When I started writing this story, I thought it was going to be a rant. Instead it's more testimony to unnecessary hassle. Obviously, we're talking about Microsoft.

Most of you know that I moved from an Exchange hosting provider to Office 365 a few years ago. Although I had Office 2013 licenses as an educator through school, I moved to Office 365 to gain access to Office 365-hosted Exchange. Then, just about a year ago, I moved off of Exchange to Gmail, and haven't looked back.

Although I cancelled my Office 365 Midsize Business plan, I still have my Office 2013 license for my PCs and my Office 2011 license for my Macs.

Yep, there it is. That's the start of this story. I get downloadable Office from the school where I teach, but they only have Office 2011 for Mac. As you probably know, Office 2016 for Mac was released a few weeks ago, and it's much more in line with the PC version of Office 2013 we're all used to.

Office 2011 for Mac is so bad that I have a Parallels install of Windows on most of my Macs, just to run Office 2013 in a Windows virtual machine.

Yesterday afternoon, I caved. I do a tremendous amount of work in Word and PowerPoint, and I just wanted them to run natively on my Macs. I wanted to use Office 2016 and stop all the weirdness that I have to go through when running a Windows instance to edit a Word file.

Unfortunately, while the university has an Office 2011 for Mac license, they haven't yet updated to Office 2016 for Mac, which will probably be sometime this fall. So, at only $89 for the year (with a ten buck academic discount), I bought my own license. You can see my receipt right there, in the screenshot below.

Are you starting to feel the dread? I wasn't. After a year or so away from doing Microsoft installs, I'd forgotten just how much of a DMV-like experience dealing with Microsoft products can be. Let the runaround begin.

One note before I begin. You don't have to read all of this if you don't want. It's just the account of the hassles I went through attempting to do what should have been a very simple process. The tl;dr of Microsoft is often the same: the hassles you go through in an attempt to do what should have been a very simple process.

And with that, the hassles...

The first install

Look at that "Thank you for your order" screenshot carefully. Do you see the nice blue "Install Office" button? Yeah, so did I. I even clicked it. The result was a downloaded installer package, which I then ran. After a little whirring and blinking, the installer ran and Office 2016 for Mac was on my Mac.

Clicking Done resulted in the installer launching Word, with a nice blue intro screen. Then came the sign in screen. I dutifully typed in my email address and then cut and pasted my password. A prompt showed up asking if I wanted to use my Office account or my company account. That was, admittedly, a bit baffling because I bought Office Home edition, but hey, I'm tough, I can handle it.

After thinking on it a bit, I ascertained that the message came up because my email address is a custom domain, not something like @gmail.com or @live.com, etc. Since I wasn't using an @live.com or an @outlook.com account, I selected the company option. It wouldn't let me go any further. The Sign In button had been replaced by a Cancel button.

Okay, fine. I still had my receipt page open in my browser, with a nice "Contact Us for help" button available, so I opened up a chat conversation with a Microsoft support rep:

DG: I am trying to sign in to activate, and it recognizes my email and password, but asks if I want to use Microsoft Account or Work Account. Which one is associated with this purchase?

Microsoft: Okay no worries, as I'd be happy to assist you with anything regarding Microsoft products! You will want to select Microsoft Account.

At this point, I should point out two things. First, my Microsoft rep was "Paris H" (yeah, not kidding) and after selecting Microsoft Account, it asked me for my username and password again. I tried logging in and was greeted with the unable to activate message below:

DG: It says unable to activate Office.

Paris H: What email address are you trying to use?

(I answered with my personal email address)

Paris H: Just a moment while I look into that for you. Please click here for Office Account Sign In. Sign into your account from there and you should be able to locate the install button.

Let's take a moment to get sidetracked about the use of, you know, the English language. Microsoft calls its product "Office" and with that comes some linguistic responsibility. I knew what she meant by using my Office Account instead of my Work Account, but seriously? That stuff can make you crazy pretty quickly.

"Click here" was a page off of stores.office.com/myaccount/. It turns out, there was an Install button there as well. So, having already installed Office 2016 and failed in activating it, I asked the obvious question:

DG: I'm signed in, but do I need to install Office again? Should I delete it first?

Paris H: If it is already installed, open up Word 2013 and then click on your name in the top right. Sign out and then sign back in.

That didn't work, because I'd already ran into the problem of opening up Word 2013. All I could think of was, "You are in a maze of twisty little passages, all alike." Okay, let's try this again.

DG: It won't let me. It insists I sign in, and is giving me the unable to activate Office message.

Paris H: What I would recommend you do is uninstall and reinstall the software.

Yep, uninstall the software I just installed and then reinstall it so that it might activate. That's got Microsoft DNA written all over it.

Uninstalling Office

Given that this is a Mac and we're talking Office here, I knew in the marrow of my bones that just taking the applications out of the Applications folder and trashing them wouldn't be enough. So I asked for advice. After all, I was still talking with Paris H., and you just don't close the window on Paris H. until the experience is complete.

DG: How do I uninstall office on a Mac?

Paris H: Please click here for Uninstall Office 2011 from a Mac

The link was to instructions for uninstalling Office 2011. I didn't have Office 2011 on this machine. I had just bought, installed, and attempted to use Office 2016. So, I tried again.

DG: No, I have Office 2016 that I need to uninstall because it won't activate. How do I uninstall the brand new Office I just bought because I can't use it?

Okay, so I might have been getting a little testy.

Paris H: I am checking on this now.

(Some time went by)

Paris H: Please click here for Uninstall Office 2016 for Mac

This time the link was more appropriate to the problem. The instructions weren't correct, but the link was right. If you follow the link, you'll see it advises three stages of activity: removing the applications from the Applications folder, deleting a .plist file from the system Library folder and deleting an indeterminate number of .plist files from the user's Library folder.

In the second stage, the instructions state "In the LaunchDaemons folder, Control+click or right-click com.microsoft.officeprefs.plist and click Move to Trash." But, as it turns out:

DG: The file specified in Library, com.microsoft.officeprefs.plist, does not exist. There is a file com.microsoft.office.licensingV2.helper.plist. Is this what should be removed?

Yepper, the instructions Microsoft provided for uninstalling Office were wrong. Can you imagine run-of-the-mill Mac users digging in their Library folder? Can you imagine how bad it could be if someone deleted the wrong .plist file? Think randomly deleting INI files in your System32 folder and you get the idea.

At this point, I'm thinking Paris H started to lose patience with me. I was instantly told "Yes, that appears to be correct." and I'm guessing that if ol' Paris had to look up how to uninstall Office, knowing which .plist file to remove wasn't something she could really confirm off the top of her head.

Right after telling me that removing com.microsoft.office.licensingV2.helper.plist appeared to be a sound strategy, I was dismissed and my celebrity Paris H experience was at an end:

Paris H: Okay, excellent and if you have troubles you can contact us back at anytime.

Paris H: Thanks again for chatting with us at the Microsoft Store, we appreciate your business!

MS (clearly not Paris H): Thank you for chatting with us. Please click the "Close" button on the top right of the chat window to tell us how we did today.

When it comes to installing Office 2016 on the Mac, at least I'll always have Paris. And I went on with the process.

Reinstalling Office 2016

This time, rather than downloading and installing Office 2016 for Mac from the Install Office button on my receipt, I went back to the link Paris provided, at stores.office.com/myaccount/ and hit that install button. The screen image below shows that I have one install (because I finally do), but when I got to this screen originally, the install count showed zero. I hit the big red button.

I was encouraged by one thing. I had started to worry that I bought the software using my personal email address and because I got an educational discount, perhaps the sign-in required one of my school email addresses. But as soon as I hit the red Install > button, I got the following screen:

In the third step, the screen showed the email address I was supposed to sign in under, and it was my personal email address, the address I used to buy the software. So at least that was something.

Eventually, the software downloaded and I subsequently ran the installer (which was functionally identical to the first installer run). Once the installation was complete, Word once again opened, and I tried logging in.

Success... sort of.

I was able to login and was, in fact, able to activate Word. Or so I thought. Satisfied with what I thought was a completed installation and activation process, I opened up the Word document I wanted to edit all along. At which point I got this message:

Special, right?

I took a moment to remind myself that it's just software and then took a couple of calming deep breaths. Then I clicked the Activate button. It went through the sign-in process again, and this time, Word reopened, but without any "you must activate" message.

I have subsequently been able to launch PowerPoint and Excel and they work without any activation messages. So, yay about that.

Final thoughts

I actively jump between three different Macs and one of the reasons I was willing to once again get into Microsoft's subscription clutches is their 5-machine deal with Office is quite reasonable. However, I'm certainly not looking forward to (okay, let's be honest: dreading) this activation hassle on the other two machines.

I once described Microsoft's mission statement thusly:

"Microsoft builds incredibly deep, powerful, and flexible software products that -- before they see the light of day -- must be infused with a level of unnecessary inconvenience, incomprehensible restrictions, and regressive policies such that all possible joy has been removed prior to customer contact."

Yep, they're on mission.

I came back to Microsoft for this product evolution. But the future? Gosh, I'm getting tired of the hassles Microsoft seems to engineer into their products. I'm certainly going to advocate for solutions that are less hassle.

The thing is, there are a lot of substitute solutions and losing hours to Microsoft's unnecessary inconvenience, incomprehensible restrictions, and regressive policies is getting really, really old.

When customers dread installing your software, you've got some serious problems.

By the way, I'm doing more updates on Twitter and Facebook than ever before. Be sure to follow me on Twitter at @DavidGewirtz and on Facebook at Facebook.com/DavidGewirtz.