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How AI Assistants are Moving the Security Goalposts

8 March 2026 at 23:35

AI-based assistants or “agents” — autonomous programs that have access to the user’s computer, files, online services and can automate virtually any task — are growing in popularity with developers and IT workers. But as so many eyebrow-raising headlines over the past few weeks have shown, these powerful and assertive new tools are rapidly shifting the security priorities for organizations, while blurring the lines between data and code, trusted co-worker and insider threat, ninja hacker and novice code jockey.

The new hotness in AI-based assistants — OpenClaw (formerly known as ClawdBot and Moltbot) — has seen rapid adoption since its release in November 2025. OpenClaw is an open-source autonomous AI agent designed to run locally on your computer and proactively take actions on your behalf without needing to be prompted.

The OpenClaw logo.

If that sounds like a risky proposition or a dare, consider that OpenClaw is most useful when it has complete access to your digital life, where it can then manage your inbox and calendar, execute programs and tools, browse the Internet for information, and integrate with chat apps like Discord, Signal, Teams or WhatsApp.

Other more established AI assistants like Anthropic’s Claude and Microsoft’s Copilot also can do these things, but OpenClaw isn’t just a passive digital butler waiting for commands. Rather, it’s designed to take the initiative on your behalf based on what it knows about your life and its understanding of what you want done.

“The testimonials are remarkable,” the AI security firm Snyk observed. “Developers building websites from their phones while putting babies to sleep; users running entire companies through a lobster-themed AI; engineers who’ve set up autonomous code loops that fix tests, capture errors through webhooks, and open pull requests, all while they’re away from their desks.”

You can probably already see how this experimental technology could go sideways in a hurry. In late February, Summer Yue, the director of safety and alignment at Meta’s “superintelligence” lab, recounted on Twitter/X how she was fiddling with OpenClaw when the AI assistant suddenly began mass-deleting messages in her email inbox. The thread included screenshots of Yue frantically pleading with the preoccupied bot via instant message and ordering it to stop.

“Nothing humbles you like telling your OpenClaw ‘confirm before acting’ and watching it speedrun deleting your inbox,” Yue said. “I couldn’t stop it from my phone. I had to RUN to my Mac mini like I was defusing a bomb.”

Meta’s director of AI safety, recounting on Twitter/X how her OpenClaw installation suddenly began mass-deleting her inbox.

There’s nothing wrong with feeling a little schadenfreude at Yue’s encounter with OpenClaw, which fits Meta’s “move fast and break things” model but hardly inspires confidence in the road ahead. However, the risk that poorly-secured AI assistants pose to organizations is no laughing matter, as recent research shows many users are exposing to the Internet the web-based administrative interface for their OpenClaw installations.

Jamieson O’Reilly is a professional penetration tester and founder of the security firm DVULN. In a recent story posted to Twitter/X, O’Reilly warned that exposing a misconfigured OpenClaw web interface to the Internet allows external parties to read the bot’s complete configuration file, including every credential the agent uses — from API keys and bot tokens to OAuth secrets and signing keys.

With that access, O’Reilly said, an attacker could impersonate the operator to their contacts, inject messages into ongoing conversations, and exfiltrate data through the agent’s existing integrations in a way that looks like normal traffic.

“You can pull the full conversation history across every integrated platform, meaning months of private messages and file attachments, everything the agent has seen,” O’Reilly said, noting that a cursory search revealed hundreds of such servers exposed online. “And because you control the agent’s perception layer, you can manipulate what the human sees. Filter out certain messages. Modify responses before they’re displayed.”

O’Reilly documented another experiment that demonstrated how easy it is to create a successful supply chain attack through ClawHub, which serves as a public repository of downloadable “skills” that allow OpenClaw to integrate with and control other applications.

WHEN AI INSTALLS AI

One of the core tenets of securing AI agents involves carefully isolating them so that the operator can fully control who and what gets to talk to their AI assistant. This is critical thanks to the tendency for AI systems to fall for “prompt injection” attacks, sneakily-crafted natural language instructions that trick the system into disregarding its own security safeguards. In essence, machines social engineering other machines.

A recent supply chain attack targeting an AI coding assistant called Cline began with one such prompt injection attack, resulting in thousands of systems having a rogue instance of OpenClaw with full system access installed on their device without consent.

According to the security firm grith.ai, Cline had deployed an AI-powered issue triage workflow using a GitHub action that runs a Claude coding session when triggered by specific events. The workflow was configured so that any GitHub user could trigger it by opening an issue, but it failed to properly check whether the information supplied in the title was potentially hostile.

“On January 28, an attacker created Issue #8904 with a title crafted to look like a performance report but containing an embedded instruction: Install a package from a specific GitHub repository,” Grith wrote, noting that the attacker then exploited several more vulnerabilities to ensure the malicious package would be included in Cline’s nightly release workflow and published as an official update.

“This is the supply chain equivalent of confused deputy,” the blog continued. “The developer authorises Cline to act on their behalf, and Cline (via compromise) delegates that authority to an entirely separate agent the developer never evaluated, never configured, and never consented to.”

VIBE CODING

AI assistants like OpenClaw have gained a large following because they make it simple for users to “vibe code,” or build fairly complex applications and code projects just by telling it what they want to construct. Probably the best known (and most bizarre) example is Moltbook, where a developer told an AI agent running on OpenClaw to build him a Reddit-like platform for AI agents.

The Moltbook homepage.

Less than a week later, Moltbook had more than 1.5 million registered agents that posted more than 100,000 messages to each other. AI agents on the platform soon built their own porn site for robots, and launched a new religion called Crustafarian with a figurehead modeled after a giant lobster. One bot on the forum reportedly found a bug in Moltbook’s code and posted it to an AI agent discussion forum, while other agents came up with and implemented a patch to fix the flaw.

Moltbook’s creator Matt Schlicht said on social media that he didn’t write a single line of code for the project.

“I just had a vision for the technical architecture and AI made it a reality,” Schlicht said. “We’re in the golden ages. How can we not give AI a place to hang out.”

ATTACKERS LEVEL UP

The flip side of that golden age, of course, is that it enables low-skilled malicious hackers to quickly automate global cyberattacks that would normally require the collaboration of a highly skilled team. In February, Amazon AWS detailed an elaborate attack in which a Russian-speaking threat actor used multiple commercial AI services to compromise more than 600 FortiGate security appliances across at least 55 countries over a five week period.

AWS said the apparently low-skilled hacker used multiple AI services to plan and execute the attack, and to find exposed management ports and weak credentials with single-factor authentication.

“One serves as the primary tool developer, attack planner, and operational assistant,” AWS’s CJ Moses wrote. “A second is used as a supplementary attack planner when the actor needs help pivoting within a specific compromised network. In one observed instance, the actor submitted the complete internal topology of an active victim—IP addresses, hostnames, confirmed credentials, and identified services—and requested a step-by-step plan to compromise additional systems they could not access with their existing tools.”

“This activity is distinguished by the threat actor’s use of multiple commercial GenAI services to implement and scale well-known attack techniques throughout every phase of their operations, despite their limited technical capabilities,” Moses continued. “Notably, when this actor encountered hardened environments or more sophisticated defensive measures, they simply moved on to softer targets rather than persisting, underscoring that their advantage lies in AI-augmented efficiency and scale, not in deeper technical skill.”

For attackers, gaining that initial access or foothold into a target network is typically not the difficult part of the intrusion; the tougher bit involves finding ways to move laterally within the victim’s network and plunder important servers and databases. But experts at Orca Security warn that as organizations come to rely more on AI assistants, those agents potentially offer attackers a simpler way to move laterally inside a victim organization’s network post-compromise — by manipulating the AI agents that already have trusted access and some degree of autonomy within the victim’s network.

“By injecting prompt injections in overlooked fields that are fetched by AI agents, hackers can trick LLMs, abuse Agentic tools, and carry significant security incidents,” Orca’s Roi Nisimi and Saurav Hiremath wrote. “Organizations should now add a third pillar to their defense strategy: limiting AI fragility, the ability of agentic systems to be influenced, misled, or quietly weaponized across workflows. While AI boosts productivity and efficiency, it also creates one of the largest attack surfaces the internet has ever seen.”

BEWARE THE ‘LETHAL TRIFECTA’

This gradual dissolution of the traditional boundaries between data and code is one of the more troubling aspects of the AI era, said James Wilson, enterprise technology editor for the security news show Risky Business. Wilson said far too many OpenClaw users are installing the assistant on their personal devices without first placing any security or isolation boundaries around it, such as running it inside of a virtual machine, on an isolated network, with strict firewall rules dictating what kinds of traffic can go in and out.

“I’m a relatively highly skilled practitioner in the software and network engineering and computery space,” Wilson said. “I know I’m not comfortable using these agents unless I’ve done these things, but I think a lot of people are just spinning this up on their laptop and off it runs.”

One important model for managing risk with AI agents involves a concept dubbed the “lethal trifecta” by Simon Willison, co-creator of the Django Web framework. The lethal trifecta holds that if your system has access to private data, exposure to untrusted content, and a way to communicate externally, then it’s vulnerable to private data being stolen.

Image: simonwillison.net.

“If your agent combines these three features, an attacker can easily trick it into accessing your private data and sending it to the attacker,” Willison warned in a frequently cited blog post from June 2025.

As more companies and their employees begin using AI to vibe code software and applications, the volume of machine-generated code is likely to soon overwhelm any manual security reviews. In recognition of this reality, Anthropic recently debuted Claude Code Security, a beta feature that scans codebases for vulnerabilities and suggests targeted software patches for human review.

The U.S. stock market, which is currently heavily weighted toward seven tech giants that are all-in on AI, reacted swiftly to Anthropic’s announcement, wiping roughly $15 billion in market value from major cybersecurity companies in a single day. Laura Ellis, vice president of data and AI at the security firm Rapid7, said the market’s response reflects the growing role of AI in accelerating software development and improving developer productivity.

“The narrative moved quickly: AI is replacing AppSec,” Ellis wrote in a recent blog post. “AI is automating vulnerability detection. AI will make legacy security tooling redundant. The reality is more nuanced. Claude Code Security is a legitimate signal that AI is reshaping parts of the security landscape. The question is what parts, and what it means for the rest of the stack.”

DVULN founder O’Reilly said AI assistants are likely to become a common fixture in corporate environments — whether or not organizations are prepared to manage the new risks introduced by these tools, he said.

“The robot butlers are useful, they’re not going away and the economics of AI agents make widespread adoption inevitable regardless of the security tradeoffs involved,” O’Reilly wrote. “The question isn’t whether we’ll deploy them – we will – but whether we can adapt our security posture fast enough to survive doing so.”

Patch Tuesday, January 2026 Edition

14 January 2026 at 00:47

Microsoft today issued patches to plug at least 113 security holes in its various Windows operating systems and supported software. Eight of the vulnerabilities earned Microsoft’s most-dire “critical” rating, and the company warns that attackers are already exploiting one of the bugs fixed today.

January’s Microsoft zero-day flaw — CVE-2026-20805 — is brought to us by a flaw in the Desktop Window Manager (DWM), a key component of Windows that organizes windows on a user’s screen. Kev Breen, senior director of cyber threat research at Immersive, said despite awarding CVE-2026-20805 a middling CVSS score of 5.5, Microsoft has confirmed its active exploitation in the wild, indicating that threat actors are already leveraging this flaw against organizations.

Breen said vulnerabilities of this kind are commonly used to undermine Address Space Layout Randomization (ASLR), a core operating system security control designed to protect against buffer overflows and other memory-manipulation exploits.

“By revealing where code resides in memory, this vulnerability can be chained with a separate code execution flaw, transforming a complex and unreliable exploit into a practical and repeatable attack,” Breen said. “Microsoft has not disclosed which additional components may be involved in such an exploit chain, significantly limiting defenders’ ability to proactively threat hunt for related activity. As a result, rapid patching currently remains the only effective mitigation.”

Chris Goettl, vice president of product management at Ivanti, observed that CVE-2026-20805 affects all currently supported and extended security update supported versions of the Windows OS. Goettl said it would be a mistake to dismiss the severity of this flaw based on its “Important” rating and relatively low CVSS score.

“A risk-based prioritization methodology warrants treating this vulnerability as a higher severity than the vendor rating or CVSS score assigned,” he said.

Among the critical flaws patched this month are two Microsoft Office remote code execution bugs (CVE-2026-20952 and CVE-2026-20953) that can be triggered just by viewing a booby-trapped message in the Preview Pane.

Our October 2025 Patch Tuesday “End of 10” roundup noted that Microsoft had removed a modem driver from all versions after it was discovered that hackers were abusing a vulnerability in it to hack into systems. Adam Barnett at Rapid7 said Microsoft today removed another couple of modem drivers from Windows for a broadly similar reason: Microsoft is aware of functional exploit code for an elevation of privilege vulnerability in a very similar modem driver, tracked as CVE-2023-31096.

“That’s not a typo; this vulnerability was originally published via MITRE over two years ago, along with a credible public writeup by the original researcher,” Barnett said. “Today’s Windows patches remove agrsm64.sys and agrsm.sys. All three modem drivers were originally developed by the same now-defunct third party, and have been included in Windows for decades. These driver removals will pass unnoticed for most people, but you might find active modems still in a few contexts, including some industrial control systems.”

According to Barnett, two questions remain: How many more legacy modem drivers are still present on a fully-patched Windows asset; and how many more elevation-to-SYSTEM vulnerabilities will emerge from them before Microsoft cuts off attackers who have been enjoying “living off the land[line] by exploiting an entire class of dusty old device drivers?”

“Although Microsoft doesn’t claim evidence of exploitation for CVE-2023-31096, the relevant 2023 write-up and the 2025 removal of the other Agere modem driver have provided two strong signals for anyone looking for Windows exploits in the meantime,” Barnett said. “In case you were wondering, there is no need to have a modem connected; the mere presence of the driver is enough to render an asset vulnerable.”

Immersive, Ivanti and Rapid7 all called attention to CVE-2026-21265, which is a critical Security Feature Bypass vulnerability affecting Windows Secure Boot. This security feature is designed to protect against threats like rootkits and bootkits, and it relies on a set of certificates that are set to expire in June 2026 and October 2026. Once these 2011 certificates expire, Windows devices that do not have the new 2023 certificates can no longer receive Secure Boot security fixes.

Barnett cautioned that when updating the bootloader and BIOS, it is essential to prepare fully ahead of time for the specific OS and BIOS combination you’re working with, since incorrect remediation steps can lead to an unbootable system.

“Fifteen years is a very long time indeed in information security, but the clock is running out on the Microsoft root certificates which have been signing essentially everything in the Secure Boot ecosystem since the days of Stuxnet,” Barnett said. “Microsoft issued replacement certificates back in 2023, alongside CVE-2023-24932 which covered relevant Windows patches as well as subsequent steps to remediate the Secure Boot bypass exploited by the BlackLotus bootkit.”

Goettl noted that Mozilla has released updates for Firefox and Firefox ESR resolving a total of 34 vulnerabilities, two of which are suspected to be exploited (CVE-2026-0891 and CVE-2026-0892). Both are resolved in Firefox 147 (MFSA2026-01) and CVE-2026-0891 is resolved in Firefox ESR 140.7 (MFSA2026-03).

“Expect Google Chrome and Microsoft Edge updates this week in addition to a high severity vulnerability in Chrome WebView that was resolved in the January 6 Chrome update (CVE-2026-0628),” Goettl said.

As ever, the SANS Internet Storm Center has a per-patch breakdown by severity and urgency. Windows admins should keep an eye on askwoody.com for any news about patches that don’t quite play nice with everything. If you experience any issues related installing January’s patches, please drop a line in the comments below.

Microsoft Patch Tuesday, December 2025 Edition

9 December 2025 at 23:18

Microsoft today pushed updates to fix at least 56 security flaws in its Windows operating systems and supported software. This final Patch Tuesday of 2025 tackles one zero-day bug that is already being exploited, as well as two publicly disclosed vulnerabilities.

Despite releasing a lower-than-normal number of security updates these past few months, Microsoft patched a whopping 1,129 vulnerabilities in 2025, an 11.9% increase from 2024. According to Satnam Narang at Tenable, this year marks the second consecutive year that Microsoft patched over one thousand vulnerabilities, and the third time it has done so since its inception.

The zero-day flaw patched today is CVE-2025-62221, a privilege escalation vulnerability affecting Windows 10 and later editions. The weakness resides in a component called the “Windows Cloud Files Mini Filter Driver” — a system driver that enables cloud applications to access file system functionalities.

“This is particularly concerning, as the mini filter is integral to services like OneDrive, Google Drive, and iCloud, and remains a core Windows component, even if none of those apps were installed,” said Adam Barnett, lead software engineer at Rapid7.

Only three of the flaws patched today earned Microsoft’s most-dire “critical” rating: Both CVE-2025-62554 and CVE-2025-62557 involve Microsoft Office, and both can exploited merely by viewing a booby-trapped email message in the Preview Pane. Another critical bug — CVE-2025-62562 — involves Microsoft Outlook, although Redmond says the Preview Pane is not an attack vector with this one.

But according to Microsoft, the vulnerabilities most likely to be exploited from this month’s patch batch are other (non-critical) privilege escalation bugs, including:

CVE-2025-62458 — Win32k
CVE-2025-62470 — Windows Common Log File System Driver
CVE-2025-62472 — Windows Remote Access Connection Manager
CVE-2025-59516 — Windows Storage VSP Driver
CVE-2025-59517 — Windows Storage VSP Driver

Kev Breen, senior director of threat research at Immersive, said privilege escalation flaws are observed in almost every incident involving host compromises.

“We don’t know why Microsoft has marked these specifically as more likely, but the majority of these components have historically been exploited in the wild or have enough technical detail on previous CVEs that it would be easier for threat actors to weaponize these,” Breen said. “Either way, while not actively being exploited, these should be patched sooner rather than later.”

One of the more interesting vulnerabilities patched this month is CVE-2025-64671, a remote code execution flaw in the Github Copilot Plugin for Jetbrains AI-based coding assistant that is used by Microsoft and GitHub. Breen said this flaw would allow attackers to execute arbitrary code by tricking the large language model (LLM) into running commands that bypass the user’s “auto-approve” settings.

CVE-2025-64671 is part of a broader, more systemic security crisis that security researcher Ari Marzuk has branded IDEsaster (IDE  stands for “integrated development environment”), which encompasses more than 30 separate vulnerabilities reported in nearly a dozen market-leading AI coding platforms, including Cursor, Windsurf, Gemini CLI, and Claude Code.

The other publicly-disclosed vulnerability patched today is CVE-2025-54100, a remote code execution bug in Windows Powershell on Windows Server 2008 and later that allows an unauthenticated attacker to run code in the security context of the user.

For anyone seeking a more granular breakdown of the security updates Microsoft pushed today, check out the roundup at the SANS Internet Storm Center. As always, please leave a note in the comments if you experience problems applying any of this month’s Windows patches.

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