Ask Paul: Has the Office 365 Personal to Office 365 Home Loophole Closed?

A few months back, I wrote about how you could convert an Office 365 Personal subscription—which comes free on many new Windows PCs and devices these days—into a more useful Office 365 Home subscription for just $9.99. This week, however, a reader is wondering whether that loophole has closed.

To understand the question, be sure to check out Tip: Convert Office 365 Personal to Office 365 Home for Just $9.99. Long story short, you can convert an Office 365 Personal subscription to an Office 365 Home subscription for just $9.99. Better yet, if you have multiple Office 365 Personal subscriptions, you can “stack” them on the same Microsoft account—which extends the time of the subscription out for one year for each subscription and then upgrade to Office 365 Home, still at a cost of just $9.99.

OK. Let’s check out today’s question.

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James D. asks:

It looks like Microsoft has closed their “loophole upgrade.” I finally had a free day to visit Microcenter, [bought] the WinBook TW802 tablet and tried to apply the key to my [Microsoft] account. But it wants to downgrade me [from Office 365 Home to Office 365 Personal]. So Microsoft saw a loophole and closed it … I tried Microsoft support and was told I could downgrade to Office 365 Personal or toss the key and pay $100/year for Office 365 Home.

So it’s not clear to me that the loophole is closed.

Doing this has always required that the Microsoft Account you sign in with does not already have an associated Office 365 subscription. I wrote about this in Tip: Convert Office 365 Personal to Office 365 Home for Just $9.99:

“Can you add an Office 365 Personal subscription to a Microsoft account that already has an Office 365 Home subscription? The answer is no. And what you see if you try will depend on whether the account is part of an Office 365 Home subscription—in which case you can leave and change to Personal, freeing up that Home license for someone else—or are the owner of the Home subscription. If it’s the latter, you will need to wait until the Home subscription runs out or simply use the Personal subscription with another Microsoft account.”

The other problem is, once you’ve added a Personal subscription and then upgrade it to Home, you can no longer add more Personal subscriptions. So if you want to stack subscriptions, you have to add two or more personal subscriptions first, and then upgrade.

Anyway, I feel like this was all adequately explained in the original tip, but I did want to raise this issue for two reasons. It’s reasonable for people with an Office 365 Home subscription to purchase a new Windows device and want to “add” that subscription to their existing one, extending it out perhaps, or just adding an addition user. But Microsoft does not allow that. And second, for all I know, that $9.99 conversion/upgrade loophole could very well be closed now regardless. I sort of doubt it, but if anyone has done this recently, I’d love to hear about it.

UPDATE: According to several people, this loophole continues to work just fine.

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