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June 7, 2020

How Darktrace AI Identified Microsoft 365 Breaches

We cover two real cases on how Darktrace stopped Microsoft 365 account takeovers by correlating insights across SaaS applications & email activity.
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
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.

Learn more about Antigena Email

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
Dan Fein
VP, Product

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April 9, 2026

Bringing Together SOC and IR teams with Automated Threat Investigations for the Hybrid World

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The investigation gap: Why incident response is slow, fragmented and reactive

Modern investigations often fall apart the moment analysts move beyond an initial alert. Whether detections originate in cloud or on-prem environments, SOC and Incident Response (IR) teams are frequently hindered by fragmented tools and data sources, closed ecosystems, and slow, manual evidence collection just to access the forensic context they need. SOC analysts receive alerts without the depth required to confidently confirm or dismiss a threat, while IR teams struggle with inconsistent visibility across cloud, on‑premises, and contained endpoints, creating delays, blind spots, and incomplete attack timelines.

This gap between SOC and Digital Forensics and Incident Response (DFIR) slows response and forces teams into reactive and inefficient investigation patterns. Security teams struggle to collect high‑fidelity forensic data during active incidents, particularly from cloud workloads, on‑prem systems, and XDR‑contained endpoints where traditional tools cannot operate without deploying new agents or disrupting containment. The result is a fragmented response process where investigations slow down, context gets lost, and critical attacker activity can slip through the cracks.

What’s new at Darktrace

Helping teams move from detection to root cause faster, more efficiently, and with greater confidence

The latest update to Darktrace / Forensic Acquisition & Investigation eliminates the traditional handoff between the SOC and IR teams, enabling analysts to seamlessly pivot from alert into forensic investigation. It also brings on-demand and automated data capture through Darktrace / ENDPOINT as well as third-party detection platforms, where investigators can safely collect critical forensic data from network contained endpoints, preserving containment while accelerating investigation and response.  

Together, this solidifies / Forensic Acquisition & Investigation as an investigation-first platform beyond the cloud, fit for any organization that has adopted a multi-technology infrastructure. In practice, when these various detection sources and host‑level forensics are combined, investigations move from limited insight to complete understanding quickly, giving security teams the clarity and deep context required to drive confident remediation and response based on the exact tactics, techniques and procedures employed.

Integrated forensic context inside every incident workflow

SOC analysts now have seamless access to forensic evidence at the exact moment they need it. There is a new dedicated Forensics tab inside Cyber AI Analyst™ incidents, allowing users to move instantly from detection to rich forensic context in a single click, without the need to export data or get other teams involved.

For investigations that previously required multiple tools, credentials, or intervention by a dedicated team, this change represents a shift toward truly embedded incident‑driven forensics – accelerating both decision‑making and response quality at the point of detection.

Figure 1: The forensic investigation associated with the Cyber AI Analyst™ incident appears in a dedicated ‘Forensics’ tab, with the ability to pivot into the / Forensic Acquisition & Investigation UI for full context and deep analysis workflows.

Reliable automated and manual hybrid evidence capture across any environment

Across cloud, on‑premises, and hybrid environments, analysts can now automate or request on‑demand forensic evidence collection the moment a threat is detected via Darktrace / ENDPOINT. This allows investigators to quickly capture high-fidelity forensic data from endpoints already under protection, accelerating investigations without additional tooling or disrupting systems. Especially in larger environments where the ability to scale is critical, automated data capture across hybrid environments significantly reduces response time and enables consistent, repeatable investigations.

Unlike EDR‑only solutions, which capture only a narrow slice of activity, these workflows provide high‑quality, cross‑environment forensic depth, even on third‑party XDR‑contained devices that many vendor ecosystems cannot reach.

The result is a single, unified process for capturing the forensic context analysts need no matter where the threat originates, even in third-party vendor protected areas.

Figure 2: The ability to acquire, process, and investigate devices with the Darktrace / ENDPOINT agent installed using the ‘Darktrace Endpoint’ import provider
Figure 3: A Linux device that has the Darktrace / ENDPOINT agent installed has been acquired and processed by / Forensic Acquisition & Investigation

Investigation‑first design flexible for hybrid organizations

Luckily, taking advantage of automated forensic data capture of non-cloud assets won’t be subject to those who purely use Darktrace / ENDPOINT. This functionality is also available where CrowdStrike, Microsoft Defender for Endpoint, or SentinelOne agents are deployed.  In the case of CrowdStrike, Darktrace / Forensic Acquisition & Investigation can also perform a triage capture of a device that has been contained using CrowdStrike’s network containment capability. What’s critical here is the fact that investigators can safely acquire additional forensic evidence without breaking or altering containment. That massively improves investigation and response time without adding more risk factors.

Figure 4: ‘cado.xdr.test2’ has been contained using CrowdStrike’s network containment capability
Figure 5: Successful triage capture of contained endpoint ‘cado.xdr.test2’ using / Forensic Acquisition & Investigation

The benefits of extending forensics to on‑premises and endpoint environments

Despite Darktrace / Forensic Acquisition & Investigation originating as a cloud‑first solution, the challenges of incident response are not limited to the cloud. Many investigations span on‑premises servers, unmanaged endpoints, legacy systems, or devices locked inside third‑party ecosystems.  

By extending automated investigation capabilities into on‑premises environments and endpoints, Darktrace delivers several critical benefits:

  • Unified investigations across hybrid infrastructure and a heterogeneous security stack
  • Consistent forensic depth regardless of asset type
  • Faster and more accurate root-cause analysis
  • Stronger incident response readiness

Figure 6: Unified alerts from cloud and on-prem environments, grouped into incident-centric investigations with forensic depth

Simplifying deep investigations across hybrid environments

These enhancements move Darktrace / Forensic Acquisition & Investigation closer to a vision out of reach for most security teams: seamless, integrated, high‑fidelity forensics across cloud, on‑prem, and endpoint environments where other solutions usually stop at detection. Automated forensics as a whole is fueling faster outcomes with complete clarity throughout the end-to-end investigation process, which now takes teams from alert to understanding in minutes compared to days or even weeks. All without added agents, disruptions, or specialized teams. The result is an incident response lifecycle that finally matches the reality of modern infrastructure.

Ready to see Darktrace / Forensic Acquisition & Investigation in your environment? Request a demo.

Hear from industry-leading experts on the latest developments in AI cybersecurity at Darktrace LIVE. Coming to a city near you.

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About the author
Paul Bottomley
Director of Product Management | Darktrace

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April 9, 2026

How to Secure AI and Find the Gaps in Your Security Operations

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What “securing AI” actually means (and doesn’t)

Security teams are under growing pressure to “secure AI” at the same pace which businesses are adopting it. But in many organizations, adoption is outpacing the ability to govern, monitor, and control it. When that gap widens, decision-making shifts from deliberate design to immediate coverage. The priority becomes getting something in place, whether that’s a point solution, a governance layer, or an extension of an existing platform, rather than ensuring those choices work together.

At the same time, AI governance is lagging adoption. 37% of organizations still lack AI adoption policies, shadow AI usage across SaaS has surged, and there are notable spikes in anomalous data uploads to generative AI services.  

First and foremost, it’s important to recognize the dual nature of AI risk. Much of the industry has focused on how attackers will use AI to move faster, scale campaigns, and evade detection. But what’s becoming just as significant is the risk introduced by AI inside the organization itself. Enterprises are rapidly embedding AI into workflows, SaaS platforms, and decision-making processes, creating new pathways for data exposure, privilege misuse, and unintended access across an already interconnected environment.

Because the introduction of complex AI systems into modern, hybrid environments is reshaping attacker behavior and exposing gaps between security functions, the challenge is no longer just having the right capabilities in place but effectively coordinating prevention, detection, investigation, response, and remediation together. As threats accelerate and systems become more interconnected, security depends on coordinated execution, not isolated tools, which is why lifecycle-based approaches to governance, visibility, behavioral oversight, and real-time control are gaining traction.

From cloud consolidation to AI systems what we can learn

We have seen a version of AI adoption before in cloud security. In the early days, tooling fragmented into posture, workload/runtime, identity, data, and more. Gradually, cloud security collapsed into broader cloud platforms. The lesson was clear: posture without runtime misses active threats; runtime without posture ignores root causes. Strong programs ran both in parallel and stitched the findings together in operations.  

Today’s AI wave stretches that lesson across every domain. Adversaries are compressing “time‑to‑tooling” using LLM‑assisted development (“vibecoding”) and recycling public PoCs at unprecedented speed. That makes it difficult to secure through siloed controls, because the risk is not confined to one layer. It emerges through interactions across layers.

Keep in mind, most modern attacks don’t succeed by defeating a single control. They succeed by moving through the gaps between systems faster than teams can connect what they are seeing. Recent exploitation waves like React2Shell show how quickly opportunistic actors operationalize fresh disclosures and chain misconfigurations to monetize at scale.

In the React2Shell window, defenders observed rapid, opportunistic exploitation and iterative payload diversity across a broad infrastructure footprint, strains that outpace signature‑first thinking.  

You can stay up to date on attacker behavior by signing up for our newsletter where Darktrace’s threat research team and analyst community regularly dive deep into threat finds.

Ultimately, speed met scale in the cloud era; AI adds interconnectedness and orchestration. Simple questions — What happened? Who did it? Why? How? Where else? — now cut across identities, SaaS agents, model/service endpoints, data egress, and automated actions. The longer it takes to answer, the worse the blast radius becomes.

The case for a platform approach in the age of AI

Think of security fusion as the connective tissue that lets you prevent, detect, investigate, and remediate in parallel, not in sequence. In practice, that looks like:

  1. Unified telemetry with behavioral context across identities, SaaS, cloud, network, endpoints, and email—so an anomalous action in one plane automatically informs expectations in others. (Inside‑the‑SOC investigations show this pays off when attacks hop fast between domains.)  
  1. Pre‑CVE and “in‑the‑wild” awareness feeding controls before signatures—reducing dwell time in fast exploitation windows.  
  1. Automated, bounded response that can contain likely‑malicious actions at machine speed without breaking workflows—buying analysts time to investigate with full context. (Rapid CVE coverage and exploit‑wave posts illustrate how critical those first minutes are.)  
  1. Investigation workflows that assume AI is in the loop—for both defenders and attackers. As adversaries adopt “agentic” patterns, investigations need graph‑aware, sequence‑aware reasoning to prioritize what matters early.

This isn’t theoretical. It’s reflected in the Darktrace posts that consistently draw readership: timely threat intel with proprietary visibility and executive frameworks that transform field findings into operating guidance.  

The five questions that matter (and the one that matters more)

When alerted to malicious or risky AI use, you’ll ask:

  1. What happened?
  1. Who did it?
  1. Why did they do it?
  1. How did they do it?
  1. Where else can this happen?

The sixth, more important question is: How much worse does it get while you answer the first five? The answer depends on whether your controls operate in sequence (slow) or in fused parallel (fast).

What to watch next: How the AI security market will likely evolve

Security markets tend to follow a familiar pattern. New technologies drive an initial wave of specialized tools (posture, governance, observability) each focused on a specific part of the problem. Over time, those capabilities consolidate as organizations realize the new challenge is coordination.

AI is accelerating the shift of focus to coordination because AI-powered attackers can move faster and operate across more systems at once. Recent exploitation waves show exactly this. Adversaries can operationalize new techniques and move across domains, turning small gaps into full attack paths.

Anticipate a continued move toward more integrated security models because fragmented approaches can’t keep up with the speed and interconnected nature of modern attacks.

Building the Groundwork for Secure AI: How to Test Your Stack’s True Maturity

AI doesn’t create new surfaces as much as it exposes the fragility of the seams that already exist.  

Darktrace’s own public investigations consistently show that modern attacks, from LinkedIn‑originated phishing that pivots into corporate SaaS to multi‑stage exploitation waves like BeyondTrust CVE‑2026‑1731 and React2Shell, succeed not because a single control failed, but because no control saw the whole sequence, or no system was able to respond at the speed of escalation.  

Before thinking about “AI security,” customers should ensure they’ve built a security foundation where visibility, signals, and responses can pass cleanly between domains. That requires pressure‑testing the seams.

Below are the key integration questions and stack‑maturity tests every organization should run.

1. Do your controls see the same event the same way?

Integration questions

  • When an identity behaves strangely (impossible travel, atypical OAuth grants), does that signal automatically inform your email, SaaS, cloud, and endpoint tools?
  • Do your tools normalize events in a way that lets you correlate identity → app → data → network without human stitching?

Why it matters

Darktrace’s public SOC investigations repeatedly show attackers starting in an unmonitored domain, then pivoting into monitored ones, such as phishing on LinkedIn that bypassed email controls but later appeared as anomalous SaaS behavior.

If tools can’t share or interpret each other's context, AI‑era attacks will outrun every control.

Tests you can run

  1. Shadow Identity Test
  • Create a temporary identity with no history.
  • Perform a small but unusual action: unusual browser, untrusted IP, odd OAuth request.
  • Expected maturity signal: other tools (email/SaaS/network) should immediately score the identity as high‑risk.
  1. Context Propagation Test
  • Trigger an alert in one system (e.g., endpoint anomaly) and check if other systems automatically adjust thresholds or sensitivity.
  • Low maturity signal: nothing changes unless an analyst manually intervenes.

2. Does detection trigger coordinated action, or does everything act alone?

Integration questions

  • When one system blocks or contains something, do other systems automatically tighten, isolate, or rate‑limit?
  • Does your stack support bounded autonomy — automated micro‑containment without broad business disruption?

Why it matters

In public cases like BeyondTrust CVE‑2026‑1731 exploitation, Darktrace observed rapid C2 beaconing, unusual downloads, and tunneling attempts across multiple systems. Containment windows were measured in minutes, not hours.  

Tests you can run

  1. Chain Reaction Test
  • Simulate a primitive threat (e.g., access from TOR exit node).
  • Your identity provider should challenge → email should tighten → SaaS tokens should re‑authenticate.
  • Weak seam indicator: only one tool reacts.
  1. Autonomous Boundary Test
  • Induce a low‑grade anomaly (credential spray simulation).
  • Evaluate whether automated containment rules activate without breaking legitimate workflows.

3. Can your team investigate a cross‑domain incident without swivel‑chairing?

Integration questions

  • Can analysts pivot from identity → SaaS → cloud → endpoint in one narrative, not five consoles?
  • Does your investigation tooling use graphs or sequence-based reasoning, or is it list‑based?

Why it matters

Darktrace’s Cyber AI Analyst and DIGEST research highlights why investigations must interpret structure and progression, not just standalone alerts. Attackers now move between systems faster than human triage cycles.  

Tests you can run

  1. One‑Hour Timeline Build Test
  • Pick any detection.
  • Give an analyst one hour to produce a full sequence: entry → privilege → movement → egress.
  • Weak seam indicator: they spend >50% of the hour stitching exports.
  1. Multi‑Hop Replay Test
  • Simulate an incident that crosses domains (phish → SaaS token → data access).
  • Evaluate whether the investigative platform auto‑reconstructs the chain.

4. Do you detect intent or only outcomes?

Integration questions

  • Can your stack detect the setup behaviors before an attack becomes irreversible?
  • Are you catching pre‑CVE anomalies or post‑compromise symptoms?

Why it matters

Darktrace publicly documents multiple examples of pre‑CVE detection, where anomalous behavior was flagged days before vulnerability disclosure. AI‑assisted attackers will hide behind benign‑looking flows until the very last moment.

Tests you can run

  1. Intent‑Before‑Impact Test
  • Simulate reconnaissance-like behavior (DNS anomalies, odd browsing to unknown SaaS, atypical file listing).
  • Mature systems will flag intent even without an exploit.
  1. CVE‑Window Test
  • During a real CVE patch cycle, measure detection lag vs. public PoC release.
  • Weak seam indicator: your detection rises only after mass exploitation begins.

5. Are response and remediation two separate universes?

Integration questions

  • When you contain something, does that trigger root-cause remediation workflows in identity, cloud config, or SaaS posture?
  • Does fixing a misconfiguration automatically update correlated controls?

Why it matters

Darktrace’s cloud investigations (e.g., cloud compromise analysis) emphasize that remediation must close both runtime and posture gaps in parallel.

Tests you can run

  1. Closed‑Loop Remediation Test
  • Introduce a small misconfiguration (over‑permissioned identity).
  • Trigger an anomaly.
  • Mature stacks will: detect → contain → recommend or automate posture repair.
  1. Drift‑Regression Test
  • After remediation, intentionally re‑introduce drift.
  • The system should immediately recognize deviation from known‑good baseline.

6. Do SaaS, cloud, email, and identity all agree on “normal”?

Integration questions

  • Is “normal behavior” defined in one place or many?
  • Do baselines update globally or per-tool?

Why it matters

Attackers (including AI‑assisted ones) increasingly exploit misaligned baselines, behaving “normal” to one system and anomalous to another.

Tests you can run

  1. Baseline Drift Test
  • Change the behavior of a service account for 24 hours.
  • Mature platforms will flag the deviation early and propagate updated expectations.
  1. Cross‑Domain Baseline Consistency Test
  • Compare identity’s risk score vs. cloud vs. SaaS.
  • Weak seam indicator: risk scores don’t align.

Final takeaway

Security teams should ask be focused on how their stack operates as one system before AI amplifies pressure on every seam.

Only once an organization can reliably detect, correlate, and respond across domains can it safely begin to secure AI models, agents, and workflows.

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About the author
Nabil Zoldjalali
VP, Field CISO
Your data. Our AI.
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