SEC536: Adversarial AI - Penetration Testing AI Systems


Experience SANS training through course previews.
Learn MoreLet us help.
Contact usBecome a member for instant access to our free resources.
Sign UpWe're here to help.
Contact UsOn Tuesday, June 9, Microsoft released fixes to address more than 200 vulnerabilities in a variety of products, making this month's release the largest on record. 38 of the flaws are considered critical, and three were previously disclosed. Among those is an actively exploited cross-site scripting issue in Microsoft Exchange Server that Microsoft first warned of in mid-May, and Microsoft offered mitigations for the vulnerability at that time. The high number of vulnerabilities addressed this month is attributable to the use of AI tools; Microsoft published a blog along with May's Patch Tuesday, which addressed nearly 140 vulnerabilities, noting that "Many of these were surfaced through AI investments and investigations across our engineering and research teams, including the use of Microsoft's new multi-model AI-driven scanning harness. A number were also credited to external researchers working in collaboration with AI."

The good news is that two of the fixes address issues discovered by Nightmare Eclipse: YellowKey Bitlocker weakness, CVE-2026-50507, and GreenPlasma Windows Collaborative Translation Framework flaw, CVE-2026-45586. Beyond the Patch Tuesday, Microsoft has addressed over 360 browser vulnerabilities, resulting in their no longer enumerating Chromium CVEs in the Security Update Guide. With the browser update cadence, you're still going to want to ensure browser updates happen weekly or better; there will simply be less background information for analysis.
The influence of advanced AI tools like Claude Mythos is rapidly reshaping the vulnerability landscape, as evidenced by the dramatic spike in both total and critical bugs addressed in recent Patch Tuesday updates. This surge represents a fundamental shift in how vulnerabilities are discovered and remediated. While Microsoft did not formally credit Anthropic, it is clear that their model has served as a primary catalyst for this acceleration, setting a new standard for automated code analysis and software assurance.

The rate of Microsoft patches over the last decade has supported the inference that there is a reservoir of both known and unknown vulnerabilities in its code base. Hopefully the use of AI (e.g., Mythos) is resulting in movement from unknown to known.
SANS ISC
KrebsOnSecurity
ZDNET
The Record
CyberScoop
SecurityWeek
Zero Day Initiative
BleepingComputer
NIST
Microsoft
The Register
Anthropic has announced that it is releasing new versions of its Claude Mythos AI models to both project Glasswing partners and to the public. Claude Mythos 5, which is described as "an upgrade to Claude Mythos Preview," will be made available to Project Glasswing partners who received access to Claude Mythos Preview in April, as well as to certain biology researchers. Claude Fable 5 will be made available to the public. Fable 5 is a Mythos-class AI model with guardrails. Anthropic acknowledges the risk inherent in releasing a model with this capability; the guardrails mean that "When Fable’s classifiers detect a request related to cybersecurity, biology and chemistry, or distillation, the response is automatically handled by Claude Opus 4.8 instead. Users will be informed whenever this occurs." WIRED journalists Lily Hay Newman and Maxwell Zeff level a measured eye at the model's release, noting "it remains to be seen how resistant Claude Fable 5’s safeguards are in the wild. Anthropic says in more than 1,000 hours of red-teaming, its testers found no universal jailbreaks for the model. Still, fears about the ability to develop adequate protections underpinned the company’s original justification for why it did not release Mythos-class models to the public in April, and these fears have seemingly persisted."

With the success of the Mythos module, having access to those capabilities will be huge for software developers, and for our adversaries as well. What we have here is Mythos using the Claude Opus 4.8 model as well as only keeping traffic for 30 days. While Anthropic has worked to verify the guardrails are sufficient, I can't help but recall the ongoing saga of AI guardrails being bypassed. Your developers are likely already checking this out, so have them explain how they are mitigating risks, as well as explaining how well it works.
The race is on. A 1,000-hour pen testing window sounds substantial, but the real variable is the caliber and volume of the pen testers involved. The immediate question is whether the guardrails will hold. But here is the stark reality: even if they do, attackers retain the ultimate advantage unless patch management is fully automated.

What could possibly go wrong?
Anthropic
WIRED
CyberScoop
SC Media
The Hacker News
The US Cybersecurity and Infrastructure Security Agency (CISA) has issued Binding Operational Directive (BOD) 26-04: Prioritizing Security Updates Based on Risk, which creates a rubric for helping civilian federal agencies (FCEBs) triage which vulnerabilities require urgent remediation. Four sequential criteria determine the required timeline for patching: whether the affected system is publicly exposed, whether the flaw is in the Known Exploited Vulnerabilities (KEV) catalog, whether exploitation is automatable, and whether the technical impact of exploitation gives an attacker full control versus partial control. These criteria are determined by CISA through their Vulnrichment program. The 16 possible timelines range between 3, 14, and 60 days, with the most urgent also requiring forensic triage, and the least urgent deemed "Fix on System Upgrade." This BOD supersedes 19-02 and 22-01, which set 15 or 30-day remediation timelines based on severity, and established the KEV and its requirements. BOD 26-04 also contains required actions for FCEBs and CISA to comply with and support the updated remediation requirements, and a visual representation of the criteria as a decision tree.

This change creates a model of continuous automated risk-based automation versus “patch all the things by KEV due date or fixed timeline.” Agencies will need to develop processes and tooling to incorporate asset exposure, vulnerability characteristics, and threat activity to sequence mitigations rather than simply relying on KEV due dates. Not a bad approach for the rest of us as well. You should already have classes of machines where updates are automatically applied so you can focus on more sensitive assets; this approach provides a way to better divide and conquer the remaining systems, once you have the needed signaling.

A step in the right direction. CISA is empowered to do both triage and prescription. This addresses risk to the government across agencies. However, it is not a substitute for a risk assessment that includes the application and environment within the FCEB. Said another way, the application and environment within an agency might make the fix even more urgent for that agency than CISA prescribes for all agencies.
CISA’s new risk criteria are a step forward, but prioritizing CVSS scoring over the KEV catalog would be more effective due to the time lag in identifying active exploitation. Ultimately, the need for this directive highlights an ongoing challenge: FCEB agencies must transition toward proactive patch management to make these types of mandates obsolete.
CISA
Nextgov/FCW
WIRED
CyberScoop
On June 8, Check Point disclosed a critical flaw in its Remote Access VPN and Mobile Access deployments configured to use the deprecated IKEv1 key exchange protocol, also stating that the flaw is being actively exploited. CVE-2026-50751, CVSS score 9.3, allows an unauthenticated remote attacker to bypass authentication requirements and establish a VPN session without a valid password, by exploiting a logic flaw in certificate validation. Check Point writes that "the observed exploitation has been limited to a few dozen targeted organizations globally," and assesses with medium confidence that the threat actor is financially motivated and uses Qilin ransomware. The company saw indications of suspicious activity on June 4, and subsequent investigation revealed exploitation as early as May 7, 2026; Check Point recommends incident responders prioritize forensic log audits and configuration reviews starting from this date. This flaw was added to the US Cybersecurity and Infrastructure Security Agency's Known Exploited Vulnerabilities catalog (CISA KEV), with a remediation deadline of June 11, three days from disclosure. Check Point Mobile Access, SSL VPN, Remote Access VPN, and Spark Firewall versions R80.20.X (EOS), R80.40 (EOS), R81 (EOS), R81.10 (EOS), R81.10.X, R81.20, R82, R82.00.X, and R82.10 configured for IKEv1 should be updated to Check Point's released hotfix. A second, high-severity flaw enabling man-in-the-middle attacks, disclosed in the same advisory, also stems from the IKEv1 protocol, but is not known to be exploited.

Bottom line: if you're running Check Point Mobile Access, SSL VPN, Remote Access VPN or affected Spark Firewall versions, apply the hotfix, and hunt for the IoCs in Check Point's blog. IKEv1 key exchange is deprecated, so you need to verify you've switched to IKEv2 only. Make sure you're not on end-of-support devices or software versions.
Check Point
HIPAA Journal
Dark Reading
BleepingComputer
The Register
On Thursday, June 11, Oracle released a security alert to address a critical vulnerability in the Oracle PeopleSoft PeopleTools enterprise resource planning (ERP) software suite that is being actively exploited. The vulnerability (CVE-2026-35273, CVSS score 9.8) is identified as a missing authentication for critical function issue that can be exploited by an unauthenticated attacker with network access via HTTP to compromise vulnerable systems. The flaw affects PeopleSoft Enterprise PeopleTools versions 8.61 and 8.62. Earlier unsupported releases are likely vulnerable as well; users are urged to update to a supported version of PeopleSoft Enterprise PeopleTools. This advisory was released outside the regular cadence of Oracle's quarterly security updates and provides a link to a Patch Availability Document, which is accessible only to customers. The advisory follows reports that threat actors have been exploiting this vulnerability in attacks targeting educational institutions, including the University of Nottingham, covered in a separate story in this edition of NewsBites.

This flaw doesn't require authentication to trigger remote code execution. The ShinyHunters gang is exploiting PeopleSoft servers, so you should jump on the update. The fix is only available for PeopleTools 8.61 and 8.62, so to get the fix you have to be on those versions. Prior versions are unsupported and should be considered vulnerable.
Help Net Security
SecurityWeek
BleepingComputer
BleepingComputer
Oracle
NIST
On Tuesday, June 9, Ivanti published a security advisory to address two critical vulnerabilities in the Ivanti Sentry (formerly known as MobileIron Sentry) mobile gateway. The first vulnerability (CVE-2026-10520, CVSS score 10.0) is an OS command injection issue that could be exploited by an unauthenticated attacker to achieve remote code execution with root level privileges. The vulnerability was exploited within 24 hours of its disclosure. In a June 10 post, the Shadowserver Foundation writes, "We are observing a large amount of Ivanti Sentry CVE-2026-10520 exploitation attempts based on the public PoC today. We see 19 vulnerable instances in our own scans, with at least 2 backdoored." The second vulnerability (CVE-2026-10523, CVSS score 9.9) is an authentication bypass issue that could be exploited by an unauthenticated attacker to create arbitrary administrative accounts and obtain full administrative access. The vulnerabilities affect Ivanti Sentry versions 10.5.1, 10.6.1, 10.7.0 and prior, and the issues are resolved in Ivanti Sentry versions 10.5.2, 10.6.2 and 10.7.1. Researchers at watchTowr and Rapid7 have published write-ups of the vulnerabilities.

Ivanti Sentry is a mobile device application gateway, sitting between your mobile fleet and back-end services, like Exchange, controlling ActiveSync email and application traffic. It's integrated with Ivanti EPMM, limiting access to only authorized/registered devices, and CVE-2026-10523 allows admin accounts to be created on the gateway, which can then bypass those restrictions. The good news is that you just need to update to the fixed versions of Sentry: 10.7.1-3, 10.6.2-4 or 10.5.2-3. Don't wait on this one.
The timeline from vulnerability announcement to weaponized AI exploit is down to hours. If you are not automating your patch management cycle from end to end, you are actively choosing to be the next victim.
The Register
Dark Reading
BleepingComputer
The Hacker News
Ivanti
Infosec Exchange
watchTowr
Rapid7
GitHub says it will change npm default settings to prevent the install command from running scripts automatically: preinstall, install, and postinstall from dependencies will not run unless explicitly allowed. The change is one of three npm install default changes that were announced as part of npm v12, which is expected to be released in July 2026. Maintainer Leo Balter writes that "Install-time lifecycle scripts are the single largest code-execution surface in the npm ecosystem." The other two default setting changes are: allow-git defaults to none — Git dependencies (direct or transitive) will not resolve unless allowed; and --allow-remote defaults to none — remote URL dependencies will not resolve unless allowed.

With the malicious npm packages leveraging postinstall options to download and run scripts, changing these to a default ‘no’ is a significant improvement; requiring explicit permission is both safer and easier to troubleshoot. To prepare for npm 12, make sure that your CI image is updated to 11.16.0 and you've verified everything is copacetic. Projects that require any of these functions need to explicitly opt-in before version 12 is released. GitHub provides the specific steps you need to follow for a smooth upgrade.
GitHub's proactive move strengthens ecosystem security. Organizations can benchmark this update — and broader pipeline configurations — against the CIS Software Supply Chain Security Benchmark. Implementing these guidelines ensures a structured, systematic approach to hardening development environments against emerging supply chain threats.
https://www.cisecurity.org/benchmark/software-supply-chain-security
GitHub
The Register
The Hacker News
BleepingComputer
The US Federal Bureau of Investigation (FBI) has seized 13 domains that were allegedly being "used to target U.S. persons, including current and former security clearance holders with access to classified and sensitive U.S. government information." The domains were set up to appear as consulting companies offering employment and are believed to have been operated by state-sponsored threat actors with ties to China. The operation dates back to November 2023. The affidavit filed in support of the seizures "alleges that the conspirators offered money to applicants and recruits in exchange for sensitive information, paid for reports using online payment accounts in the names of fictitious individuals, and used cryptocurrency to conceal the conspirators’ identities and the true source of the payments. These payments allowed for the flow of money from places outside the United States to places inside the United States in furtherance of the conspiracy."
This operation underscores a highly sophisticated nation-state capability, specifically leveraging publicly available data on former government employees to construct precise targeting matrices. Verification of online professional opportunities must become a standard security practice. As defensive measures mature, you can anticipate that adversaries will evolve their methods to continuously target sensitive national security assets.

Cleared individuals are well aware they are targets, and are frequently recruited when they are leaving a position by a company seeking to avoid the cost and time of the background investigation. With all that, it can be difficult to discern which contacts are legitimate versus foreign intelligence. Shutting down those domains will knock back the volume. When in doubt, cleared individuals need to contact their security or counter intelligence groups for guidance.
Nextgov/FCW
Help Net Security
CNN
Justice
Mackay Sugar, a major Australian sugar producer, has disclosed that it has halted operations at two of its mills following a cybersecurity incident that has affected some of the company's operations. Mackay Sugar's sugar milling and cane haulage processes have been disrupted at the Farleigh and Racecourse mills, and Mackay has advised cane growers to cease harvesting until further notice. The shutdown comes at the start of the sugarcane crushing season. Production at Mackay's third sugar mill in Marian was not scheduled to start operations until next week. In a brief statement on the website, Mackay Sugar says they "have engaged specialist cyber security experts and are working closely with relevant authorities to investigate the incident and restore systems safely. Interim processes are in place to support critical business functions and minimise disruption where possible."

The most interesting detail is that harvesting was halted. That suggests the issue went beyond lost or ransomed data, or unavailable email. Operators apparently lacked sufficient confidence in the systems needed to safely and efficiently receive, transport, or process cane. In this case, operational resilience is measured not by whether systems are compromised, but by whether critical business and industrial processes can safely continue after a cyber incident.

While the exact nature of the attack is unknown, the timing of the attack is before the peak harvesting season, and their third mill had not started operations for the season yet, reducing the impact. One hopes Mackay releases more detailed information on the attack that others can leverage to prevent recurrence. Mackay is currently heads-down restoring services, and hopes to resume operations next week.
Great Marlow School in Buckinghamshire, England, sent home the majority of its students for two days this week following "a cybersecurity incident affecting [the high school's] ICT systems." The school allowed students sitting GCSE and A-Level exams to attend. According to a statement on the Great Marlow School website, the school "will be fully open and operational for all students on Friday 12th June 2026." The University of Nottingham has confirmed that threat actors accessed "a significant amount of data in [the university's] student record system." The university is investigating claims by threat actors that data of students at Nottingham's campuses in Malaysia and China were accessed as well. The Powys (Wales) Council also recently disclosed "a cyber security incident affecting some school systems, which has resulted in unauthorised access to some personal data."

Schools and their online learning environments remain an attractive target. Shutting down those systems is extremely disruptive, and the personal data contained in them is a boon for those seeking information for ID theft. While schools need to focus on resiliency and contingency plans, students (and their parents) need to make sure they have appropriate ID protection in place, and look at locking down (freezing) their credit. Note that if you're under 18, it's a manual process that must be completed by a parent or guardian, but still can be done.
GMS
The Record
The Register
Nottingham
The Record
The Register
BleepingComputer
Powys
SANS Internet Storm Center StormCast Friday, June 12, 2026
Bitlocker Trouble; Ivanti and Oracle Exploited; macOS Malicious Installers
https://isc.sans.edu/podcastdetail/9970
More Bitlocker Issues: GreatXML
Security Advisory Ivanti Sentry (CVE-2026-10520, CVE-2026-10523)
Oracle Security Alert Advisory - CVE-2026-35273
https://www.oracle.com/security-alerts/alert-cve-2026-35273.html
How Deceptive Installers Are Targeting macOS Users
https://www.huntress.com/blog/deceptive-installers-macos-infostealers
SANS Internet Storm Center StormCast Thursday, June 11, 2026
Framing Protections; npm improvements; Adobe Patches; New Defender 0-day
https://isc.sans.edu/podcastdetail/9968
How has use of framing protection security headers changed in the past 3 years?
Preparing for npm v12: install scripts and non-registry sources become opt-in
https://github.com/orgs/community/discussions/198547
Adobe Patches
https://helpx.adobe.com/security.html
Rogue Planet new Microsoft Defender Vulnerability
https://github.com/MSNightmare/RoguePlanet
SANS Internet Storm Center StormCast Wednesday, June 10, 2026
Microsoft Patch Tuesday; Miasma Source Published; Fortinet Patches
https://isc.sans.edu/podcastdetail/9966
Microsoft June 2026 Patch Tuesday
https://isc.sans.edu/diary/Microsoft+June+2026+Patch+Tuesday/33064
Miasma Software Supply Chain Attack Toolkit Source Published
https://safedep.io/inside-the-miasma-supply-chain-attack-toolkit/
Fortinet FortiSandbox Vulnerability
https://fortiguard.fortinet.com/psirt/FG-IR-26-141
My Upcoming Classes
Catch up on recent editions of NewsBites or browse our full archive of expert-curated cybersecurity news.
Snyk released a new ebook, Stabilize, Optimize, Scale: A Prescriptive Path for AI Security! Learn how to establish visibility across models, prompts, and agents; implement real-time guardrails; and use risk-based prioritization to clear backlogs 60% faster.
Survey Insights Event | 2026 SANS SOC Survey Insights: A Decade of Evolution in Cyber Defense | Wednesday, June 17 | Christopher Crowley | Learn key global SOC trends and challenges from alert fatigue to budget priorities.
Webinar | Reengineering the SOC: A Roadmap to AI-Enhanced Cyber Defense | Monday, June 22 | Christopher Crowley & Vaibhav Dutta
SANS Demo Day 2026 | Wednesday, June 24, 10AM - 5PM EDT | See cutting-edge cybersecurity tools in action, compare solutions side by side, and gain expert insights to make smarter, faster security decisions for your organization.