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A Shifting Email Conversation: Email Security is Stuck Looking to the Past
In an escalating threat landscape with email as the primary target, IT teams need to move far beyond traditional methods of email security that haven’t evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. By design, they are permanently playing catch up to continually innovating attackers, taking an average of 13 days to recognize new attacks[1].
Phishing attacks are getting more targeted and sophisticated as attackers innovate in two key areas: delivery tactics, and social engineering. On the malware delivery side, attackers are increasingly ‘piggybacking’ off the legitimate infrastructure and reputations of services like SharePoint and OneDrive, as well as legitimate email accounts, to evade security tools.
To evade the human on the other end of the email, attackers are tapping into new social engineering tactics, exploiting fear, uncertainty, and doubt (FUD) and evoking a sense of urgency as ever, but now have tools at their disposal to enable tailored and personalized social engineering at scale.
With the help of tools such as ChatGPT, threat actors can leverage AI technologies to impersonate trusted organizations and contacts – including damaging business email compromises, realistic spear phishing, spoofing, and social engineering. In fact, Darktrace found that the average linguistic complexity of phishing emails has jumped by 17% since the release of ChatGPT.
This is just one example of accelerating attack sophistication – lowering the barrier to entry and improving outcomes for attackers. It forms part of a wider trend of the attack landscape moving from low-sophistication, low-impact, and generic phishing tactics - a 'spray and pray' approach - to more targeted, sophisticated, and higher impact attacks that fall outside of the typical detection remit for any tool relying on rules and signatures. Generative AI and other technologies in the attackers' toolkit will soon enable the launch of these attacks at scale, and only being able to catch known threats that have been seen before will no longer be enough.
In an escalating threat landscape with email as the primary target, the vast majority of email security tools haven't evolved fast enough – they’re trained on historical attack data, so only catch what they’ve seen before. They look to the past to try and predict the next attack, and are designed to catch today’s attacks tomorrow.
Organizations are increasingly moving towards AI systems, but not all AI is the same, and the application of that AI is crucial. IT and security teams need to move towards email security that is context-aware and leverages AI for deep behavioral analysis. And it’s a proven approach, successfully catching attacks that slip by other tools across thousands of organizations. And email security today needs to be more about just protecting the inbox. It needs to address not just malicious emails, but the full 360-degree view of a user across their email messages and accounts, as well as extended coverage where email bleeds into collaboration tools/SaaS. For many organizations, the question is not if they should upgrade their email security, but when – how much longer can they risk relying on email security that’s stuck looking to the past?
The Email Security Industry: Playing Catch-Up
Gateways and ICES (Integrated Cloud Email Security) providers have something in common: they look to past attacks in order to try to predict the future. They often rely on previous threat intelligence and on assembling ‘deny-lists’ of known bad elements of emails already identified as malicious – these tools fail to meet the reality of the contemporary threat landscape. Some of these tools attempt to use AI to improve this flawed approach, looking not only for direct matches, but using "data augmentation" to try and find similar-looking emails. But this approach is still inherently blind to novel threats.
These tools tend to be resource-intensive, requiring constant policy maintenance combined with the hand-to-hand combat of releasing held-but-legitimate emails and holding back malicious phishing emails. This burden of manually releasing individual emails typically falls on security teams, teams that are frequently small with multiple areas of responsibility. The solution is to deploy technology that autonomously stops the bad while allowing the good through, and adapts to changes in the organization – technology that actually fits the definition of ‘set and forget’.
Becoming behavioral and context-aware
There is a seismic shift underway in the industry, from “secure” email gateways to intelligent AI-driven thinking. The right approach is to understand the behaviors of end users – how each person uses their inbox and what constitutes ‘normal’ for each user – in order to detect what’s not normal. It makes use of context – how and when people communicate, and with who – to spot the unusual and to flag to the user when something doesn’t look quite right – and why. Basically, a system that understands you. Not past attacks.
Darktrace has developed a fundamentally different approach to AI, one that doesn’t learn what’s dangerous from historical data but from a deep continuous understanding of each organization and their users. Only a complex understanding of the normal day-to-day behavior of each employee can accurately determine whether or not an email actually belongs in that recipient’s inbox.
Whether it’s phishing, ransomware, invoice fraud, executive impersonation, or a novel technique, leveraging AI for behavioral analysis allows for faster decision-making – it doesn’t need to wait for a Patient Zero to contain a new attack because it can stop malicious threats on first encounter. This increased confidence in detection allows for more a precise response – targeted action to remove only the riskiest parts of an email, rather than taking a broad blanket response out of caution – in order to reduce risk with minimal disruption to the business.
Returning to our attack spectrum, as the attack landscape moves increasingly towards highly sophisticated attacks that use novel or seemingly legitimate infrastructure to deliver malware and induce victims, it has never been more important to detect and issue an appropriate response to these high-impact and targeted attacks.
Understanding you and a 360° view of the end user
We know that modern email security isn’t limited to the inbox alone – it has to encompass a full understanding of a user’s normal behavior across email and beyond. Traditional email tools are focused solely on inbound email as the point of breach, which fails to protect against the potentially catastrophic damage caused by a successful email attack once an account has been compromised.
In order to have complete context around what is normal for a user, it’s crucial to understand their activity within Microsoft 365, Google Workspace, Salesforce, Dropbox, and even their device on the network. Monitoring devices (as well as inboxes) for symptoms of infection is crucial to determining whether or not an email has been malicious, and if similar emails need to be withheld in the future. Combining with data from cloud apps enables a more holistic view of identity-based attacks.
Understanding a user in the context of the whole organization – which also means network, cloud, and endpoint data – brings additional context to light to improve decision making, and connecting email security with external data on the attack surface can help proactively find malicious domains, so that defenses can be hardened before an attack is even launched.
Educating and Engaging Your Employees
Ultimately, it’s employees who interact with any given email. If organizations can successfully empower this user base, they will end up with a smarter workforce, fewer successful attacks, and a security team with more time on their hands for better, strategic work.
The tools that succeed best will be those that can leverage AI to help employees become more security-conscious. While some emails are evidently malicious and should never enter an employee’s inbox, there is a significant grey area of emails that have potentially risky elements. The majority of security tools will either withhold these emails completely – even though they might be business critical – or let them through scot-free. But what if these grey-area emails could in fact be used as training opportunities?
As opposed to phishing simulation vendors, behavioral AI can improve security awareness holistically throughout organizations by training users with a light touch via their own inboxes – bringing the end user into the loop to harden defenses.
The new frontier of email security fights AI with AI, and organizations who lag behind might end up learning the hard way. Read on for our blog series about how these technologies can transform the employee experience, dynamize deployment, augment security teams and form part of an integrated defensive loop.
[1] 13 days is the mean average of phishing payloads active in the wild between the response of Darktrace/Email compared to the earliest of 16 independent feeds submitted by other email security technologies.
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PurpleFox in a Henhouse: How Darktrace Hunted Down a Persistent and Dynamic Rootkit
Versatile Malware: PurpleFox
As organizations and security teams across the world move to bolster their digital defenses against cyber threats, threats actors, in turn, are forced to adopt more sophisticated tactics, techniques and procedures (TTPs) to circumvent them. Rather than being static and predictable, malware strains are becoming increasingly versatile and therefore elusive to traditional security tools.
One such example is PurpleFox. First observed in 2018, PurpleFox is a combined fileless rootkit and backdoor trojan known to target Windows machines. PurpleFox is known for consistently adapting its functionalities over time, utilizing different infection vectors including known vulnerabilities (CVEs), fake Telegram installers, and phishing. It is also leveraged by other campaigns to deliver ransomware tools, spyware, and cryptocurrency mining malware. It is also widely known for using Microsoft Software Installer (MSI) files masquerading as other file types.
The Evolution of PurpleFox
The Original Strain
First reported in March 2018, PurpleFox was identified to be a trojan that drops itself onto Windows machines using an MSI installation package that alters registry values to replace a legitimate Windows system file [1]. The initial stage of infection relied on the third-party toolkit RIG Exploit Kit (EK). RIG EK is hosted on compromised or malicious websites and is dropped onto the unsuspecting system when they visit browse that site. The built-in Windows installer (MSIEXEC) is leveraged to run the installation package retrieved from the website. This, in turn, drops two files into the Windows directory – namely a malicious dynamic-link library (DLL) that acts as a loader, and the payload of the malware. After infection, PurpleFox is often used to retrieve and deploy other types of malware.
Subsequent Variants
Since its initial discovery, PurpleFox has also been observed leveraging PowerShell to enable fileless infection and additional privilege escalation vulnerabilities to increase the likelihood of successful infection [2]. The PowerShell script had also been reported to be masquerading as a .jpg image file. PowerSploit modules are utilized to gain elevated privileges if the current user lacks administrator privileges. Once obtained, the script proceeds to retrieve and execute a malicious MSI package, also masquerading as an image file. As of 2020, PurpleFox no longer relied on the RIG EK for its delivery phase, instead spreading via the exploitation of the SMB protocol [3]. The malware would leverage the compromised systems as hosts for the PurpleFox payloads to facilitate its spread to other systems. This mode of infection can occur without any user action, akin to a worm.
The current iteration of PurpleFox reportedly uses brute-forcing of vulnerable services, such as SMB, to facilitate its spread over the network and escalate privileges. By scanning internet-facing Windows computers, PurpleFox exploits weak passwords for Windows user accounts through SMB, including administrative credentials to facilitate further privilege escalation.
Darktrace detection of PurpleFox
In July 2023, Darktrace observed an example of a PurpleFox infection on the network of a customer in the healthcare sector. This observation was a slightly different method of downloading the PurpleFox payload. An affected device was observed initiating a series of service control requests using DCE-RPC, instructing the device to make connections to a host of servers to download a malicious .PNG file, later confirmed to be the PurpleFox rootkit. The device was then observed carrying out worm-like activity to other external internet-facing servers, as well as scanning related subnets.
Darktrace DETECT™ was able to successfully identify and track this compromise across the cyber kill chain and ensure the customer was able to take swift remedial action to prevent the attack from escalating further.
While the customer in question did have Darktrace RESPOND™, it was configured in human confirmation mode, meaning any mitigative actions had to be manually applied by the customer’s security team. If RESPOND had been enabled in autonomous response mode at the time of the attack, it would have been able to take swift action against the compromise to contain it at the earliest instance.
Attack Overview
Initial Scanning over SMB
On July 14, 2023, Darktrace detected the affected device scanning other internal devices on the customer’s network via port 445. The numerous connections were consistent with the aforementioned worm-like activity that has been reported from PurpleFox behavior as it appears to be targeting SMB services looking for open or vulnerable channels to exploit.
This initial scanning activity was detected by Darktrace DETECT, specifically through the model breach ‘Device / Suspicious SMB Scanning Activity’. Darktrace’s Cyber AI Analyst™ then launched an autonomous investigation into these internal connections and tied them into one larger-scale network reconnaissance incident, rather than a series of isolated connections.
As Darktrace RESPOND was configured in human confirmation mode, it was unable to autonomously block these internal connections. However, it did suggest blocking connections on port 445, which could have been manually applied by the customer’s security team.
Privilege Escalation
The device successfully logged in via NTLM with the credential, ‘administrator’. Darktrace recognized that the endpoint was external to the customer’s environment, indicating that the affected device was now being used to propagate the malware to other networks. Considering the lack of observed brute-force activity up to this point, the credentials for ‘administrator’ had likely been compromised prior to Darktrace’s deployment on the network, or outside of Darktrace’s purview via a phishing attack.
Exploitation
Darktrace then detected a series of service control requests over DCE-RPC using the credential ‘admin’ to make SVCCTL Create Service W Requests. A script was then observed where the controlled device is instructed to launch mshta.exe, a Windows-native binary designed to execute Microsoft HTML Application (HTA) files. This enables the execution of arbitrary script code, VBScript in this case.
There are a few MSIEXEC flags to note:
- /i : installs or configures a product
- /Q : sets the user interface level. In this case, it is set to ‘No UI’, which is used for “quiet” execution, so no user interaction is required
Evidently, this was an attempt to evade detection by endpoint users as it is surreptitiously installed onto the system. This corresponds to the download of the rootkit that has previously been associated with PurpleFox. At this stage, the infected device continues to be leveraged as an attack device and scans SMB services over external endpoints. The device also appeared to attempt brute-forcing over NTLM using the same ‘administrator’ credential to these endpoints. This activity was identified by Darktrace DETECT which, if enabled in autonomous response mode would have instantly blocked similar outbound connections, thus preventing the spread of PurpleFox.
Installation
On August 9, Darktrace observed the device making initial attempts to download a malicious .PNG file. This was a notable change in tactics from previously reported PurpleFox campaigns which had been observed utilizing .MOE files for their payloads [3]. The .MOE payloads are binary files that are more easily detected and blocked by traditional signatured-based security measures as they are not associated with known software. The ubiquity of .PNG files, especially on the web, make identifying and blacklisting the files significantly more difficult.
The first connection was made with the URI ‘/test.png’. It was noted that the HTTP method here was HEAD, a method similar to GET requests except the server must not return a message-body in the response.
The metainformation contained in the HTTP headers in response to a HEAD request should be identical to the information sent in response to a GET request. This method is often used to test hypertext links for validity and recent modification. This is likely a way of checking if the server hosting the payload is still active. Avoiding connections that could possibly be detected by antivirus solutions can help keep this activity under-the-radar.
The server responds with a status code of 200 before the download begins. The HEAD request could be part of the attacker’s verification that the server is still running, and that the payload is available for download. The ‘/test.png’ HEAD request was sent twice, likely for double confirmation to begin the file transfer.
Subsequent analysis using a Packet Capture (PCAP) tool revealed that this connection used the Windows Installer user agent that has previously been associated with PurpleFox. The device then began to download a payload that was masquerading as a Microsoft Word document. The device was thus able to download the payload twice, from two separate endpoints.
By masquerading as a Microsoft Word file, the threat actor was likely attempting to evade the detection of the endpoint user and traditional security tools by passing off as an innocuous text document. Likewise, using a Windows Installer user agent would enable threat actors to bypass antivirus measures and disguise the malicious installation as legitimate download activity.
Darktrace DETECT identified that these were masqueraded file downloads by correctly identifying the mismatch between the file extension and the true file type. Subsequently, AI Analyst was able to correctly identify the file type and deduced that this download was indicative of the device having been compromised.
In this case, the device attempted to download the payload from several different endpoints, many of which had low antivirus detection rates or open-source intelligence (OSINT) flags, highlighting the need to move beyond traditional signature-base detections.
If Darktrace RESPOND was enabled in autonomous response mode at the time of the attack it would have acted by blocking connections to these suspicious endpoints, thus preventing the download of malicious files. However, as RESPOND was in human confirmation mode, RESPOND actions required manual application by the customer’s security team which unfortunately did not happen, as such the device was able to download the payloads.
Schlussfolgerung
The PurpleFox malware is a particularly dynamic strain known to continually evolve over time, utilizing a blend of old and new approaches to achieve its goals which is likely to muddy expectations on its behavior. By frequently employing new methods of attack, malicious actors are able to bypass traditional security tools that rely on signature-based detections and static lists of indictors of compromise (IoCs), necessitating a more sophisticated approach to threat detection.
Darktrace DETECT’s Self-Learning AI enables it to confront adaptable and elusive threats like PurpleFox. By learning and understanding customer networks, it is able to discern normal network behavior and patterns of life, distinguishing expected activity from potential deviations. This anomaly-based approach to threat detection allows Darktrace to detect cyber threats as soon as they emerge.
By combining DETECT with the autonomous response capabilities of RESPOND, Darktrace customers are able to effectively safeguard their digital environments and ensure that emerging threats can be identified and shut down at the earliest stage of the kill chain, regardless of the tactics employed by would-be attackers.
Credit to Piramol Krishnan, Cyber Analyst, Qing Hong Kwa, Senior Cyber Analyst & Deputy Team Lead, Singapore
Appendices
Darktrace Model Detections
- Device / Increased External Connectivity
- Device / Large Number of Connections to New Endpoints
- Device / SMB Session Brute Force (Admin)
- Compliance / External Windows Communications
- Anomalous Connection / New or Uncommon Service Control
- Compromise / Unusual SVCCTL Activity
- Compromise / Rare Domain Pointing to Internal IP
- Anomalous File / Masqueraded File Transfer
RESPOND Models
- Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
- Antigena / Network / External Threat / Antigena Suspicious Activity Block
- Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block
- Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block
- Antigena / Network / External Threat / Antigena Suspicious File Block
- Antigena / Network / External Threat / Antigena File then New Outbound Block
List of IoCs
IoC - Type - Description
/C558B828.Png - URI - URI for Purple Fox Rootkit [4]
5b1de649f2bc4eb08f1d83f7ea052de5b8fe141f - File Hash - SHA1 hash of C558B828.Png file (Malware payload)
190.4.210[.]242 - IP - Purple Fox C2 Servers
218.4.170[.]236 - IP - IP for download of .PNG file (Malware payload)
180.169.1[.]220 - IP - IP for download of .PNG file (Malware payload)
103.94.108[.]114:10837 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
221.199.171[.]174:16543 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
61.222.155[.]49:14098 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
178.128.103[.]246:17880 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
222.134.99[.]132:12539 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
164.90.152[.]252:18075 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
198.199.80[.]121:11490 - IP - IP from Service Control MSIEXEC script to download PNG file (Malware payload)
MITRE ATT&CK Mapping
Tactic - Technique
Reconnaissance - Active Scanning T1595, Active Scanning: Scanning IP Blocks T1595.001, Active Scanning: Vulnerability Scanning T1595.002
Resource Development - Obtain Capabilities: Malware T1588.001
Initial Access, Defense Evasion, Persistence, Privilege Escalation - Valid Accounts: Default Accounts T1078.001
Initial Access - Drive-by Compromise T1189
Defense Evasion - Masquerading T1036
Credential Access - Brute Force T1110
Discovery - Network Service Discovery T1046
Command and Control - Proxy: External Proxy T1090.002
References
- https://blog.360totalsecurity.com/en/purple-fox-trojan-burst-out-globally-and-infected-more-than-30000-users/
- https://www.trendmicro.com/en_us/research/19/i/purple-fox-fileless-malware-with-rookit-component-delivered-by-rig-exploit-kit-now-abuses-powershell.html
- https://www.akamai.com/blog/security/purple-fox-rootkit-now-propagates-as-a-worm
- https://www.foregenix.com/blog/an-overview-on-purple-fox
- https://www.trendmicro.com/en_sg/research/21/j/purplefox-adds-new-backdoor-that-uses-websockets.html
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$70 Million in Cyber Security Funding for Electric Cooperatives & Utilities
What is the Bipartisan Infrastructure Deal?
The Bipartisan Infrastructure Law passed by congress in 2021 aimed to upgrade power and infrastructure to deliver clean, reliable energy across the US to achieve zero-emissions. To date, the largest investment in clean energy, the deal will fund new programs to support the development and deployment of clean energy technology.
Why is it relevant to electric municipalities?
Section 40124 of the Bipartisan Infrastructure Law allocates $250 million over a 5-year period to create the Rural and Municipal Utility Cybersecurity (RMUC) Program to help electric cooperative, municipal, and small investor-owned utilities protect against, detect, respond to, and recover from cybersecurity threats.1 This act illuminates the value behind a full life-cycle approach to cyber security. Thus, finding a cyber security solution that can provide all aspects of security in one integrated platform would enhance the overall security posture and ease many of the challenges that arise with adopting multiple point solutions.
On November 16, 2023 the Office of Cybersecurity, Energy Security, and Emergency Response (CESER) released the Advanced Cybersecurity Technology (ACT) for electric utilities offering a $70 million funding opportunity that aims to enhance the cybersecurity posture of electric cooperative, municipal, and small investor-owned utilities.
Funding Details
10 projects will be funded with application submissions due November 29, 2023, 5:00 pm ET with $200,000 each in cash prizes in the following areas:
- Direct support for eligible utilities to make investments in cybersecurity technologies, tools, training, and improvements in utility processes and procedures;
- Funding to strengthen the peer-to-peer and not-for-profit cybersecurity technical assistance ecosystem currently serving eligible electric utilities; and
- Increasing access to cybersecurity technical assistance and training for eligible utilities with limited cybersecurity resources. 2
To submit for this award visit: https://www.herox.com/ACT1Prize
How can electric municipalities utilize the funding?
While the adoption of hybrid working patterns increase cloud and SaaS usage, the number of industrial IoT devices also continues to rise. The result is decrease in visibility for security teams and new entry points for attackers. Particularly for energy and utility organizations.
Electric cooperatives seeking to enhance their cyber security posture can aim to invest in cyber security tools that provide the following:
Compliance support: Consider finding an OT security solution that maps out how its solutions and features help your organization comply with relevant compliance mandates such as NIST, ISA, FERC, TSA, HIPAA, CIS Controls, and more.
Anomaly based detection: Siloed security solutions also fail to detect attacks that span
the entire organization. Anomaly-based detection enhances an organization’s cyber security posture by proactively defending against potential attacks and maintaining a comprehensive view of their attack surface.
Integration capabilities: Implementation of several point solutions that complete individual tasks runs the risk of increasing workloads for operators and creates additional challenges with compliance, budgeting, and technical support. Look for cyber security tools that integrate with your existing technologies.
Passive and active asset tracking: Active Identification offers accurate enumeration, real time updates, vulnerability assessment, asset validation while Passive Identification eliminates the risk of operational disruption, minimizes risk, does not generate additional network traffic. It would be ideal to find a security solution that can do both.
Can secure both IT and OT in unison: Given that most OT cyber-attacks actually start in IT networks before pivoting into OT, a mature security posture for critical infrastructure would include a single solution for both IT and OT. Separate solutions for IT and OT present challenges when defending network boundaries and detecting incidents when an attacker pivots from IT to OT. These independent solutions also significantly increase operator workload and materially diminish risk mitigation efforts.
Darktrace/OT for Electric Cooperatives and Utilities
For smaller teams with just one or two dedicated employees, Darktrace’s Cyber AI Analyst and Investigation features allow end users to spend less time in the platform as it compiles critical incidents into comprehensive actionable event reports. AI Analyst brings all the information into a centralized view with incident reporting in natural language summaries and can be generated for compliance reports specific to regulatory requirements.
For larger teams, Darktrace alerts can be forwarded to 3rd party platforms such as a SIEM, where security team decision making is augmented. Additionally, executive reports and autonomous response reduce the alert fatigue generally associated with legacy tools. Most importantly, Darktrace’s unique understanding of normal allows security teams to detect zero-days and signatureless attacks regardless of the size of the organization and how alerts are consumed.
Key Benefits of Darktrace/OT
- Anomaly-based detection and real-time response
- Secures IT, OT, and IoT in unison
- Active and Passive Asset Identification
- Automated security reporting
- Attack surface management and vulnerability assessment
- Covers all levels of the Purdue Model
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References
