macOS keeps asking my ssh passphrase since I updated to Sierra

Question

It used to remember the passphrase, but now it's asking it to me each time.

I've read that I need to regenerate the public key with this command, which I did:

ssh-keygen -y -f id_rsa > id_rsa.pub

but it didn't fix anything.

How can I make macOS remember my passphrase again?

Answer 1

In the latest version of macOS (10.12.2), this is easy to fix. Just edit your ~/.ssh/config and enable the UseKeychain option:

Host *
    UseKeychain yes

There is no need to change anything else. Now everything works the way it used to work before the latest updates. You do not need to add keys to ssh-agent.

---

Edit: You may still need to enter your passphrase once. If you don't know it, follow these instructions to reveal it.

Answer 2

I had the same problem. MacOS Sierra keychain keeps asking for the passphrase. Your id_rsa should be encrypted with a passphrase for security. Then try adding it to the keychain ssh-add -K ~/.ssh/id_rsa

If your key is in another folder than ~/.ssh then substitute with the correct folder.

Keychain now knows your ssh key and, hopefully, all works now (mine did)

Answer 3

This fixed my similar issue:

/usr/bin/ssh-add -K

This stores passphrases in your keychain.

Update (thanks @EasyCo):

This works but does not persist between restarts. @jukka-suomela's solution on this page does work across restarts. You can find that answer here:

https://superuser.com/a/1158050/234685

Second update (thanks @user5359531):

In macOS Sonoma 14.x:

The -K and -A flags are deprecated and have been replaced by the --apple-use-keychain and --apple-load-keychain flags, respectively.

Answer 4

I only had to enter the correct passphrase once and it started working. The problem was that I didn't remember my original SSH passphrase, but I recovered it by following these steps from Github:

• In Finder, search for the Keychain Access app.
• In Keychain Access, search for SSH.
• Double click on the entry for your SSH key to open a new dialog box.
• Keychain access dialogIn the lower-left corner, select Show password.
• You'll be prompted for your administrative password. Type it into the "Keychain Access" dialog box.
• Your password will be revealed.

Answer 5

One fix is to add the following to your ~/.ssh/config file:

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

Taken from: https://www.reddit.com/r/osx/comments/52zn5r/difficulties_with_sshagent_in_macos_sierra/ Also see: https://apple.stackexchange.com/a/264974/3810

Answer 6

None of the above solutions worked after installing Sierra over El Capitan on a new MacBook Pro. Sierra by design does not save SSH keys in the keychain.

Two solutions worked for me. One is to add the command ssh-add -A &> /dev/null to ~/.bash_profile. Every time you open the terminal, this command will be executed (the &> /dev/null part sends the output of the command the file /dev/null).

A more complicated but slightly slicker solution is to create a plist with the command that is executed every time the OS is booted as suggested in Saving SSH keys in macOS Sierra keychain. This involves using Xcode to create the file.

Answer 7

I tried multiple answers here, but was still having issues with remote keys passing (such as when using capistrano). To solve it, I read the technote from apple and made this my config file. No more asking for my password!

https://developer.apple.com/library/content/technotes/tn2449/_index.html

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

Answer 8

This morning, I had the same problem as you after updating to Sierra. In my case, the id_rsa file was encrypted and after decrypting it was working like a charm.

1. Verify if your id_rsa file is encrypted with the following command: cat ~/.ssh/id_rsa | head -2
2. If the second line says Proc-Type: 4,ENCRYPTED, it's encrypted and you could try decrypting it
3. Important: make a backup of your original id_rsa file! Use the command cp ~/.ssh/id_rsa ~/.ssh/id_rsa.bak
4. Decrypt your private key with openssl rsa -in ~/.ssh/id_rsa -out ~/.ssh/id_rsa.decrypted
5. Remove the original key (rm ~/.ssh/id_rsa) and replace it with the decrypted one: mv ~/.ssh/id_rsa.decrypted ~/.ssh/id_rsa

After these steps, you should be able to use ssh again.

Answer 9

I started suffering from the same problem using MacOS Monterrey. I just noticed that when I tried to add my key using:

 /usr/bin/ssh-add -K /path/to/my-key

I saw this:

WARNING: The -K and -A flags are deprecated and have been replaced
         by the --apple-use-keychain and --apple-load-keychain
         flags, respectively.  To suppress this warning, set the
         environment variable APPLE_SSH_ADD_BEHAVIOR as described in
         the ssh-add(1) manual page.

So I used:

/usr/bin/ssh-add --apple-use-keychain /path/to/my-key

Added this answer if someone else is suffering from this using MacOS Monterrey.

Answer 10

I had this issue as well when attempting to deploy some code using Capistrano. Very frustrating. Here are two methods I know of to deal with this issue.

Method 1: Add all known keys to the SSH agent.

So one solution I found is to run ssh-add with the -A option—which adds all known identities to the SSH agent using any passphrases stored in your keychain—like this:

ssh-add -A

Now this works but it won’t persist across reboots. So if you want to never worry about this again, just open up your user’s ~/.bash_profile file like this:

nano ~/.bash_profile

And add this line to the bottom:

ssh-add -A 2>/dev/null;

Now when you open a new Terminal window, all should be good!

Method 2: Add only SSH keys that are in the keychain to the agent.

So while the ssh-add -A option should work for most basic cases, I ran into an issue recently where I had 6-7 Vagrant boxes (which uses SSH keys/identities for access) setup on a machine on top of the more common id_rsa.pub in place.

Long story short, I ended up being locked out of a remote server due to too many failed tries based on SSH keys/identities since the server access was based on a password and SSH keys/identities are SSH keys/identities. So the SSH agent tried all of my SSH keys, failed and I couldn’t even get to the password prompt.

The problem is that ssh-add -A will just arbitrarily add every single SSH key/identity you have to the agent even if it’s not necessary to do so; such as in the case of Vagrant boxes.

My solution after much testing was as follows.

First, if you have more SSH keys/identities added to your agent than you need—as shown with ssh-add -l then purge them all from the agent like so:

ssh-add -D

With that done, then start the SSH agent as a background process like so:

eval "$(ssh-agent -s)"

Now, it gets weird and I am not too sure why. In some cases you can specifically add the ~/.ssh/id_rsa.pub key/identity to the agent like so:

ssh-add ~/.ssh/id_rsa.pub

Type in your passphrase, hit Return and you should be good to go.

But in other cases simply running this is enough to get the key/identity added:

ssh-add -K

If that’s all worked, type in ssh-add -l and you should see one lone SSH key/identity listed.

All good? Now open up your .bash_profile:

nano ~/.bash_profile

And add this line to the bottom; comment or remove the -A version if you have that in place:

ssh-add -K 2>/dev/null;

That will allow the SSH key/identity to be reloaded to the SSH agent on each startup/reboot.

UPDATE: Apple has now added a UseKeychain option to the open SSH config options and considers ssh-add -A a solution as well.

As of macOS Sierra 10.12.2, Apple (I assume) has added a UseKeychain config option for SSH configs. Checking the man page (via man ssh_config) shows the following info:

UseKeychain
        On macOS, specifies whether the system should search for
        passphrases in the user's keychain when attempting to use a par-
        ticular 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''.

Which boils down to Apple seeing the solution as either adding ssh-add -A to your .bash_profile as explained in this Open Radar ticket or adding UseKeychain as one of the options in a per user ~/.ssh/config.

Answer 11

Jukka Suomela's answer is correct, but if you are using openssh installed from homebrew, then you also need to uninstall it with:

brew remove openssh

...to switch back to system default openssh, because homebrew's one doesn't support UseKeychain ssh config entry.

Answer 12

You need a .plist file added to ~/Library/LaunchAgents/ to run ssh-add -A on every startup of macOS.

There's a single command which does this (from SSH-keys-in-macOS-Sierra-keychain):

curl -o ~/Library/LaunchAgents/ssh.add.a.plist https://raw.githubusercontent.com/jirsbek/SSH-keys-in-macOS-Sierra-keychain/master/ssh.add.a.plist

Answer 13

I tried all solutions suggested here, but I don't have keychain set up in my Mac.

Adding to following line at top .ssh/config file on both the local and the remote machine worked for me.

PubkeyAcceptedKeyTypes=+ssh-dss 

Answer 14

Updated for Sonoma 14.x...

I was able to add my SSH key to Tower without being repeatedly asked for the password by running this in Terminal:

ssh-add --apple-use-keychain ~/.ssh/id_ed25519

In Mac's newest OS, "The -K and -A flags are deprecated and have been replaced by the --apple-use-keychain and --apple-load-keychain flags, respectively."

You should not need to add/modify ~/.ssh/config using this solution.

Answer 15

In my case, ssh asked for passprase, because i tried to connect without specifying a username:

ssh hostname.com

Remote host considers it as connecting under root. Fixed using my remote host username:

ssh [email protected]