It seems that ssh-add -K ~/.ssh/id_rsa will load your key but will ask for the password each time you reboot.

I am looking for a solution that would not require me to re-enter the key password between logins.

  • 1
    Can you say a little more about when the password prompt comes up for you? I ask because I have an ssh-key for a remote server, which I assure you is not the same as my Mac login password or anything, and I haven't had to enter the password for the ssh-key for years. I can just open up a terminal, type "ssh <server>", and I'm there. I think I first set this key up under OSX 10.5. id_dsa, but I don't think that should matter.
    – Michael H.
    Apr 13 '12 at 16:39
  • My id_rsa key has a password on it.
    – sorin
    Apr 13 '12 at 16:46
  • I also have the problem that I solved this so long ago that I can't remember exactly what I did. But I think the idea is to not run ssh-add, but just run ssh directly. You should get a window popping up that will as the pass phrase for the key, and with a checkbox to let you store it in your keychain. Apr 13 '12 at 18:19
  • 1
    @Sorin - so does mine! I had to enter it once, long ago, and the Mac has saved it for me ever since. Hopefully Harald's advice will help.
    – Michael H.
    Apr 13 '12 at 18:35
  • Do you mean the Keychain password (i.e. your login password) or the key's passphrase? If it's the latter, re your passphrases definitely stored in Keychain? You can check this by opening Keychain Access and looking for it in the login keychain. Apr 20 '12 at 11:41

On OSX, the native ssh-add client has a special argument to save the private key's passphrase in the OSX keychain, which means that your normal login will unlock it for use with ssh. On OSX Sierra and later, you also need to configure SSH to always use the keychain (see Step 2 below).

Alternatively you can use a key without a passphrase, but if you prefer the security that's certainly acceptable with this workflow.

Step 1 - Store the key in the keychain

Just do this once:

ssh-add -K ~/.ssh/[your-private-key]

Enter your key passphrase, and you won't be asked for it again.

(If you're on a pre-Sierra version of OSX, you're done, Step 2 is not required.)

Step 2 - Configure SSH to always use the keychain

It seems that OSX Sierra removed the convenient behavior of persisting your keys between logins, and the update to ssh no longer uses the keychain by default. Because of this, you will get prompted to enter the passphrase for a key after you upgrade, and again after each restart.

The solution is fairly simple, and is outlined in this github thread comment. Here's how you set it up:

  1. Ensure you've completed Step 1 above to store the key in the keychain.

  2. If you haven't already, create an ~/.ssh/config file. In other words, in the .ssh directory in your home dir, make a file called config.

  3. In that .ssh/config file, add the following lines:

     Host *
       UseKeychain yes
       AddKeysToAgent yes
       IdentityFile ~/.ssh/id_rsa

    Change ~/.ssh/id_rsa to the actual filename of your private key. If you have other private keys in your ~/.ssh directory, also add an IdentityFile line for each of them. For example, I have one additional line that reads IdentityFile ~/.ssh/id_ed25519 for a 2nd private key.

    The UseKeychain yes is the key part, which tells SSH to look in your OSX keychain for the key passphrase.

  4. That's it! Next time you load any ssh connection, it will try the private keys you've specified, and it will look for their passphrase in the OSX keychain. No passphrase typing required.

  • 8
    @Poulsbo & @Abram -- see my update, Sierra changed the automatic behavior and now you have to run ssh-add -A manually to load your saved keychain. Some possible solutions referenced above.
    – trisweb
    Jan 3 '17 at 22:20
  • 3
    @trisweb Thanks for the tip. joshbuchea's solution of modifying the .ssh/config file looks promising! See github.com/lionheart/openradar-mirror/issues/…
    – Poulsbo
    Jan 6 '17 at 21:19
  • 18
    Works great! In my case I needed to use the A flag in addition to the K one to add my keys to the keychain and register the passphrase into it (ssh-add -AK ~/.ssh/[your-private-key]). Thanks!
    – youssman
    Mar 7 '17 at 22:28
  • 4
    Even with the usekeychain option, I still find that my keychain will drop the .ssh/id_rsa key on reboot.
    – Chogg
    May 2 '18 at 18:39
  • 4
    I did exactly the same and my Mac still drops the key on reboot. Nov 22 '18 at 8:57

I had a similar problem, in that I was being asked every time for my pub-key passphrase. Per suggestion of user "trisweb" above, I turned on these options to ~/.ssh/config:

Host *
  UseKeychain yes
  AddKeysToAgent yes
  IdentityFile ~/.ssh/id_rsa

But it still prompted every time I wanted to use ssh. Eventually I turned on ssh -v and found this debug line:

debug1: key_load_private: incorrect passphrase supplied to decrypt private key

I then opened my keychain in "Keychain Access.app", found the key named "SSH: /Users/username/.ssh/id_rsa" and opened it up. I clicked "Show password" to disclose the password and indeed found that the passphrase in the keyring was an old passphrase. I updated the passphrase in Keychain Access, and now password-free works.

I could have also updated the passphrase with this phrase:

ssh-keygen -p -f ~/.ssh/id_rsa
  • In my Mac the password is saved in “password” category of “iCloud” chain. I thought it was in “log in” chain. Mar 31 '20 at 4:53

To all where the above did not work, my issue appears to have been because I was duplicating the UseKeychain yes & AddKeysToAgent yes in all ssh key profiles / shortcuts. I updated my ~/.ssh/config file to declare these only once and they now all load on login without prompting for passwords on startup, e.g:

Host *
  UseKeychain yes
  AddKeysToAgent yes
  IdentityFile ~/.ssh/foo
  IdentityFile ~/.ssh/bar

Host foo
  HostName foo.com
  User fooUser
  IdentityFile ~/.ssh/foo

Host bar
  HostName bar.com
  User barUser
  IdentityFile ~/.ssh/bar
  • 3
    I would recommend Host * be after specific host rules. See man ssh_config for details. Mar 31 '20 at 4:31
  • 1
    Thank you so much for this. Where are the docs for this i.e. how did you work this out? Jun 15 at 16:06
  • 1
    ...actually, this did not work for me: I have a setup where Host bar has HostName foo.com too (i.e. two different configs for the same site). IdentityFile ~/.ssh/foo was always used. To fix, I had to move the Host * section to the bottom, as @FranklinYu suggests. I think this is because > For each parameter, the first obtained value will be used. linux.die.net/man/5/ssh_config Jun 18 at 3:34

Also, in macOS Sierra and HighSierra (don't know about previous versions), running ssh-add -A will get the agent to load all keys whose passphrases are stored on Keychain... So very handy


Add the public key in:


Public key usually are on:


Hope that helps

  • 9
    I think mean the authorized_keys May 23 '12 at 18:47
  • Anyway, this doesn't work if you have more than one key!
    – sorin
    May 24 '12 at 10:01

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