Since upgrading to High Sierra, I’ve had to manually add keys after every reboot using ssh-add like this:
ssh-add -K
I don’t reboot often but for a while I was rebooting often enough to make it annoying. So I found that you can link ssh with MacOS keychain using your .ssh/config file, add all the keys to your agent, and everything works smoothly.
Host *
UseKeychain yes
AddKeysToAgent yes
Then add all your keys to the keychain using
ssh-add -KA