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April 5, 2023

Understanding Qakbot Infections and Attack Paths

Explore the network-based analysis of Qakbot infections with Darktrace. Learn about the various attack paths used by cybercriminals and Darktrace's response.
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
Sam Lister
SOC Analyst
Written by
Connor Mooney
SOC Analyst
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05
Apr 2023

Security vendors around the world are forced to quickly adapt, react, and respond to known attack vectors and threats. In the face of this, malicious actors are constantly looking for novel ways to gain access to networks. Whether that’s through new exploitations of network vulnerabilities or new delivery methods, attackers and their methods are continually evolving. Although it is valuable for organizations to leverage threat intelligence to keep abreast of known threats to their networks, intelligence alone is not enough to defend against increasingly versatile attackers. Having an autonomous decision maker able to detect and respond to emerging threats, even those employing novel or unknown techniques, is paramount to defend against network compromise.

At the end of January 2023, threat actors began to abuse OneNote attachments to deliver the malware strain, Qakbot, onto users' devices. Widespread adoption of this novel delivery method resulted in a surge in Qakbot infections across Darktrace's customer base between the end of January 2023 and the end of February 2023. Using its Self-Learning AI, Darktrace was able to uncover and respond to these so-called ‘QakNote’ infections as the new trend emerged. Darktrace detected and responded to the threat at multiple stages of the kill chain, preventing damaging and widespread compromise to customer networks.

Qakbot and The Recent Weaponization of OneNote

Qakbot first appeared in 2007 as a banking trojan designed to steal sensitive data such as banking credentials. Since then, Qakbot has evolved into a highly modular, multi-purpose tool, with backdoor, payload delivery, reconnaissance, lateral movement, and data exfiltration capabilities. Although Qakbot's primary delivery method has always been email-based, threat actors have been known to modify their email-based delivery methods of Qakbot in the face of changing circumstances. In the first half of 2022, Microsoft started rolling out versions of Office which block XL4 and VBA macros by default [1]/[2]/[3]. Prior to this change, Qakbot email campaigns typically consisted in the spreading of deceitful emails with Office attachments containing malicious macros. In the face of Microsoft's default blocking of macros, threat actors appeared to cease delivering Qakbot via Office attachments, and shifted to primarily using HTML attachments, through a method known as 'HTML smuggling' [4]/[5]. After the public disclosure [6] of the Follina vulnerability (CVE-2022-30190) in Microsoft Support Diagnostic Tool (MSDT) in May 2022, Qakbot actors were seen capitalizing on the vulnerability to facilitate their email-based delivery of Qakbot payloads [7]/[8]/[9]. 

Given the inclination of Qakbot actors to adapt their email-based delivery methods, it is no surprise that they were quick to capitalize on the novel OneNote-based delivery method which emerged in December 2022. Since December 2022, threat actors have been seen using OneNote attachments to deliver a variety of malware strains, ranging from Formbook [10] to AsynRAT [11] to Emotet [12]. The abuse of OneNote documents to deliver malware is made possible by the fact that OneNote allows for the embedding of executable file types such as HTA files, CMD files, and BAT files. At the end of January 2023, actors started to leverage OneNote attachments to deliver Qakbot [13]/[14]. The adoption of this novel delivery method by Qakbot actors resulted in a surge in Qakbot infections in the wider threat landscape and across the Darktrace customer base.

Observed Activity Chains

Between January 31 and February 24, 2023, Darktrace observed variations of the following pattern of activity across its customer base:

1. User's device contacts OneNote-related endpoint 

2. User's device makes an external GET request with an empty Host header, a target URI whose final segment consists in 5 or 6 digits followed by '.dat', and a User-Agent header referencing either cURL or PowerShell. The GET request is responded to with a DLL file

3. User's device makes SSL connections over ports 443 and 2222 to unusual external endpoints, and makes TCP connections over port 65400 to 23.111.114[.]52

4. User's device makes SSL connections over port 443 to an external host named 'bonsars[.]com' (IP: 194.165.16[.]56) and TCP connections over port 443 to 78.31.67[.]7

5. User’s device makes call to Endpoint Mapper service on internal systems and then connects to the Service Control Manager (SCM) 

6. User's device uploads files with algorithmically generated names and ‘.dll’ or ‘.dll.cfg’ file extensions to SMB shares on internal systems

7. User's device makes Service Control requests to the systems to which it uploaded ‘.dll’ and ‘.dll.cfg’ files 

Further investigation of these chains of activity revealed that they were parts of Qakbot infections initiated via interactions with malicious OneNote attachments. 

Figure 1: Steps of observed QakNote infections.

Delivery Phase

Users' interactions with malicious OneNote attachments, which were evidenced by devices' HTTPS connections to OneNote-related endpoints, such as 'www.onenote[.]com', 'contentsync.onenote[.]com', and 'learningtools.onenote[.]com', resulted in the retrieval of Qakbot DLLs from unusual, external endpoints. In some cases, the user's interaction with the malicious OneNote attachment caused their device to fetch a Qakbot DLL using cURL, whereas, in other cases, it caused their device to download a Qakbot DLL using PowerShell. These different outcomes reflected variations in the contents of the executable files embedded within the weaponized OneNote attachments. In addition to having cURL and PowerShell User-Agent headers, the HTTP requests triggered by interaction with these OneNote attachments had other distinctive features, such as empty host headers and target URIs whose last segment consists in 5 or 6 digits followed by '.dat'. 

Figure 2: Model breach highlighting a user’s device making a HTTP GET request to 198.44.140[.]78 with a PowerShell User-Agent header and the target URI ‘/210/184/187737.dat’.
Figure 3: Model breach highlighting a user’s device making a HTTP GET request to 103.214.71[.]45 with a cURL User-Agent header and the target URI ‘/70802.dat’.
Figure 4: Event Log showing a user’s device making a GET request with a cURL User-Agent header to 185.231.205[.]246 after making an SSL connection to contentsync.onenote[.]com.
Figure 5: Event Log showing a user’s device making a GET request with a cURL User-Agent header to 185.231.205[.]246 after making an SSL connection to www.onenote[.]com.

Command and Control Phase

After fetching Qakbot DLLs, users’ devices were observed making numerous SSL connections over ports 443 and 2222 to highly unusual, external endpoints, as well as large volumes of TCP connections over port 65400 to 23.111.114[.]52. These connections represented Qakbot-infected devices communicating with command and control (C2) infrastructure. Qakbot-infected devices were also seen making intermittent connections to legitimate endpoints, such as 'xfinity[.]com', 'yahoo[.]com', 'verisign[.]com', 'oracle[.]com', and 'broadcom[.]com', likely due to Qakbot making connectivity checks. 

Figure 6: Event Log showing a user’s device contacting Qakbot C2 infrastructure and making connectivity checks to legitimate domains.
Figure 7: Event Log showing a user’s device contacting Qakbot C2 infrastructure and making connectivity checks to legitimate domains.

Cobalt Strike and VNC Phase

After Qakbot-infected devices established communication with C2 servers, they were observed making SSL connections to the external endpoint, bonsars[.]com, and TCP connections to the external endpoint, 78.31.67[.]7. The SSL connections to bonsars[.]com were C2 connections from Cobalt Strike Beacon, and the TCP connections to 78.31.67[.]7 were C2 connections from Qakbot’s Virtual Network Computing (VNC) module [15]/[16]. The occurrence of these connections indicate that actors leveraged Qakbot infections to drop Cobalt Strike Beacon along with a VNC payload onto infected systems. The deployment of Cobalt Strike and VNC likely provided actors with ‘hands-on-keyboard’ access to the Qakbot-infected systems. 

Figure 8: Advanced Search logs showing a user’s device contacting OneNote endpoints, fetching a Qakbot DLL over HTTP, making SSL connections to Qakbot infrastructure and connectivity checks to legitimate domains, and then making SSL connections to the Cobalt Strike endpoint, bonsars[.]com.
Figure 9: Event Log showing a user’s device contacting the Cobalt Strike C2 endpoint, bonsars[.]com, and the VNC C2 endpoint, 78.31.67[.]7, whilst simultaneously contacting the Qakbot C2 endpoint, 47.32.78[.]150.

Lateral Movement Phase

After dropping Cobalt Strike Beacon and a VNC module onto Qakbot-infected systems, actors leveraged their strengthened foothold to connect to the Service Control Manager (SCM) on internal systems in preparation for lateral movement. Before connecting to the SCM, infected systems were seen making calls to the Endpoint Mapper service, likely to identify exposed Microsoft Remote Procedure Call (MSRPC) services on internal systems. The MSRPC service, Service Control Manager (SCM), is known to be abused by Cobalt Strike to create and start services on remote systems. Connections to this service were evidenced by OpenSCManager2  (Opnum: 0x40) and OpenSCManagerW (Opnum: 0xf) calls to the svcctl RPC interface. 

Figure 10: Advanced Search logs showing a user’s device contacting the Endpoint Mapper and Service Control Manager (SCM) services on internal systems. 

After connecting to the SCM on internal systems, infected devices were seen using SMB to distribute files with ‘.dll’ and ‘.dll.cfg’ extensions to SMB shares. These uploads were followed by CreateWowService (Opnum: 0x3c) calls to the svcctl interface, likely intended to execute the uploaded payloads. The naming conventions of the uploaded files indicate that they were Qakbot payloads. 

Figure 11: Advanced Search logs showing a user’s device making Service Control DCE-RPC requests to internal systems after uploading ‘.dll’ and ‘.dll.cfg’ files to them over SMB.

Fortunately, none of the observed QakNote infections escalated further than this. If these infections had escalated, it is likely that they would have resulted in the widespread detonation of additional malicious payloads, such as ransomware.  

Darktrace Coverage of QakNote Activity

Figure 1 shows the steps involved in the QakNote infections observed across Darktrace’s customer base. How far attackers got along this chain was in part determined by the following three factors:

The presence of Darktrace/Email typically stopped QakNote infections from moving past the initial infection stage. The presence of RESPOND/Network significantly slowed down observed activity chains, however, infections left unattended and not mitigated by the security teams were able to progress further along the attack chain. 

Darktrace observed varying properties in the QakNote emails detected across the customer base. OneNote attachments were typically detected as either ‘application/octet-stream’ files or as ‘application/x-tar’ files. In some cases, the weaponized OneNote attachment embedded a malicious file, whereas in other cases, the OneNote file embedded a malicious link (typically a ‘.png’ or ‘.gif’ link) instead. In all cases Darktrace observed, QakNote emails used subject lines starting with ‘RE’ or ‘FW’ to manipulating their recipients into thinking that such emails were part of an existing email chain/thread. In some cases, emails impersonated users known to their recipients by including the names of such users in their header-from personal names. In many cases, QakNote emails appear to have originated from likely hijacked email accounts. These are highly successful methods of social engineering often employed by threat actors to exploit a user’s trust in known contacts or services, convincing them to open malicious emails and making it harder for security tools to detect.

The fact that observed QakNote emails used the fake-reply method, were sent from unknown email accounts, and contained attachments with unusual MIME types, caused such emails to breach the following Darktrace/Email models:

  • Association / Unknown Sender
  • Attachment / Unknown File
  • Attachment / Unsolicited Attachment
  • Attachment / Highly Unusual Mime
  • Attachment / Unsolicited Anomalous Mime
  • Attachment / Unusual Mime for Organisation
  • Unusual / Fake Reply
  • Unusual / Unusual Header TLD
  • Unusual / Fake Reply + Unknown Sender
  • Unusual / Unusual Connection from Unknown
  • Unusual / Off Topic

QakNote emails impersonating known users also breached the following DETECT & RESPOND/Email models:

  • Unusual / Unrelated Personal Name Address
  • Spoof / Basic Known Entity Similarities
  • Spoof / Internal User Similarities
  • Spoof / External User Similarities
  • Spoof / Internal User Similarities + Unrelated Personal Name Address
  • Spoof / External User Similarities + Unrelated Personal Name Address
  • Spoof / Internal User Similarities + Unknown File
  • Spoof / External User Similarities + Fake Reply
  • Spoof / Possible User Spoof from New Address - Enhanced Internal Similarities
  • Spoof / Whale

The actions taken by Darktrace on the observed emails is ultimately determined by Darktrace/Email models are breached. Those emails which did not breach Spoofing models (due to lack of impersonation indicators) received the ‘Convert Attachment’ action. This action converts suspicious attachments into neutralized PDFs, in this case successfully unweaponizing the malicious OneNote attachments. QakNote emails which did breach Spoofing models (due to the presence of impersonation indicators) received the strongest possible action, ‘Hold Message’. This action prevents suspicious emails from reaching the recipients’ mailbox. 

Figure 12: Email log showing a malicious OneNote email (without impersonation indicators) which received a 87% anomaly score, a ‘Move to junk’ action, and a ‘Convert attachment’ actions from Darktrace/Email.
Figure 13: Email log showing a malicious OneNote email (with impersonation indicators) which received an anomaly score of 100% and a ‘Hold message’ action from Darktrace/Email.
Figure 14: Email log showing a malicious OneNote email (with impersonation indicators) which received an anomaly score of 100% and a ‘Hold message’ action from Darktrace/Email.

If threat actors managed to get past the first stage of the QakNote kill chain, likely due to the absence of appropriate email security tools, the execution of the subsequent steps resulted in strong intervention from Darktrace/Network. 

Interactions with malicious OneNote attachments caused their devices to fetch a Qakbot DLL from a remote server via HTTP GET requests with an empty Host header and either a cURL or PowerShell User-Agent header. These unusual HTTP behaviors caused the following Darktrace/Network models to breach:

  • Device / New User Agent
  • Device / New PowerShell User Agent
  • Device / New User Agent and New IP
  • Anomalous Connection / New User Agent to IP Without Hostname
  • Anomalous Connection / Powershell to Rare External
  • Anomalous File / Numeric File Download
  • Anomalous File / EXE from Rare External Location
  • Anomalous File / New User Agent Followed By Numeric File Download

For customers with RESPOND/Network active, these breaches resulted in the following autonomous actions:

  • Enforce group pattern of life for 30 minutes
  • Enforce group pattern of life for 2 hours
  • Block connections to relevant external endpoints over relevant ports for 2 hours   
  • Block all outgoing traffic for 10 minutes
Figure 15: Event Log showing a user’s device receiving Darktrace RESPOND/Network actions after downloading a Qakbot DLL. 
Figure 16: Event Log showing a user’s device receiving Darktrace RESPOND/Network actions after downloading a Qakbot DLL.

Successful, uninterrupted downloads of Qakbot DLLs resulted in connections to Qakbot C2 servers, and subsequently to Cobalt Strike and VNC C2 connections. These C2 activities resulted in breaches of the following DETECT/Network models:

  • Compromise / Suspicious TLS Beaconing To Rare External
  • Compromise / Large Number of Suspicious Successful Connections
  • Compromise / Large Number of Suspicious Failed Connections
  • Compromise / Sustained SSL or HTTP Increase
  • Compromise / Sustained TCP Beaconing Activity To Rare Endpoint
  • Compromise / Beaconing Activity To External Rare
  • Compromise / Slow Beaconing Activity To External Rare
  • Anomalous Connection / Multiple Connections to New External TCP Port
  • Anomalous Connection / Multiple Failed Connections to Rare Endpoint
  • Device / Initial Breach Chain Compromise

For customers with RESPOND/Network active, these breaches caused RESPOND to autonomously perform the following actions:

  • Block connections to relevant external endpoints over relevant ports for 1 hour
Figure 17: Event Log showing a user’s device receiving RESPOND/Network actions after contacting the Qakbot C2 endpoint,  Cobalt Strike C2 endpoint, bonsars[.]com.

In cases where C2 connections were allowed to continue, actors attempted to move laterally through usage of SMB and Service Control Manager. This lateral movement activity caused the following DETECT/Network models to breach:

  • Device / Possible SMB/NTLM Reconnaissance
  • Anomalous Connection / New or Uncommon Service Control 

For customers with RESPOND/Network enabled, these breaches caused RESPOND to autonomously perform the following actions:

  • Block connections to relevant internal endpoints over port 445 for 1 hour
Figure 18: Event Log shows a user’s device receiving RESPOND/Network actions after contacting the Qakbot C2 endpoint, 5.75.205[.]43, and distributing ‘.dll’ and ‘.dll.cfg’ files internally.

The QakNote infections observed across Darktrace’s customer base involved several steps, each of which elicited alerts and autonomous preventative actions from Darktrace. By autonomously investigating the alerts from DETECT, Darktrace’s Cyber AI Analyst was able to connect the distinct steps of observed QakNote infections into single incidents. It then produced incident logs to present in-depth details of the activity it uncovered, provide full visibility for customer security teams.

Figure 19: AI Analyst incident entry showing the steps of a QakNote infection which AI Analyst connected following its autonomous investigations.

Conclusion

Faced with the emerging threat of QakNote infections, Darktrace demonstrated its ability to autonomously detect and respond to arising threats in a constantly evolving threat landscape. The attack chains which Darktrace observed across its customer base involved the delivery of Qakbot via malicious OneNote attachments, the usage of ports 65400 and 2222 for Qakbot C2 communication, the usage of Cobalt Strike Beacon and VNC for ‘hands-on-keyboard’ activity, and the usage of SMB and Service Control Manager for lateral movement. 

Despite the novelty of the OneNote-based delivery method, Darktrace was able to identify QakNote infections across its customer base at various stages of the kill chain, using its autonomous anomaly-based detection to identify unusual activity or deviations from expected behavior. When active, Darktrace/Email neutralized malicious QakNote attachments sent to employees. In cases where Darktrace/Email was not active, Darktrace/Network detected and slowed down the unusual network activities which inevitably ensued from Qakbot infections. Ultimately, this intervention from Darktrace’s products prevented infections from leading to further harmful activity, such as data exfiltration and the detonation of ransomware.

Darktrace is able to offer customers an unparalleled level of network security by combining both Darktrace/Network and Darktrace/Email, safeguarding both their email and network environments. With its suite of products, including DETECT and RESPOND, Darktrace can autonomously uncover threats to customer networks and instantaneously intervene to prevent suspicious activity leading to damaging compromises. 

Appendices

MITRE ATT&CK Mapping 

Initial Access:

T1566.001 – Phishing: Spearphishing Attachment

Execution:

T1204.001 – User Execution: Malicious Link

T1204.002 – User Execution: Malicious File

T1569.002 – System Services: Service Execution

Lateral Movement:

T1021.002 – Remote Services: SMB/Windows Admin Shares

Command and Control:

T1573.002 – Encrypted Channel : Asymmetric Cryptography

T1571 – Non-Standard Port 

T1105 – Ingress Tool Transfer

T1095 –  Non-Application Layer Protocol

T1219 – Remote Access Software

List of IOCs

IP Addresses and/or Domain Names:

- 103.214.71[.]45 - Qakbot download infrastructure 

- 141.164.35[.]94 - Qakbot download infrastructure 

- 95.179.215[.]225 - Qakbot download infrastructure 

- 128.254.207[.]55 - Qakbot download infrastructure

- 141.164.35[.]94 - Qakbot download infrastructure

- 172.96.137[.]149 - Qakbot download infrastructure

- 185.231.205[.]246 - Qakbot download infrastructure

- 216.128.146[.]67 - Qakbot download infrastructure 

- 45.155.37[.]170 - Qakbot download infrastructure

- 85.239.41[.]55 - Qakbot download infrastructure

- 45.67.35[.]108 - Qakbot download infrastructure

- 77.83.199[.]12 - Qakbot download infrastructure 

- 45.77.63[.]210 - Qakbot download infrastructure 

- 198.44.140[.]78 - Qakbot download infrastructure

- 47.32.78[.]150 - Qakbot C2 infrastructure

- 197.204.13[.]52 - Qakbot C2 infrastructure

- 68.108.122[.]180 - Qakbot C2 infrastructure

- 2.50.48[.]213 - Qakbot C2 infrastructure

- 66.180.227[.]60 - Qakbot C2 infrastructure

- 190.206.75[.]58 - Qakbot C2 infrastructure

- 109.150.179[.]236 - Qakbot C2 infrastructure

- 86.202.48[.]142 - Qakbot C2 infrastructure

- 143.159.167[.]159 - Qakbot C2 infrastructure

- 5.75.205[.]43 - Qakbot C2 infrastructure

- 184.176.35[.]223 - Qakbot C2 infrastructure 

- 208.187.122[.]74 - Qakbot C2 infrastructure

- 23.111.114[.]52 - Qakbot C2 infrastructure 

- 74.12.134[.]53 – Qakbot C2 infrastructure

- bonsars[.]com • 194.165.16[.]56 - Cobalt Strike C2 infrastructure 

- 78.31.67[.]7 - VNC C2 infrastructure

Target URIs of GET Requests for Qakbot DLLs:

- /70802.dat 

- /51881.dat

- /12427.dat

- /70136.dat

- /35768.dat

- /41981.dat

- /30622.dat

- /72286.dat

- /46557.dat

- /33006.dat

- /300332.dat

- /703558.dat

- /760433.dat

- /210/184/187737.dat

- /469/387/553748.dat

- /282/535806.dat

User-Agent Headers of GET Requests for Qakbot DLLs:

- curl/7.83.1

- curl/7.55.1

- Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.19041.2364

- Mozilla/5.0 (Windows NT; Windows NT 10.0; en-US) WindowsPowerShell/5.1.17763.3770

- Mozilla/5.0 (Windows NT; Windows NT 10.0; en-GB) WindowsPowerShell/5.1.19041.2364

SHA256 Hashes of Downloaded Qakbot DLLs:  

- 83e9bdce1276d2701ff23b1b3ac7d61afc97937d6392ed6b648b4929dd4b1452

- ca95a5dcd0194e9189b1451fa444f106cbabef3558424d9935262368dba5f2c6 

- fa067ff1116b4c8611eae9ed4d59a19d904a8d3c530b866c680a7efeca83eb3d

- e6853589e42e1ab74548b5445b90a5a21ff0d7f8f4a23730cffe285e2d074d9e

- d864d93b8fd4c5e7fb136224460c7b98f99369fc9418bae57de466d419abeaf6

- c103c24ccb1ff18cd5763a3bb757ea2779a175a045e96acbb8d4c19cc7d84bea

Names of Internally Distributed Qakbot DLLs: 

- rpwpmgycyzghm.dll

- rpwpmgycyzghm.dll.cfg

- guapnluunsub.dll

- guapnluunsub.dll.cfg

- rskgvwfaqxzz.dll

- rskgvwfaqxzz.dll.cfg

- hkfjhcwukhsy.dll

- hkfjhcwukhsy.dll.cfg

- uqailliqbplm.dll

- uqailliqbplm.dll.cfg

- ghmaorgvuzfos.dll

- ghmaorgvuzfos.dll.cfg

Links Found Within Neutralized QakNote Email Attachments:

- hxxps://khatriassociates[.]com/MBt/3.gif

- hxxps://spincotech[.]com/8CoBExd/3.gif

- hxxps://minaato[.]com/tWZVw/3.gif

- hxxps://famille2point0[.]com/oghHO/01.png

- hxxps://sahifatinews[.]com/jZbaw/01.png

- hxxp://87.236.146[.]112/62778.dat

- hxxp://87.236.146[.]112/59076.dat

- hxxp://185.231.205[.]246/73342.dat

References

[1] https://techcommunity.microsoft.com/t5/excel-blog/excel-4-0-xlm-macros-now-restricted-by-default-for-customer/ba-p/3057905

[2] https://techcommunity.microsoft.com/t5/microsoft-365-blog/helping-users-stay-safe-blocking-internet-macros-by-default-in/ba-p/3071805

[3] https://learn.microsoft.com/en-us/deployoffice/security/internet-macros-blocked

[4] https://www.cyfirma.com/outofband/html-smuggling-a-stealthier-approach-to-deliver-malware/

[5] https://www.trustwave.com/en-us/resources/blogs/spiderlabs-blog/html-smuggling-the-hidden-threat-in-your-inbox/

[6] https://twitter.com/nao_sec/status/1530196847679401984

[7] https://www.fortiguard.com/threat-signal-report/4616/qakbot-delivered-through-cve-2022-30190-follina

[8] https://isc.sans.edu/diary/rss/28728

[9] https://darktrace.com/blog/qakbot-resurgence-evolving-along-with-the-emerging-threat-landscape

[10] https://www.trustwave.com/en-us/resources/blogs/spiderlabs-blog/trojanized-onenote-document-leads-to-formbook-malware/

[11] https://www.proofpoint.com/uk/blog/threat-insight/onenote-documents-increasingly-used-to-deliver-malware

[12] https://www.malwarebytes.com/blog/threat-intelligence/2023/03/emotet-onenote

[13] https://blog.cyble.com/2023/02/01/qakbots-evolution-continues-with-new-strategies/

[14] https://news.sophos.com/en-us/2023/02/06/qakbot-onenote-attacks/

[15] https://isc.sans.edu/diary/rss/29210

[16] https://unit42.paloaltonetworks.com/feb-wireshark-quiz-answers/

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
Sam Lister
SOC Analyst
Written by
Connor Mooney
SOC Analyst

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October 14, 2025

Inside Akira’s SonicWall Campaign: Darktrace’s Detection and Response

akira sonicwallDefault blog imageDefault blog image

Introduction: Background on Akira SonicWall campaign

Between July and August 2025, security teams worldwide observed a surge in Akira ransomware incidents involving SonicWall SSL VPN devices [1]. Initially believed to be the result of an unknown zero-day vulnerability, SonicWall later released an advisory announcing that the activity was strongly linked to a previously disclosed vulnerability, CVE-2024-40766, first identified over a year earlier [2].

On August 20, 2025, Darktrace observed unusual activity on the network of a customer in the US. Darktrace detected a range of suspicious activity, including network scanning and reconnaissance, lateral movement, privilege escalation, and data exfiltration. One of the compromised devices was later identified as a SonicWall virtual private network (VPN) server, suggesting that the incident was part of the broader Akira ransomware campaign targeting SonicWall technology.

As the customer was subscribed to the Managed Detection and Response (MDR) service, Darktrace’s Security Operations Centre (SOC) team was able to rapidly triage critical alerts, restrict the activity of affected devices, and notify the customer of the threat. As a result, the impact of the attack was limited - approximately 2 GiB of data had been observed leaving the network, but any further escalation of malicious activity was stopped.

Threat Overview

CVE-2024-40766 and other misconfigurations

CVE-2024-40766 is an improper access control vulnerability in SonicWall’s SonicOS, affecting Gen 5, Gen 6, and Gen 7 devices running SonicOS version 7.0.1 5035 and earlier [3]. The vulnerability was disclosed on August 23, 2024, with a patch released the same day. Shortly after, it was reported to be exploited in the wild by Akira ransomware affiliates and others [4].

Almost a year later, the same vulnerability is being actively targeted again by the Akira ransomware group. In addition to exploiting unpatched devices affected by CVE-2024-40766, security researchers have identified three other risks potentially being leveraged by the group [5]:

*The Virtual Office Portal can be used to initially set up MFA/TOTP configurations for SSLVPN users.

Thus, even if SonicWall devices were patched, threat actors could still target them for initial access by reusing previously stolen credentials and exploiting other misconfigurations.

Akira Ransomware

Akira ransomware was first observed in the wild in March 2023 and has since become one of the most prolific ransomware strains across the threat landscape [6]. The group operates under a Ransomware-as-a-Service (RaaS) model and frequently uses double extortion tactics, pressuring victims to pay not only to decrypt files but also to prevent the public release of sensitive exfiltrated data.

The ransomware initially targeted Windows systems, but a Linux variant was later observed targeting VMware ESXi virtual machines [7]. In 2024, it was assessed that Akira would continue to target ESXi hypervisors, making attacks highly disruptive due to the central role of virtualisation in large-scale cloud deployments. Encrypting the ESXi file system enables rapid and widespread encryption with minimal lateral movement or credential theft. The lack of comprehensive security protections on many ESXi hypervisors also makes them an attractive target for ransomware operators [8].

Victimology

Akira is known to target organizations across multiple sectors, most notably those in manufacturing, education, and healthcare. These targets span multiple geographic regions, including North America, Latin America, Europe and Asia-Pacific [9].

Geographical distribution of organization’s affected by Akira ransomware in 2025 [9].
Figure 1: Geographical distribution of organization’s affected by Akira ransomware in 2025 [9].

Common Tactics, Techniques and Procedures (TTPs) [7][10]

Initial Access
Targets remote access services such as RDP and VPN through vulnerability exploitation or stolen credentials.

Reconnaissance
Uses network scanning tools like SoftPerfect and Advanced IP Scanner to map the environment and identify targets.

Lateral Movement
Moves laterally using legitimate administrative tools, typically via RDP.

Persistence
Employs techniques such as Kerberoasting and pass-the-hash, and tools like Mimikatz to extract credentials. Known to create new domain accounts to maintain access.

Command and Control
Utilizes remote access tools including AnyDesk, RustDesk, Ngrok, and Cloudflare Tunnel.

Exfiltration
Uses tools such as FileZilla, WinRAR, WinSCP, and Rclone. Data is exfiltrated via protocols like FTP and SFTP, or through cloud storage services such as Mega.

Darktrace’s Coverage of Akira ransomware

Reconnaissance

Darktrace first detected of unusual network activity around 05:10 UTC, when a desktop device was observed performing a network scan and making an unusual number of DCE-RPC requests to the endpoint mapper (epmapper) service. Network scans are typically used to identify open ports, while querying the epmapper service can reveal exposed RPC services on the network.

Multiple other devices were also later seen with similar reconnaissance activity, and use of the Advanced IP Scanner tool, indicated by connections to the domain advanced-ip-scanner[.]com.

Lateral movement

Shortly after the initial reconnaissance, the same desktop device exhibited unusual use of administrative tools. Darktrace observed the user agent “Ruby WinRM Client” and the URI “/wsman” as the device initiated a rare outbound Windows Remote Management (WinRM) connection to two domain controllers (REDACTED-dc1 and REDACTED-dc2). WinRM is a Microsoft service that uses the WS-Management (WSMan) protocol to enable remote management and control of network devices.

Darktrace also observed the desktop device connecting to an ESXi device (REDACTED-esxi1) via RDP using an LDAP service credential, likely with administrative privileges.

Credential access

At around 06:26 UTC, the desktop device was seen fetching an Active Directory certificate from the domain controller (REDACTED-dc1) by making a DCE-RPC request to the ICertPassage service. Shortly after, the device made a Kerberos login using the administrative credential.

Figure 3: Darktrace’s detection of the of anomalous certificate download and subsequent Kerberos login.

Further investigation into the device’s event logs revealed a chain of connections that Darktrace’s researchers believe demonstrates a credential access technique known as “UnPAC the hash.”

This method begins with pre-authentication using Kerberos’ Public Key Cryptography for Initial Authentication (PKINIT), allowing the client to use an X.509 certificate to obtain a Ticket Granting Ticket (TGT) from the Key Distribution Center (KDC) instead of a password.

The next stage involves User-to-User (U2U) authentication when requesting a Service Ticket (ST) from the KDC. Within Darktrace's visibility of this traffic, U2U was indicated by the client and service principal names within the ST request being identical. Because PKINIT was used earlier, the returned ST contains the NTLM hash of the credential, which can then be extracted and abused for lateral movement or privilege escalation [11].

Flowchart of Kerberos PKINIT pre-authentication and U2U authentication [12].
Figure 4: Flowchart of Kerberos PKINIT pre-authentication and U2U authentication [12]
Figure 5: Device event log showing the Kerberos Login and Kerberos Ticket events

Analysis of the desktop device’s event logs revealed a repeated sequence of suspicious activity across multiple credentials. Each sequence included a DCE-RPC ICertPassage request to download a certificate, followed by a Kerberos login event indicating PKINIT pre-authentication, and then a Kerberos ticket event consistent with User-to-User (U2U) authentication.

Darktrace identified this pattern as highly unusual. Cyber AI Analyst determined that the device used at least 15 different credentials for Kerberos logins over the course of the attack.

By compromising multiple credentials, the threat actor likely aimed to escalate privileges and facilitate further malicious activity, including lateral movement. One of the credentials obtained via the “UnPAC the hash” technique was later observed being used in an RDP session to the domain controller (REDACTED-dc2).

C2 / Additional tooling

At 06:44 UTC, the domain controller (REDACTED-dc2) was observed initiating a connection to temp[.]sh, a temporary cloud hosting service. Open-source intelligence (OSINT) reporting indicates that this service is commonly used by threat actors to host and distribute malicious payloads, including ransomware [13].

Shortly afterward, the ESXi device was observed downloading an executable named “vmwaretools” from the rare external endpoint 137.184.243[.]69, using the user agent “Wget.” The repeated outbound connections to this IP suggest potential command-and-control (C2) activity.

Cyber AI Analyst investigation into the suspicious file download and suspected C2 activity between the ESXI device and the external endpoint 137.184.243[.]69.
Figure 6: Cyber AI Analyst investigation into the suspicious file download and suspected C2 activity between the ESXI device and the external endpoint 137.184.243[.]69.
Packet capture (PCAP) of connections between the ESXi device and 137.184.243[.]69.
Figure 7: Packet capture (PCAP) of connections between the ESXi device and 137.184.243[.]69.

Data exfiltration

The first signs of data exfiltration were observed at around 7:00 UTC. Both the domain controller (REDACTED-dc2) and a likely SonicWall VPN device were seen uploading approximately 2 GB of data via SSH to the rare external endpoint 66.165.243[.]39 (AS29802 HVC-AS). OSINT sources have since identified this IP as an indicator of compromise (IoC) associated with the Akira ransomware group, known to use it for data exfiltration [14].

Cyber AI Analyst incident view highlighting multiple unusual events across several devices on August 20. Notably, it includes the “Unusual External Data Transfer” event, which corresponds to the anomalous 2 GB data upload to the known Akira-associated endpoint 66.165.243[.]39.
Figure 8: Cyber AI Analyst incident view highlighting multiple unusual events across several devices on August 20. Notably, it includes the “Unusual External Data Transfer” event, which corresponds to the anomalous 2 GB data upload to the known Akira-associated endpoint 66.165.243[.]39.

Cyber AI Analyst

Throughout the course of the attack, Darktrace’s Cyber AI Analyst autonomously investigated the anomalous activity as it unfolded and correlated related events into a single, cohesive incident. Rather than treating each alert as isolated, Cyber AI Analyst linked them together to reveal the broader narrative of compromise. This holistic view enabled the customer to understand the full scope of the attack, including all associated activities and affected assets that might otherwise have been dismissed as unrelated.

Overview of Cyber AI Analyst’s investigation, correlating all related internal and external security events across affected devices into a single pane of glass.
Figure 9: Overview of Cyber AI Analyst’s investigation, correlating all related internal and external security events across affected devices into a single pane of glass.

Containing the attack

In response to the multiple anomalous activities observed across the network, Darktrace's Autonomous Response initiated targeted mitigation actions to contain the attack. These included:

  • Blocking connections to known malicious or rare external endpoints, such as 137.184.243[.]69, 66.165.243[.]39, and advanced-ip-scanner[.]com.
  • Blocking internal traffic to sensitive ports, including 88 (Kerberos), 3389 (RDP), and 49339 (DCE-RPC), to disrupt lateral movement and credential abuse.
  • Enforcing a block on all outgoing connections from affected devices to contain potential data exfiltration and C2 activity.
Autonomous Response actions taken by Darktrace on an affected device, including the blocking of malicious external endpoints and internal service ports.
Figure 10: Autonomous Response actions taken by Darktrace on an affected device, including the blocking of malicious external endpoints and internal service ports.

Managed Detection and Response

As this customer was an MDR subscriber, multiple Enhanced Monitoring alerts—high-fidelity models designed to detect activity indicative of compromise—were triggered across the network. These alerts prompted immediate investigation by Darktrace’s SOC team.

Upon determining that the activity was likely linked to an Akira ransomware attack, Darktrace analysts swiftly acted to contain the threat. At around 08:05 UTC, devices suspected of being compromised were quarantined, and the customer was promptly notified, enabling them to begin their own remediation procedures without delay.

A wider campaign?

Darktrace’s SOC and Threat Research teams identified at least three additional incidents likely linked to the same campaign. All targeted organizations were based in the US, spanning various industries, and each have indications of using SonicWall VPN, indicating it had likely been targeted for initial access.

Across these incidents, similar patterns emerged. In each case, a suspicious executable named “vmwaretools” was downloaded from the endpoint 85.239.52[.]96 using the user agent “Wget”, bearing some resemblance to the file downloads seen in the incident described here. Data exfiltration was also observed via SSH to the endpoints 107.155.69[.]42 and 107.155.93[.]154, both of which belong to the same ASN also seen in the incident described in this blog: S29802 HVC-AS. Notably, 107.155.93[.]154 has been reported in OSINT as an indicator associated with Akira ransomware activity [15]. Further recent Akira ransomware cases have been observed involving SonicWall VPN, where no similar executable file downloads were observed, but SSH exfiltration to the same ASN was. These overlapping and non-overlapping TTPs may reflect the blurring lines between different affiliates operating under the same RaaS.

Lessons from the campaign

This campaign by Akira ransomware actors underscores the critical importance of maintaining up-to-date patching practices. Threat actors continue to exploit previously disclosed vulnerabilities, not just zero-days, highlighting the need for ongoing vigilance even after patches are released. It also demonstrates how misconfigurations and overlooked weaknesses can be leveraged for initial access or privilege escalation, even in otherwise well-maintained environments.

Darktrace’s observations further reveal that ransomware actors are increasingly relying on legitimate administrative tools, such as WinRM, to blend in with normal network activity and evade detection. In addition to previously documented Kerberos-based credential access techniques like Kerberoasting and pass-the-hash, this campaign featured the use of UnPAC the hash to extract NTLM hashes via PKINIT and U2U authentication for lateral movement or privilege escalation.

Credit to Emily Megan Lim (Senior Cyber Analyst), Vivek Rajan (Senior Cyber Analyst), Ryan Traill (Analyst Content Lead), and Sam Lister (Specialist Security Researcher)

Appendices

Darktrace Model Detections

Anomalous Connection / Active Remote Desktop Tunnel

Anomalous Connection / Data Sent to Rare Domain

Anomalous Connection / New User Agent to IP Without Hostname

Anomalous Connection / Possible Data Staging and External Upload

Anomalous Connection / Rare WinRM Incoming

Anomalous Connection / Rare WinRM Outgoing

Anomalous Connection / Uncommon 1 GiB Outbound

Anomalous Connection / Unusual Admin RDP Session

Anomalous Connection / Unusual Incoming Long Remote Desktop Session

Anomalous Connection / Unusual Incoming Long SSH Session

Anomalous Connection / Unusual Long SSH Session

Anomalous File / EXE from Rare External Location

Anomalous Server Activity / Anomalous External Activity from Critical Network Device

Anomalous Server Activity / Outgoing from Server

Anomalous Server Activity / Rare External from Server

Compliance / Default Credential Usage

Compliance / High Priority Compliance Model Alert

Compliance / Outgoing NTLM Request from DC

Compliance / SSH to Rare External Destination

Compromise / Large Number of Suspicious Successful Connections

Compromise / Sustained TCP Beaconing Activity To Rare Endpoint

Device / Anomalous Certificate Download Activity

Device / Anomalous SSH Followed By Multiple Model Alerts

Device / Anonymous NTLM Logins

Device / Attack and Recon Tools

Device / ICMP Address Scan

Device / Large Number of Model Alerts

Device / Network Range Scan

Device / Network Scan

Device / New User Agent To Internal Server

Device / Possible SMB/NTLM Brute Force

Device / Possible SMB/NTLM Reconnaissance

Device / RDP Scan

Device / Reverse DNS Sweep

Device / Suspicious SMB Scanning Activity

Device / UDP Enumeration

Unusual Activity / Unusual External Data to New Endpoint

Unusual Activity / Unusual External Data Transfer

User / Multiple Uncommon New Credentials on Device

User / New Admin Credentials on Client

User / New Admin Credentials on Server

Enhanced Monitoring Models

Compromise / Anomalous Certificate Download and Kerberos Login

Device / Initial Attack Chain Activity

Device / Large Number of Model Alerts from Critical Network Device

Device / Multiple Lateral Movement Model Alerts

Device / Suspicious Network Scan Activity

Unusual Activity / Enhanced Unusual External Data Transfer

Antigena/Autonomous Response Models

Antigena / Network / External Threat / Antigena File then New Outbound Block

Antigena / Network / External Threat / Antigena Suspicious Activity Block

Antigena / Network / External Threat / Antigena Suspicious File Block

Antigena / Network / Insider Threat / Antigena Large Data Volume Outbound Block

Antigena / Network / Insider Threat / Antigena Network Scan Block

Antigena / Network / Insider Threat / Antigena Unusual Privileged User Activities Block

Antigena / Network / Manual / Quarantine Device

Antigena / Network / Significant Anomaly / Antigena Alerts Over Time Block

Antigena / Network / Significant Anomaly / Antigena Controlled and Model Alert

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Client Block

Antigena / Network / Significant Anomaly / Antigena Enhanced Monitoring from Server Block

Antigena / Network / Significant Anomaly / Antigena Significant Anomaly from Client Block

Antigena / Network / Significant Anomaly / Antigena Significant Server Anomaly Block

Antigena / Network / Significant Anomaly / Repeated Antigena Alerts

List of Indicators of Compromise (IoCs)

·      66.165.243[.]39 – IP Address – Data exfiltration endpoint

·      107.155.69[.]42 – IP Address – Probable data exfiltration endpoint

·      107.155.93[.]154 – IP Address – Likely Data exfiltration endpoint

·      137.184.126[.]86 – IP Address – Possible C2 endpoint

·      85.239.52[.]96 – IP Address – Likely C2 endpoint

·      hxxp://85.239.52[.]96:8000/vmwarecli  – URL – File download

·      hxxp://137.184.126[.]86:8080/vmwaretools – URL – File download

MITRE ATT&CK Mapping

Initial Access – T1190 – Exploit Public-Facing Application

Reconnaissance – T1590.002 – Gather Victim Network Information: DNS

Reconnaissance – T1590.005 – Gather Victim Network Information: IP Addresses

Reconnaissance – T1592.004 – Gather Victim Host Information: Client Configurations

Reconnaissance – T1595 – Active Scanning

Discovery – T1018 – Remote System Discovery

Discovery – T1046 – Network Service Discovery

Discovery – T1083 – File and Directory Discovery

Discovery – T1135 – Network Share Discovery

Lateral Movement – T1021.001 – Remote Services: Remote Desktop Protocol

Lateral Movement – T1021.004 – Remote Services: SSH

Lateral Movement – T1021.006 – Remote Services: Windows Remote Management

Lateral Movement – T1550.002 – Use Alternate Authentication Material: Pass the Hash

Lateral Movement – T1550.003 – Use Alternate Authentication Material: Pass the Ticket

Credential Access – T1110.001 – Brute Force: Password Guessing

Credential Access – T1649 – Steal or Forge Authentication Certificates

Persistence, Privilege Escalation – T1078 – Valid Accounts

Resource Development – T1588.001 – Obtain Capabilities: Malware

Command and Control – T1071.001 – Application Layer Protocol: Web Protocols

Command and Control – T1105 – Ingress Tool Transfer

Command and Control – T1573 – Encrypted Channel

Collection – T1074 – Data Staged

Exfiltration – T1041 – Exfiltration Over C2 Channel

Exfiltration – T1048 – Exfiltration Over Alternative Protocol

References

[1] https://thehackernews.com/2025/08/sonicwall-investigating-potential-ssl.html

[2] https://www.sonicwall.com/support/notices/gen-7-and-newer-sonicwall-firewalls-sslvpn-recent-threat-activity/250804095336430

[3] https://psirt.global.sonicwall.com/vuln-detail/SNWLID-2024-0015

[4] https://arcticwolf.com/resources/blog/arctic-wolf-observes-akira-ransomware-campaign-targeting-sonicwall-sslvpn-accounts/

[5] https://www.rapid7.com/blog/post/dr-akira-ransomware-group-utilizing-sonicwall-devices-for-initial-access/

[6] https://www.ic3.gov/AnnualReport/Reports/2024_IC3Report.pdf

[7] https://www.cisa.gov/news-events/cybersecurity-advisories/aa24-109a

[8] https://blog.talosintelligence.com/akira-ransomware-continues-to-evolve/

[9] https://www.ransomware.live/map?year=2025&q=akira

[10] https://attack.mitre.org/groups/G1024/
[11] https://labs.lares.com/fear-kerberos-pt2/#UNPAC

[12] https://www.thehacker.recipes/ad/movement/kerberos/unpac-the-hash

[13] https://www.s-rminform.com/latest-thinking/derailing-akira-cyber-threat-intelligence)

[14] https://fieldeffect.com/blog/update-akira-ransomware-group-targets-sonicwall-vpn-appliances

[15] https://arcticwolf.com/resources/blog/arctic-wolf-observes-july-2025-uptick-in-akira-ransomware-activity-targeting-sonicwall-ssl-vpn/

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September 30, 2025

Out of Character: Detecting Vendor Compromise and Trusted Relationship Abuse with Darktrace

vendor email compromiseDefault blog imageDefault blog image

What is Vendor Email Compromise?

Vendor Email Compromise (VEC) refers to an attack where actors breach a third-party provider to exploit their access, relationships, or systems for malicious purposes. The initially compromised entities are often the target’s existing partners, though this can extend to any organization or individual the target is likely to trust.

It sits at the intersection of supply chain attacks and business email compromise (BEC), blending technical exploitation with trust-based deception. Attackers often infiltrate existing conversations, leveraging AI to mimic tone and avoid common spelling and grammar pitfalls. Malicious content is typically hosted on otherwise reputable file sharing platforms, meaning any shared links initially seem harmless.

While techniques to achieve initial access may have evolved, the goals remain familiar. Threat actors harvest credentials, launch subsequent phishing campaigns, attempt to redirect invoice payments for financial gain, and exfiltrate sensitive corporate data.

Why traditional defenses fall short

These subtle and sophisticated email attacks pose unique challenges for defenders. Few busy people would treat an ongoing conversation with a trusted contact with the same level of suspicion as an email from the CEO requesting ‘URGENT ASSISTANCE!’ Unfortunately, many traditional secure email gateways (SEGs) struggle with this too. Detecting an out-of-character email, when it does not obviously appear out of character, is a complex challenge. It’s hardly surprising, then, that 83% of organizations have experienced a security incident involving third-party vendors [1].  

This article explores how Darktrace detected four different vendor compromise campaigns for a single customer, within a two-week period in 2025.  Darktrace / EMAIL successfully identified the subtle indicators that these seemingly benign emails from trusted senders were, in fact, malicious. Due to the configuration of Darktrace / EMAIL in this customer’s environment, it was unable to take action against the malicious emails. However, if fully enabled to take Autonomous Response, it would have held all offending emails identified.

How does Darktrace detect vendor compromise?

The answer lies at the core of how Darktrace operates: anomaly detection. Rather than relying on known malicious rules or signatures, Darktrace learns what ‘normal’ looks like for an environment, then looks for anomalies across a wide range of metrics. Despite the resourcefulness of the threat actors involved in this case, Darktrace identified many anomalies across these campaigns.

Different campaigns, common traits

A wide variety of approaches was observed. Individuals, shared mailboxes and external contractors were all targeted. Two emails originated from compromised current vendors, while two came from unknown compromised organizations - one in an associated industry. The sender organizations were either familiar or, at the very least, professional in appearance, with no unusual alphanumeric strings or suspicious top-level domains (TLDs). Subject line, such as “New Approved Statement From [REDACTED]” and “[REDACTED] - Proposal Document” appeared unremarkable and were not designed to provoke heightened emotions like typical social engineering or BEC attempts.

All emails had been given a Microsoft Spam Confidence Level of 1, indicating Microsoft did not consider them to be spam or malicious [2]. They also passed authentication checks (including SPF, and in some cases DKIM and DMARC), meaning they appeared to originate from an authentic source for the sender domain and had not been tampered with in transit.  

All observed phishing emails contained a link hosted on a legitimate and commonly used file-sharing site. These sites were often convincingly themed, frequently featuring the name of a trusted vendor either on the page or within the URL, to appear authentic and avoid raising suspicion. However, these links served only as the initial step in a more complex, multi-stage phishing process.

A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Figure 1: A legitimate file sharing site used in phishing emails to host a secondary malicious link.
Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.
Figure 2: Another example of a legitimate file sharing endpoint sent in a phishing email and used to host a malicious link.

If followed, the recipient would be redirected, sometimes via CAPTCHA, to fake Microsoft login pages designed to capturing credentials, namely http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html and https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html#.

The latter made use of homoglyphs to deceive the user, with a link referencing ‘s3cure0line’, rather than ‘secureonline’. Post-incident investigation using open-source intelligence (OSINT) confirmed that the domains were linked to malicious phishing endpoints [3] [4].

Fake Microsoft login page designed to harvest credentials.
Figure 3: Fake Microsoft login page designed to harvest credentials.
Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.
Figure 4: Phishing kit with likely AI-generated image, designed to harvest user credentials. The URL uses ‘s3cure0line’ instead of ‘secureonline’, a subtle misspelling intended to deceive users.

Darktrace Anomaly Detection

Some senders were unknown to the network, with no previous outbound or inbound emails. Some had sent the email to multiple undisclosed recipients using BCC, an unusual behavior for a new sender.  

Where the sender organization was an existing vendor, Darktrace recognized out-of-character behavior, in this case it was the first time a link to a particular file-sharing site had been shared. Often the links themselves exhibited anomalies, either being unusually prominent or hidden altogether - masked by text or a clickable image.

Crucially, Darktrace / EMAIL is able to identify malicious links at the time of processing the emails, without needing to visit the URLs or analyze the destination endpoints, meaning even the most convincing phishing pages cannot evade detection – meaning even the most convincing phishing emails cannot evade detection. This sets it apart from many competitors who rely on crawling the endpoints present in emails. This, among other things, risks disruption to user experience, such as unsubscribing them from emails, for instance.

Darktrace was also able to determine that the malicious emails originated from a compromised mailbox, using a series of behavioral and contextual metrics to make the identification. Upon analysis of the emails, Darktrace autonomously assigned several contextual tags to highlight their concerning elements, indicating that the messages contained phishing links, were likely sent from a compromised account, and originated from a known correspondent exhibiting out-of-character behavior.

A summary of the anomalous email, confirming that it contained a highly suspicious link.
Figure 5: Tags assigned to offending emails by Darktrace / EMAIL.

Figure 6: A summary of the anomalous email, confirming that it contained a highly suspicious link.

Out-of-character behavior caught in real-time

In another customer environment around the same time Darktrace / EMAIL detected multiple emails with carefully crafted, contextually appropriate subject lines sent from an established correspondent being sent to 30 different recipients. In many cases, the attacker hijacked existing threads and inserted their malicious emails into an ongoing conversation in an effort to blend in and avoid detection. As in the previous, the attacker leveraged a well-known service, this time ClickFunnels, to host a document containing another malicious link. Once again, they were assigned a Microsoft Spam Confidence Level of 1, indicating that they were not considered malicious.

The legitimate ClickFunnels page used to host a malicious phishing link.
Figure 7: The legitimate ClickFunnels page used to host a malicious phishing link.

This time, however, the customer had Darktrace / EMAIL fully enabled to take Autonomous Response against suspicious emails. As a result, when Darktrace detected the out-of-character behavior, specifically, the sharing of a link to a previously unused file-sharing domain, and identified the likely malicious intent of the message, it held the email, preventing it from reaching recipients’ inboxes and effectively shutting down the attack.

Figure 8: Darktrace / EMAIL’s detection of malicious emails inserted into an existing thread.*

*To preserve anonymity, all real customer names, email addresses, and other identifying details have been redacted and replaced with fictitious placeholders.

Legitimate messages in the conversation were assigned an Anomaly Score of 0, while the newly inserted malicious emails identified and were flagged with the maximum score of 100.

Key takeaways for defenders

Phishing remains big business, and as the landscape evolves, today’s campaigns often look very different from earlier versions. As with network-based attacks, threat actors are increasingly leveraging legitimate tools and exploiting trusted relationships to carry out their malicious goals, often staying under the radar of security teams and traditional email defenses.

As attackers continue to exploit trusted relationships between organizations and their third-party associates, security teams must remain vigilant to unexpected or suspicious email activity. Protecting the digital estate requires an email solution capable of identifying malicious characteristics, even when they originate from otherwise trusted senders.

Credit to Jennifer Beckett (Cyber Analyst), Patrick Anjos (Senior Cyber Analyst), Ryan Traill (Analyst Content Lead), Kiri Addison (Director of Product)

Appendices

IoC - Type - Description + Confidence  

- http://pub-ac94c05b39aa4f75ad1df88d384932b8.r2[.]dev/offline[.]html#p – fake Microsoft login page

- https://s3.us-east-1.amazonaws[.]com/s3cure0line-0365cql0.19db86c3-b2b9-44cc-b339-36da233a3be2ml0qin/s3cccql0.19db86c3-b2b9-44cc-b339-36da233a3be2%26l0qn[.]html# - link to domain used in homoglyph attack

MITRE ATT&CK Mapping  

Tactic – Technique – Sub-Technique  

Initial Access - Phishing – (T1566)  

References

1.     https://gitnux.org/third-party-risk-statistics/

2.     https://learn.microsoft.com/en-us/defender-office-365/anti-spam-spam-confidence-level-scl-about

3.     https://www.virustotal.com/gui/url/5df9aae8f78445a590f674d7b64c69630c1473c294ce5337d73732c03ab7fca2/detection

4.     https://www.virustotal.com/gui/url/695d0d173d1bd4755eb79952704e3f2f2b87d1a08e2ec660b98a4cc65f6b2577/details

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

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