Upgrading to Catalina from Mojave stuck at "Estimating time remaining" for days! I was upgrading my 2015 Macbook Pro running Mojave to Catalina. It is stuck at a black screen with the Apple logo and &quot;Estimating time remaining&quot; 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 &quot;Estimating time remaining&quot;. 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 &quot;Estimating time remaining&quot; 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?
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?