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November 27, 2024

Behind the veil: Darktrace's detection of VPN exploitation in SaaS environments

A recent phishing attack compromised an internal email account, but Darktrace’s advanced AI quickly intervened. By identifying unusual activity across email and SaaS environments, Darktrace uncovered the attacker’s use of VPNs to mask their location and shut down the threat.
Inside the SOC
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
Priya Thapa
Cyber Analyst
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27
Nov 2024

Introduction

In today’s digital landscape, Software-as-a-Service (SaaS) platforms have become indispensable for businesses, offering unparalleled flexibly, scalability, and accessibly across locations. However, this convenience comes with a significant caveat - an expanded attack surface that cyber criminals are increasingly exploiting. In 2023, 96.7% of organizations reported security incidents involving at least one SaaS application [1].

Virtual private networks (VPNs) play a crucial role in SaaS security, acting as gateways for secure remote access and safeguarding sensitive data and systems when properly configured. However, vulnerabilities in VPNs can create openings for attacks to exploit, allowing them to infiltrate SaaS environments, compromise data, and disrupt business operations. Notably, in early 2024, the Darktrace Threat Research team investigated the exploitation of zero-day vulnerabilities in Ivanti Connect Secure VPNs, which would allow threat actors to gain access to sensitive systems and execute remote code.

More recently, in August, Darktrace identified a SaaS compromise where a threat actor logged into a customer’s VPN from an unusual IP address, following an initial email compromise. The attacker then used a separate VPN to create a new email rule designed to obfuscate the phishing campaign they would later launch.

Attack Overview

The initial attack vector in this case appeared to be through the customer’s email environment. A trusted external contact received a malicious email from another mutual contact who had been compromised and forwarded it to several of the organization’s employees, believing it to be legitimate. Attackers often send malicious emails from compromised accounts to their past contacts, leveraging the trust associated with familiar email addresses. In this case, that trust caused an external victim to unknowingly propagate the attack further. Unfortunately, an internal user then interacted with a malicious payload included in the reply section of the forwarded email.

Later the same day, Darktrace / IDENTITY detected unusual login attempts from the IP 5.62.57[.]7, which had never been accessed by other SaaS users before. There were two failed attempts prior to the successful logins, with the error messages “Authentication failed due to flow token expired” and “This occurred due to 'Keep me signed in' interrupt when the user was signing in.” These failed attempts indicate that the threat actor may have been attempting to gain unauthorized access using stolen credentials or exploiting session management vulnerabilities. Furthermore, there was no attempt to use multi-factor authentication (MFA) during the successful login, suggesting that the threat actor had compromised the account’s credentials.

Following this, Darktrace detected the now compromised account creating a new email rule named “.” – a telltale sign of a malicious actor attempting to hide behind an ambiguous or generic rule name.

The email rule itself was designed to archive incoming emails and mark them as read, effectively hiding them from the user’s immediate view. By moving emails to the “Archive” folder, which is not frequently checked by end users, the attacker can conceal malicious communications and avoid detection. The settings also prevent any automatic deletion of the rules or forced overrides, indicating a cautious approach to maintaining control over the mailbox without raising suspicion. This technique allows the attacker to manipulate email visibility while maintaining a façade of normality in the compromised account.

Email Rule:

  • AlwaysDeleteOutlookRulesBlob: False
  • Force: False
  • MoveToFolder: Archive
  • Name: .
  • MarkAsRead: True
  • StopProcessingRules: True

Darktrace further identified that this email rule had been created from another IP address, 95.142.124[.]42, this time located in Canada. Open-source intelligence (OSINT) sources indicated this endpoint may have been malicious [2].

Given that this new email rule was created just three minutes after the initial login from a different IP in a different country, Darktrace recognized a geographic inconsistency. By analyzing the timing and rarity of the involved IP addresses, Darktrace identified the likelihood of malicious activity rather than legitimate user behavior, prompting further investigation.

Figure 1: The compromised SaaS account making anomalous login attempts from an unusual IP address in the US, followed by the creation of a new email rule from another VPN IP in Canada.

Just one minute later, Darktrace observed the attacker sending a large number of phishing emails to both internal and external recipients.

Figure 2: The compromised SaaS user account sending a high volume of outbound emails to new recipients or containing suspicious content.

Darktrace / EMAIL detected a significant spike in inbound emails for the compromised account, likely indicating replies to phishing emails.

Figure 3: The figure demonstrates the spike in inbound emails detected for the compromised account, including phishing-related replies.

Furthermore, Darktrace identified that these phishing emails contained a malicious DocSend link. While docsend[.]com is generally recognized as a legitimate file-sharing service belonging to Dropbox, it can be vulnerable to exploitation for hosting malicious content. In this instance, the DocSend domain in question, ‘hxxps://docsend[.]com/view/h9t85su8njxtugmq’, was flagged as malicious by various OSINT vendors [3][4].

Figure 4: Phishing emails detected containing a malicious DocSend link.

In this case, Darktrace Autonomous Response was not in active mode in the customer’s environment, which allowed the compromise to escalate until their security team intervened based on Darktrace’s alerts. Had Autonomous Response been enabled during the incident, it could have quickly mitigated the threat by disabling users and inbox rules, as suggested by Darktrace as actions that could be manually applied, exhibiting unusual behavior within the customer’s SaaS environment.

Figure 5: Suggested Autonomous Response actions for this incident that required human confirmation.

Despite this, Darktrace’s Managed Threat Detection service promptly alerted the Security Operations Center (SOC) team about the compromise, allowing them to conduct a thorough investigation and inform the customer before any further damage could take place.

Conclusion

This incident highlights the role of Darktrace in enhancing cyber security through its advanced AI capabilities. By detecting the initial phishing email and tracking the threat actor's actions across the SaaS environment, Darktrace effectively identified the threat and brought it to the attention of the customer’s security team.

Darktrace’s proactive monitoring was crucial in recognizing the unusual behavior of the compromised account. Darktrace / IDENTITY detected unauthorized access attempts from rare IP addresses, revealing the attacker’s use of a VPN to hide their location.

Correlating these anomalies allowed Darktrace to prompt immediate investigation, showcasing its ability to identify malicious activities that traditional security tools might miss. By leveraging AI-driven insights, organizations can strengthen their defense posture and prevent further exploitation of compromised accounts.

Credit to Priya Thapa (Cyber Analyst), Ben Atkins (Senior Model Developer) and Ryan Traill (Analyst Content Lead)

Appendices

Real-time Detection Models

  • SaaS / Compromise / Unusual Login and New Email Rule
  • SaaS / Compromise / High Priority New Email Rule
  • SaaS / Compromise / New Email Rule and Unusual Email Activity
  • SaaS / Compromise / Unusual Login and Outbound Email Spam
  • SaaS / Compliance / Anomalous New Email Rule
  • SaaS / Compromise / Suspicious Login and Suspicious Outbound Email(s)
  • SaaS / Email Nexus / Possible Outbound Email Spam

Autonomous Response Models

  • Antigena / SaaS / Antigena Email Rule Block
  • Antigena / SaaS / Antigena Enhanced Monitoring from SaaS User Block
  • Antigena / SaaS / Antigena Suspicious SaaS Activity Block

MITRE ATT&CK Mapping

Technique Name Tactic ID Sub-Technique of

  • Cloud Accounts. DEFENSE EVASION, PERSISTENCE, PRIVILEGE ESCALATION, INITIAL ACCESS T1078.004 T1078
  • Compromise Accounts RESOURCE DEVELOPMENT T1586
  • Email Accounts RESOURCE DEVELOPMENT T1586.002 T1586
  • Internal Spearphishing LATERAL MOVEMENT T1534 -
  • Outlook Rules PERSISTENCE T1137.005 T1137
  • Phishing INITIAL ACCESS T1566 -

Indicators of Compromise (IoCs)

IoC – Type – Description

5.62.57[.]7 – Unusual Login Source

95.142.124[.]42– IP – Unusual Source for Email Rule

hxxps://docsend[.]com/view/h9t85su8njxtugmq - Domain - Phishing Link

References

[1] https://wing.security/wp-content/uploads/2024/02/2024-State-of-SaaS-Report-Wing-Security.pdf

[2] https://www.virustotal.com/gui/ip-address/95.142.124.42

[3] https://urlscan.io/result/0caf3eee-9275-4cda-a28f-6d3c6c3c1039/

[4] https://www.virustotal.com/gui/url/8631f8004ee000b3f74461e5060e6972759c8d38ea8c359d85da9014101daddb

Inside the SOC
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
Priya Thapa
Cyber Analyst

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September 9, 2025

The benefits of bringing together network and email security

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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.

Check out the white paper, The Modern Security Stack: Why Your NDR and Email Security Solutions Need to Work Together, to explore these benefits in more depth, with real-world examples and practical steps for unifying your defenses.

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Mikey Anderson
Product Marketing Manager, Network Detection & Response

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September 9, 2025

Unpacking the Salesloft Incident: Insights from Darktrace Observations

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Introduction

On August 26, 2025, Google Threat intelligence Group released a report detailing a widespread data theft campaign targeting the sales automation platform Salesloft, via compromised OAuth tokens used by the third-party Drift AI chat agent [1][2].  The attack has been attributed to the threat actor UNC6395 by Google Threat Intelligence and Mandiant [1].

The attack is believed to have begun in early August 2025 and continued through until mid-August 2025 [1], with the threat actor exporting significant volumes of data from multiple Salesforce instances [1]. Then sifting through this data for anything that could be used to compromise the victim’s environments such as access keys, tokens or passwords. This had led to Google Threat Intelligence Group assessing that the primary intent of the threat actor is credential harvesting, and later reporting that it was aware of in excess of 700 potentially impacted organizations [3].

Salesloft previously stated that, based on currently available data, customers that do not integrate with Salesforce are unaffected by this campaign [2]. However, on August 28, Google Threat Intelligence Group announced that “Based on new information identified by GTIG, the scope of this compromise is not exclusive to the Salesforce integration with Salesloft Drift and impacts other integrations” [2]. Google Threat Intelligence has since advised that any and all authentication tokens stored in or connected to the Drift platform be treated as potentially compromised [1].

This campaign demonstrates how attackers are increasingly exploiting trusted Software-as-a-Service (SaaS) integrations as a pathway into enterprise environment.

By abusing these integrations, threat actors were able to exfiltrate sensitive business data at scale, bypassing traditional security controls. Rather than relying on malware or obvious intrusion techniques, the adversaries leveraged legitimate credentials and API traffic that resembled legitimate Salesforce activity to achieve their goals. This type of activity is far harder to detect with conventional security tools, since it blends in with the daily noise of business operations.

The incident underscores the escalating significance of autonomous coverage within SaaS and third-party ecosystems. As businesses increasingly depend on interconnected platforms, visibility gaps become evident that cannot be managed by conventional perimeter and endpoint defenses.

By developing a behavioral comprehension of each organization's distinct use of cloud services, anomalies can be detected, such as logins from unexpected locations, unusually high volumes of API requests, or unusual document activity. These indications serve as an early alert system, even when intruders use legitimate tokens or accounts, enabling security teams to step in before extensive data exfiltration takes place

What happened?

The campaign is believed to have started on August 8, 2025, with malicious activity continuing until at least August 18. The threat actor, tracked as UNC6395, gained access via compromised OAuth tokens associated with Salesloft Drift integrations into Salesforce [1]. Once tokens were obtained, the attackers were able to issue large volumes of Salesforce API requests, exfiltrating sensitive customer and business data.

Initial Intrusion

The attackers first established access by abusing OAuth and refresh tokens from the Drift integration. These tokens gave them persistent access into Salesforce environments without requiring further authentication [1]. To expand their foothold, the threat actor also made use of TruffleHog [4], an open-source secrets scanner, to hunt for additional exposed credentials. Logs later revealed anomalous IAM updates, including unusual UpdateAccessKey activity, which suggested attempts to ensure long-term persistence and control within compromised accounts.

Internal Reconnaissance & Data Exfiltration

Once inside, the adversaries began exploring the Salesforce environments. They ran queries designed to pull sensitive data fields, focusing on objects such as Cases, Accounts, Users, and Opportunities [1]. At the same time, the attackers sifted through this information to identify secrets that could enable access to other systems, including AWS keys and Snowflake credentials [4]. This phase demonstrated the opportunistic nature of the campaign, with the actors looking for any data that could be repurposed for further compromise.

Lateral Movement

Salesloft and Mandiant investigations revealed that the threat actor also created at least one new user account in early September. Although follow-up activity linked to this account was limited, the creation itself suggested a persistence mechanism designed to survive remediation efforts. By maintaining a separate identity, the attackers ensured they could regain access even if their stolen OAuth tokens were revoked.

Accomplishing the mission

The data taken from Salesforce environments included valuable business records, which attackers used to harvest credentials and identify high-value targets. According to Mandiant, once the data was exfiltrated, the actors actively sifted through it to locate sensitive information that could be leveraged in future intrusions [1]. In response, Salesforce and Salesloft revoked OAuth tokens associated with Drift integrations on August 20 [1], a containment measure aimed at cutting off the attackers’ primary access channel and preventing further abuse.

How did the attack bypass the rest of the security stack?

The campaign effectively bypassed security measures by using legitimate credentials and OAuth tokens through the Salesloft Drift integration. This rendered traditional security defenses like endpoint protection and firewalls ineffective, as the activity appeared non-malicious [1]. The attackers blended into normal operations by using common user agents and making queries through the Salesforce API, which made their activity resemble legitimate integrations and scripts. This allowed them to operate undetected in the SaaS environment, exploiting the trust in third-party connections and highlighting the limitations of traditional detection controls.

Darktrace Coverage

Anomalous activities have been identified across multiple Darktrace deployments that appear associated with this campaign. This included two cases on customers based within the United States who had a Salesforce integration, where the pattern of activities was notably similar.

On August 17, Darktrace observed an account belonging to one of these customers logging in from the rare endpoint 208.68.36[.]90, while the user was seen active from another location. This IP is a known indicator of compromise (IoC) reported by open-source intelligence (OSINT) for the campaign [2].

Cyber AI Analyst Incident summarizing the suspicious login seen for the account.
Figure 1: Cyber AI Analyst Incident summarizing the suspicious login seen for the account.

The login event was associated with the application Drift, further connecting the events to this campaign.

Advanced Search logs showing the Application used to login.
Figure 2: Advanced Search logs showing the Application used to login.

Following the login, the actor initiated a high volume of Salesforce API requests using methods such as GET, POST, and DELETE. The GET requests targeted endpoints like /services/data/v57.0/query and /services/data/v57.0/sobjects/Case/describe, where the former is used to retrieve records based on a specific criterion, while the latter provides metadata for the Case object, including field names and data types [5,6].

Subsequently, a POST request to /services/data/v57.0/jobs/query was observed, likely to initiate a Bulk API query job for extracting large volumes of data from the Ingest Job endpoint [7,8].

Finally, a DELETE request to remove an ingestion job batch, possibly an attempt to obscure traces of prior data access or manipulation.

A case on another US-based customer took place a day later, on August 18. This again began with an account logging in from the rare IP 208.68.36[.]90 involving the application Drift. This was followed by Salesforce GET requests targeting the same endpoints as seen in the previous case, and then a POST to the Ingest Job endpoint and finally a DELETE request, all occurring within one minute of the initial suspicious login.

The chain of anomalous behaviors, including a suspicious login and delete request, resulted in Darktrace’s Autonomous Response capability suggesting a ‘Disable user’ action. However, the customer’s deployment configuration required manual confirmation for the action to take effect.

An example model alert for the user, triggered due to an anomalous API DELETE request.
Figure 3: An example model alert for the user, triggered due to an anomalous API DELETE request.
Figure 4: Model Alert Event Log showing various model alerts for the account that ultimately led to an Autonomous Response model being triggered.

Conclusion

In conclusion, this incident underscores the escalating risks of SaaS supply chain attacks, where third-party integrations can become avenues for attacks. It demonstrates how adversaries can exploit legitimate OAuth tokens and API traffic to circumvent traditional defenses. This emphasizes the necessity for constant monitoring of SaaS and cloud activity, beyond just endpoints and networks, while also reinforcing the significance of applying least privilege access and routinely reviewing OAuth permissions in cloud environments. Furthermore, it provides a wider perspective into the evolution of the threat landscape, shifting towards credential and token abuse as opposed to malware-driven compromise.

Credit to Emma Foulger (Global Threat Research Operations Lead), Calum Hall (Technical Content Researcher), Signe Zaharka (Principal Cyber Analyst), Min Kim (Senior Cyber Analyst), Nahisha Nobregas (Senior Cyber Analyst), Priya Thapa (Cyber Analyst)

Appendices

Darktrace Model Detections

·      SaaS / Access / Unusual External Source for SaaS Credential Use

·      SaaS / Compromise / Login From Rare Endpoint While User Is Active

·      SaaS / Compliance / Anomalous Salesforce API Event

·      SaaS / Unusual Activity / Multiple Unusual SaaS Activities

·      Antigena / SaaS / Antigena Unusual Activity Block

·      Antigena / SaaS / Antigena Suspicious Source Activity Block

Customers should consider integrating Salesforce with Darktrace where possible. These integrations allow better visibility and correlation to spot unusual behavior and possible threats.

IoC List

(IoC – Type)

·      208.68.36[.]90 – IP Address

References

1.     https://cloud.google.com/blog/topics/threat-intelligence/data-theft-salesforce-instances-via-salesloft-drift

2.     https://trust.salesloft.com/?uid=Drift+Security+Update%3ASalesforce+Integrations+%283%3A30PM+ET%29

3.     https://thehackernews.com/2025/08/salesloft-oauth-breach-via-drift-ai.html

4.     https://unit42.paloaltonetworks.com/threat-brief-compromised-salesforce-instances/

5.     https://developer.salesforce.com/docs/atlas.en-us.api_rest.meta/api_rest/resources_query.htm

6.     https://developer.salesforce.com/docs/atlas.en-us.api_rest.meta/api_rest/resources_sobject_describe.htm

7.     https://developer.salesforce.com/docs/atlas.en-us.api_asynch.meta/api_asynch/get_job_info.htm

8.     https://developer.salesforce.com/docs/atlas.en-us.api_asynch.meta/api_asynch/query_create_job.htm

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About the author
Emma Foulger
Global Threat Research Operations Lead
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