • Krish

Icelock210 karma

Do you secretly use gMail at home for your personal email?

OutlookOnReddit464 karma

Hey, Dick again. I have a Gmail account, too, and I use it fairly frequently to understand the competition. It's a great service, for sure. We have a different point-of-view than Gmail for a bunch of things, like connecting to other services, collecting your data, showing ads in personal email, etc., and I honest-to-gosh like using Outlook better on a day-to-day basis. I just find it faster and easier to use. But you should try 'em both and decide for yourself.

OutlookOnReddit142 karma

Hi I'm Gruia - one of the Outlook.com folks! I do have a GMail account, but Outlook.com is my main account. I encourage all to switch :)

secondinnings194 karma

I have mainly 2 questions.

Why did you remove the functionality of switching between two outlook accounts. I have two accounts one I use it as my main email and the other I use it as a personal email, for like sexting, sending dick pictures to girlfriend and etc.. so now i have to login/logout everytime. I really really really need this feature.. You guys said that it was removed to improve security.. etc.. but im not convinced.. change it immediately..

Also when I receive a message in messenger in outlook.com there is no indication to me that I got one if I am in a different tab. earlier in hotmail, the tab text used to change from the message i received and the outlook.com blablabla.. I hope you understand what I mean. Some sort of notification to new messages even when I'm invisible is what I'm asking for..

thank you..

also fuck the haters..

imo outlook >>>> gmail..

i forward my old gmail to outlook and all the emails that are forwarded from gmail are spam.. gmail's spam filters are shit..

OutlookOnReddit728 karma

Dick, here. Yeah, I really liked this feature, too, and sucked to have to take it out. The truth is that just wasn't supportable from a security standpoint. Eric Doerr, who manages that Microsoft Account team, wrote a blog post about it that explains more.

Eric's post also talks about setting up aliases which is a good way to do what you want with the Dick pictures.

Also: Please stop sending pics of me to your gf. No kidding. That's just creepy.

Laserblaster179 karma

Can outlook have the feature when you say the word "attachment" or "attached" in an email without an attachment, it let's you know.

OutlookOnReddit267 karma

done! krish

oscargamble153 karma

I love outlook.com but there are a few things keeping me from completely switching from Gmail (and I really do want to switch):

  1. In conversation view, when I delete a conversation from my inbox, the corresponding sent mail isn't deleted from my sent folder. In Gmail, deleting a conversation from the inbox causes the sent mail to be deleted as well. Why isn't that the default behavior on outlook.com? It's a pretty big usability oversight in my opinion.

  2. When I email someone, their address is automatically added to my address book and there's no way to remove it. This is particularly annoying when you email with ebay/Amazon/Craigslist sellers once but their addresses pop up as suggestions forever.

  3. I use Firefox, and every time I open outlook.com, the page completely refreshes after 5-10 seconds—usually right in the middle of my doing something. It's infuriating.

Is there any chance of these things getting fixed or, in the case of the first two, at least adding options to delete sent mail and mailed-to email addresses.

OutlookOnReddit130 karma

Thanks for feedback. On #1, it's something we're considering. It's a tough one given that that's not the behavior everyone wants be default. Giving you some options there would be good, though.

On #2, you can hover over the suggestion and click the X and it shouldn't show up again. We don't have a way to block that forever, but when you're done communicating with them the X approach should work.

On #3, I'll look into that. We haven't had reports of that.

  • David

falconer150 karma

More of an organizational question-- does the Outlook.com team also run everything that used to be known as "Windows Live"? I noticed all those services (Outlook.com, SkyDrive, Microsoft account, etc.) are still on the "live.com" domain. Just wondering if the same people are in charge of all that.

On a related note, does your team have anything to do with the other "Outlook" products and services at Microsoft, like Office 365?

OutlookOnReddit347 karma

We are the MSN, I mean Windows Live, I mean Outlook.com team.

Seriously though, a lot of us have been working on mail for a long time. We do work closely with other teams at Microsoft like Office 365 and the Outlook desktop client (and the Windows 8 mail team, Windows Phone team).


Synxx69150 karma

Why does the Android app suck so much? It's the worst, slowest app I have on my phone.

OutlookOnReddit173 karma

Hi this is Anu from outlook.com team. We are working on fixing the Seven app on Android. Apologies for the inconvenience till then.

mattstache107 karma

What browser do you use to test your code first?

OutlookOnReddit308 karma

Dick here. We test against a whole bunch of browsers, including latest versions of all the major browsers and a bunch of older browsers, except IE6, because honestly, it's time for that thing to die die die.

We have a bunch of automated testing that happens for all those browsers in parallel for every build, so we don't really test on one "first".

OutlookOnReddit259 karma

Dick again. Fun fact: In an earlier life, I worked on IE 5 for the Macintosh. Good times, good times.

DrBountyHunter96 karma


OutlookOnReddit342 karma

Fantastic question. Any suggestions? I'm thinking EarthWindAndFireDrive, but I suspect that's not going to fly. (Dick, now probably fired)

reel_big_work82 karma

Are you guys working on a way to filter spam as well as Gmail does?

My Hotmail address is x10 better than my Gmail, but is constantly flooded with spam.. I'd move back to Hotmail/Outlook if you fixed it!

OutlookOnReddit112 karma

We made tremendous progress on filtering spam and keeping our users safe. Both internal and external metrics put us on par with Gmail. But I would be the first to admit that all accounts don't have the same great experience due to several variables that impact our filtering like usage of the account, mailing lists the account is part of, account age and such. The next big thing we are working on is to identify the small pockets of users with sub par experience and improve it.

  • Krish

Salacious-82 karma

What awesome email feature would you like to implement but it is currently impossible or unfeasible?

OutlookOnReddit92 karma

I work on the back end team, and one of the things we'd like to do is move to a container model for our data centers. Working toward it, but not something we can do immediately.

shaggorama47 karma

Can you elaborate what you mean by a "container model?"

Sekonda43 karma

I think be means a modular approach to Data Centres. Like stacking shipping containers on top of each other to provide more compute (for example).

If you YouTube Container Data centres you'll find something similar to this.

OutlookOnReddit43 karma

Yup, that is the general thought for me. We are deeply committed to reliability, availability, and performance. So, as you consider moving to more efficient datacenters, the software has to adjust accordingly such that we never impact our customers negatively. We've made a ton of infrastructure improvements and are continually investing further. As we make improvements, we'll keep assessing what kind of data center we actually host the data on.

In general, this is, and will continue to be a long term investment for us.


joaoluisac63 karma


OutlookOnReddit105 karma

It's something we had in the past, but we found that very few people used it or wanted it and it was costly to maintain so we decided to remove the feature. - David

DAL8260 karma

How do you really feel about Windows 8?

OutlookOnReddit78 karma

Andrew here, I like it! It's not perfect, but overall it's an improvement over Windows 7. 8.1 adds some nice things too, like unified search and of course the start button :)

FlaccidExplosion50 karma

I haven't researched this yet so pardon my ignorance, but how would I go about migrating a [email protected] email address to a [email protected] email address, and bring EVERYTHING over with me to use outlook.com? Is that possible?

OutlookOnReddit91 karma

The easiest way is to add an alias. That way, you own both e-mail addresses and they point to the same inbox.

barboa48 karma

Hi, and thanks for doing this.

What is the best feature that I don't know about?

OutlookOnReddit93 karma

Unsubscribe? Sweep? Keyboard shortcuts? Google chat and Facebook chat interop? Those are just a few of my personal favorites. Others on the team probably have their own.


Nebulaeus38 karma

When will Outlook.com finally support IMAP and CardDAV/CalDAV so i can use it with native mail clients and calendering applications?

OutlookOnReddit45 karma

We have added support for IMAP. With EAS (Exchange ActiveSync), you can sync mail, contacts and calendars across a wide variety of devices. We listen closely to our customers’ feedback, and, just as we have done with IMAP, we will continue to evaluate how best to ensure our customers have access to all their data wherever they are.

usctrojan9830 karma

What is the best way to access Outlook.com email, calendar and contacts on a Mac?

OutlookOnReddit60 karma

We've just announced IMAP here on this AMA! We'll consider CardDAV and CalDAV for the future. Of course, you can always access everything via Safari at Outlook.com :-). - David

astenast22 karma

Hey i love your service! I have noticed that my unread messages that is shown with bold font in my inbox differs when it comes to english and other languages such as greek. The whole subject of the unread email doesn't seem to be equally bolded. Here is an example http://i.imgur.com/eDIIDgh.png Please fix this. Thank you! :)

OutlookOnReddit28 karma

We're working on fixing that. Thanks for raising the issue. - David

brownboy1316 karma

What's the next major development you guys want to see in the way outlook (or email in general) works?

soyjesus23 karma

They want people to prefer outlook over gmail.

OutlookOnReddit79 karma

Confirmed. Source: I work for outlook.com (this is Dick)

OutlookOnReddit34 karma

Seriously, though. I think we're entering a pretty excited time for email. Email is ubiquitous. It is both indispensable and maddening. People use email for all kinds of new things, like getting receipts for the stuff they buy (even cab rides and lattes), or getting deals, or communicating with companies they do business with. And today's Inboxes are pretty bad at dealing with that stuff. We're investing heavily in doing more with the stuff that shows up in your Inbox, and lots of other people are, too. It's fun to watch and be a part of. (edit: this is still Dick)

1amongmany5 karma

How do I convince my boss to shift our small company's mail server of 30 accounts to Outlook from a lame unheard of service called net4?

ramstoria4 karma

I've set up an outlook.com account and I'm slowly moving things over from gmail to outlook. I really like the UI of outlook, but it seems like the settings and customization options are pretty slim, particularly with setting up custom filters. Will I get to see custom filters soon, or any other cool new features coming out in the near future I should know about?

OutlookOnReddit22 karma

or any other cool new features coming out in the near future I should know about?

nice try, Gmail product manager.

Nebulaeus3 karma

Any plans to update the Hotmail branding in Windows Phone 8? Maybe for the GDR 3 release? ;-)

OutlookOnReddit7 karma

Stay tuned! :-)

taxidriver11382 karma

Any plans to get rid of the ads on the right without making us pay?

OutlookOnReddit7 karma

Tell me more. I'd love to hear some ideas that you have about how we'd at least recover the costs of the service without showing ads. It's very expensive to run a "free" email services with 100s of millions of users. We've done a lot of work in Outlook.com to make the ads less intrusive and to respect privacy more than others in the industry. If you have ideas for us, we'd love to hear them, though. - David