Outlook.com: A few quirks away from perfection

Outlook.com launched at the end of July and after more than two solid months of use, we wanted to give our insight, at a deeper level than when Outlook.com first launched, about how Microsoft can improve the platform.

When Outlook.com was announced, it signaled the end of the Hotmail era and brought with it a new interface, which we covered extensively here. The interface is familiar and designed with your content being front and center but despite all of the changes, there are still a few areas that need tweaking to take the service to the next level.

In general, though, we do enjoy the service as the customization is plentiful and the existing integration with smartphones using EAS made setting up accounts a breeze. Navigating around the interface, Skydrive integration and contact import from other services (Gmail, Facebook, etc) all worked seamlessly and made the transition from Gmail to Outlook.com a snap.

Despite speaking highly of the service, there are a few areas that need to be improved in future revisions that can refine and expand the service to make it holistically the best option for email on the Internet.

Spam/Filters:

Apple.com email being flagged as insecure

Oh boy, getting up and running we had some issues with the spam filter, notably, emails coming from other Outlook.com accounts were flagged as spam (oops!). Now, this issue has been resolved (for outlook.com domains) and the filter certainly “learns” the more you identify content which reduces these flags, but it is still not perfect.

For instance, legitimate insurance emails were flagged as spam, causing me to miss them for a few weeks, and we have also seen Apple.com emails being flagged for being insecure. While it is getting better, the upstart was a bit rough and we still find the need to check the spam folder to make sure legitimate emails were not flagged.

We asked Microsoft about the incorrect flagging and David Law, who works on the Outlook.com team, stated the following response:

Our internal metrics show that, in aggregate, Outlook is actually doing better than Hotmail and other competitors at keeping spam out of our customers’ inboxes

On a high note, we should mention that we have not received any of the traditional spam such as Viagra offers or cash payments from a prince in Nigeria,

UI Quirks:

Border shading does not vertically align to scroll bar

Beyond the spam, there are few UI quirks that we have noticed that need to be cleaned up; such as the image you see below when trying to send an email with an attachment that has not been fully uploaded. The options presented don’t make it easy to cancel the action, you can hit escape to stop sending the email but with no cancel button, it could be confusing for some users.

No cancel button to stop the action

The design inconsistencies are apparent throughout the email service but rarely inhibit the use of the platform. Another quirk (image below) is that new items in the Junk folder cause the text field to be bold indicating that new items have been diverted from your inbox. Why would I want to know that I have new, unread, junk email that needs to be viewed? Of course, when you read the issue above about not trusting the spam filter, maybe it's a good thing as you now have two inboxes that need to be maintained until the filter is properly trained.

The settings area could also use a bit of tweaking as well, as it appears to be a massive wall of text and locating the different settings segments is a bit of a headache as there is not enough distinction in the headings. Simply making the header text bold for each segment could turn this cluttered page into a more organized feature.

Wall of text, headings should be emphasized.

Another issue that can be seen across the UI is inconsistent border width. The image below shows a 1 pixel border gap between the scroll bar and the email field (right side) but on the left side there is no gap between the email field and the sidebar.

Inconsistent border spacing

Archiving

One of the compelling features that most users complain about not being available in Outlook.com is the ability to archive content, rather than delete it. There is a work around for this feature and Outlook.com does a great job of allowing you to quickly add a folder shortcut to create a manual archive instead of the automated process, but it is not a perfect solution.

Google (top) allows for native archiving, Outlook (bottom) only allows deletion

Where this shortcoming shows through is with the mobile experience. When using the email service on iOS, Gmail’s archive option works seamlessly but outlook.com only allows you to delete the email; unless you take the additional steps to open the item and assign it to a new folder.

Fin:

These issues are relatively minor in the grand scheme of the email service but it's the small tweaks that make big impact on user perception. For Microsoft, they need to build the best email platform, not a competing service. 

Outlook.com is off to a great start and the overall experience is positive. If Microsoft can address the spam and design issues, it will help Outlook.com keep the momentum it has already established and ensure that the service builds a quality rapport with its users.

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Here are some quirks, in my opinion:

Quirk 1. You lose access to your account on some bs grounds like "someone is trying to use your account". Some days later they even try to be funny sending you an e-mail asking "how was your experience in recovering access to your account". My experience was dreadful. Losing many important e-mails (and maybe access to Skydrive, I didn't bother to check) was not funny at all.

Quirt 2. It's a shame you have to use other browser than IE to check your Outlook.com e-mail account because sometimes it doesn't work in IE.

gallo68 said,
Here are some quirks, in my opinion:

Quirk 1. You lose access to your account on some bs grounds like "someone is trying to use your account". Some days later they even try to be funny sending you an e-mail asking "how was your experience in recovering access to your account". My experience was dreadful. Losing many important e-mails (and maybe access to Skydrive, I didn't bother to check) was not funny at all.

Quirt 2. It's a shame you have to use other browser than IE to check your Outlook.com e-mail account because sometimes it doesn't work in IE.

At Q2, Oh the irony

Rappy said,
I love it, I have left Google Mail for this and not been disappointed by the move

I assume you don't have anything important or work related tied to your gmail then? Clients relying on getting in contact etc? Just leaving a long term email is something most will never do

When I first read outlook.com I thought it would be an online version of outlook, meaning a tool where I could link my other emails (in my case just a gmail) accounts to and use it as a mail manager. To my big disappointment it's just a new version of hotmail, with new annoying things. Commercials? I mean wtf! It's your email!! Some people make a loving from their emails!! I stopped using ms msn client years ago when they started filling they with commercials as well... I would for my gmail interface to work like the actual outlook program, without having to install outlook. ( multiple computers etc)

The most annoying thing about Outlook is the stupid sidebar advertising that you have to wait to load before you can click on anything. So irritating. I had to use adblock just so it wouldn't load.

They made it fully functional in IE10. When you upload files, you don't get the progress bar. And when you want to use bcc the recently sent addresses gets in the way until you click anywhere on the screen.

Labels, filters based on labels, and a better use of grey in the submenu
This is what i want from outlook, not fixing problem that i've never be able to spot

We all need to be more proactive about our personal account security. One thing that can't be stressed enough is taking advantage of the 2FA (2-Factor Authentication). Maybe now that they have purchased a phone verification company they will start offering better security with 2FA. Until then Gmail wins.

Another needed feature; they need to add a Search function to the Calendar when they finally switch it over from Hotmail.

A nice feature request would be to have different email signatures for different aliases/email addresses. I pull all my mail into outlook, but it can only attach the same signature across all email addresses.

I have had trouble with folks switching and then getting denied the ability to "mass mail" the 50 or so contacts in there address book to inform people of their new address. It takes them to a verification process that a lot of people seem to miss the steps and process with. And then there is a whole other group that can seriously not make out the "captcha". So If MS could somehow automate that process for people it would be a big deal to get people to switch.

Just yesterday when I updated the "Mail App", my outlook.com contacts dissappeared altogether. I finally had to uninstall the app altogether and then reinstall. Took a REALLY long time to sync back the 1500 contacts.

Still not clear on the contact limit either. I think it is 1500, they really need to bump that up as I have more then 1500 in the Outlook Software, and it basically randomly deletes people from Outlook.com and the Phone to keep inline with that limit.

Other than the glitches, it was long overdue and I have a long list of similar Win 8 glitches that REALLY need to be addressed before launch. Help section still refers to "release preview", my printer stopped working this morning, 4th time this week after that latest update. Had to delete it, AND reboot. Printer cue issues are calls I get from a LOT of consumers.

A couple features I miss in Outlook.com are Gmail's 1. conversation view, 2a. labels, 2b. priority inbox, and 3. filters.

1. Although Outlook supposedly does have a threaded view, I find it does not work as well as Gmail's. Often times a list of emails will appear (much) shorter in Gmail because of the grouping.

2. I like to label my emails as a means to immediately see what the email is related to. Combined with the Priority Inbox, I can have my emails separated by labels without segregating them into folders which I have to view individually. It would be nice if Gmail's priority inbox had more than 4 sections though.

3. Gmail's filters are more flexible than Outlook's rules. The use of the OR operator is very handy and lets me make one filter for multiple addresses instead of one rule for each address.

It has it's problems, like any other Email service. But i still prefer it to Gmail and it's now become my main Email. Also love the SkyDrive integration.

Drossel said,
About password security:

1. allow more than 16 characters

2. allow spaces

For some reason the 16 character limit was recently imposed. Mine was a lot longer now I get told to just enter the first 16 characters when I log in.

I think Outlook.com is excellent! I switched from Gmail to Outlook.com and will never go back to Gmail. It's super fast, and dare I say funner to use? lol I do agree there are a few little tiny quirks here and there that I'm sure they'll fix soon. Looking at that Gmail screenshot makes me irk at how outdated and bulky it looks... lol.

Speaking of the scroll bar, didn't Outlook.com feature Windows 8 classic-style scroll bars? Now I'm seeing Windows 7-style scroll bars.

Whine...complain...whine....complain

Another issue that can be seen across the UI is inconsistent border width. The image below shows a 1 pixel border gap between the scroll bar and the email field (right side) but on the left side there is no gap between the email field and the sidebar.

Never noticed. Don't care 1 bit about 1 single pixel.

Another quirk (image below) is that new items in the Junk folder cause the text field to be bold indicating that new items have been diverted from your inbox. Why would I want to know that I have new, unread, junk email that needs to be viewed?

are you kidding me??? All email clients do this.

It's a constructive piece, if you read the entire post, you would know that I love the service.

Also, Gmail does not highlight items in the junk folder.

bdsams said,
It's a constructive piece, if you read the entire post, you would know that I love the service.

Also, Gmail does not highlight items in the junk folder.

No, it's a nitpicky pedantic post about a bunch of things that your average Joe User will neither notice nor care about. There are far more productive things to be written about than this.

jamieakers said,

No, it's a nitpicky pedantic post about a bunch of things that your average Joe User will neither notice nor care about. There are far more productive things to be written about than this.

Also, all the nitpicks about the browser-based UI can be dealt with by moving to a desktop client (I use Outlook 2013 as mine - I also use it for GMail and my ISP).

If it weren't that Yahoo Mail (US) charges for POP3 (and doesn't support IMAP4), I could actually have a single e-mail application for all.

bdsams said,

Odd, mine is not highlighted.

I too find the Outlook highlighting junk to be annoying.

Gmail highlights spam, but at least gives one the option of hiding the spam folder in the directory.

Not that different from Hotmail. More of a skin than anything at the moment.

Another issue is messenger, lack of options there even compared to Hotmail.

WooHoo!!! said,
Not that different from Hotmail. More of a skin than anything at the moment.

Another issue is messenger, lack of options there even compared to Hotmail.


It has been built from the ground up. So nope, not a skin.

My biggest issue is I haven't been able to convert my hosted custom Windows Live domain to an Outlook.com account. Anyone else get the same thing and have any advice?

Chris Breeden said,
My biggest issue is I haven't been able to convert my hosted custom Windows Live domain to an Outlook.com account. Anyone else get the same thing and have any advice?

I may be wrong on this, but if I recall, custom WL domains are being ended. You need to get an Office 365 account for that I believe.

nesl247 said,

I may be wrong on this, but if I recall, custom WL domains are being ended. You need to get an Office 365 account for that I believe.

This is the first time I've heard that, good to know if it's true. I guess I'll be moving my domain away from MS then, since I don't want to pay for the few accounts I use.

This sucks because I was just transitioning away from Google Apps domains because of their terrible support and how few free domain accounts you can have now.

Chris Breeden said,
My biggest issue is I haven't been able to convert my hosted custom Windows Live domain to an Outlook.com account. Anyone else get the same thing and have any advice?

You have to do it one email account at a time, sign in with the account you wish to convert then simply go to outlook.com and you can get the new outlook interface. Works perfectly on a domain I've just setup and on one which has been using windows live domains for years.

Chris Breeden said,

This is the first time I've heard that, good to know if it's true. I guess I'll be moving my domain away from MS then, since I don't want to pay for the few accounts I use.

This sucks because I was just transitioning away from Google Apps domains because of their terrible support and how few free domain accounts you can have now.


I wouldn't go and move away just like that. As I said, I seem to remember something about it closing, but I could be wrong, or they could have changed it since then. It's been a long time since I heard about it to be honest.

Custom domains still work fine, we only lost the free web hosting via OfficeLive beta.

Not sure what your issue was, mine converted automatically.

Chris Breeden said,
My biggest issue is I haven't been able to convert my hosted custom Windows Live domain to an Outlook.com account. Anyone else get the same thing and have any advice?

Nope. All of mine converted over just fine.

Chris Breeden said,

Interesting, mine are still stuck using the old Live interface.

Chris,
If you're using a custom logo for your domain pages (in the top left corner), you need to remove that logo. Then simply go to outlook.com and your account will convert to an outlook.com account.

MsftGaurav said,
One of the "quirks" is Metro style design that doesn't make you feel like using it.

Must be one of your quirks, if nothing else the modern UI looks clean and is easy to understand and use.

The inability to manually sort filters under "Rules for sorting new messages" is driving me nuts.

I hope I've just overlooked something...

JimmyJamesRoS said,

What kind of issues I have yet to have any problems with it.


Same, I have yet to encounter any issues with attachments while using Chrome.