Securing Your Work From Home

UnlockedDoor

Wanna make your security team’s blood run cold? Remind them that all that time and effort they put in to securing the enterprise from attackers and data exfiltration is currently sitting unused while we all work from home. You might have even heard them screaming at the sky just now.

Enterprise security isn’t easy, nor should it be. We constantly have to be on the offensive to find new attack vectors and hunt down threats and exploits. We have spent years and careers building defense-in-depth to an artform not unlike making buttery croissants. It’s all great when that apparatus is protecting our enterprise data center and cloud presence like a Scottish castle repelling invaders. Right now we’re in the wilderness with nothing but a tired sentry to protect us from the marauders.

During Security Field Day 4, I led a discussion panel with the delegates about the challenges of working from home securely. Here’s a link to our discussion that I wanted to spend some time elaborating on:

Home Is Where the Exploits Are

BYOD was a huge watershed moment for the enterprise because we realized for the first time that we had to learn to secure other people’s devices. We couldn’t rely on locked-down laptops and company-issued phones to keep us safe. Security exploded when we no longer had control of the devices we were trying to protect. We all learned hard lessons about segmenting networks and stopping lateral attacks from potentially compromised machines. It’s all for naught now because we’re staring at those protections gathering dust in an empty office. With the way that commercial real estate agents are pronouncing a downturn in their market, we may not see them again soon.

Now, we have to figure out how to protect devices we don’t own on networks we don’t control. For all the talk of VPNs for company devices and SD-WAN devices at the edge to set up on-demand protection, we’re still in the dark when it comes to the environment around our corporate assets. Sure, the company Thinkpad is safe and sound and isolated at the CEO’s house. But what about his wife’s laptop? Or the kids and their Android tablets? Or even the smart speakers and home IoT devices around it? How can we be sure those are all safe?

Worse still, how do you convince the executives of a company that their networks aren’t up to par? How can you tell someone that controls your livelihood they need to install more firewalls or segment their network for security? If the PlayStation suddenly needs to authenticate to the wireless and is firewalled away from the TV to play movies over AirPlay, you’re going to get a lot of panicked phone calls.

Security As A Starting Point

If we’re going to make Build Your Own Office (BYOO) security work for our enterprise employees, we need to reset our goals. Are we really trying to keep everyone 100% safe and secure 100% of the time? Are we trying for total control over all assets? Or is there a level of insecurity we are willing to accept to make things work more smoothly?

On-demand VPNs are a good example. It’s fine to require them to access company resources behind a firewall in the enterprise data center. But does it need to be enabled to access things in the public cloud? Should the employee have to have it enabled if they decide to work on the report at 8:00pm when they haven’t ever needed it on before? These challenges are more about policy than technology.

Policy is the heart of how we need to rebuild BYOO security. We need to examine which policies are in place now and determine if they make sense for people that may never come back into the office. Don’t want to use the VPN for connectivity? Fine. However, you will need to enable two-factor authentication (2FA) on your accounts and use a software token on your phone to access our systems. Don’t want to install the apps on your laptop to access cloud resources? We’re going to lock you out until we’ve evaluated everything remotely for security purposes.

Policy has an important role to play. It is the reason for our technology and the driver for our work. Policy is why I have 2FA enabled on all my corporate accounts. Policy is why I don’t have superuser rights to certain devices but instead authenticate changes as needed with suitable logging. Policy is why I can’t log in to a corporate email server from a vacation home in the middle of nowhere because I’m not using a secured connection. It’s all relevant to the way we do business.

Pushing Policy Buttons

You, as a security professional, need to spend the rest of 2020 doing policy audits. You’re going to get crosseyed. You’re going to hate it. So will anyone you contact about it. Trust me, they hate it just like you do. But you have to make it happen., You have to justify why you’re doing things the way you’re doing them. “This is how we’ve always done it” is no longer justification for a policy. We’re still trying to pull through a global pandemic that has costs thousands their jobs and displaced thousands more to a home they never thought was going to support actual work. Now is not the time to get squeamish.

It’s time to scrub your policies down to the baseboards and get to cleaning and building them back up. Figure out what you need and what is required. Implement changes you’ve always needed to make, like software updates or applications that enhance security. If you want to make it stick in this new world of working from home you need to put it in place at the deepest levels now. And it needs to stick for everyone. No executive workarounds. No grace extensions for them to keep their favorite insecure apps or allowing them to not have 2FA enabled on everything. They need to lead by example from the front, not lag in the back being insecure.


Tom’s Take

I loved the talk at Security Field Day about security at home. We weighed a lot of things that people aren’t really thinking about right now because we haven’t had a major breach in “at home” security. Yet. We know it’s coming and if it happens the current state of network segementation isn’t going to be kind to whomever is under the gun. Definitely watch the video above and tell me your thoughts, either on the video comments or here. We can keep things safe and secure no matter where we are. We just need to think about what that looks like at the lowest policy level and build up from there.

Some Random Thoughts From Security Field Day

I’m spending the week in some great company at Security Field Day with awesome people. They’re really making me think about security in some different ways. Between our conversations going to the presentations and the discussions we’re having after hours, I’m starting to see some things that I didn’t notice before.

  • Security is a hard thing to get into because it’s so different everywhere. Where everyone just sees one big security community, it is in fact a large collection of small communities. Thinking that there is just one security community would be much more like thinking enterprise networking, wireless networking, and service provider networking are the same space. They may all deal with packets flying across the wires but they are very different under the hood. Security is a lot of various communities with the name in common.
  • Security isn’t about tools. It’s not about software or hardware or a product you can buy. It’s about thinking differently. It’s about looking at the world through a different lens. How to protect something. How to attack something. How to figure all of that out. That’s not something you learn from a book or a course. It’s a way of adjusting your thinking to look at problems in a different way. It’s not unlike being in an escape room. Don’t look at the objects like you normally would. Instead, think about them with unique combinations that get you somewhere different than where you thought you needed to be.
  • Security is one of the only IT disciplines where failure is an acceptable outcome. If we can’t install a router or a wireless access point, it’s a bad job. However, in security if you fail to access something that should have been secured it was a success. That can lead to some very interesting situations that you can find yourself in. It’s important to realize that you also have to properly document your “failure” so people know what you tried to do to get there. Otherwise your success may just be a lack of proper failure.

Tom’s Take

I’m going to have some more thoughts from Security Field Day coming up another time. There’s just too much to digest at one time. Stay tuned for some more great discussions and highlights of my first real foray in the security community!