Few angles make for a better email-borne attack than the impersonation of a trusted service. Organizations such as Microsoft, Google, Bank of America, Citigroup, DocuSign, Dropbox, FedEx, UPS, and countless others are brands recognized throughout the world that host or access trusted financial data, personally identifiable information, confidential data, and other exploitable content desired by criminals.

Better yet for attackers, these organizations frequently send a variety of notifications: updated terms of service, account changes and alerts, new documents being shared, etc. Recipients don’t just trust these brands, they’ve been conditioned to expect email notifications from these companies. As a result, they often interact with emails from trusted brands without giving as much thought to it as they might take with an email from a stranger. This provides a ripe environment for attackers to exploit.

These types of emails are often attempting to gain any number of different pieces of information: names, addresses, social security numbers, account numbers, routing numbers, but what is commonplace at nearly every organization are credential theft attempts by way of a fake notification email like one of the aforementioned. Attackers have realized the value of these credentials; with password reuse as rampant as it is, one password could be the key to everything from a corporate account to a personal email account to a bank account, and even without widespread reuse of the password, email addresses are the most common means of resetting passwords for every other account a person utilizes.

There are a number of ways to detect and prevent these types of attacks, but detection and prevention specifically based upon analysis of URLs (and to a lesser extent attachments) has been viewed as a central component to email security technologies for some time now. This is not nearly as infallible as many would be led to believe and when the system gets it right, everyone sleeps soundly, but there are a number of these payloads still reaching end users precisely because of the shortcomings of the specific analytical approach taken and end users are then left to their own devices to figure out which URLs are safe and which are not.

Over time, attackers have become craftier and craftier in their approach to these emails meaning the payloads getting through are more and more pernicious. Regardless of who or what business service might be spoofed by an attacker, destination URLs are often “hidden” behind hyperlinked text (e.g. “Click here”), made to look like a common file share URL, or are even legitimate file sharing URLs. Because of this, they can be difficult to spot and identify as unsafe. Coupled with users’ inherent level of trust with these respected brands (or members of their organization) and the sense of urgency an attacker creates (Data will be deleted in the next 24 hours if you do not take action!), users often feel compelled to do exactly as the URL advises: they click.

Many existing email security solutions are heavily reliant on threat intelligence feeds to identify these URLs as malicious at the time of delivery. While undeniably useful, threat intelligence has its shortcomings. It goes without saying, but someone need be the first (or possibly second, third, fourth, fifth…) victim before the URL can be classified as malicious and that intelligence can be disseminated. Other solutions stop short in performing their analysis on the full URL but instead focus only on the root domain. The idea is that, given their available dataset coupled with their threat intelligence and other data feeds, malicious URLs are bound to be spotted based solely on being anomalous. This, of course, ignores the fact that web certificates do expire or that attackers can hijack otherwise innocuous websites through other means, they can utilize URL shorteners, redirects, and a host of other means that ultimately obfuscate the true intent of the destination page of the attacker’s URL.

GreatHorn recently identified a fairly compelling example of a business services impersonation email in one of our client environments that would have almost certainly bypassed many of these existing methods of detection. The message appeared to be from business service provider LogMeIn, which makes a suite of popular access and communications products, including GoToMeeting and LastPass among others. As anyone familiar with LogMeIn can see here – save for the font – the notification was exceptionally close in appearance to a real LogMeIn notification email. There was a link in the message purportedly leading the user to a LogMeIn account login page where “6 months of free subscription” awaited him.

In this instance, the attacker utilized a domain for the URL (logme-in.com) similar enough to LogMeIn’s actual domain (logmein.com) that it would likely pass as legitimate to an end user’s eye test. At the time of attack, the URL in this email was not showing up on dozens of threat intelligence feeds and the root domain of the URL redirected to a Google search page showing results for a LogMeIn-related search. With threat intelligence coming up blank, if a solution were to check the root domain, it would ultimately find a legitimate Google webpage.

As is shown in this example, the term “detecting malicious URLs” can be misleading. This particular email, at least in regard to the URL, could easily have bypassed any number of security solutions if they used one of the above approaches. With attackers getting more savvy, it’s important for security teams to ensure that their link protection options are robust enough to protect them from attacks.

We recently announced GreatHorn Link Protection – a new turnkey module that’s available as a core component of our email security platform. In addition to all the proprietary threat detection techniques we use that would flag a message such as this as a concern, GreatHorn Link Protection provides multiple levels of protection regardless of the URL’s presence on our threat intelligence feeds.

Stay tuned for more blogs on GreatHorn Link Protection, but in the meantime, you can learn more about GreatHorn’s Malicious URL capabilities here. Also consider checking out our recent blog on the recent rise in business service impersonations to learn more about real-world credential theft attempts.