Why I Deleted the iOS Outlook App… Three Times!

Let me be clear from the beginning. I am a happy iOS and OS X user for about five years now, but I also like the new way Microsoft is going, by shifting its strategy through mobile environment, by acquiring Nokia mobile phones unit, Acompli, Sunrise or (just announced) LiveLoop and also by the way they integrated Windows 10 and turning towards free or subscription based services for its Office applications. Good competition is beneficial to the consumer. But now, let’s get back to Outlook.

I really enjoy being up to speed when it comes to tech news, so just seconds after reading about Microsoft’s new iOS Outlook launch back in January (only two months after acquiring Acompli), I was eager to install it out of curiosity in the beginning, but also with some high hopes, since — let’s face it — the Mail application from iOS is far from perfect when it comes to managing conversations and showing only the most relevant items in its main screen.

Marketing slogans such as Mobile email just got a promotion, Sharper focus on your important email or Easier than ever attachments fueled my hopes even higher.

I just wanted to add two accounts to Outlook: my email account (from an IMAP server) and the Google Drive one. They both shared the same email address (yes, you can create a Google Account using a company email such as your.name@example.com).

Strike One — IMAP Support

I reached a dead-end faster than I thought, because the first iteration of the app didn’t have support for IMAP. So, after less than 60 seconds of Outlook on my iPhone, I tapped the delete button.

Strike Two — Which Came First, the Chicken or the Egg?

Microsoft added support for IMAP, in an update, just two weeks later. Still excited about the marketing materials mentioned above, I reinstalled it.

Two screens later, I encountered another challenge for Outlook. First, I chose to add an IMAP email. Then I added my credentials.

My reaction, after seeing the error message

But, regardless of what I added in the previous screens, my IMAP mail always appeared to be a Gmail account! WAT?! Just because this is the email address for a Google Account, it doesn’t automatically mean it’s also Gmail account, right?

I contacted their support team and tried to explain the problem. It was almost as complicated as the chicken or the egg causality dilemma but I nailed it, in the end. After tens of exchanged messages, print screens, online tools and a hard reset for my account from the Microsoft Engineers, on the 17th of March and two iterations later, they proudly recommended me to delete the application and reinstall it. It will work.

Strike Three — The Final Encounter

I was happy, while the application reinstalled for the second time. Adding my IMAP email worked like a charm. Perfect! While the emails were downloading, I tried to attach my Google Drive, which had the same email address.

For me, this message eventually became the screen of death for the iOS Outlook application

WAT?! You are kidding me, right? Apparently the team “worked” at this bug by repositioning the cases in the switch statement. Until now, my email address was only a Google account. Now, it is only an IMAP email. It was too much for them make it be both, based on what I selected in the initial screen. Definitely disappointed with this new experience, I came back to the support team explaining them, once more, the situation.

One week later and after several failed attempts to make this work, I deleted the application and decided not to use iOS Outlook for a while.

Bonus Chapter — How to Solve the Greatest Programming Challenge?

Working in the IT industry for my whole life, I know initial wrong assumptions can be difficult to repair. I know the code could be messy sometimes. But knowing to code a little bit, I also know the solution was there, in their face.

I drew below a really really really simplistic scheme explaining how the current algorithm works. At a glance, the logic behind it appears to be a pretty good one.

It does have an Achilles’ heel, though. The script doesn’t use all the information provided by the user. It only checks the email address based on its own rules, dumping the user’s choice. So, the address cannot be both an IMAP account and a Google account in the same time.

Now, let’s see how this can be improved. As I previously stated, the solution is right in front of us. We just have to listen to the user! Assume the user is right and you’ll go to the right switch. Take a look below.

As you can see, the above algorithm makes the code simpler, does the job done and — most important — satisfies the users’ needs.


If you know someone at Microsoft, please send her/him the link to this article. Who knows, maybe they will fix this after all. And, who knows, it might come a time when I will install the iOS Outlook again on my iPhone.

For the rest of us, I think this could also be a lesson learned. Listening to our users should be the most important aspect of a project, regardless its size.

Did you have similar issues with other applications, devices or websites? Please share them with us.