this post was submitted on 23 Jul 2023
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I have too many machines floating around, some virtual, some physical, and they're getting added and removed semi-frequently as I play around with different tools/try out ideas. One recurring pain point is I have no easy way to manage SSH keys around them, and it's a pain to deal with adding/removing/cycling keys. I know I can use AuthorizedKeysCommand on sshd_config to make the system fetch a remote key for validation, I know I could theoretically publish my pub key to github or alike, but I'm wondering if there's something more flexible/powerful where I can manage multiple users (essentially roles) such that each machine can be assigned a role and automatically allow access accordingly?

I've seen Keyper before, but the container haven't been updated for years, and the support discord owner actively kicks everyone from the server, even after asking questions.

Is there any other solution out there that would streamline this process a bit?

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[–] [email protected] 23 points 1 year ago (1 children)

I would switch to certificate based SSH authentication.

All the server keys gets signed by your CA, all clients also gets signed by your CA. Everyone implicitly trust eachother though the CA and it's as safe as regular SSH keys.

You can also sign short lived client keys if you want to make revocations easier, the servers don't care because now all it cares is that it's a valid cert issues by the CA, which can be done entirely offline!

HashiCorp Vault can also help managing the above, but it's also pretty easy to do manually.

[–] [email protected] 7 points 1 year ago (2 children)

I do this, use the small step ca/Cli to manage the lot. It's amazing

[–] [email protected] 8 points 1 year ago (1 children)

It's such an underrated feature. It baffles me how people immediately turn to overly complicated solutions solving a problem they don't really have to solve, just because everyone assumes the only way is the default commonly known way. Like OP, people immediately jump to the conclusion you need extra software to manage the keys, rather than using another authentication method natively supported, and keep filling their known_hosts file with junk, making the whole validation process useless because everyone just accepts whatever key the host presents.

It's amazing how simple it is. Developer needs temporary access to debug a web server? Sure, here's your 2h valid cert to log in as the web user on the server, don't even need to actually log into the server to put their key in and then remove it. I mint a cert and it's ready to go on whichever users and servers I specified in the cert. Can't even gain persistence because regular authorized_keys is disabled and we have limited session durations.

I regularly leave people baffled at work because I come up with a clever and built-in super simple solution to something they expected to just slap more scripts and software to work around the only way they know to use the software. Read your manpages in full folks, it'll save you so much work. Know what your software is capable of.

[–] [email protected] 5 points 1 year ago

That's a long rant, but your on point with it. I have a colleague who refuses to try new things cuz they don't understand that it makes life easier, I do tend to find the solutions that are simpler and easier to work

[–] [email protected] 0 points 1 year ago (1 children)

Is smallstep free to self host? Looking at their pricing page it's kind of unclear, and their saas is pretty pricey.

[–] [email protected] 1 points 1 year ago

It sure is, give this a read DIY-Single-Sign-On-for-SSH

[–] [email protected] 9 points 1 year ago (1 children)

You could use an LDAP and/or Kerberos solution to centralize user management. Alternatively you could use ansible

[–] kylian0087 1 points 1 year ago

To add to this. If everything is just linux based take a look at freeipa/rhel idm.

[–] BrianTheeBiscuiteer 9 points 1 year ago

I've been using https://github.com/warp-tech/warpgate for essentially this purpose. It does kind of put all of your eggs in one basket so don't expose this to the Internet and probably keep at least one other machine that has all the keys. I haven't had any catastrophic issues so far other than my host going down (unrelated to this tool).

[–] [email protected] 8 points 1 year ago (1 children)

Terrible idea of the day: You could use something like NFS and map the drive on all clients. On that drive you can have the latest keys then use symlinking to update, etc.

Something like puppet, chef, ansible are likely better choices.

[–] solidgrue 8 points 1 year ago

You're the devil.

Did we work together, maybe?

[–] RegalPotoo 7 points 1 year ago (1 children)

You could try SSH certificates using something like https://smallstep.com/sso-ssh/ - essentially you delegate validation of your public key to a IDP, which your servers are configured to trust.

The other approach would be something like ansible or puppet to deploy trusted keys to all servers

[–] [email protected] 1 points 1 year ago

Hm... these are both interesting but might be a bit overkill IMO.

I don't think I'd need a CA and intermediary step if all SSHd needs to do is check if a key is a currently approved key for this particular service or not; and I last looked at chef/puppet many years ago, and it was way too much orchestration work that we no longer need w/ Docker containers and smaller footprint host OSes.

[–] [email protected] 6 points 1 year ago

I quite like Tailscale SSH for this, but I don't have as many machines, so not sure how it will scale. You can definitely assign roles here to allow/deny SSH between hosts in your fleet though.

[–] FlexibleToast 4 points 1 year ago

This is one of the jobs of OpenLDAP.

[–] MajorHavoc 3 points 1 year ago* (last edited 1 year ago)

Sometimes the obvious solution is the way to go.

Your idea sounds good to go ahead and publish your pubkey(s) to fully public URL you control and can memorize.

Then you can stash or memorize the curl command needed to grab it (them) and authorize something to it (them).

A lot of more complicated solutions are just fancy ways to safely move private keys around.

For my private keys, I prefer to generate a new one for each use case, and throw them out when I'm done with them. That way I don't need a solution to move, share or store them.

Edit: Full disclosure - I do also use Ansible to deploy my public keys.

[–] [email protected] 3 points 1 year ago

You could use ldap with OpenLdap, Keycloak, freeipa, etc to set ssh keys for users.

If you want something simpler, you could use Ansible (or another cm) or just have a startup script that downloads the authorized keys file from GitHub or wherever you can store it.

And if you want something less simple, hashicorp Vault supports dynamic ssh keys using certificates.

[–] vegetaaaaaaa 2 points 1 year ago

I use ansible for that: https://docs.ansible.com/ansible/latest/collections/ansible/posix/authorized_key_module.html

Keys stored alongside my playbook in a git repository.

[–] alsobrsp 2 points 1 year ago

Some options

  • Use a build system like Foreman to automate the builds putting the key in place, uses puppet for config management after the build
  • Use vanilla puppet without Foreman
  • Use Ansible
[–] c2c2 2 points 1 year ago
[–] [email protected] -4 points 1 year ago (1 children)

all I know is that on NixOS you can declare the authorized keys for each user in the config

[–] [email protected] 2 points 1 year ago (1 children)

Yeah, the problem is that I have 2 physical servers, each with 5 to 10 VMs on it, and a bunch of other VMs scattered across different cloud providers; it gets tricky to edit the ~/.ssh/authorized_keys file on each of them to reflect a new SSH key (i.e.: new machine on the "network") or replace an existing SSH key (i.e.: annual key cycle).

[–] [email protected] -3 points 1 year ago (1 children)

yeah what i mean is on nixos you make 1 config for them all and you’d just change the key in 1 spot

[–] [email protected] 1 points 1 year ago

You do realize that those machines are not necessarily NixOS right? It is best to separate the management of SSH from NixOS declarative nature since what you would really want to be declarative is ACL rules, not network topology/SSH keys. For example you can use Netbird or Tailscale and their respective SSH feature.