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Native Secure Enclave backed SSH keys on macOS

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Re: Native Secure Enclave backed SSH keys on macOS

#12
post #2

It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac. Nothing better that another way to make it even more painful and complicated, so that people will just store plain text keys to not be annoyed.

> It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac. Who uses password encrypted keys anyway ? No exfiltration protection, and a sitting duck for unlimited automated password guessing attempts. Pre-Tahoe people used Yubikeys or Secretive. But now this native tool is a better option than Secretive, even if Yubikeys still have their uses for the power-users.

> Who uses password encrypted keys anyway ?

Edit: I'm not suggesting an ssh key with a passphrase (or password) is better than what the article suggests; I'm only saying that adding a passphrase (or password) to an ssh key at least buys time to address the situation while the attacker is trying to break the encryption on the stolen key.

I am anti-Mac in every way, but I do use passphrase protected ssh keys so if someone were to get a copy of my ssh key, they would have to be able to break the encryption to use the key. I see a lot of devs using blank passphrases on their ssh keys, smh.

> sitting duck for unlimited automated password guessing attempts.

Using a passphrase on your ssh key has nothing to do with whether the ssh service is configured to allow or deny passwords.

Re: Native Secure Enclave backed SSH keys on macOS

#13
If I understand correctly, this means you can't back up the private key, correct? It's in the Secure Enclave, so if you lose your laptop, you also lose the key? Since it looks like export only really exports the public key not the private one?

Probably not the worst thing, you most likely have another way to get into the remote machine, or an admin who can reset you, but still feels like a hole.

Or am I missing something?

ps. It amuses me that my Mac won't let me type Secure Enclave without automatically capitalizing it.

Edit: I understand good security is having multiple keys, I was simply asking if this one can be backed up. OP answered below and is updating their webpage accordingly.

Re: Native Secure Enclave backed SSH keys on macOS

#15
post #2

It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac. Nothing better that another way to make it even more painful and complicated, so that people will just store plain text keys to not be annoyed.

> It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac

I'm anti-Mac but for the year recently that I had to use one at work, no choice...I had no issues, none, using gpg or using a passphrase on my ssh keys.

Re: Native Secure Enclave backed SSH keys on macOS

#16
post #13

If I understand correctly, this means you can't back up the private key, correct? It's in the Secure Enclave, so if you lose your laptop, you also lose the key? Since it looks like export only really exports the public key not the private one? Probably not the worst thing, you most likely have another way to get into the remote machine, or an admin who can reset you, but still feels like a hole. Or am I missing somet…

Correct. Set up multiple keys as backups. Thats also a positive, as nothing can leak the key.

Re: Native Secure Enclave backed SSH keys on macOS

#17
post #13

If I understand correctly, this means you can't back up the private key, correct? It's in the Secure Enclave, so if you lose your laptop, you also lose the key? Since it looks like export only really exports the public key not the private one? Probably not the worst thing, you most likely have another way to get into the remote machine, or an admin who can reset you, but still feels like a hole. Or am I missing somet…

Inability to export the private key is no different from using an YubiKey? You can't "backup" the private key they generate either.

Re: Native Secure Enclave backed SSH keys on macOS

#18

Earlier quoted context omitted.

> It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac. Who uses password encrypted keys anyway ? No exfiltration protection, and a sitting duck for unlimited automated password guessing attempts. Pre-Tahoe people used Yubikeys or Secretive. But now this native tool is a better option than Secretive, even if Yubikeys still have their uses for the power-users.

> Who uses password encrypted keys anyway ? Edit: I'm not suggesting an ssh key with a passphrase (or password) is better than what the article suggests; I'm only saying that adding a passphrase (or password) to an ssh key at least buys time to address the situation while the attacker is trying to break the encryption on the stolen key. I am anti-Mac in every way, but I do use passphrase protected ssh keys so if some…

> whether the ssh service is configured to allow or deny passwords.

Given the consistent use of "password" instead of "passphrase", I think they meant an exfil'ed encrypted key is vulnerable to no-rate-limit bruteforcing, in contrast with hardware-backed keys.

Re: Native Secure Enclave backed SSH keys on macOS

#19
post #14

I’m a bit confused as to why you can export the keys. Can someone explain this?

TFA: > Note that the "private" key here is just a reference to the FIDO credential. It does not contain any secret key material.

Ah, ok, I missed that bit. Thank you!

Re: Native Secure Enclave backed SSH keys on macOS

#20

Earlier quoted context omitted.

> It's a total pain in the ass to try to have password encrypted gpg or ssh keys in mac. Who uses password encrypted keys anyway ? No exfiltration protection, and a sitting duck for unlimited automated password guessing attempts. Pre-Tahoe people used Yubikeys or Secretive. But now this native tool is a better option than Secretive, even if Yubikeys still have their uses for the power-users.

> Who uses password encrypted keys anyway ? Edit: I'm not suggesting an ssh key with a passphrase (or password) is better than what the article suggests; I'm only saying that adding a passphrase (or password) to an ssh key at least buys time to address the situation while the attacker is trying to break the encryption on the stolen key. I am anti-Mac in every way, but I do use passphrase protected ssh keys so if some…

The parent means that an attacker has unlimited attempts at breaking the passphrase on an exfiltrated key. Once the key passphrase is broken, they can log in using the key.
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