Today I Learned

We need to tell macOS to add the keys to the agent, in order to make them persistent after reboot.

We have to create new file in ~/.ssh/ called config

vi ~/.ssh/config

with the following content:

Host *
   AddKeysToAgent yes
   UseKeychain yes   

Then, we need to add our keys to the agent and macOS keychain (so your private key password is remembered).

ssh-add -D
ssh-add -K ~/.ssh/*

To verify that our keys are present in the agent:

ssh-add -l