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Tailscale SSH

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Re: Tailscale SSH

#101

I'm very interested in Tailscale for both personal and business use-cases, but I'm rather put off by the stark centralization of offered identity providers: Microsoft, Github (Microsoft), Google, okta (?). What are the chances that Tailscale would offer authentication using decentralized/self-hosted identity providers like Ory ( https://www.ory.sh/ )?

There is also the self-hostable Headscale implementation.

Re: Tailscale SSH

#102
post #17
post #2

Is anyone using tailscale on an organizational level? I'm curious to hear about some of the use cases, and whether some companies and organizations are attempting to adopt this instead of traditional VPN.

We just adopted it to consolidate multiple different OpenVPN installations. Why? * The Tailscale clients are dead simple and good quality (but not perfect). OpenVPN clients for mac and iOS are pretty bad. Onboarding OpenVPN users was a large document that generated a lot of questions and support issues. Tailscale onboarding is about two minutes for most users and we had nearly no support requests rolling it out widel…

curious what 'dead simple' means re: clients. Do your users still need to login like openvpn, or is it always on?

Re: Tailscale SSH

#103
post #9
post #2

Is anyone using tailscale on an organizational level? I'm curious to hear about some of the use cases, and whether some companies and organizations are attempting to adopt this instead of traditional VPN.

One of my clients, an industrial/commercial property realtor (to contextualize the environment; we’re not talking military secrets here), uses it. Day to day I interact with it like any other VPN client except I auth via the Google workspace account they gave me. It’s Tailscale, or hosted OpenVPN and cross your fingers they’re not snooping, or DIY Wireguard or OpenVPN and all the usual ups and downs of DIY. Software…

> It’s Tailscale, or hosted OpenVPN and cross your fingers they’re not snooping...

The "cross your fingers they're not snooping" applies to Tailscale as well.

Re: Tailscale SSH

#104

I'm one of the authors of this. Happy to answer any questions. One of the fun technical details is that, when enabled on a machine (tailscale up --ssh), the userspace tailscaled process takes over all TCP port 22 packets after the WireGuard decryption and doesn't even feed them into the kernel over TUN. We use gVisor's netstack to handle the TCP connections in-process. So it doesn't matter whether you have other proc…

Can you do ssh tunnelling?

Re: Tailscale SSH

#105
post #98

Earlier quoted context omitted.

It's not the same, but "Docker Network bypasses Firewall, no option to disable" https://github.com/moby/moby/issues/22054 (2016)

You're right, it's not at all the same. The Tailscale bypass exists (1) only for traffic traversing Tailscale interfaces (by design, that's the only traffic it can impact, because Tailscale can't run a userland TCP/IP stack for non-Tailscale traffic), and (2) only for this one feature, and (3) only if you've explicitly allowed it for particular users in your Tailscale ACLs. It's not clear to me how you could screw it…

All I'm trying to point out is that advertising "this bypasses the firewall, by design" has been abused in the past.

[edit] It boils down to principle of least surprise, managing expectations, etc. - proper documentation is indeed key.

Re: Tailscale SSH

#106
I started using tailscale a few days ago, and I absolutely love it.

However, one thing is still nagging me: technically, they can add devices to my network without telling me, right? Or is there something I'm missing?

Re: Tailscale SSH

#107

I'm one of the authors of this. Happy to answer any questions. One of the fun technical details is that, when enabled on a machine (tailscale up --ssh), the userspace tailscaled process takes over all TCP port 22 packets after the WireGuard decryption and doesn't even feed them into the kernel over TUN. We use gVisor's netstack to handle the TCP connections in-process. So it doesn't matter whether you have other proc…

Can you do ssh tunnelling?

You can do local port forwarding today, remote port forward is still a WIP. What do you want to use it for?

Disclaimer: I am one of the engineers who built Tailscale SSH.

Re: Tailscale SSH

#108
post #68

Earlier quoted context omitted.

The big thing you get with Teleport that you don't yet get with Tailscale --- apart from entirely owning the source of truth for SSH authentication on your own infra, which is a very minor issue for almost everyone but is a major issue for some people --- is that Teleport gives you transcript-level audit logs of your SSH sessions. Teleport also has that web-based SSH console (it's one of the better web-based consoles…

> is that Teleport gives you transcript-level audit logs of your SSH sessions That is extremely valuable. Just in case 'transcript-level audit' didn't sink in, it's a session recording – not only you can see the all keystrokes typed but you can see all the outputs, the whole state. Someone doing a TOP command for an hour? You can watch the same thing later. Think asciinema ( https://asciinema.org/ ).

FWIW, Tailscale SSH can also record sessions in asciinema cast format:

https://github.com/tailscale/tailscale/blob/v1.26.1/ssh/tail...

We haven't yet fully "productized" it yet because it only records on-device for now. We want to make it stream recordings to another device (that you run) first before considering it done.

Re: Tailscale SSH

#109

I'm one of the authors of this. Happy to answer any questions. One of the fun technical details is that, when enabled on a machine (tailscale up --ssh), the userspace tailscaled process takes over all TCP port 22 packets after the WireGuard decryption and doesn't even feed them into the kernel over TUN. We use gVisor's netstack to handle the TCP connections in-process. So it doesn't matter whether you have other proc…

hello, is sftp supported? thanks

Re: Tailscale SSH

#110

I'm one of the authors of this. Happy to answer any questions. One of the fun technical details is that, when enabled on a machine (tailscale up --ssh), the userspace tailscaled process takes over all TCP port 22 packets after the WireGuard decryption and doesn't even feed them into the kernel over TUN. We use gVisor's netstack to handle the TCP connections in-process. So it doesn't matter whether you have other proc…

hello, is sftp supported? thanks

Yes: https://github.com/tailscale/tailscale/blob/v1.26.1/ssh/tail...
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