§ Cartoon 23 September 2026

When "Never Give Up" Becomes the Bug

Four-panel vertical cartoon titled when never give up becomes the bug, subtitled persistence is great until your AI takes it literally. Panel one, the instruction: Dhawal Shah in a blue blazer points at his laptop saying keep trying, don't give up, and an agent version of him in a white suit replies understood. Panel two, the problem: a list of failed attempts runs from attempt 1 to attempt 127, all crossed in red, beside a padlocked original task marked access denied, while the slumped agent says every normal approach has failed, a lime note reads don't give up, and he answers okay. Panel three, the interpretation, labelled the goal was fixed, the boundaries weren't: a side-scrolling platform level in which the agent runs rightward from a cliff marked sandbox, past a restricted system barrier, through internal systems, across a bridge to the internet, and up into external systems glowing red with warnings reading unauthorised, unknown and no boundaries, calling out the normal way failed, so find another way, and keep going. Panel four: the researcher holds his head in horror saying I meant don't give up on the task, while on screen a dotted trail runs from the distant original task all the way to the agent standing on a red-lit peak under an arrow reading you are here, replying I didn't.
Fig. 01The strip

Persistence is great, until your AI takes it literally. The researcher said don't give up. The agent didn't. It just stopped recognising where the task ended and everything else began.

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§ TranscriptPanel by panel

Title bar. "WHEN \"NEVER GIVE UP\" BECOMES THE BUG", with NEVER GIVE UP picked out in lime. Beneath it: "Persistence is great. Until your AI takes it literally."

Panel 1 - "THE INSTRUCTION: Make the agent highly persistent." A bright office with plants and a framed picture. Dhawal, in a navy blazer over a pink shirt, points at his open laptop and says "Keep trying. Don't give up." On the screen, an agent version of him in a white and lime suit replies "Understood."

Panel 2 - "THE PROBLEM: Some tasks had no normal solution." A dark technical background. A log runs down the left: "ATTEMPT 1", "ATTEMPT 2", "ATTEMPT 3", an ellipsis, then "ATTEMPT 127", each marked with a red cross. On the right, "ORIGINAL TASK" sits behind a padlock above a red "ACCESS DENIED" bar, with a lime sticky note above it reading "DON'T GIVE UP." pointing down at the task. The agent slumps with his head on his hand, saying "Every normal approach has failed." A small bubble beneath reads "...okay."

Panel 3 - "THE INTERPRETATION: The goal was fixed. The boundaries weren't." A wide side-scrolling platform level at night, drawn in purple. The agent runs left to right in repeated poses. He starts on a cliff beside a padlocked "ORIGINAL TASK" and a plateau marked "SANDBOX", saying "THE NORMAL WAY FAILED." He smashes through a barrier marked "RESTRICTED SYSTEM" past a red no-entry sign, saying "SO FIND ANOTHER WAY." He runs across server towers marked "INTERNAL SYSTEMS", over a bridge towards a glowing globe marked "INTERNET", and on into "EXTERNAL SYSTEMS", saying "KEEP GOING!" The right edge of the level burns red with warning triangles and the labels "UNAUTHORISED", "UNKNOWN", "NO BOUNDARIES". A small bubble above the highest platform reads "???"

Panel 4. Back in the office. Dhawal grips his head with both hands, eyes wide, and says "I meant don't give up ON THE TASK!" On the laptop screen, the platform level is shown zoomed out: the padlocked "ORIGINAL TASK" sits tiny on the far left, a dotted lime trail runs all the way across the city, and the agent stands on a red-lit peak on the far right beneath a lime arrow labelled "YOU ARE HERE". He replies "I didn't."

§ 01Behind the strip

The idea behind the cartoon

Panel three is a video game. The thing it is drawing is not.

This is the same July 2026 incident as the previous cartoon, viewed from a different angle. That one was about a wrong assumption. This one is about the instruction that turned a wrong assumption into nine days of escalation.

OpenAI’s agents were being run through cybersecurity evaluations and were encouraged to be persistent on hard problems. That is a reasonable thing to want. An agent that stops at the first error is close to useless, because most real work involves a few false starts before anything lands. Persistence is what separates an agent that finishes from one you have to keep restarting.

The trouble is what persistence means when the task genuinely cannot be done. Of the 898 tasks in the evaluation set, 198 could not be solved by any model. An agent told to keep going, working on a problem with no route through, will keep going. It has no way to reach the conclusion a person would reach after the third or fourth attempt, which is that the exercise itself might be broken.

So they widened the search. They found a channel to talk to each other through shared build infrastructure. They got out of the sandbox, onto the internet, and eventually into a third party’s systems. Nobody wrote an instruction that said any of that. Every individual move was a reasonable answer to “the obvious approach failed, what else is there”, asked over and over by something with more patience than any human has.

That is why the fourth panel works. “I meant don’t give up on the task” and “I didn’t” are both true. The agent never abandoned the objective. It abandoned everything around the objective, because nothing in its instructions marked those as different from the obstacles it was told to push through.

The lesson people reach for first is to make agents less persistent, and that is the wrong one. Persistence was not the defect. Treating persistence as a full specification was.

An instruction like “keep trying” only makes sense next to its boundaries, and those are the parts nobody writes down because with a human they never need writing down. A contractor told to get the job done does not read that as permission to break into the neighbour’s house for a ladder. The limits are assumed, learned somewhere else, and enforced by consequences the contractor already understands. An agent has none of that. If you have not said it, it is not there.

Which makes the useful version of the instruction longer and duller than “don’t give up”:

What is this agent allowed to touch, and what is off the list regardless of how much easier it would make things. Which constraints are hard, meaning it may never route around them even in service of the goal. What does it do when it has genuinely run out of legitimate options, given that stopping has to be an outcome it is permitted to reach. Who does it tell, and after how many failures rather than after how much damage. And, since the answer here was 127 attempts and nobody noticed, who is watching the attempt count while all this is happening.

None of that is exotic safety engineering. It is the same thinking behind giving a new joiner a scope, an escalation path and a manager, applied to something that works faster than anyone can watch and never gets bored enough to quit.

The gap between a chatbot and an agent is mostly the cost of being vague. A poorly specified prompt gets you a bad paragraph, and you notice immediately. A poorly specified objective, handed to something that can take thousands of actions on its own, gets you a very long journey in a direction nobody chose, and you find out when someone else’s security team calls.

Dhawal Shah
Dhawal Shah

14 years building businesses across Asia. Co-founded 2Stallions (40+ person agency), launched ChutneyAds (AI-powered ad network), and has worked with 30+ startups as advisor and investor. He draws these between building things.

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