Feb 21, 2019  The next video is starting stop. Local Items Keychain asking for password - Duration. Folder Lock without additional software in Mac OS Mojave 2018. Duration: 4:26. Oct 28, 2014  In this post, I’ll show you how to stop macOS from asking for a password after waking up your Mac. How to stop having to log in to your Mac every time. Obviously, if security is important to you, you should avoid what I’m about to share. If you work in an office or if you have people around your computer, again, skip all that and maintain a. Sep 15, 2019 2 How to Disable the Login Password on Mac when Waking Up. 2.1 Follow these steps to disable the password when waking up: 3 How to Disable the Login Password on Mac When Switching Users. 3.1 Follow these steps to create a blank password on your Mac; 3.2 Creating a new Mac user and want a blank password? 4 Always have an additional Mac Admin.

I recently upgraded my MacOS Sierra and now ssh command keep asking for passphrase as follows when I try to login to my remote Linux/Unix server:

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Enter passphrase for key ‘/Users/vivek/.ssh/id_ed25519’:
How do I fix MacOS Sierra upgrade that keep breaking ssh keys in terminal?
My MacOS used to remember the ssh passphrase, but now it is asking it to me each time when I try to login to local FreeBSD nas server or remote Ubuntu server when I type:
$ ssh user@server
$ ssh vivek@server1.cyberciti.biz

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Sample outputs:
Let us see how to fix the MacOS sierra upgrade breaking my SSH keys using various methods.

Method #1: Fix when macOS keeps asking ssh passphrase after updated to Sierra or after reboots

You need to use the UseKeychain option in your ~/.ssh/config file. From the ssh_config man page:

On macOS, specifies whether the system should search for passphrases in the user’s keychain when attempting to use a particular key. When the passphrase is provided by the user, this option also specifies whether the passphrase should be stored into the keychain once it has been verified to be correct. The argument must be yes or no. The default is no.

This is the easiest and recommended solution for all users. Edit your ~/.ssh/config file:
$ vi ~/.ssh/config
Append the following line in Host * section:

Here is my sample file:

Save and close the file. This should force ssh to remember user’s key in the keychain:
$ ssh user@server
$ ssh vivek@server1.cyberciti.biz

Method #2: Use ssh-agent/ssh-add to add all known keys to the SSH agent

The syntax is as follows to use SSH Keys on a Linux / Unix / MacOS System:

Method #3: Use keychain

OpenSSH offers RSA and DSA authentication to remote systems without supplying a password. keychain is a special bash script designed to make key-based authentication incredibly convenient and flexible. It offers various security benefits over passphrase-free keys.

Install the keychain as follows:

$ brew install keychain
Sample outputs:

Append the following code in your ssh profile (assuming that you are using id_rsa file):

See “keychain: Set Up Secure Passwordless SSH Access For Backup Scripts” for more info.