Posey's Tips & Tricks

Ten Years with Microsoft 365, Part 1: Making the Switch

Was giving up the control of my self-hosted email worth it to hand Microsoft over the keys completely?

This month marks ten years since I began using Microsoft 365 (formerly Office 365) in my own organization. That being the case, I wanted to take a step back and take a look at my experiences. More specifically, I want to talk about what has worked for me, what hasn’t worked, and whether or not adopting Microsoft 365 was a good decision.

Why Did I Adopt Microsoft 365?

As someone who writes about all things Microsoft, I have always used Microsoft products both in my lab environment and in my production environment. In case you’re wondering, my production use of Microsoft products doesn’t stem from brand loyalty or business necessity. There are actually several reasons why I use Microsoft products in my production environment, but one of the big reasons is that it helps to keep my writing real. I find that I sometimes run into issues in production that I would never encounter in a lab environment. When that happens, it forces me to look for a solution, and, in many cases, I have been able to write about those solutions and help other people.

The reason why I mention this is because in the years leading up to my Microsoft 365 adoption I was writing heavily about Microsoft Exchange Server. As such, I had a Microsoft Exchange deployment in my house and hosted my email on those servers. Aside from the occasional glitch, it usually worked out pretty well.

Back in 2012, I was recruited for what turned out to be a three-year international speaking tour. My second stop on the tour was London, England. Upon my arrival in London, I connected to the hotel Wi-Fi and had planned to send an email to my wife to let her know that I had arrived safely. Unfortunately, the mobile device that I was using at the time only worked in the United States, so calling home really wasn’t an option. Email was my only means of communication. Imagine my surprise when I discovered that my email was down.

So there I was, thousands of miles from home with no way of contacting anyone and with no way of reading any of the emails that were being sent to me. Not only did the outage prevent me from communicating with my wife until I got back to the States, but it also meant that the tour organizer was not able to reach me either.

Unfortunately, I could not fix the problem until I got back home, and was left without email access for the better part of a week. I’m sure that you can imagine the problems that this caused.

Ultimately, the outage was related to something really simple and one of my Exchange boxes just needed to be rebooted. Even so, I was traveling five days a week and I knew that I just couldn’t risk having another failure. That’s what made me switch to Microsoft 365.

How Did Microsoft 365 Work?

I did not take the decision to switch to Microsoft 365 lightly. After all, I had always hosted my own infrastructure at my home. Making the switch to the Microsoft cloud meant giving up a degree of control (I’m kind of a control freak, so giving up autonomy was hard for me to do), and it also meant walking away from a substantial investment that I had made in server infrastructure.

Ultimately, I think that my decision to switch everything over to Microsoft 365 was a good choice. In the ten years since I made the switch, I haven’t suffered any major outages that I am aware of. I know that Microsoft has had a few Microsoft 365 outages over the years, but it’s possible that those outages may have occurred when I was taking a day off, or they just simply did not affect me. In any case, the service has been reliable.

When I first made the switch, I did encounter a few issues with making the service work properly with my domain name. Thankfully, Microsoft has greatly improved its support for domain name use over the years, and I haven’t had any domain name problems in quite a few years.

Of course reliability is not the only reason for switching to Microsoft 365. In the second part of this series, I want to talk about some of my experiences over the last ten years as they relate to operating costs and administrative burden.

About the Author

Brien Posey is a 20-time Microsoft MVP with decades of IT experience. As a freelance writer, Posey has written thousands of articles and contributed to several dozen books on a wide variety of IT topics. Prior to going freelance, Posey was a CIO for a national chain of hospitals and health care facilities. He has also served as a network administrator for some of the country's largest insurance companies and for the Department of Defense at Fort Knox. In addition to his continued work in IT, Posey has spent the last several years actively training as a commercial scientist-astronaut candidate in preparation to fly on a mission to study polar mesospheric clouds from space. You can follow his spaceflight training on his Web site.

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