iMac prompting for password after setting 'Require Password' to 'never'

This setting refers to when you lock the screen or the screen saver starts.

It does not change what happens if you log out or restart your mac.

Now you could make it so you do not have to type your password when starting.

I have to advise against it, but it's possible - unless, as dialabrain suggested, you have FileVault (then you will always need the password).

Here is how: In System Settings->Users & Groups, turn on "Automatically log in as", and choose your account.

Again, this is probably a bad idea, but it's your call.

Let's go over it again:

Setting that to "never" is only for the screen saver and lock screen.

If you want you mac to start an log you in without a password, you have to go to

System Settings->Users & Groups and change "Automatically log in as " from "Off" to the name of your account.

ALSO.... you will want to make sure that you are not logged out automatically after some period of inactivity/

In

System Settings->Privacy & Security

go all the way to the bottom, click "Advanced..." and turn OFF "log out after inactivity":

Crowsfeet48 wrote:

Are you saying I shouldn't turn off filevault?

If you want the ability to log in without password, you HAVE to turn File Vault OFF.

By the way, it is normal that it is taking a long time, since it needs to decrypt the whole drive.

Once it finishes, you can do as I wrote above, to enable automatic login.

If after you've tried everything and you still have to log into your user account when starting up give this a try: boot into Safe Mode according to How to use safe mode on your Mac and reboot normally and test.

NOTE 1: Safe Mode boot can take up to 3 - 5 minutes as it's doing the following; 

• Verifies your startup disk and attempts to repair directory issues, if needed

• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)

• Prevents Startup Items and Login Items from opening automatically

• Disables user-installed fonts 

• Deletes font caches, kernel cache, and other system cache files

NOTE 2: if you have a wireless keyboard with rechargeable batteries connect it with its charging cable before booting into Safe Mode. This makes it act as a wired keyboard as will insure a successful boot into Safe Mode.

Did you enable FileVault?

After File Vault is un-encrypted go to the Systgem ➙ Users & Groups settings pane and set you to be automatically logged in when booting us like this:

Crowsfeet48 wrote:

Nevermind, I found it and it is on

You would need to disable it.