WTH is happening with Office 365?

Okay, so Windows 10 updates have had issues, shall we say, for years. But, really, Microsoft, you're going to roll out the same kinds of problems for your services now, too?

Red flag warning button [alert / danger / disaster]
Matejmo / Getty Images

I'm used to having Windows updates being a complete crap show, but Outlook? Office!? What's going on here?

Every few months I take a swing at yet another disastrous Windows update or patch. I really don't want to. But, darn it, when it comes to fixing Windows 10 or adding a new feature, Microsoft is the gang that can't shoot straight. Until recently, I thought it was doing a great job with Software-as-a-Service (SaaS) offerings such as Office 365 and Outlook.

So much for that idea.

Starting last June, Microsoft's services plunged downhill. First, Outlook just stopped working for many users. Then, in July, all Outlook clients and services came to an abrupt halt.

Come on, Microsoft. This is e-mail 101. How hard can it be? If I could do it back in the 1980s when I was a NASA e-mail administrator, when connecting disparate e-mail systems was equal parts hacking and black magic, you can certainly keep fundamental e-mail clients running in the ‘20s.

At least, I thought you could. I mean, while Outlook is my least favorite e-mail client (Evolution on Linux happens to be my fave), you've only had, what, 23 years since you released it as part of Exchange Server 5 in 1997 to get it right?

I mean, sure, there are weird corner cases where things can go wrong, but this is your e-mail system coming to a smoking collapse. How can you keep blundering like this?

But as it turned out, there was worse -- far worse--to come. Microsoft and all its Office 365 and Outlook users got a nasty September surprise.

Starting on Sept. 28 and lasting through the next day, Microsoft users around the world found they couldn't sign into Microsoft and other programs that use Azure Active Directory (Azure AD) for authentication. Can you say, "Whoops?" Sure, you can. Can you repeat all the other things users had to say about this revolting development? You can, but this is a PG-rated publication.

Microsoft quickly figured out what was wrong--a beta service update made it into Azure AD backend services, and everything went haywire. So, the company "fixed" it using an automated rollback…, which failed. Six hours later, the services were finally up again.

But wait, there’s more. This was followed by yet another Exchange/Outlook issue, which knocked out European and Indian Office 365/Microsoft 365 customers. By now, you'd think Microsoft would have a handle on what was what.


On Oct. 7, Microsoft once more saw its services go crashing down. This time, it was Microsoft's Office 365 services and Outlook users throughout the U.S. For this go-around, the trouble lingered through the next day.

What happened? Microsoft said this time that if customers were using resources that operated between regions on Azure network infrastructure they would run into these problems. How do you know, when using Office 365, whether you're working on, say, a document residing in a US East availability zone, while your application's running in on Pacific time?

Short answer: You don't.

This time the problem was a “deliberate change (that) was applied to [Wide Area Networking] WAN resources causing connectivity latency or failures between regions." To fix it, the Azure team rolled things back to a healthy configuration. This time, thank God for small miracles, it worked.

The common theme here is one I keep harping on in when writing about Windows 10's woes. Microsoft isn't doing enough work to make sure its fixes and upgrades don't break systems. Quality assurance needs to be job one.

Microsoft had been doing better at the cloud. As I've said before, the cloud, not the Windows desktop, is where it’ll be making money in the years to come. If it can get its  act together again.

Microsoft’s corporate vice president of the Enterprise Client & Mobility (ECM) team, Brad Anderson, recently said:  "You think about what enterprises commercial organizations use to collaborate and to be productive. It’s Office 365, Microsoft 365 that is the language of business.

That's all nice and good to hear. But if your users can't count on getting their work done, the only language Microsoft will hear, as customers flee to Google Workplace, is a string of obscenities.

Copyright © 2020 IDG Communications, Inc.

7 inconvenient truths about the hybrid work trend
Shop Tech Products at Amazon