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Re:Protecting SSH Keys with macOS Secure Enclave by larusso on Wednesday November 11, 2026 @12:14AM (#50449973)
I used yubikeys for ssh for years. First via the older clunky gpg as ssh key feature. Then via the FIDO api. My biggest issue was the chicken and egg issue when using this setup on a new machine or god forbid in a container etc. windows and WLS wasn’t super thrilled either. I switched to 1Password ssh because I actually like the fact that I can simply share my keys. It’s still not perfect. Agent forwarding needs an extra configuration and depending how many keys you have and how verbose your ssh config gets it becomes also very finicky. This solution feels for me like a slight setback because it’s a macOS only solution. If you have a Linux or windows machine next to a Mac you have to deal with the insecure key file on your hard drive again either via yubi keys or software solutions.

But I think I would take this over a yubikey. I really disliked the fact that one usb port was constantly in use.

Re:Protecting SSH Keys with macOS Secure Enclave by nubb on Wednesday November 11, 2026 @12:26AM (#50450010)
you can’t just pop it out once you’re logged in?
Re:Protecting SSH Keys with macOS Secure Enclave by larusso on Wednesday November 11, 2026 @12:43AM (#50450077)
Sure and pop in whenever I do a git commit? I also sign my commits. I used GPG (different key on the same hardware key) and now via SSH key. I had both a compact and bigger key. I got the compact key because my very first yubikey nearly broke. I lifted my Mac while it was connected and it cracked in the middle. I bought a compact one next which can stay inside and that one you don’t want to take out. It’s so small you’ll lose it. I know because that happened to my backup key … (that was actually the idea for the bigger one I bought but I lost the damn thing during the setup phase) But having the yubikey bound to your Mac at all times is also stupid because it doesn’t come with a fingerprint or other biometric sensor. The idea is that you use this thing as a token not that you leave the key in the lock at all times. For that alone I would favor the enclave solution.
Re:Protecting SSH Keys with macOS Secure Enclave by LeBit on Wednesday November 11, 2026 @01:26AM (#50450291)
The Yubikey 5 Nano and 5C Nano DO come with touch.

The idea is precisely that you keep them permanently connected in the laptop.

Re:Protecting SSH Keys with macOS Secure Enclave by what on Wednesday November 11, 2026 @11:42AM (#50455442)
Touch is not the same as biometrics. I think they’re saying that leaving it plugged in means that anyone that can unlock your computer can also use/touch your yubikey.
Re:Protecting SSH Keys with macOS Secure Enclave by 0xCMP on Wednesday November 11, 2026 @01:36AM (#50450347)
The way I think of it is YubiKeys should be used to basically provision a computer with an approved device specific key. Whether it's a passkey or SE/TPM secured SSH/GPG/TLS key: the Yubikey holds the credential everyone trusts and therefore can be used from any device to gain access and enroll a new approved key.
Re:Protecting SSH Keys with macOS Secure Enclave by LeBit on Wednesday November 11, 2026 @01:36AM (#50450348)
Why do you share private keys?

SSH private keys should be passphrase protected.

You don’t have to do that if you use FIDO2 with a Yubikey.

Re:Protecting SSH Keys with macOS Secure Enclave by larusso on Wednesday November 11, 2026 @02:07AM (#50450515)
Share as in storing my key in 1Password and use it from different machines. I generated the key from 1Password and don’t intend to export it.
Re:Protecting SSH Keys with macOS Secure Enclave by LeBit on Wednesday November 11, 2026 @06:29AM (#50452159)
You should reevaluate if you can instead use multiple public keys where you need to connect.

It’s a mind shift worth considering.

You then can accept that your ssh keys are different per hardware token (because the private key cannot be extracted).

No more sharing of private keys in your password manager.

Re:Protecting SSH Keys with macOS Secure Enclave by larusso on Wednesday November 11, 2026 @03:33PM (#50458287)
I’m a bit lost and maybe something also got lost in translation. I use 1Password to store multiple ssh keys for different services. I have a very restrictive ssh config because I don’t like to use ssh agent which hands out all keys to different connections. I use one key for a set of machines for work. One for GitHub etc etc etc. I connect to these machines from different endpoints. And I don’t want to register each of these with a new custom keypair to all the services. Like GitHub. I have 1Password installed on all desktops I use so I pull them from there. I share the same dot files and configuration. For GitHub I actually need 3 keys. My private key, 2 for work that have special SSO permissions. I don’t want my private key to have access to the work repos that’s why I split and my company has 2 different enterprise accounts where I have 2 different user accounts.
Re:Protecting SSH Keys with macOS Secure Enclave by dboreham on Wednesday November 11, 2026 @08:29AM (#50453163)
You can use CA signed -sk keys to avoid the provisioning hassle. Provision the CA public key only onto hosts. Disclosure: Claude taught me this trick.