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No matter where your employees go, there you are

With increasingly flexible remote-work options (for keeps or just for the holidays), security’s got to push left to keep pace
Chester Wisniewski

I live in a city center and the lunch hour certainly isn’t like it once was. While some people have returned to working in an office, it seems that the majority have not. Looking back, the pandemic will likely have been a turning point for many things around the world, and the rhythms of office-centered worklife will be something that will never return to the old ways.

With this increased flexibility employees are not just working from home behind consumer-grade Wi-Fi routers; they are also spending part of the day at the park or coffee shop, or perhaps even having a “working holiday.” Those in charge of protecting enterprise assets have to assume these endpoints are always in hostile territory.

Even before the pandemic, organizations working toward improving their security maturity were often trying to “push left.” What is pushing left? At its most basic level it means moving things closer to the start. It originates from software development where the stages of the development process are conceptualized from left to right, left being the beginning. In applied security we also use the term “pushing left,” but rather than referring to the software development process we are referring to the attack chain, which moves from reconnaissance on the left through action (exfiltration or other attacker goal) on the right.

For many years, the most comprehensive security strategies have involved defense in depth. The idea is that not all technologies are suitable for detecting a given threat type, so it is best to deploy them in layers. These layers often directly correspond to how far “left” something is in the attack chain. If you can detect something at the network border through your firewall, email, or web filters, you have contained the threat before it has any negative impact on operations.

Ideally you want to detect and block an attacker as far left as possible, i.e., as early as possible. Pushing detections left also alerts security analysts that an intrusion may be underway, initiating more focused threat hunting to anticipate gaps in defenses your attacker may be attempting to exploit.

For employees at the office, you can centralize control of these defenses and provide optimum protection. The question is, are you able to provide the same protection for remote workers regardless of their location? Can you monitor and respond to threats being detected on those assets when they are out of the office? As many have observed, this did not work as well as we would have liked when we all went into lockdown, many of us without a plan.

While there are still many benefits to monitoring the network when you have control of it, including reduced endpoint overhead and the ability to keep threats at a distance from sensitive assets, we need to ensure we can take as much of this protection as possible with us when we are out and about.

We must ensure not only that protection is optimized, but also that we don’t lose our ability to monitor, detect, and respond to attacks targeting these remote assets. Most organizations have moved to utilizing EDR/XDR solutions (or plan to in the very near future) , which is a great start, but not all solutions are comprehensive.

In the remote-work era, insufficiently protected remote users can encounter plenty of issues – malicious URLs and downloads, and networks attacks, to name only the most mundane – that in the Before Times would have been handled by machines guarding the corporate “fort.” The biggest missing components when users are “outside the fort” are HTTPS filtering and web content inspection of the sort that is typically implemented within next-generation firewalls. When you add these technologies to pre-execution protection, behavioral detection, machine learning models, client firewalls, DLP, application control, and XDR, you are starting to look at a comprehensive stack of defenses for attackers to overcome – even if the endpoints themselves are now free-range.

For initiatives like zero trust network access (ZTNA) to be effective, we must not only wrap the applications we interact with, but we must also wrap the endpoints that connect to them. Simple checks like whether the OS up-to-date and whether it has security software installed may be a good start, but not all protection is created equal.

With most devices being connected to the internet whenever they’re in use, we can leverage the power of the cloud to help provide ubiquitous protection and monitoring. Modern security solutions must assume the endpoint device or phone is in a hostile environment at all times. The old idea of inside and outside is not only outdated, it’s downright dangerous.

About the authors

Chester Wisniewski

Chester Wisniewski

Chester Wisniewski is Director, Global Field CTO at next-generation security leader Sophos. With more than 25 years of security experience, his interest in security and privacy first peaked while learning to hack from bulletin board text files in the 1980s, and has since been a lifelong pursuit.

Chester works with Sophos X-Ops researchers around the world to understand the latest trends, research and criminal behaviors. This perspective helps advance the industry's understanding of evolving threats, attacker behaviors and effective security defenses. Having worked in product management and sales engineering roles earlier in his career, this knowledge enables him to help organizations design enterprise-scale defense strategies and consult on security planning with some of the largest global brands.

Based in Vancouver, Chester regularly speaks at industry events, including RSA Conference, Virus Bulletin, Security BSides (Vancouver, London, Wales, Perth, Austin, Detroit, Los Angeles, Boston, and Calgary) and others. He’s widely recognized as one of the industry’s top security researchers and is regularly consulted by press, appearing on BBC News, ABC, NBC, Bloomberg, Washington Post, CBC, NPR, and more.

When not busy fighting cybercrime, Chester spends his free time cooking, cycling, and mentoring new entrants to the security field through his volunteer work with InfoSec BC. Chester is available on Mastodon (securitycafe.ca/@chetwisniewski).

For press inquiries, email chesterw [AT] sophos [.] com.