Microsoft inactivating Office 2019 demanding I get 365

I own a copy of Microsoft office 2019 which is installed and running on my Intel MacBook Pro (running Sonoma). I recently had to restore that machine from my Time Machine (TM) backup and everything, including office, works. Thats the good news.

The bad and ugly part? I bought a new M4 Max laptop and restored my computer using the same TM backup. all is well EXCEPT office which is now inactivated (cannot modify files, read only) until I activate office 365 which I do not want. that is the bad part- what right do they have to prevent me from using a software I own?


The ugly part? what is it in the latest OS that enables Microsoft to inactivate a legitimate piece of software and how can I restore my 2019 office?


MacBook Pro 14″, macOS 15.5

Posted on Jul 4, 2025 9:44 AM

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Posted on Jul 4, 2025 11:34 AM

MS made the decision some years back to support the perpetual license versions of Office for only three major Mac OS releases. For Office 2019, that means Catalina, Big Sur and Monterey. If you don't include Catalina, since that came out the same year as Office 2019, then it would be Big Sur, Monterey and Ventura. That's why you can't activate it on your new M4 laptop.


But then it gets kind of messy. As you of course know, 2019 is running under Sonoma on your Intel based Mac, even though it's past the three year support period. That's because it's already activated for that Mac, and most importantly, the file(s) Office uses to check and see if the suite has been activated are on the Mac itself. As long as it can find those files, it will keep running. If there were any, it would refuse to install any further updates for Office 2019. But MS doesn't even list updates for the 2019 versions anymore.


You really have only one choice to avoid the subscription based 365 on the new Mac, and that's to purchase the latest perpetual license, Microsoft 2024, for the new Mac.


The Group Containers folder in your user account (~/Library/Group Containers) you restored to the new Mac do have the activation files in them. This is what Office looks for when you launch an app to see if it's been activated or not. But they're not just simple yes/no files. They hold identifying data of the hardware it was activated under, and they of course do not match the new Mac.


Assuming if you purchase Microsoft 2024 with the standard 5 user license, you'll be able to install it on both the older and new Mac as its three year support span is Sequoia, Sonoma and Ventura. Which is nonsensical, but that's what MS is saying now, despite the fact the 2024 version didn't arrive until macOS Sonoma was the current OS. So it should really cover Sonoma, Sequoia and the upcoming Tahoe.

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Jul 4, 2025 11:34 AM in response to RKopan

MS made the decision some years back to support the perpetual license versions of Office for only three major Mac OS releases. For Office 2019, that means Catalina, Big Sur and Monterey. If you don't include Catalina, since that came out the same year as Office 2019, then it would be Big Sur, Monterey and Ventura. That's why you can't activate it on your new M4 laptop.


But then it gets kind of messy. As you of course know, 2019 is running under Sonoma on your Intel based Mac, even though it's past the three year support period. That's because it's already activated for that Mac, and most importantly, the file(s) Office uses to check and see if the suite has been activated are on the Mac itself. As long as it can find those files, it will keep running. If there were any, it would refuse to install any further updates for Office 2019. But MS doesn't even list updates for the 2019 versions anymore.


You really have only one choice to avoid the subscription based 365 on the new Mac, and that's to purchase the latest perpetual license, Microsoft 2024, for the new Mac.


The Group Containers folder in your user account (~/Library/Group Containers) you restored to the new Mac do have the activation files in them. This is what Office looks for when you launch an app to see if it's been activated or not. But they're not just simple yes/no files. They hold identifying data of the hardware it was activated under, and they of course do not match the new Mac.


Assuming if you purchase Microsoft 2024 with the standard 5 user license, you'll be able to install it on both the older and new Mac as its three year support span is Sequoia, Sonoma and Ventura. Which is nonsensical, but that's what MS is saying now, despite the fact the 2024 version didn't arrive until macOS Sonoma was the current OS. So it should really cover Sonoma, Sequoia and the upcoming Tahoe.

Jul 5, 2025 6:07 AM in response to RKopan

Another thought occurred to me: the code for Office 2019 and for Microsoft 365 (from several years ago) might be the same code, with the functionality that you get depending on whether you activate it with a Microsoft 365 "key" or an Office "key". If so, it is possible that initially, the user interface will always say that you need to activate "365" but that if you enter the "key" you used to activate Office (or log in to your Microsoft Account, or whatever it is that they want you to do to satisfy the DRM), the code will activate and you will get Office 2019 back. (Depending upon how Microsoft arranges their DRM, you might need to deactivate it on the old machine first - with the possible risk of not being able to reactivate it on either machine. If in doubt, contact Microsoft Support for help.)


--------------------


If that doesn't work out, or you just want to move on …


Microsoft 365 – Compare All Microsoft 365 Products has a table comparing the Microsoft 365 "subscription" plans with Office Home 2024.


If you want to try LibreOffice, it's free (although the developers will be happy to accept donations).

Jul 5, 2025 5:55 AM in response to RKopan

RKopan wrote:

The ugly part? what is it in the latest OS that enables Microsoft to inactivate a legitimate piece of software


Applications can check to see what version of macOS is running. There doesn't have to be anything special in the latest OS to "enable Microsoft" to do this to you. It would just be a matter of Microsoft deciding to do this to you. They could have put code to let them do that into Office 2019 from the start – where it lay dormant, just waiting for them to trigger it. Or they could have introduced it in an Office 2019 update.


Microsoft Support – Upgrade macOS to continue receiving Microsoft 365 and Office for Mac updates


and how can I restore my 2019 office?


If Microsoft is deliberately blocking you, the answer might be "You can't." But for whatever it's worth:


Microsoft Support – Activate Office for Mac

Microsoft Support – What to try if you can't install or activate Office for Mac

Jul 6, 2025 12:16 PM in response to RKopan

RKopan wrote:

Actually I did own it- it was perpetual use license.


Perpetual licenses don’t usually convey software compatibility with newer configurations and newer versions.


The apps will work for what they were sold for, in the configuration they were sold for, but may not or will not work for newer versions of the licensed app, or for newer or different configurations outside what the licensed app was originally supported with.


If you’re in the original licensed configuration, then the perpetual licenses will run until either the hardware fails, or some other part of the system configuration fails. It is perpetual.


However, there are few (no?) non-trivial apps software that can exist and continue to function without ongoing maintenance and updates, across newer versions or newer architectures or other changes.


No commercial vendor can survive financially by offering a perpetual license and forever support. That can be a great deal for a buyer certainly, and can be initially workable for the vendor. Until the vendor then financially implodes.


AFAIK, Office 2019 is not supported in the configuration you want:


For issues, questions, or concerns about Microsoft apps and licensing, best contact Microsoft, or the Microsoft forums.

Jul 4, 2025 11:59 AM in response to RKopan

If you want to use Microsoft tools, then Windows 11 is your preferred platform, and Azure is your preferred hosting provider, and Microsoft will do what they can to steer all other users elsewhere onto those platforms.


If you decide you don’t want to do that, then you will still need to maintain the current versions of the Microsoft 365 Copilot tools, and maintain one of the three most recent macOS versions, and the “perpetual” license.


If you don’t want to do that either, then your options can include the Apple iWork tools, as well as LibreOffice or OnlyOffice, among other fine choices. These and other tools can successfully read and write most Office documents.


For assistance with Microsoft licensing, contact Microsoft. I’d expect they’ll want you to buy a new license here, too. Options for migrating Microsoft products to other computers was limited, when last I checked.

Jul 5, 2025 6:22 AM in response to RKopan

RKopan wrote:

that is the bad part- what right do they have to prevent me from using a software I own?


Along the same lines – Adobe got rid of "one-time purchase" options for most of their products long ago. Now the remaining one-time purchase products – Photoshop and Premiere Elements – have time bombs.


E.g., for Photoshop Elements,



"The license enables you to use Photoshop Elements for a full 3-year term. It’s a one-time purchase with no additional fees. The license is non-renewing — it expires 3 years after redemption. When your 3-year term license expires, the Photoshop Elements Editor will no longer be accessible."


So even if there are no changes in future versions of macOS that break Photoshop Elements 2025, it is designed to (partially) self-destruct three years after you start using it!!!

Jul 5, 2025 12:32 PM in response to RKopan

RKopan wrote:

Exactly as you would expect: I ** not registered as an owner of 365. no mention of my previous license.


Then you have your answer.


For legitimate access to Microsoft 365 Copilot, available options include a new perpetual license, or a subscription, or a license transfer where permissible.


Transfer info:


Alternatively, you can migrate to one of the other fine tools available.


This is how Microsoft designs, operates, and licenses their wares.

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Microsoft inactivating Office 2019 demanding I get 365

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