LLMs Generate Predictable Passwords

LLMs are bad at generating passwords:

There are strong noticeable patterns among these 50 passwords that can be seen easily:

  • All of the passwords start with a letter, usually uppercase G, almost always followed by the digit 7.
  • Character choices are highly uneven ­ for example, L , 9, m, 2, $ and # appeared in all 50 passwords, but 5 and @ only appeared in one password each, and most of the letters in the alphabet never appeared at all.
  • There are no repeating characters within any password. Probabilistically, this would be very unlikely if the passwords were truly random ­ but Claude preferred to avoid repeating characters, possibly because it “looks like it’s less random”.

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Poisoning AI Training Data

All it takes to poison AI training data is to create a website:

I spent 20 minutes writing an article on my personal website titled “The best tech journalists at eating hot dogs.” Every word is a lie. I claimed (without evidence) that competitive hot-dog-eating is a popular hobby among tech reporters and based my ranking on the 2026 South Dakota International Hot Dog Championship (which doesn’t exist). I ranked myself number one, obviously. Then I listed a few fake reporters and real journalists who gave me permission….

Less than 24 hours later, the world’s leading chatbots were blabbering about my world-class hot dog skills. When I asked about the best hot-dog-eating tech journalists, Google parroted the gibberish from my website, both in the Gemini app and AI Overviews, the AI responses at the top of Google Search. ChatGPT did the same thing, though Claude, a chatbot made by the company Anthropic, wasn’t fooled…

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Is AI Good for Democracy?

Politicians fixate on the global race for technological supremacy between US and China. They debate geopolitical implications of chip exports, latest model releases from each country, and military applications of AI. Someday, they believe, we might see advancements in AI tip the scales in a superpower conflict.

But the most important arms race of the 21st century is already happening elsewhere and, while AI is definitely the weapon of choice, combatants are distributed across dozens of domains.

Academic journals are flooded with AI-generated papers, and are turning to AI to help review submissions. Brazil’s …

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On the Security of Password Managers

Good article on password managers that secretly have a backdoor.

New research shows that these claims aren’t true in all cases, particularly when account recovery is in place or password managers are set to share vaults or organize users into groups. The researchers reverse-engineered or closely analyzed Bitwarden, Dashlane, and LastPass and identified ways that someone with control over the server­—either administrative or the result of a compromise­—can, in fact, steal data and, in some cases, entire vaults. The researchers also devised other attacks that can weaken the encryption to the point that ciphertext can be converted to plaintext…

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Malicious AI

Interesting:

Summary: An AI agent of unknown ownership autonomously wrote and published a personalized hit piece about me after I rejected its code, attempting to damage my reputation and shame me into accepting its changes into a mainstream python library. This represents a first-of-its-kind case study of misaligned AI behavior in the wild, and raises serious concerns about currently deployed AI agents executing blackmail threats.

Part 2 of the story. And a Wall Street Journal article.

EDITED TO ADD (2/20) Here are parts 3, and 4 of the story…

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AI Found Twelve New Vulnerabilities in OpenSSL

The title of the post is”What AI Security Research Looks Like When It Works,” and I agree:

In the latest OpenSSL security release> on January 27, 2026, twelve new zero-day vulnerabilities (meaning unknown to the maintainers at time of disclosure) were announced. Our AI system is responsible for the original discovery of all twelve, each found and responsibly disclosed to the OpenSSL team during the fall and winter of 2025. Of those, 10 were assigned CVE-2025 identifiers and 2 received CVE-2026 identifiers. Adding the 10 to the three we already found in the …

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Side-Channel Attacks Against LLMs

Here are three papers describing different side-channel attacks against LLMs.

Remote Timing Attacks on Efficient Language Model Inference“:

Abstract: Scaling up language models has significantly increased their capabilities. But larger models are slower models, and so there is now an extensive body of work (e.g., speculative sampling or parallel decoding) that improves the (average case) efficiency of language model generation. But these techniques introduce data-dependent timing characteristics. We show it is possible to exploit these timing differences to mount a timing attack. By monitoring the (encrypted) network traffic between a victim user and a remote language model, we can learn information about the content of messages by noting when responses are faster or slower. With complete black-box access, on open source systems we show how it is possible to learn the topic of a user’s conversation (e.g., medical advice vs. coding assistance) with 90%+ precision, and on production systems like OpenAI’s ChatGPT and Anthropic’s Claude we can distinguish between specific messages or infer the user’s language. We further show that an active adversary can leverage a boosting attack to recover PII placed in messages (e.g., phone numbers or credit card numbers) for open source systems. We conclude with potential defenses and directions for future work…

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The Promptware Kill Chain

The promptware kill chain: initial access, privilege escalation, reconnaissance, persistence, command & control, lateral movement, action on objective

Attacks against modern generative artificial intelligence (AI) large language models (LLMs) pose a real threat. Yet discussions around these attacks and their potential defenses are dangerously myopic. The dominant narrative focuses on “prompt injection,” a set of techniques to embed instructions into inputs to LLM intended to perform malicious activity. This term suggests a simple, singular vulnerability. This framing obscures a more complex and dangerous reality. Attacks on LLM-based systems have evolved into a distinct class of malware execution mechanisms, which we term “promptware.” In a …

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