Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
Written by
Dan Fein
VP, Product
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07
Jun 2020
‘Social engineering’. ‘Credential theft’. ‘Account takeover’. If you were a fly on the wall of a Security Operations Center in 2020, you would have heard these phrases far more often than ‘banking trojan’, ‘SQL injection’ or ‘exploit kit’. The reason for this is simple – the reality for most security teams now is that their perimeter has shifted into the cloud. Identities are being attacked more than devices.
‘Microsoft 365 account compromise’ is the current favorite, with 29% of organizations reporting a related incident in one month alone. Security teams struggle with these attacks because the evidence needed to detect them is scattered across the enterprise: they begin via email, are executed over the network, and progress in the cloud. This broad and spread out digital footprint means that following the breadcrumbs is not easy.
Darktrace’s Cyber AI Platform is designed to understand a user’s behavior as they move between devices and cloud services, tracking their activity to identify a compromise. To help understand how these attacks avoid detection, it is useful to look at a couple of examples of Microsoft Office 365 compromise detected recently in one of our customers.
Microsoft 365 compromised to launch external email threat
A Microsoft 365 account was recently compromised at a public accounting firm based in the United States. Darktrace initially picked up on several anomalies, including a sudden surge in outbound email traffic as well as the unusual login location – while the company and nearly all of its users were located in Wisconsin, an IP address located in Kansas was used to log in to the Microsoft 365 account. Along with the unusual login, a login to Microsoft Teams from the same Kansas IP address was detected.
Figure 1: Just after the new email rule was created, a Microsoft Teams 100% rare IP login occurred.
‘Impossible travel’ rules alone would have missed these anomalies, but an understanding of activity and behavior across different SaaS applications allowed Darktrace’s AI to recognize these events as one systematic case of credential theft. When the threat-actor subsequently created a new email rule, Darktrace was able to connect this event with the other anomalous behavior and understand its potentially malicious nature.
Figure 2: Darktrace’s SaaS Module noted a 100% rare IP logging into the user’s Microsoft 365 account and the creation of a new mailbox rules. All factors indicated 100% unusual SaaS activity.
Five minutes later, Antigena Email alerted on a large number of outbound emails containing a generic subject line and an attached PDF. The technology also detected that there was a clear spike in outbound emails from this user and flagged each of these emails with the “Out of Character” tag, which in this case denoted a change from normal behavior with the surge in recipients, and likely internal compromise.
Figure 3: Antigena Email detected a surge in recipients that indicated a serious breach of normal behavior for this user.
The unusual login behavior detected by Darktrace’s SaaS Module could be connected to the anomalous outbound email behavior flagged by Antigena Email, allowing the security team to see the extent of the attack and neutralize it as it emerged. It was clear that the account was being used to engage in malicious activity, as each of the 220 outbound emails used a generic subject line and contained a suspicious attachment. The security team therefore immediately disabled the compromised account.
Figure 4: A recreation of the email sent by the attacker, containing the malicious attachment.
‘Change of bank details’ sent from accounts department
When an Accounts Department’s Microsoft 365 account was compromised and used to send targeted phishing emails, Darktrace was able to track the attacker’s movement within the inbox, tying together information from Darktrace’s SaaS Module with Antigena Email’s alerts to understand the full picture of the threat and stop the attack.
The SaaS account appears to have been compromised via an inbound spear phishing attack, or some other form of attack that occurred before Darktrace began monitoring the organization. While Darktrace Cyber AI had no oversight of the initial compromise, it was still able to distinguish later attacker behavior as malicious, based on its actively evolving understanding of the organization and its workforce.
When the account user logged in from a 100% rare French IP address, Darktrace’s SaaS Module picked up on the anomaly immediately, and further detected a series of activities carried out after the unusual login. At the same time, Antigena Email noted an email being sent.
Figure 5: The login from a French IP was noted as 100% rare for this user and SaaS account.
Darktrace then identified more activity occurring from a second rare login location, a Swiss IP address. Very little email activity occurred when the account was logged in from this IP. Instead, Cyber AI saw the threat-actor using their illegitimate SaaS access to view information on the legitimate account user and files related to banking, invoices, and payments.
Antigena Email then identified a series of email communications that, when seen in the context of the SaaS account compromise, pointed to a clear threat. There were no obvious malicious attachments or links in the emails. However, the subject of the final reply was ‘Change of Bank Details’, and the email prompted a high Solicitation Inducement Score within Antigena Email, strongly implying that the malicious actor had sent emails instructing the destination to change payment details in order to route money to the attacker, instead of the company.
It seems the attackers went through the banking and invoicing files in order to find a customer with a big bill to pay, then used the compromised email account to launch an outbound phishing attack, changing the billing details. With Darktrace AI correlating information within the SaaS platform and insights from Antigena Email, this targeted phishing attack could be contained before further compromise or damage could occur.
The below screenshot also indicates a series of inbox processing rules made on the compromised account, showing actions that are typical of an account takeover.
Figure 6: Darktrace’s records of new inbox rules being set up on the compromised SaaS account.
The benefits of a unified approach
These stories are all too familiar. Most security tools would not be able to take action on any one of these steps individually. But the combination reveals the tell-tale sign of a Microsoft 365 account hijack. Organizations are struggling to manage their user identities across their cloud infrastructure, and rule and policy-based detection is no longer feasible.
However, by learning identities and behavior across the enterprise, Darktrace is able to detect, and seamlessly respond, to combat these threats. Hundreds of organizations are now using Antigena Email to protect their email and cloud environments continuously, trusting it to dynamically enforce MFA, lock accounts, block network traffic, and withhold emails when necessary.
As cloud-native applications become more popular, organizations face the growing problem of separate end-to-end security solutions for each type of workload. With Antigena Email working in conjunction with Darktrace’s Enterprise Immune System, defenders can be assured that a single, unified platform is tracking every suspicious behavior, wherever it arises in the organization.
Darktrace cyber analysts are world-class experts in threat intelligence, threat hunting and incident response, and provide 24/7 SOC support to thousands of Darktrace customers around the globe. Inside the SOC is exclusively authored by these experts, providing analysis of cyber incidents and threat trends, based on real-world experience in the field.
SEO Poisoning and Fake PuTTY sites: Darktrace’s Investigation into the Oyster backdoor
What is SEO poisoning?
Search Engine Optimization (SEO) is the legitimate marketing technique of improving the visibility of websites in organic search engine results. Businesses, publishers, and organizations use SEO to ensure their content is easily discoverable by users. Techniques may include optimizing keywords, creating backlinks, or even ensuring mobile compatibility.
SEO poisoning occurs when attackers use these same techniques for malicious purposes. Instead of improving the visibility of legitimate content, threat actors use SEO to push harmful or deceptive websites to the top of search results. This method exploits the common assumption that top-ranking results are trustworthy, leading users to click on URLs without carefully inspecting them.
As part of SEO poisoning, the attacker will first register a typo-squatted domain, slightly misspelled or otherwise deceptive versions of real software sites, such as putty[.]run or puttyy[.]org. These sites are optimized for SEO and often even backed by malicious Google ads, increasing the visibility when users search for download links. To achieve that, threat actors may embed pages with strategically chosen, high-value keywords or replicate content from reputable sources to elevate the domain’s perceived authority in search engine algorithms [4]. In more advanced operations, these tactics are reinforced with paid promotion, such as Google ads, enabling malicious domains to appear above organic search results as sponsored links. This placement not only accelerates visibility but also impacts an unwarranted sense of legitimacy to unsuspected users.
Once a user lands on one of these fake pages, they are presented with what looks like a legitimate software download option. Upon clicking the download indicator, the user will be redirected to another separate domain that actually hosts the payload. This hosting domain is usually unrelated to the nominally referenced software. These third-party sites can involve recently registered domains but may also include legitimate websites that have been recently compromised. By hosting malware on a variety of infrastructure, attackers can prolong the availability of distribution methods for these malicious files before they are taken down.
What is the Oyster backdoor?
Oyster, also known as Broomstick or CleanUpLoader, is a C++ based backdoor malware first identified in July 2023. It enables remote access to infected systems, offering features such as command-line interaction and file transfers.
Oyster has been widely adopted by various threat actors, often as an entry point for ransomware attacks. Notable examples include Vanilla Tempest and Rhysida ransomware groups, both of which have been observed leveraging the Oyster backdoor to enhance their attack capabilities. Vanilla Tempest is known for using Oyster’s stealth persistence to maintain long-term access within targeted networks, often aligning their operations with ransomware deployment [5]. Rhysida has taken this further by deploying Oyster as an initial access tool in ransomware campaigns, using it to conduct reconnaissance and move laterally before executing encryption activities [6].
Once installed, the backdoor gathers basic system information before communicating with a command-and-control (C2) server. The malware largely relies on a ‘cmd.exe’ instance to execute commands and launch other files [1].
In previous SEO poisoning cases, the file downloaded from the fake pages is not just PuTTY, but a trojanized version that includes the stealthy Oyster backdoor. PuTTY is a free and open-source terminal emulator for Windows that allows users to connect to remote servers and devices using protocols like SSH and Telnet. In the recent campaign, once a user visits the fake software download site, ranked highly through SEO poisoning, the malicious payload is downloaded through direct user interaction and subsequently installed on the local device, initiating the compromise. The malware then performs two actions simultaneously: it installs a fully functional version of PuTTY to avoid user suspicion, while silently deploying the Oyster backdoor. Given PuTTY’s nature, it is prominently used by IT administrators with highly privileged account as opposed to standard users in a business, possibly narrowing the scope of the targets.
Oyster’s persistence mechanism involves creating a Windows Scheduled Task that runs every few minutes. Notably, the infection uses Dynamic Link Library (DLL) side loading, where a malicious DLL, often named ‘twain_96.dll’, is executed via the legitimate Windows utility ‘rundll32.exe’, which is commonly used to run DLLs [2]. This technique is frequently used by malicious actors to blend their activity with normal system operations.
Darktrace’s Coverage of the Oyster Backdoor
In June 2025, security analysts at Darktrace identified a campaign leveraging search engine manipulation to deliver malware masquerading as the popular SSH client, PuTTY. Darktrace / NETWORK’s anomaly-based detection identified signs of malicious activity, and when properly configured, its Autonomous Response capability swiftly shut down the threar before it could escalate into a more disruptive attack. Subsequent analysis by Darktrace’s Threat Research team revealed that the payload was a variant of the Oyster backdoor.
The first indicators of an emerging Oyster SEO campaign typically appeared when user devices navigated to a typosquatted domain, such as putty[.]run or putty app[.]naymin[.]com, via a TLS/SSL connection.
Figure 1: Darktrace’s detection of a device connecting to the typosquatted domain putty[.]run.
The device would then initiate a connection to a secondary domain that hosts the malicious installer, likely triggered by user interaction with redirect elements on the landing page. This secondary site may not have any immediate connection to PuTTY itself but is instead a hijacked blog, a file-sharing service, or a legitimate-looking content delivery subdomain.
Figure 2: Darktrace’s detection of the device making subsequent connections to the payload domain.
Following installation, multiple affected devices were observed attempting outbound connectivity to rare external IP addresses, specifically requesting the ‘/secure’ endpoint as noted within the declared URIs. After the initial callback, the malware continued communicating with additional infrastructure, maintaining its foothold and likely waiting for tasking instructions. Communication patterns included:
· Endpoints with URIs /api/kcehc and /api/jgfnsfnuefcnegfnehjbfncejfh
· Endpoints with URI /reg and user agent “WordPressAgent”, “FingerPrint” or “FingerPrintpersistent”
This tactic has been consistently linked to the Oyster backdoor, which has shown similar URI patterns across multiple campaigns [3].
Darktrace analysts also noted the sophisticated use of spoofed user agent strings across multiple investigated customer networks. These headers, which are typically used to identify the application making an HTTP request, are carefully crafted to appear benign or mimic legitimate software. One common example seen in the campaign is the user agent string “WordPressAgent”. While this string references a legitimate web application or plugin, it does not appear to correspond to any known WordPress services or APIs. Its inclusion is most likely designed to mimic background web traffic commonly associated with WordPress-based content management systems.
Figure 3: Cyber AI Analyst investigation linking the HTTP C2 activity.
Case-Specific Observations
While the previous section focused on tactics and techniques common across observed Oyster infections, a closer examination reveals notable variations and unique elements in specific cases. These distinct features offer valuable insights into the diverse operational approaches employed by threat actors. These distinct features, from unusual user agent strings to atypical network behavior, offer valuable insights into the diverse operational approaches employed by the threat actors. Crucially, the divergence in post-exploitation activity reflects a broader trend in the use of widely available malware families like Oyster as flexible entry points, rather than fixed tools with a single purpose. This modular use of the backdoor reflects the growing Malware-as-a-Service (MaaS) ecosystem, where a single initial infection can be repurposed depending on the operator’s goals.
From Infection to Data Egress
In one observed incident, Darktrace observed an infected device downloading a ZIP file named ‘host[.]zip’ via curl from the URI path /333/host[.]zip, following the standard payload delivery chain. This file likely contained additional tools or payloads intended to expand the attacker’s capabilities within the compromised environment. Shortly afterwards, the device exhibited indicators of probable data exfiltration, with outbound HTTP POST requests featuring the URI pattern: /upload?dir=NAME_FOLDER/KEY_KEY_KEY/redacted/c/users/public.
This format suggests the malware was actively engaged in local host data staging and attempting to transmit files from the target machine. The affected device, identified as a laptop, aligns with the expected target profile in SEO poisoning scenarios, where unsuspecting end users download and execute trojanized software.
Irregular RDP Activity and Scanning Behavior
Several instances within the campaign revealed anomalous or unexpected Remote Desktop Protocol (RDP) sessions occurring shortly after DNS requests to fake PuTTY domains. Unusual RDP connections frequently followed communication with Oyster backdoor C2 servers. Additionally, Darktrace detected patterns of RDP scanning, suggesting the attackers were actively probing for accessible systems within the network. This behavior indicates a move beyond initial compromise toward lateral movement and privilege escalation, common objectives once persistence is established.
The presence of unauthorized and administrative RDP sessions following Oyster infections aligns with the malware’s historical role as a gateway for broader impact. In previous campaigns, Oyster has often been leveraged to enable credential theft, lateral movement, and ultimately ransomware deployment. The observed RDP activity in this case suggests a similar progression, where the backdoor is not the final objective but rather a means to expand access and establish control over the target environment.
Cryptic User Agent Strings?
In multiple investigated cases, the user agent string identified in these connections featured formatting that appeared nonsensical or cryptic. One such string containing seemingly random Chinese-language characters translated into an unusual phrase: “Weihe river is where the water and river flow.” Legitimate software would not typically use such wording, suggesting that the string was intended as a symbolic marker rather than a technical necessity. Whether meant as a calling card or deliberately crafted to frame attribution, its presence highlights how subtle linguistic cues can complicate analysis.
Figure 4: Darktrace’s detection of malicious connections using a user agent with randomized Chinese-language formatting.
Strategic Implications
What makes this campaign particularly noteworthy is not simply the use of Oyster, but its delivery mechanism. SEO poisoning has traditionally been associated with cybercriminal operations focused on opportunistic gains, such as credential theft and fraud. Its strength lies in casting a wide net, luring unsuspecting users searching for popular software and tricking them into downloading malicious binaries. Unlike other campaigns, SEO poisoning is inherently indiscriminate, given that the attacker cannot control exactly who lands on their poisoned search results. However, in this case, the use of PuTTY as the luring mechanism possibly indicates a narrowed scope - targeting IT administrators and accounts with high privileges due to the nature of PuTTY’s functionalities.
This raises important implications when considered alongside Oyster. As a backdoor often linked to ransomware operations and persistent access frameworks, Oyster is far more valuable as an entry point into corporate or government networks than small-scale cybercrime. The presence of this malware in an SEO-driven delivery chain suggests a potential convergence between traditional cybercriminal delivery tactics and objectives often associated with more sophisticated attackers. If actors with state-sponsored or strategic objectives are indeed experimenting with SEO poisoning, it could signal a broadening of their targeting approaches. This trend aligns with the growing prominence of MaaS and the role of initial access brokers in today’s cybercrime ecosystem.
Whether the operators seek financial extortion through ransomware or longer-term espionage campaigns, the use of such techniques blurs the traditional distinctions. What looks like a mass-market infection vector might, in practice, be seeding footholds for high-value strategic intrusions.
Credit to Christina Kreza (Cyber Analyst) and Adam Potter (Senior Cyber Analyst)
Appendices
MITRE ATT&CK Mapping
· T1071.001 – Command and Control – Web Protocols
· T1008 – Command and Control – Fallback Channels
· T0885 – Command and Control – Commonly Used Port
· T1571 – Command and Control – Non-Standard Port
· T1176 – Persistence – Browser Extensions
· T1189 – Initial Access – Drive-by Compromise
· T1566.002 – Initial Access – Spearphishing Link
· T1574.001 – Persistence – DLL
Indicators of Compromise (IoCs)
· 85.239.52[.]99 – IP address
· 194.213.18[.]89/reg – IP address / URI
· 185.28.119[.]113/secure – IP address / URI
· 185.196.8[.]217 – IP address
· 185.208.158[.]119 – IP address
· putty[.]run – Endpoint
· putty-app[.]naymin[.]com – Endpoint
· /api/jgfnsfnuefcnegfnehjbfncejfh
· /api/kcehc
Darktrace Model Detections
· Anomalous Connection / New User Agent to IP Without Hostname
· Anomalous Connection / Posting HTTP to IP Without Hostname
· Compromise / HTTP Beaconing to Rare Destination
· Compromise / Large Number of Suspicious Failed Connections
· Compromise / Beaconing Activity to External Rare
· Compromise / Quick and Regular Windows HTTP Beaconing
· Device / Large Number of Model Alerts
· Device / Initial Attack Chain Activity
· Device / Suspicious Domain
· Device / New User Agent
· Antigena / Network / Significant Anomaly / Antigena Breaches Over Time Block
The content provided in this blog is published by Darktrace for general informational purposes only and reflects our understanding of cybersecurity topics, trends, incidents, and developments at the time of publication. While we strive to ensure accuracy and relevance, the information is provided “as is” without any representations or warranties, express or implied. Darktrace makes no guarantees regarding the completeness, accuracy, reliability, or timeliness of any information presented and expressly disclaims all warranties.
Nothing in this blog constitutes legal, technical, or professional advice, and readers should consult qualified professionals before acting on any information contained herein. Any references to third-party organizations, technologies, threat actors, or incidents are for informational purposes only and do not imply affiliation, endorsement, or recommendation.
Darktrace, its affiliates, employees, or agents shall not be held liable for any loss, damage, or harm arising from the use of or reliance on the information in this blog.
The cybersecurity landscape evolves rapidly, and blog content may become outdated or superseded. We reserve the right to update, modify, or remove any content without notice.
The benefits of bringing together network and email security
In many organizations, network and email security operate in isolation. Each solution is tasked with defending its respective environment, even though both are facing the same advanced, multi-domain threats.
This siloed approach overlooks a critical reality: email remains the most common vector for initiating cyber-attacks, while the network is the primary stage on which those attacks progress. Without direct integration between these two domains, organizations risk leaving blind spots that adversaries can exploit.
A modern security strategy needs to unify email and network defenses, not just in name, but in how they share intelligence, conduct investigations, and coordinate response actions. Let’s take a look at how this joined-up approach delivers measurable technical, operational, and commercial benefits.
Technical advantages
Pre-alert intelligence: Gathering data before the threat strikes
Most security tools start working when something goes wrong – an unusual login, a flagged attachment, a confirmed compromise. But by then, attackers may already be a step ahead.
By unifying network and email security under a single AI platform (like the Darktrace Active AI Security Platform), you can analyze patterns across both environments in real time, even when there are no alerts. This ongoing monitoring builds a behavioral understanding of every user, device, and domain in your ecosystem.
That means when an email arrives from a suspicious domain, the system already knows whether that domain has appeared on your network before – and whether its behavior has been unusual. Likewise, when new network activity involves a domain first spotted in an email, it’s instantly placed in the right context.
This intelligence isn’t built on signatures or after-the-fact compromise indicators – it’s built on live behavioral baselines, giving your defenses the ability to flag threats before damage is done.
Alert-related intelligence: Connecting the dots in real time
Once an alert does fire, speed and context matter. The Darktrace Cyber AI Analyst can automatically investigate across both environments, piecing together network and email evidence into a single, cohesive incident.
Instead of leaving analysts to sift through fragmented logs, the AI links events like a phishing email to suspicious lateral movement on the recipient’s device, keeping the full attack chain intact. Investigations that might take hours – or even days – can be completed in minutes, with far fewer false positives to wade through.
This is more than a time-saver. It ensures defenders maintain visibility after the first sign of compromise, following the attacker as they pivot into network infrastructure, cloud services, or other targets. That cross-environment continuity is impossible to achieve with disconnected point solutions or siloed workflows.
Operational advantages
Streamlining SecOps across teams
In many organizations, email security is managed by IT, while network defense belongs to the SOC. The result? Critical information is scattered between tools and teams, creating blind spots just when you need clarity.
When email and network data flow into a single platform, everyone is working from the same source of truth. SOC analysts gain immediate visibility into email threats without opening another console or sending a request to another department. The IT team benefits from the SOC’s deeper investigative context.
The outcome is more than convenience: it’s faster, more informed decision-making across the board.
Reducing time-to-meaning and enabling faster response
A unified platform removes the need to manually correlate alerts between tools, reducing time-to-meaning for every incident. Built-in AI correlation instantly ties together related events, guiding analysts toward coordinated responses with higher confidence.
Instead of relying on manual SIEM rules or pre-built SOAR playbooks, the platform connects the dots in real time, and can even trigger autonomous response actions across both environments simultaneously. This ensures attacks are stopped before they can escalate, regardless of where they begin.
Commercial advantages
While purchasing “best-of-breed" for all your different tools might sound appealing, it often leads to a patchwork of solutions with overlapping costs and gaps in coverage. However good a “best-in-breed" email security solution might be in the email realm, it won't be truly effective without visibility across domains and an AI analyst piecing intelligence together. That’s why we think “best-in-suite" is the only “best-in-breed" approach that works – choosing a high-quality platform ensures that every new capability strengthens the whole system.
On top of that, security budgets are under constant pressure. Managing separate vendors for email and network defense means juggling multiple contracts, negotiating different SLAs, and stitching together different support models.
With a single provider for both, procurement and vendor management become far simpler. You deal with one account team, one support channel, and one unified strategy for both environments. If you choose to layer on managed services, you get consistent expertise across your whole security footprint.
Even more importantly, an integrated AI platform sets the stage for growth. Once email and network are under the same roof, adding coverage for other attack surfaces – like cloud or identity – is straightforward. You’re building on the same architecture, not bolting on new point solutions that create more complexity.
