That iMac will run the current Big Sur, but likely won’t be supported with the upcoming Monterey it’s not supported by the Monterey beta. hypervisor guest), or learning more about how to manage an older OS X version that’s fallen off support. The Adobe tools and Microsoft Office (2011 and earlier, 2016 and newer should work) will probably continue to work as expected through Mojave, but you’re not going to get around not upgrading older apps forever, and will be looking at alternatives for those apps, or for upgrades, or for other approaches (e.g. Use only Safari to download the macOS version you choose: How to get old versions of macOS - Apple Support But there have been upgrades, with those arriving roughly yearly in recent years. As a guess here, you’ve probably been checking for software updates on occasion, and there have been few or no updates. Software updates are offered easily, while you have to specifically request an upgrade. Upgrades can be and usually are larger changes, and some upgrades can or will disrupt apps or can then require app updates. Some other background about macOS updates and upgrades: Apple differentiates “updates” from “upgrades”, with updates being smaller fixes and changes not expected to disrupt apps. …If you post the Mac model year here, we we tailor upgrade information and info about known wrinkles to your available upgrade options. If you are not sure which model year your iMac 27” is, you can use □ > About This Mac to see that info. If yet newer, yet newer upgrade choices are available. If your iMac is late 2012 or newer, it can be upgraded to Mojave. If your iMac 27” is late 2009 or newer, it can be upgraded to High Sierra. Upgrading to High Sierra or newer will resolve this certificate case, yes.
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