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🔒 SSH Command Logging

Presented by Kenny Johnson
Originally aired on 

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Transcript (Beta)

Hello. Good morning.

Good afternoon or good evening, depending on where you're joining from the world.

My name is Kenny Johnson.

I'm the product manager here at Cloudflare, My specific product is Cloudflare Access.

And today I'm excited to go through our a new feature that we just announced today as part of Security Week, SSH Command Logging.

So really the idea today is I want to do just a quick background on kind of the feature set and the product set that this this.

New idea falls under what products it belongs to within Cloudflare.

And then really I want to spend the majority of the time digging into the specifics of how this product works and showing a live demo.

So starting off really quickly, I always like to set the scene and show this quickly of where of all the different products that we offer at Cloudflare and then where this particular feature sets.

So the area that we're going to be focused on today is Cloudflare's Zero Trust Services, because SSH Command Logging is a key component of protecting and understanding what's going on with your resources that can be accessed via SSH.

So the majority of the time we're going to go ahead and dig into our Zero Trust Network Access solution and how SSH Command Logging works within that solution.

One piece I always like to dig into as well is that the reason that we're approaching and using Cloudflare's network to secure access to various applications is that we're seeing more and more companies need to move away from a perimeter based approach where they're creating either MPLS lines or VPN links across their branches, in between their data centers, and having their remote users use a VPN client to drop into their data center to then be able to access resources across their local network more to a software defined perimeter or SASE, is the analyst term that has become popular as in Secure Access Service Edge.

Basically what this allows you to do is wrap a perimeter around your hosted applications, your Internet based applications and protect your users from both inbound and outbound threats.

Part of this also allows us to inspect and protect traffic over search bound for specific resources within your data center or within your public clouds.

The last thing that I'll say is part of what makes Cloudflare so special is that we've built one of the largest networks in the world.

We had to build that to support our CDN and security products like our Web Application Firewall.

We have over 90% of the Internet connected population is within 50 milliseconds of our data centers across the world.

And everything that I'm about to show you today runs in every single Cloudflare data center.

So it's really fast in terms of latency as well as resiliency. Even if one data center goes down, we are able to route to the to the next closest one.

Awesome. So then diving into our command logging function a little bit more kind of where this sits is it's within our Zero Trust Network Access solution.

And what this allows us to do is we're able to hook into your cell, into your either your data center or your public clouds, GCP, AWS, Azure, any of those tools we're able to set up and proxy SSH commands coming from a user's machine with an agent or a client running on the device, we proxy that traffic to Cloudflare.

And then from Cloudflare, we're able to, as an SSH proxy, pass into that individual machine and using certificate based authentication, it really feels like magic to the user.

However, we're doing zero trust based authentication on whether or not that user should or shouldn't have access.

Excellent.

So what I'm going to go ahead and do is demonstrate how this feature actually works.

So what I've got is this probably looks familiar to folks who use GCP, but this works the same for something that you're hosting in your own infrastructure or any of the other public clouds.

I've got just a basic VM that I've spun up in GCP.

It really doesn't do anything other than the fact that we're going to be able to access it over SSH.

If I go to view network details.

I've got this particular VM up and open at a specific public IP address.

Alternatively, we can also make this available only over private the private IP as well.

I can talk a little bit about how that would work, but for today's demo, we're just going to go ahead and take a look at how this works within it with an external IP.

So the first step is to actually Proxy and make Cloudflare aware of this external IP.

So what I'm going to go ahead and do is I'll pull up my demo account here within the secure web gateway, which is basically the forward proxy from a user device.

I'm able to route all my traffic to Cloudflare and then out to the public internet.

And this is where I'm able to run various policies over that traffic. What I need to do is I need to go ahead and create an audit.

As a rule, in this case, I've already created one for GCP.

So what this looks like is I'm able to save for a specific destination IP.

I want to audit that.

S-h and a piece that's coming in the next few weeks is we're actually going to be able to enable full command logging to do a full session replay.

Right now, what this does is it supports event logging.

So it basically shows ongoing SSH connections as well as duration of the SSH session.

How long was it which and which specific user was logging into that particular sage section?

The piece that we're finalizing is will also capture all of the commands, run on a particular machine, and we'll dump that into an encrypted file that then you're able to download on your side.

The reason we encrypt that is because you can run really sensitive things on Sage and really only you should be able to see what's being run on an individual box.

We don't even want to see that information at Cloudflare and all that's required there.

Is that we that you provide us a public key that then we use to encrypt that data.

So it just drops it into an encrypted file.

And then if I go and look at the actual search logs, this is where I should I'm able to see either active sessions or ongoing sessions, which we'll look at in a moment or past sessions.

So this gives me a basic overview of, Hey, here's my email address.

I logged in to my destination IP and here's the overall session timing for that particular.

Ssa event.

And then in a few weeks we'll also have the ability to download the actual logs and to be able to play back exactly what was run on a given SSH machine.

Great. So now that we have the audit, as the policy stood up for GCP.

The other steps, I'll actually show you what's required from the box that we SSH to.

So the next step I'm going to do is actually SSH to this. And what I'm going to go ahead and check here is I don't yet have the Zero Trust client running on this call.

So if I pull up my command prompt here, let me pull this into the screen.

I've got my command.

Prompt up.

If I go ahead and try to switch to this machine.

It's going to go ahead and give me a permission tonight because it's not seeing the public key, because the public key actually lives at Cloudflare's Edge and I need to be able to proxy my traffic to Cloudflare and then through to the to the machine.

So what I'm going to go ahead and do is I'm going to switch on the Zero Trust client.

I might freeze for a second. Just bear with me here because I'm going to switch my Internet to being proxy to over to via Cloudflare.

So just one moment as I switch this on.

All right.

And I should be back now. All my traffic's being routed to Cloudflare.

So from my home office here up to Cloudflare Workers point of presence up in Dallas.

And then this is where we're actually going to be able to proxy that SSH to this GCP VM.

So I'm going to go ahead and rerun this SSH command now, and this is going to then drop me on to my GCP VM and I can do things like Run ls, CD now you can see I'm actually on this individual instance.

One other caveat that's worth pointing out.

That's a piece we're still working through.

As you saw, I had to add a couple security bypasses here.

Sorry about that.

Looks like I lost y'all for a second, but I am back now.

That was.

That was just a piece I didn't get just blip because I switched on the on the Warp client or on the Zero Trust client.

But here we are.

We're back.

And now I'm asked to fit into this box. Anything can and happens in a in a live demo.

Thanks for bearing with me there.

So you can see I'm on this, this individual machine.

And then if we actually go to the logs themselves, we should see an active ongoing connection to that particular machine.

So you can see that I've got an ongoing connection to that, to that machine, which is which is great.

It's something where I'm able to see across the world all the ongoing connections to individual machines, a piece we're hoping to add in the future, as well as the ability to actually terminate connections to specific machines if you see something anomalous.

Awesome.

So what I'm then going to go ahead and do now is just talk about the setup that's required on the individual VM in order to get this talk, because there's no setup required on the user device other than being logged into the Zero Trust client.

I don't have to mess around with keys. I don't have to put certs onto the user device because we're Proxying all of this traffic from Cloudflare directly to the server that's being SSH'd to.

Awesome.

So let's go ahead and pull up the individual things that need to be done on this server.

And I'll do it via proxy to SSH here. So I'm going to go ahead and jump into my ETC file and then my SSH directory.

So within SSH here, there's two things that I need to add and that's all.

And then this is set up and configured to work.

One is I need to add a root CA to this device and that root CA is generated using the Cloudflare API.

And then the other component is if I go into.

My SSH config.

The two things that I had to switch on to get this to work are public key authentication, which generally most associated boxes are already going to have that enabled.

That's kind of the best practice for managing SSH access. There's a lot of reasons why password based authentication is generally discouraged when it comes to S-H.

And then the only other piece is adding the trusted user keys to the to the root certificate that I added to this particular configuration.

So and that's it.

That's all I needed to add because that, that then tells the end machine what root certificate to trust.

And within the Zero Trust client running on the device.

I have an associated user account, so I've authenticated to my test account under my identity.

I've actually logged in using Okta credentials.

So on the Zero Trust client side, we know my identity and then I've added that or I already had that Unix username on my device, I've just had Tae Johnson.

So we look at it and see Kid Johnson at Cloudflare dot com is.

Is the identity associated with this end user machine.

So then what happens is I make the request.

It goes to Cloudflare's Edge.

Cloudflare recognizes that I am who I say I am.

I'm coming from the right device.

It then uses the public key that lives at Cloudflare's Edge for this account and uses that as a means of authentication into the SSH server using public key authentication with my particular associated username.

And this is a really big deal because it it means that you're not having to pass certificates or keys or anything like that out to your entire employee base.

You just have them enroll into the agent, which you might already be doing if you're using Cloudflare Secure web gateway and you get S-H secure, logged, audited s h to these individual devices.

And all you need to do is, is put a certificate and add it to its trusted key store for that particular device.

So we are very excited about this feature in terms of it's kind of the future of what we're going to be able to add and what it's capable of already today.

So then I'm going to go ahead and I can just log out of this guy and then that just takes me and ends my session and then this will update.

And show the log of the actual session.

That's that's been ended.

And I can take this a lot further.

I can actually in these network policies, I don't have to just configure network based checks.

I can also configure identity based checks as well as device posture checks.

So I can say things like, I need you to be. I need you to be running my instance of CrowdStrike, or I need to have you running carbon black for you to be able to ssh into an individual machine.

Or I need you to be in a specific user group, so I need you to be part of my Okta developers group in order for you to be able to access to my S-H.

So instead of having to mess around with your PAM style controls on your search box and limit down to specific usernames and keep all that stuff straight, you can do this at an IEP level now, just like your web applications, just like you're used to there.

This is kind of true. Zero trust for SSA where you can configure down to individual user emails or individual user groups with device posture checks before allowing access to a particular box set box.

And you can do this at a network overlay layer.

You don't have to go box to box to configure these security policies anymore.

You can do this at layer four and say for any search that I'm going to proxy through Cloudflare, I need to require specific device posture checks and specific users can only access them before they're able to access a given machine.

So there's a lot of power in that in terms of being able to control those specific users as opposed to having to do it either at a firewall level or an individual origin server level.

So we're very excited about this one.

We're going to continue to make it better.

We just announced it on the Cloudflare blog today.

I can actually pull that up and show you guys where to go.

Read more if you want.

I think it's our second or third blog we announced today for Zero Trust week.

So if you go to the blog, you'll see more information about Zero Trust command logging and definitely keep your eyes out.

Over the next few weeks, this is going to start getting rolled out as a beta product more broadly into zero trust accounts.

So we're very excited about this and I can't wait to get this out more broadly for folks to get their hands on it.

If there's specific things that you want to see with this, don't hesitate to reach out.

Don't hesitate to tweet at us to let us know on the on the blog post. We want to get this into folks hands and hear how we can do even better in terms of of SSH command logging.

So again, thank you all so much for joining.

Really looking forward to getting this out in the world and getting everybody's feedback on how we can make this better.

And thank you again.

Thanks for tuning in and thank you for riding along with us during security week at Cloudflare.

With that, I will go ahead and conclude for today. Thanks very much.

We're betting on the technology for the future, not the technology for the past.

So having a broad network, having global companies now running at full enterprise scale gives us great comfort.

It's dead clear that no one is innovating in this space as fast as Cloudflare is.

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Cloudflare has helped save lives through Project Fair Shot.

We will forever be grateful for your participation in getting the vaccine to those who need it most in an elegant, efficient and ethical manner.

Thank you.

The real privilege of working at Mozilla is that we're a mission driven organization.

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Mozilla's values are similar to Cloudflare service.

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Hi.

We're Cloudflare. We're building one of the world's largest global cloud networks to help make the Internet more secure, faster and more reliable.

Meet our customer Neto.

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Helping Build a Better Internet. Hi.

We're Cloudflare. We're building one of the world's largest global cloud networks to help make the Internet faster, more secure and more reliable.

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Helping Build a Better Internet. 80.

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