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Inside the SOC
Better the Devil You Know? Darktrace’s Detection of Unattributed Ransomware







In the current threat landscape, much of the conversation around ransomware focusses on high-profile strains and notorious threat groups. While organizations and their security teams are justified in these concerns, it is important not to underestimate the danger posed by smaller scale, unattributed ransomware attacks.
Unlike attributed ransomware strains, there are often no playbooks or lists of previously observed indicators of compromise (IoCs) that security teams can consult to help them shore up their cyber defenses. As such, anomaly detection is critical to ensure that emerging threats can be detected based on their abnormality on the network, rather than relying heavily on threat intelligence.
In mid-March 2023, a Darktrace customer requested analytical support from the Darktrace Security Operations Center (SOC) after they had been hit by a ransomware attack a few hours earlier. Darktrace was able to uncover a myriad of malicious activity that preceded the eventual ransomware deployment, ultimately assisting the customer to identify compromised devices and contain the ransomware attack.
Attack Overview
While there were a small number of endpoints that had been flagged as malicious by open-source intelligence (OSINT), Darktrace DETECT™ focused on the unusualness of the activity surrounding this emerging ransomware attack. This provided unparalleled visibility over this ransomware attack at every stage of the cyber kill chain, whilst also revealing the potential origins of the compromise which came months area.
Initial Compromise
Initial investigation revealed that several devices that Darktrace were observed performing suspicious activity had previously engaged in anomalous behavior several months before the ransomware event, indicating this could be a part of a repeated compromise or the result of initial access brokers.
Most notably, in late January 2023 there was a spike in unusual activity when some of the affected devices were observed performing activity indicative of network and device scanning.
Darktrace DETECT identified some of the devices establishing unusually high volumes of internal failed connections via TCP and UDP, and the SMB protocol. Various key ports, such as 135, 139, and 445, were also scanned.
Due to the number of affected devices, the exact initial attack vector is unclear; however, one likely scenario is associated with an internet-facing DNS server. Towards the end of January 2023, the server began to receive unusual TCP DNS requests from the rare external endpoint, 103.203.59[.]3, which had been flagged as potentially malicious by OSINT [4]. Based on a portion of the hostname of the device, dc01, we can assume that this server served as a gateway to the domain controller. If a domain controller is compromised, a malicious actor would gain access to usernames and passwords within a network allowing attackers to obtain administrative-level access to an organization’s digital estate.
Around the same time as the unusual TCP DNS requests, Darktrace DETECT observed the domain controller engaging in further suspicious activity. As demonstrated in Figure 1, Darktrace recognized that this server was not responding to common requests from multiple internal devices, as it would be expected to. Following this, the device was observed carrying out new or uncommon Windows Management Instrumentation (WMI) activity. WMI is typically used by network administrators to manage remote and local Windows systems [3].

Had Darktrace RESPOND™ been enabled in autonomous response mode, it would have to blocked connections originating from the compromised internal devices as soon as they were detected, while also limiting affected devices to their pre-established patterns of file to prevent them from carrying out any further malicious activity.
Darktrace subsequently observed multiple devices establishing various chains of connections that are indicative of lateral movement activity, such as unusual internal RDP and WMI requests. While there may be devices within an organization that do regularly partake these types of connections, Darktrace recognized that this activity was extremely unusual for these devices.
Darktrace’s Self-Learning AI allows for a deep understanding of customer networks and the devices within them. It’s anomaly-based threat detection capability enables it to recognize subtle deviations in a device’s normal patterns of behavior, without depending on known IoCs or signatures and rules to guide it.

Persistence
Darktrace DETECT observed several affected devices communicating with rare external endpoints that had also been flagged as potentially malicious by OSINT tools. Multiple devices were observed performing activity indicative of NTLM brute-forcing activity, as seen in the Figure 3 which highlights the event log of the aforementioned domain controller. Said domain controller continuously engaged in anomalous behavior throughout the course of the attack. The same device was seen using a potentially compromise credential, ‘cvd’, which was observed via an SMB login event.

Affected devices, including the domain controller, continued to engage in consistent communication with the endpoints prior to the actual ransomware attack. Darktrace identified that some of these malicious endpoints had likely been generated by Domain Generation Algorithms (DGA), a classic tactic utilized by threat actors. Subsequent OSINT investigation revealed that one such domain had been associated with malware such as TrojanDownloader:Win32/Upatre!rfn [5].
All external engagements were observed by Darktrace DETECT and would have been actioned on by Darktrace RESPOND, had it been configured in autonomous response mode. It would have blocked any suspicious outgoing connections originating from the compromised devices, thus preventing additional external engagement from taking place. Darktrace RESPOND works in tandem with DETECT to autonomously take action against suspicious activity based on its unusualness, rather than relying on static lists of ‘known-bads’ or malicious IoCs.
Reconnaissance
On March 14, 2023, a few days before the ransomware attack, Darktrace observed multiple internal devices failing to establish connections in a manner that suggests SMB, RDP and network scanning. Among these devices once more was the domain controller, which was seen performing potential SMB brute-forcing, representing yet another example of malicious activity carried out by this device.
Lateral Movement
Immediately prior to the attack, many compromised devices were observed mobilizing to conduct an array of high-severity lateral movement activity. Darktrace detected one device using two administrative credentials, namely ‘Administrator’ and ‘administrator’, while it also observed a notable spike in the volume of successful SMB connections from the device around the same time.
At this point, Darktrace DETECT was observing the progression of this attack along the cyber kill chain. What had started as internal recognisance, had escalated to exploitation and ensuing command-and-control activity. Following an SMB brute-force attempt, Darktrace DETECT identified a successful DCSync attack.
A DCSync attack occurs when a malicious actor impersonates a domain controller in an effort to gather sensitive information, such as user credentials and passwords hashes, by replicating directory services [1]. In this case, a device sent various successful DRSGetNCChanges operation requests to the DRSUAPI endpoint.
Data Exfiltration
Around the same time, Darktrace detected the compromised server transferring a high volume of data to rare external endpoints associated with Bublup, a third-party project management application used to save and share files. Although the actors attempted to avoid the detection of security tools by using a legitimate file storage service, Darktrace understood that this activity represented a deviation in this device’s expected pattern of life.
In one instance, around 8 GB of data was transferred, and in another, over 4 GB, indicating threat actors were employing a tactic known as ‘low and slow’ exfiltration whereby data is exfiltrated in small quantities via multiple connections, in an effort to mask their suspicious activity. While this tactic may have evaded the detection of traditional security measures, Darktrace’s anomaly-based detection allowed it to recognize that these two incidents represented a wider exfiltration event, rather than viewing the transfers in isolation.
Impact
Finally, Darktrace began to observe a large amount of suspicious SMB activity on the affected devices, most of which was SMB file encryption. DETECT observed the file extension ‘uw9nmvw’ being appended to many files across various internal shares and devices. In addition to this, a potential ransom note, ‘RECOVER-uw9nmvw-FILES.txt’, was detected on the network shortly after the start of the attack.

Conclusion
Ultimately, this incident show cases how Darktrace was able to successfully identify an emerging ransomware attack using its unrivalled anomaly-based detection capabilities, without having to rely on any previously established threat intelligence. Not only was Darktrace DETECT able to identify the ransomware at multiple stages of the kill chain, but it was also able to uncover the anomalous activity that took place in the buildup to the attack itself.
As the attack progressed along the cyber kill chain, escalating in severity at every juncture, DETECT was able to provide full visibility over the events. Through the successful identification of compromised devices, anomalous administrative credentials usage and encrypted files, Darktrace was able to greatly assist the customer, ensuring they were well-equipped to contain the incident and begin their incident management process.
Darktrace would have been able to aid the customer even further had they enabled its autonomous response technology on their network. Darktrace RESPOND would have taken targeted, mitigative action as soon as suspicious activity was detected, preventing the malicious actors from achieving their goals.
Credit to: Natalia Sánchez Rocafort, Cyber Security Analyst, Patrick Anjos, Senior Cyber Analyst.
MITRE Tactics/Techniques Mapping
RECONNAISSANCE
Scanning IP Blocks (T1595.001)
RECONNAISSANCE
Vulnerability Scanning (T1595.002)
IMPACT
Service Stop (T1489)
LATERAL MOVEMENT
Taint Shared Content (T1080)
IMPACT
Data Encrypted for Impact (T1486)
INITIAL ACCESS
Replication Through Removable Media (T1200)
DEFENSE EVASION
Rogue Domain Controller (T1207)
COMMAND AND CONTROL
Domain Generation Algorithms (T1568.002)
EXECUTION
Windows Management Instrumentation (T1047)
INITIAL ACCESS
Phishing (T1190)
EXFILTRATION
Exfiltration Over C2 Channel (T1041)
IoC Table
IoC ----------- TYPE ------------- DESCRIPTION + PROBABILITY
CVD --------- credentials -------- Possible compromised credential
.UW9NMVW - File extension ----- Possible appended file extension
RECOVER-UW9NMVW-FILES.TXT - Ransom note - Possible ransom note observed
84.32.188[.]186 - IP address ------ C2 Endpoint
AS.EXECSVCT[.]COM - Hostname - C2 Endpoint
ZX.EXECSVCT[.]COM - Hostname - C2 Endpoint
QW.EXECSVCT[.]COM - Hostname - C2 Endpoint
EXECSVCT[.]COM - Hostname ------ C2 Endpoint
15.197.130[.]221 --- IP address ------ C2 Endpoint
AS59642 UAB CHERRY SERVERS - ASN - Possible ASN associated with C2 Endpoints
108.156.28[.]43
108.156.28[.]22
52.84.93[.]26
52.217.131[.]241
54.231.193[.]89 - IP addresses - Possible IP addresses associated with data exfiltration
103.203.59[.]3 -IP address ---- Possible IP address associated with initial attack vector
References:
[1] https://blog.netwrix.com/2021/11/30/what-is-dcsync-an-introduction/
[2] https://www.easeus.com/computer-instruction/delete-system32.html#:~:text=System32%20is%20a%20folder%20on,DLL%20files%2C%20and%20EXE%20files.
[3] https://www.techtarget.com/searchwindowsserver/definition/Windows-Management-Instrumentation#:~:text=WMI%20provides%20users%20with%20information,operational%20environments%2C%20including%20remote%20systems.
[4] https://www.virustotal.com/gui/ip-address/103.203.59[.]3
[5] https://otx.alienvault.com/indicator/ip/15.197.130[.]221
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Inside the SOC
Protecting Prospects: How Darktrace Detected an Account Hijack Within Days of Deployment



Cloud Migration Expanding the Attack Surface
Cloud migration is here to stay – accelerated by pandemic lockdowns, there has been an ongoing increase in the use of public cloud services, and Gartner has forecasted worldwide public cloud spending to grow around 20%, or by almost USD 600 billion [1], in 2023. With more and more organizations utilizing cloud services and moving their operations to the cloud, there has also been a corresponding shift in malicious activity targeting cloud-based software and services, including Microsoft 365, a prominent and oft-used Software-as-a-Service (SaaS).
With the adoption and implementation of more SaaS products, the overall attack surface of an organization increases – this gives malicious actors additional opportunities to exploit and compromise a network, necessitating proper controls to be in place. This increased attack surface can leave organization’s open to cyber risks like cloud misconfigurations, supply chain attacks and zero-day vulnerabilities [2]. In order to achieve full visibility over cloud activity and prevent SaaS compromise, it is paramount for security teams to deploy sophisticated security measures that are able to learn an organization’s SaaS environment and detect suspicious activity at the earliest stage.
Darktrace Immediately Detects Hijacked Account
In May 2023, Darktrace observed a chain of suspicious SaaS activity on the network of a customer who was about to begin their trial of Darktrace/Cloud™ and Darktrace/Email™. Despite being deployed on the network for less than a week, Darktrace DETECT™ recognized that the legitimate SaaS account, belonging to an executive at the organization, had been hijacked. Darktrace/Email was able to provide full visibility over inbound and outbound mail and identified that the compromised account was subsequently used to launch an internal spear-phishing campaign.
If Darktrace RESPOND™ were enabled in autonomous response mode at the time of this compromise, it would have been able to take swift preventative action to disrupt the account compromise and prevent the ensuing phishing attack.
Account Hijack Attack Overview
Unusual External Sources for SaaS Credentials
On May 9, 2023, Darktrace DETECT/Cloud detected the first in a series of anomalous activities performed by a Microsoft 365 user account that was indicative of compromise, namely a failed login from an external IP address located in Virginia.

Just a few minutes later, Darktrace observed the same user credential being used to successfully login from the same unusual IP address, with multi-factor authentication (MFA) requirements satisfied.

A few hours after this, the user credential was once again used to login from a different city in the state of Virginia, with MFA requirements successfully met again. Around the time of this activity, the SaaS user account was also observed previewing various business-related files hosted on Microsoft SharePoint, behavior that, taken in isolation, did not appear to be out of the ordinary and could have represented legitimate activity.
The following day, May 10, however, there were additional login attempts observed from two different states within the US, namely Texas and Florida. Darktrace understood that this activity was extremely suspicious, as it was highly improbable that the legitimate user would be able to travel over 2,500 miles in such a short period of time. Both login attempts were successful and passed MFA requirements, suggesting that the malicious actor was employing techniques to bypass MFA. Such MFA bypass techniques could include inserting malicious infrastructure between the user and the application and intercepting user credentials and tokens, or by compromising browser cookies to bypass authentication controls [3]. There have also been high-profile cases in the recent years of legitimate users mistakenly (and perhaps even instinctively) accepting MFA prompts on their token or mobile device, believing it to be a legitimate process despite not having performed the login themselves.
New Email Rule
On the evening of May 10, following the successful logins from multiple US states, Darktrace observed the Microsoft 365 user creating a new inbox rule, named “.’, in Microsoft Outlook from an IP located in Florida. Threat actors are often observed naming new email rules with single characters, likely to evade detection, but also for the sake of expediency so as to not expend any additional time creating meaningful labels.
In this case the newly created email rules included several suspicious properties, including ‘AlwaysDeleteOutlookRulesBlob’, ‘StopProcessingRules’ and “MoveToFolder”.
Firstly, ‘AlwaysDeleteOutlookRulesBlob’ suppresses or hides warning messages that typically appear if modifications to email rules are made [4]. In this case, it is likely the malicious actor was attempting to implement this property to obfuscate the creation of new email rules.
The ‘StopProcessingRules’ rule meant that any subsequent email rules created by the legitimate user would be overridden by the email rule created by the malicious actor [5]. Finally, the implementation of “MoveToFolder” would allow the malicious actor to automatically move all outgoing emails from the “Sent” folder to the “Deleted Items” folder, for example, further obfuscating their malicious activities [6]. The utilization of these email rule properties is frequently observed during account hijackings as it allows attackers to delete and/or forward key emails, delete evidence of exploitation and launch phishing campaigns [7].
In this incident, the new email rule would likely have enabled the malicious actor to evade the detection of traditional security measures and achieve greater persistence using the Microsoft 365 account.

Account Update
A few hours after the creation of the new email rule, Darktrace observed the threat actor successfully changing the Microsoft 365 user’s account password, this time from a new IP address in Texas. As a result of this action, the attacker would have locked out the legitimate user, effectively gaining full access over the SaaS account.

Phishing Emails
The compromised SaaS account was then observed sending a high volume of suspicious emails to both internal and external email addresses. Darktrace was able to identify that the emails attempting to impersonate the legitimate service DocuSign and contained a malicious link prompting users to click on the text “Review Document”. Upon clicking this link, users would be redirected to a site hosted on Adobe Express, namely hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/.
Adobe Express is a free service that allows users to create web pages which can be hosted and shared publicly; it is likely that the threat actor here leveraged the service to use in their phishing campaign. When clicked, such links could result in a device unwittingly downloading malware hosted on the site, or direct unsuspecting users to a spoofed login page attempting to harvest user credentials by imitating legitimate companies like Microsoft.

The malicious site hosted on Adobe Express was subsequently taken down by Adobe, possibly in response to user reports of maliciousness. Unfortunately though, platforms like this that offer free webhosting services can easily and repeatedly be abused by malicious actors. Simply by creating new pages hosted on different IP addresses, actors are able to continue to carry out such phishing attacks against unsuspecting users.
In addition to the suspicious SaaS and email activity that took place between May 9 and May 10, Darktrace/Email also detected the compromised account sending and receiving suspicious emails starting on May 4, just two days after Darktrace’s initial deployment on the customer’s environment. It is probable that the SaaS account was compromised around this time, or even prior to Darktrace’s deployment on May 2, likely via a phishing and credential harvesting campaign similar to the one detailed above.

Darktrace Coverage
As the customer was soon to begin their trial period, Darktrace RESPOND was set in “human confirmation” mode, meaning that any preventative RESPOND actions required manual application by the customer’s security team.
If Darktrace RESPOND had been enabled in autonomous response mode during this incident, it would have taken swift mitigative action by logging the suspicious user out of the SaaS account and disabling the account for a defined period of time, in doing so disrupting the attack at the earliest possible stage and giving the customer the necessary time to perform remediation steps. As it was, however, these RESPOND actions were suggested to the customer’s security team for them to manually apply.

Nevertheless, with Darktrace DETECT/Cloud in place, visibility over the anomalous cloud-based activities was significantly increased, enabling the swift identification of the chain of suspicious activities involved in this compromise.
In this case, the prospective customer reached out to Darktrace directly through the Ask the Expert (ATE) service. Darktrace’s expert analyst team then conducted a timely and comprehensive investigation into the suspicious activity surrounding this SaaS compromise, and shared these findings with the customer’s security team.
Conclusion
Ultimately, this example of SaaS account compromise highlights Darktrace’s unique ability to learn an organization’s digital environment and recognize activity that is deemed to be unexpected, within a matter of days.
Due to the lack of obvious or known indicators of compromise (IoCs) associated with the malicious activity in this incident, this account hijack would likely have gone unnoticed by traditional security tools that rely on a rules and signatures-based approach to threat detection. However, Darktrace’s Self-Learning AI enables it to detect the subtle deviations in a device’s behavior that could be indicative of an ongoing compromise.
Despite being newly deployed on a prospective customer’s network, Darktrace DETECT was able to identify unusual login attempts from geographically improbable locations, suspicious email rule updates, password changes, as well as the subsequent mounting of a phishing campaign, all before the customer’s trial of Darktrace had even begun.
When enabled in autonomous response mode, Darktrace RESPOND would be able to take swift preventative action against such activity as soon as it is detected, effectively shutting down the compromise and mitigating any subsequent phishing attacks.
With the full deployment of Darktrace’s suite of products, including Darktrace/Cloud and Darktrace/Email, customers can rest assured their critical data and systems are protected, even in the case of hybrid and multi-cloud environments.
Credit: Samuel Wee, Senior Analyst Consultant & Model Developer
Appendices
References
[2] https://www.upguard.com/blog/saas-security-risks
[4] https://learn.microsoft.com/en-us/powershell/module/exchange/disable-inboxrule?view=exchange-ps
[7] https://blog.knowbe4.com/check-your-email-rules-for-maliciousness
Darktrace Model Detections
Darktrace DETECT/Cloud and RESPOND Models Breached:
SaaS / Access / Unusual External Source for SaaS Credential Use
SaaS / Unusual Activity / Multiple Unusual External Sources for SaaS Credential
Antigena / SaaS / Antigena Unusual Activity Block (RESPOND Model)
SaaS / Compliance / New Email Rule
Antigena / SaaS / Antigena Significant Compliance Activity Block
SaaS / Compromise / Unusual Login and New Email Rule (Enhanced Monitoring Model)
Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)
SaaS / Compromise / SaaS Anomaly Following Anomalous Login (Enhanced Monitoring Model)
SaaS / Compromise / Unusual Login and Account Update
Antigena / SaaS / Antigena Suspicious SaaS Activity Block (RESPOND Model)
IoC – Type – Description & Confidence
hxxps://express.adobe[.]com/page/A9ZKVObdXhN4p/ - Domain – Probable Phishing Page (Now Defunct)
37.19.221[.]142 – IP Address – Unusual Login Source
35.174.4[.]92 – IP Address – Unusual Login Source
MITRE ATT&CK Mapping
Tactic - Techniques
INITIAL ACCESS, PRIVILEGE ESCALATION, DEFENSE EVASION, PERSISTENCE
T1078.004 – Cloud Accounts
DISCOVERY
T1538 – Cloud Service Dashboards
CREDENTIAL ACCESS
T1539 – Steal Web Session Cookie
RESOURCE DEVELOPMENT
T1586 – Compromise Accounts
PERSISTENCE
T1137.005 – Outlook Rules

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Darktrace/Email in Action: Why AI-Driven Email Security is the Best Defense Against Sustained Phishing Campaigns
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Stopping the bad while allowing the good
Since its inception, email has been regarded as one of the most important tools for businesses, revolutionizing communication and allowing global teams to become even more connected. But besides organizations heavily relying on email for their daily operations, threat actors have also recognized that the inbox is one of the easiest ways to establish an initial foothold on the network.
Today, not only are phishing campaigns and social engineering attacks becoming more prevalent, but the level of sophistication of these attacks are also increasing with the help of generative AI tools that allow for the creation of hyper-realistic emails with minimal errors, effectively lowering the barrier to entry for threat actors. These diverse and stealthy types of attacks evade traditional email security tools based on rules and signatures, because they are less likely to contain the low-sophistication markers of a typical phishing attack.
In a situation where the sky is the limit for attackers and security teams are lean, how can teams equip themselves to tackle these threats? How can they accurately detect increasingly realistic malicious emails and neutralize these threats before it is too late? And importantly, how can email security block these threats while allowing legitimate emails to flow freely?
Instead of relying on past attack data, Darktrace’s Self-Learning AI detects the slightest deviation from a user’s pattern of life and responds autonomously to contain potential threats, stopping novel attacks in their tracks before damage is caused. It doesn’t define ‘good’ and ‘bad’ like traditional email tools, rather it understands each user and what is normal for them – and what’s not.
This blog outlines how Darktrace/Email™ used its understanding of ‘normal’ to accurately detect and respond to a sustained phishing campaign targeting a real-life company.
Responding to a sustained phishing attack
Over the course of 24 hours, Darktrace detected multiple emails containing different subjects, all from different senders to different recipients in one organization. These emails were sent from different IP addresses, but all came from the same autonomous system number (ASN).

The emails themselves had many suspicious indicators. All senders had no prior association with the recipient, and the emails generated a high general inducement score. This score is generated by structural and non-specific content analysis of the email – a high score indicates that the email is trying to induce the recipient into taking a particular action, which may lead to account compromise.
Additionally, each email contained a visually prominent link to a file storage service, hidden behind a shortened bit.ly link. The similarities across all these emails pointed to a sustained campaign targeting the organization by a single threat actor.


With all these suspicious indicators, many models were breached. This drove up the anomaly score, causing Darktrace/Email to hold all suspicious emails from the recipients’ inboxes, safeguarding the recipients from potential account compromise and disallowing the threats from taking hold in the network.
Imagining a phishing attack without Darktrace/Email
So what could have happened if Darktrace had not withheld these emails, and the recipients had clicked on the links? File storage sites have a wide variety of uses that allow attackers to be creative in their attack strategy. If the user had clicked on the shortened link, the possible consequences are numerous. The link could have led to a login page for unsuspecting victims to input their credentials, or it could have hosted malware that would automatically download if the link was clicked. With the compromised credentials, threat actors could even bypass MFA, change email rules, or gain privileged access to a network. The downloaded malware might also be a keylogger, leading to cryptojacking, or could open a back door for threat actors to return to at a later time.


The limits of traditional email security tools
Secure email gateways (SEGs) and static AI security tools may have found it challenging to detect this phishing campaign as malicious. While Darktrace was able to correlate these emails to determine that a sustained phishing campaign was taking place, the pattern among these emails is far too generic for specific rules as set in traditional security tools. If we take the characteristic of the freemail account sender as an example, setting a rule to block all emails from freemail accounts may lead to more legitimate emails being withheld, since these addresses have a variety of uses.
With these factors in mind, these emails could have easily slipped through traditional security filters and led to a devastating impact on the organization.
Conclusion
As threat actors step up their attacks in sophistication, prioritizing email security is more crucial than ever to preserving a safe digital environment. In response to these challenges, Darktrace/Email offers a set-and-forget solution that continuously learns and adapts to changes in the organization.
Through an evolving understanding of every environment in which it is deployed, its threat response becomes increasingly precise in neutralizing only the bad, while allowing the good – delivering email security that doesn’t come at the expense of business growth.