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I was upgrading my 2015 Macbook Pro running Mojave to Catalina. It is stuck at a black screen with the Apple logo and "Estimating time remaining" for several days now.

During that time, I hard rebooted several times out of frustration after hours of waiting, each time I got a normal-looking login window and I then input my username and password and got logged in, after which it resumed to the same black screen with the Apple logo and "Estimating time remaining". But the progress indicator kept at approximately the same location which is about 1/6 of the entire length. There were also a few times when the machine shut down itself and when I found out about it I pressed the power button to start it manually. After that the normal-looking login window showed up again and I then input my username and password to log in. And the same black screen with the Apple logo and "Estimating time remaining" show up again but the progress indicator stayed at approximately the same place. It is the third day it has been doing that now. What should I do?

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3 Answers 3

Reset to default
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One thing you can try is to start up to your previous system and try the upgrade again. Press the option key on start and choose macOS Mojave or whatever your root volume is called. This will get you out of the recurring upgrade process.

Regarding the login window, do you have FileVault enabled?

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    How do I exactly tell if FileVault is enabled? All I remember seeing is a login window as normal, my avatar above, and an input field for password. text indicating "FileVault" visible anywhere.
    – qazwsx
    Commented Jun 25, 2020 at 3:57
  • You can tell from System Preferences (Security and Privacy>Firevault), or from Disk Utility (look under your root volume. If it says APFS Volume • APFS (Encrypted), then it's FileVault enabled)
    – Joy Jin
    Commented Jun 25, 2020 at 9:45
  • I checked. FileVault is indeed on. Does it matter? Is it making the upgrade easier to be stucked?
    – qazwsx
    Commented Jun 27, 2020 at 11:28
  • Is there anything I may do with my current FileVault setting to help with the situation in the OP?
    – qazwsx
    Commented Jun 27, 2020 at 23:57
  • FileVault being on means that the login screen is normal. It does not make the upgrade easier to be stuck. It matters because I'm confident now that this is a normal update being stuck situation, because the login screen should NOT appear before the progress bar in normal update (i.e. without FileVault).
    – Joy Jin
    Commented Jun 29, 2020 at 2:09
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The end of the story is that I basically kept trying rebooting and allowing the installation process to retry itself and after a few days, for whatever reason, it went through and finished the installation. So it stays a mystery both why it was repeatedly stuck and why it got thorough the last time. It was a through test of my patience, I have to say.

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After trying every possible suggestion I could find online, I managed to succeed by using Disk Utility to erase my SSD and have a fresh install.

My hypothesis that the file system might have been corrupted made even more sense when I found out that a particular file in the ~/Library dir would never finish copying.

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