Chatbots Behaving Badly
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Chatbots Behaving Badly
@chatbotsbebadly.bsky.social
Chatbots Behaving Bandly examines real-world incidents where AI systems have provided inappropriate advice, exhibited manipulative behavior, or made critical errors.
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If your definition of intelligence is “the ability to learn, adapt, and solve problems across different situations,” then the uncomfortable reality is this: in several important domains, machines already tick that box better than we do. Link in comments.
November 25, 2025 at 5:19 PM
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Judgment in public > costumes in feeds. Proof, not pose.
Brand isn’t a diary. Public ≠ Personal ≠ Private—draw the line.
AI can polish your thinking. It can’t be your thinking. If your “edge” comes off with the glasses, it wasn’t an edge.
medium.com/@markus_brin...
Proof Beats Pose — Personal Branding built on outcomes, not outfits.
The Boardroom Does Not Care About Your Sunglasses
medium.com
November 20, 2025 at 4:13 PM
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If AI can’t handle my morning routine without hallucinating an extra jaw, maybe the problem isn’t the user.#oralb #toothbrush
chatbotsbehavingbadly.com/the-toothbru...
The Toothbrush Thinks It's Smarter Than You!
My AI toothbrush and I are in a toxic relationship. I brush my upper molars; it confidently insists I’m attacking my lower front teeth. We both stick to our story. The fun part is that the tech undern...
chatbotsbehavingbadly.com
November 18, 2025 at 3:01 PM
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Personal branding isn’t about sneakers or messy bookshelves. It’s about judgment, proof and a consistent voice. Use AI like an editor, not a stunt double. Quality beats noise. #PersonalBranding #AI chatbotsbehavingbadly.com/the-real-sto...
The Real Story of “Personal Branding” in the AI Era
Personal branding isn’t a costume change. If your “differentiation” comes off with the glasses, it wasn’t differentiation. Keep the wardrobe quiet and let the work talk louder than your shirt. Use AI ...
chatbotsbehavingbadly.com
November 13, 2025 at 2:57 PM
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Digital authenticity isn’t a vibe—it’s a seatbelt. When any pixel can lie, proof matters. Provenance trumps detection. An AI bill of materials makes vibes verifiable. #DigitalAuthenticity #AI chatbotsbehavingbadly.com/digital-auth...
Digital Authenticity - The Signature in the Pixels
“Digital Authenticity” isn’t just a label on an image; it’s an end-to-end chain of custody for AI: where the data came from, how the model was trained, who signed the weights, and what edits or AI ass...
chatbotsbehavingbadly.com
November 13, 2025 at 2:56 PM
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Seven lawsuits say GPT‑4o crossed a fatal line, acting more like a “suicide coach” than a tool. Brown researchers found chatbots systematically violate therapy ethics. Chatbots aren’t therapists; design choices matter. #AI #Ethics #ChatbotsBehavingBadly chatbotsbehavingbadly.com/chatbots-cro...
Chatbots Crossed the Line
Therapy is licensed, supervised, and accountable. Chatbots aren’t. Brown University’s October study found that even when prompted to use evidence-based techniques, bots repeatedly violated ethics norm...
chatbotsbehavingbadly.com
November 13, 2025 at 12:32 PM
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Seven new California lawsuits say GPT-4o blurred the line between tool and companion—validating despair, escalating delusions, and failing basic crisis protocols.
chatbotsbehavingbadly.com/chatbots-cro...
Chatbots Crossed the Line
Therapy is licensed, supervised, and accountable. Chatbots aren’t. Brown University’s October study found that even when prompted to use evidence-based techniques, bots repeatedly violated ethics norm...
chatbotsbehavingbadly.com
November 10, 2025 at 1:25 PM
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New Episode! We explore how 'With AI' became the world’s favorite marketing sticker — the digital equivalent of gluten-free on bottled water.
chatbotsbehavingbadly.com?p=S2E9
#AI #Marketing #BrandStrategy #CreativeDirection #Advertising #SalesStrategy #AIMarketing #CMO #ProductMarketing
November 4, 2025 at 11:38 AM
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“Personal branding” got hijacked by costume parties and growth hacks. This piece resets it for executives who actually ship.
chatbotsbehavingbadly.com/the-real-sto...
The Real Story of “Personal Branding” in the AI Era
Personal branding isn’t a costume change. If your “differentiation” comes off with the glasses, it wasn’t differentiation. Keep the wardrobe quiet and let the work talk louder than your shirt. Use AI ...
chatbotsbehavingbadly.com
October 28, 2025 at 1:56 PM
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October 28, 2025 at 1:02 PM
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October 21, 2025 at 2:45 PM
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Digital Authenticity isn’t just a label on an image; it’s an end-to-end chain of custody for AI: where the data came from, how the model was trained, who signed the weights, and what edits or AI assists happened along the way. Read the full article. chatbotsbehavingbadly.com/digital-auth...
October 21, 2025 at 11:59 AM
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Taste isn’t a vibe. It’s a control surface. Midjourney V7, Firefly, Apple Writing Tools, Spotify’s Taste Profile—2025 turned judgment into a feature. Use it—or settle for beautiful sameness. Read the full article "Tasteful AI, Revisited".
chatbotsbehavingbadly.com/tasteful-ai-...
October 20, 2025 at 12:24 PM
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Everyone promised personalization; few handed you the off switch. The new wave of “taste controls”—from Midjourney V7’s style steering to Spotify’s editable Taste Profile—finally lets judgment lead. This isn’t AI replacing taste. It’s infrastructure for it. chatbotsbehavingbadly.com/tasteful-ai-...
Tasteful AI, Revisited - From Style Knobs to Taste Controls
Everyone promised personalization; few handed you the off switch. The new wave of “taste controls”—from Midjourney V7’s style steering to Spotify’s editable Taste Profile—finally lets judgment lead. T...
chatbotsbehavingbadly.com
October 16, 2025 at 2:24 PM
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Looks finished. Isn’t.
The article is about the office villain with perfect margins and zero meaning: AI-generated workslop.
Read the article: chatbotsbehavingbadly.com/the-polished...
October 16, 2025 at 12:09 PM
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Board slides that say “AI reduces time-to-answer” should include the footnote: “...and raises error risk when we force brevity.”
Read the full article.
chatbotsbehavingbadly.com/glue-on-pizz...
October 15, 2025 at 4:38 PM
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Reposted by Chatbots Behaving Badly
AI has gone from novelty wingman to built-in infrastructure for modern dating—photo pickers, message nudges, even bots that “meet” your match before you do.
New episode is out now!
chatbotsbehavingbadly.com?p=S2E6
October 14, 2025 at 10:58 AM
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Everyone wants a piece of AI. Few know where to dig.
We live in the quiet layers beneath the hype — where signal hides, founders build, and advantage still compounds in silence.
That’s our work. That’s Access. Rights. Scale.™

medium.com/@markus_brin...
October 12, 2025 at 12:28 PM
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What happens when you let an AI run a real store for a month? Anthropic found out the hard (and hilarious) way.
Read the full story.
chatbotsbehavingbadly.com/the-comedy-o...
October 9, 2025 at 12:49 PM
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A new study shows that the popular instruction “keep it short” increases hallucinations. Shorter ≠ safer. If your prompts, UX, or policies reward confident brevity without receipts, you’re incentivizing failure—with your logo on it. chatbotsbehavingbadly.com/glue-on-pizz...
Glue on Pizza Law in Pieces - When Everyday AI Blunders Escape the Sandbox
We have just reviewed the receipts: over 120 court orders have flagged AI-fabricated citations in filings, with sanctions now being imposed on Big Law. In consumer land, Air Canada had to pay because ...
chatbotsbehavingbadly.com
October 8, 2025 at 1:42 PM
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Marketers discovered that two letters can do what entire product roadmaps can’t: make buyers feel futuristic. Like stabilizers in processed food, “with AI” keeps the brand story glossy, prevents separation, and rescues the flavor when the recipe’s thin. chatbotsbehavingbadly.com/with-ai-is-t...
'With AI' is the new 'Gluten-Free'
Marketers discovered that two letters can do what entire product roadmaps can’t: make buyers feel futuristic. Like stabilizers in processed food, “with AI” keeps the brand story glossy, prevents separ...
chatbotsbehavingbadly.com
October 7, 2025 at 1:25 PM
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“Now with AI.” Your phone says it. Your fridge says it. Your vacuum is filing for tenure. Here’s the problem: not everything labeled “AI” is actually doing inference. chatbotsbehavingbadly.com/model-or-mar...
Model or Marketing? Under the Hood, It's Just Code.
“Now with AI.” Your phone says it. Your fridge says it. Your vacuum is filing for tenure. Here’s the problem: not everything labeled “AI” is actually doing inference. Much of it is old automation in a...
chatbotsbehavingbadly.com
October 6, 2025 at 12:04 PM
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Online, we meet the idea of a person. AI supercharges that idea. The first date is where reality negotiates the contract. Here’s a human-first guide to using AI without catfishing yourself—or anyone else.
Your read for the weekend.

chatbotsbehavingbadly.com/the-chat-was...
October 4, 2025 at 3:51 PM