Jun 16, 2020 If you're using OS X El Capitan v10.11.5 or later and your App Store preferences or Software Update preferences are set to download new updates when available, macOS Catalina will download conveniently in the background, making it even easier to upgrade. A notification will inform you when macOS Catalina is ready to be installed. Oct 09, 2019 Mac doesn’t start after macOS Catalina installation. Some users report no issues with downloading and installing the macOS Catalina but their Mac hangs with the spinning icon when trying to startup following the update. Other issue that is often reported is that the boot sequence starts correctly and then shows a progress bar.
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Welcome to Apple Support Communities. I understand you're unable to update to macOS Catalina as you continue to see 'Upgrade Now.' I'll be happy to help and point you in the right direction.
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If you haven't tried yet, I recommend to start up your Mac in safe mode. You can review the benefits and details of how to start up your Mac in safe mode through this helpful article: Use safe mode to isolate issues with your Mac Once that's done, you can then restart your Mac normally and attempt the update for macOS Catalina. In addition, please be sure you have enough available storage space for the update. Here's how: How to free up storage space on your Mac
For any reason you continue to experience the same behavior, I suggest creating another user account on your Mac and attempt to update the software. If needed, here's how to create a user account on your Mac: How to test an issue in another user account on your Mac
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