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Catch-22 when upgrading both OS and Microsoft

I seem to be caught in an upgrade bind. I want to upgrade my OS from my current Mojave (10.14.6), but the only option is Ventura and it will not support my ancient Word program (Word Office 2008) and I can't risk losing the files I created with Word 2008. Would that even happen?

I also want to upgrade to Microsoft 365 but it requires at least Catalina (11.1). It looks like I can maintain my use of Word 2008 if I upgrade to Catalina (true/false?) and also install MS 365 (then trash the old Word once the 365 is in place), but I can't see any way to upgrade to anything lower than Ventura! Can anyone confirm that Catalina supports the old Word program? Is there any way to upgrade to Catalina?


iMac 21.5″, 10.14

Posted on Feb 8, 2023 2:41 PM

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Question marked as Top-ranking reply

Posted on Feb 8, 2023 2:44 PM

❗️ Do NOT upgrade until you have made a Time Machine or other backup of your startup drive.

Learn How to Back up your Mac with Time Machine


How to Upgrade  macOS:

The macOS version you can upgrade to depends on the year your Mac was released.

Click the  (Apple) menu at the top of your screen and choose About This Mac.


Check the Compatibility of your Mac with newer versions of macOS:

➡️ macOS 10.15 Catalina is compatible with the Macs listed here

➡️ macOS 11 Big Sur is compatible with the Macs listed here 

➡️ macOS 12 Monterey is compatible with the Macs listed here

➡️ macOS 13 Ventura is compatible with the Macs listed here


❗️ – IMPORTANT – None of your 32-bit apps will work in macOS Catalina or newer.

32-bit app compatibility with macOS High Sierra 10.13.4 and later - Apple Support

Use the free utility Go64 to check the compatibility of your apps:

https://www.stclairsoft.com/Go64/


✅ - IF your Mac and apps are compatible, then using Safari only, download the macOS upgrade installer app:

Click > CatalinaBig SurMonterey  or  Ventura.

Once downloaded, double-click the “Install macOS…” app in the Applications folder to begin the upgrade.


Please see > How to download macOS.


4 replies
Question marked as Top-ranking reply

Feb 8, 2023 2:44 PM in response to GonzoJoey

❗️ Do NOT upgrade until you have made a Time Machine or other backup of your startup drive.

Learn How to Back up your Mac with Time Machine


How to Upgrade  macOS:

The macOS version you can upgrade to depends on the year your Mac was released.

Click the  (Apple) menu at the top of your screen and choose About This Mac.


Check the Compatibility of your Mac with newer versions of macOS:

➡️ macOS 10.15 Catalina is compatible with the Macs listed here

➡️ macOS 11 Big Sur is compatible with the Macs listed here 

➡️ macOS 12 Monterey is compatible with the Macs listed here

➡️ macOS 13 Ventura is compatible with the Macs listed here


❗️ – IMPORTANT – None of your 32-bit apps will work in macOS Catalina or newer.

32-bit app compatibility with macOS High Sierra 10.13.4 and later - Apple Support

Use the free utility Go64 to check the compatibility of your apps:

https://www.stclairsoft.com/Go64/


✅ - IF your Mac and apps are compatible, then using Safari only, download the macOS upgrade installer app:

Click > CatalinaBig SurMonterey  or  Ventura.

Once downloaded, double-click the “Install macOS…” app in the Applications folder to begin the upgrade.


Please see > How to download macOS.


Feb 8, 2023 2:56 PM in response to GonzoJoey

There is no Catch 22. If you upgrade to a newer operating system you must also upgrade your Microsoft Office to use it on the newer operating system. This has no impact on your existing documents. You will still have access to your documents.

Make sure you have a data backup before upgrading your OS. You should maintain backups regularly.

Feb 9, 2023 3:30 AM in response to GonzoJoey

Whether current Microsoft 365 or Office 2021 for Mac, Microsoft no longer supports new installations on macOS Catalina as they dropped support for that operating system. Catalina and later versions of macOS require 64-bit applications and Office 2008/2011 fail that test.


Your Office 2008 for Mac documents are preserved on future versions of macOS. I have Word documents created by Word 95 that I still open on Ventura.

Catch-22 when upgrading both OS and Microsoft

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