Upgrading Office 365 from Personal to Home - it could be easier

I like Office 365 Personal. The Mac version has bugs of course, but it seems to improve with each incremental release. For $70 a year I have a version running on my Mac and a version running in a Windows 10 VM (in theory it only installs one either 1 Mac or 1 Windows machine, but in practice it seems to allow both at once). The cost seems entirely reasonable to me. There’s little data lock because so many apps read and write (more or less) Office files. It’s the kind of subscription software I love.

So I didn’t mind when I had to get another license to cover my son. I figured I’d just upgrade to Home. 

Except it’s quite unclear how you do that. This 2015 article suggests there’s a bit of an underhanded trick to it: How I upgraded Office 365 Personal to Office 365 Home for $10. That’s sort of how it works except it’s as designed, it’s not a bug or trick.

I had a month left on my Personal (1 machine) subscription. I bought Home (5 machine) for $10/month (renewable). MSFT switched my remaining month from Personal to Home. Then a month from now, it was to start charging me $10 a month. In MSFT parlance the subscriptions “stack”.

I suppose the trick deal is to buy a year of Personal, then immediately get a $10/month subscription to Home. Then you’d get a year of Home at the Personal price.

In my case it took a call to support for me to understand what had happened. Microsoft could improve this process. Once I figured it out I switched from $10/month to $99 a year. That switch was easy — and MSFT threw in a free month (standard behavior).