My MacBook Pro (ret. mid 2014) in having issues updating to macOS Catalina 10.15.6. When i press "Install Now", it displays that I need to restart my computer. When I click the tab, it restarts but doesn't update.

iflyproductions Said:

"My MacBook Pro (ret. mid 2014) in having issues updating to macOS Catalina 10.15.6. When I press "Install Now", it displays that I need to restart my computer. When I click the tab, it restarts but doesn't update."

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Try a Manual Update:

Perform the following in the order provided.

1. Back up your Mac:

Start by creating a Time Machine backup of your Mac, so that you can have something to restore your Mac from, should anything go wrong with the install. Use an external hard drive at least 1.5 (one-and-a-half) times the size of the built in drive's total storage capacity)

2. Download the Installer

Get it Here: macOS Catalina 10.15.6 Update - Apple

3. Run the Installer:

Try installing it in the current user. If it still does not work, then create a new Administrator user and try the install once more. If that does not work, then install it through Safe Mode (Hold Down: shift key upon boot)

Here is how it is supposed to work:

Installer sets startup to the new MacOS Base System you downloaded (as if it were a disk) and does a Restart.

>> a failure right here means you still have everything on your old drive, (plus about 6GB or more of MacOS Base system that does not work)

ONLY if Restart was successful do you begin replacing files to move to the new version of macOS. Time 30 minutes to 3/4 hour.

Restart again and comes up running the new version, in Setup Assistant. 

¿Do you have a firmware-lock password in place?