Simon Willison's Weblog: ai-assisted-programming

datasette PR #2689: Replace token-based CSRF with Sec-Fetch-Site header protection

2026-04-14T23:58:53+00:00

datasette PR #2689: Replace token-based CSRF with Sec-Fetch-Site header protection

Datasette has long protected against CSRF attacks using CSRF tokens, implemented using my asgi-csrf Python library. These are something of a pain to work with - you need to scatter forms in templates with <input type="hidden" name="csrftoken" value="{{ csrftoken() }}"> lines and then selectively disable CSRF protection for APIs that are intended to be called from outside the browser.

I've been following Filippo Valsorda's research here with interest, described in this detailed essay from August 2025 and shipped as part of Go 1.25 that same month.

I've now landed the same change in Datasette. Here's the PR description - Claude Code did much of the work (across 10 commits, closely guided by me and cross-reviewed by GPT-5.4) but I've decided to start writing these PR descriptions by hand, partly to make them more concise and also as an exercise in keeping myself honest.

New CSRF protection middleware inspired by Go 1.25 and this research by Filippo Valsorda. This replaces the old CSRF token based protection.

Removes all instances of <input type="hidden" name="csrftoken" value="{{ csrftoken() }}"> in the templates - they are no longer needed.

Removes the def skip_csrf(datasette, scope): plugin hook defined in datasette/hookspecs.py and its documentation and tests.

Updated CSRF protection documentation to describe the new approach.

Upgrade guide now describes the CSRF change.

Tags: csrf, security, datasette, ai-assisted-programming

Quoting Bryan Cantrill

2026-04-13T02:44:24+00:00

The problem is that LLMs inherently lack the virtue of laziness. Work costs nothing to an LLM. LLMs do not feel a need to optimize for their own (or anyone's) future time, and will happily dump more and more onto a layercake of garbage. Left unchecked, LLMs will make systems larger, not better — appealing to perverse vanity metrics, perhaps, but at the cost of everything that matters.

As such, LLMs highlight how essential our human laziness is: our finite time forces us to develop crisp abstractions in part because we don't want to waste our (human!) time on the consequences of clunky ones.

— Bryan Cantrill, The peril of laziness lost

Tags: bryan-cantrill, ai, llms, ai-assisted-programming, generative-ai

Eight years of wanting, three months of building with AI

2026-04-05T23:54:18+00:00

Eight years of wanting, three months of building with AI

Lalit Maganti provides one of my favorite pieces of long-form writing on agentic engineering I've seen in ages.

They spent eight years thinking about and then three months building syntaqlite, which they describe as "high-fidelity devtools that SQLite deserves".

The goal was to provide fast, robust and comprehensive linting and verifying tools for SQLite, suitable for use in language servers and other development tools - a parser, formatter, and verifier for SQLite queries. I've found myself wanting this kind of thing in the past myself, hence my (far less production-ready) sqlite-ast project from a few months ago.

Lalit had been procrastinating on this project for years, because of the inevitable tedium of needing to work through 400+ grammar rules to help build a parser. That's exactly the kind of tedious work that coding agents excel at!

Claude Code helped get over that initial hump and build the first prototype:

AI basically let me put aside all my doubts on technical calls, my uncertainty of building the right thing and my reluctance to get started by giving me very concrete problems to work on. Instead of “I need to understand how SQLite’s parsing works”, it was “I need to get AI to suggest an approach for me so I can tear it up and build something better". I work so much better with concrete prototypes to play with and code to look at than endlessly thinking about designs in my head, and AI lets me get to that point at a pace I could not have dreamed about before. Once I took the first step, every step after that was so much easier.

That first vibe-coded prototype worked great as a proof of concept, but they eventually made the decision to throw it away and start again from scratch. AI worked great for the low level details but did not produce a coherent high-level architecture:

I found that AI made me procrastinate on key design decisions. Because refactoring was cheap, I could always say “I’ll deal with this later.” And because AI could refactor at the same industrial scale it generated code, the cost of deferring felt low. But it wasn’t: deferring decisions corroded my ability to think clearly because the codebase stayed confusing in the meantime.

The second attempt took a lot longer and involved a great deal more human-in-the-loop decision making, but the result is a robust library that can stand the test of time.

It's worth setting aside some time to read this whole thing - it's full of non-obvious downsides to working heavily with AI, as well as a detailed explanation of how they overcame those hurdles.

The key idea I took away from this concerns AI's weakness in terms of design and architecture:

When I was working on something where I didn’t even know what I wanted, AI was somewhere between unhelpful and harmful. The architecture of the project was the clearest case: I spent weeks in the early days following AI down dead ends, exploring designs that felt productive in the moment but collapsed under scrutiny. In hindsight, I have to wonder if it would have been faster just thinking it through without AI in the loop at all.

But expertise alone isn’t enough. Even when I understood a problem deeply, AI still struggled if the task had no objectively checkable answer. Implementation has a right answer, at least at a local level: the code compiles, the tests pass, the output matches what you asked for. Design doesn’t. We’re still arguing about OOP decades after it first took off.

Via Hacker News

Tags: vibe-coding, ai-assisted-programming, sqlite, generative-ai, agentic-engineering, ai, llms

Syntaqlite Playground

2026-04-05T19:32:59+00:00

Tool: Syntaqlite Playground

Lalit Maganti's syntaqlite is currently being discussed on Hacker News thanks to Eight years of wanting, three months of building with AI, a deep dive into how it was built.

This inspired me to revisit a research project I ran when Lalit first released it a couple of weeks ago, where I tried it out and then compiled it to a WebAssembly wheel so it could run in Pyodide in a browser (the library itself uses C and Rust).

This new playground loads up the Python library and provides a UI for trying out its different features: formating, parsing into an AST, validating, and tokenizing SQLite SQL queries.

Update: not sure how I missed this but syntaqlite has its own WebAssembly playground linked to from the README.

Tags: sql, ai-assisted-programming, sqlite, tools, agentic-engineering

scan-for-secrets 0.1

2026-04-05T03:27:13+00:00

Release: scan-for-secrets 0.1

I like publishing transcripts of local Claude Code sessions using my claude-code-transcripts tool but I'm often paranoid that one of my API keys or similar secrets might inadvertently be revealed in the detailed log files.

I built this new Python scanning tool to help reassure me. You can feed it secrets and have it scan for them in a specified directory:

uvx scan-for-secrets $OPENAI_API_KEY -d logs-to-publish/

If you leave off the -d it defaults to the current directory.

It doesn't just scan for the literal secrets - it also scans for common encodings of those secrets e.g. backslash or JSON escaping, as described in the README.

If you have a set of secrets you always want to protect you can list commands to echo them in a ~/.scan-for-secrets.conf.sh file. Mine looks like this:

llm keys get openai
llm keys get anthropic
llm keys get gemini
llm keys get mistral
awk -F= '/aws_secret_access_key/{print $2}' ~/.aws/credentials | xargs

I built this tool using README-driven-development: I carefully constructed the README describing exactly how the tool should work, then dumped it into Claude Code and told it to build the actual tool (using red/green TDD, naturally.)

Tags: projects, security, agentic-engineering, coding-agents, ai-assisted-programming, claude-code

Quoting Soohoon Choi

2026-04-01T02:07:16+00:00

I want to argue that AI models will write good code because of economic incentives. Good code is cheaper to generate and maintain. Competition is high between the AI models right now, and the ones that win will help developers ship reliable features fastest, which requires simple, maintainable code. Good code will prevail, not only because we want it to (though we do!), but because economic forces demand it. Markets will not reward slop in coding, in the long-term.

— Soohoon Choi, Slop Is Not Necessarily The Future

Tags: slop, ai-assisted-programming, generative-ai, agentic-engineering, ai, llms

Mr. Chatterbox is a (weak) Victorian-era ethically trained model you can run on your own computer

2026-03-30T14:28:34+00:00

Trip Venturella released Mr. Chatterbox, a language model trained entirely on out-of-copyright text from the British Library. Here's how he describes it in the model card:

Mr. Chatterbox is a language model trained entirely from scratch on a corpus of over 28,000 Victorian-era British texts published between 1837 and 1899, drawn from a dataset made available by the British Library. The model has absolutely no training inputs from after 1899 — the vocabulary and ideas are formed exclusively from nineteenth-century literature.

Mr. Chatterbox's training corpus was 28,035 books, with an estimated 2.93 billion input tokens after filtering. The model has roughly 340 million paramaters, roughly the same size as GPT-2-Medium. The difference is, of course, that unlike GPT-2, Mr. Chatterbox is trained entirely on historical data.

Given how hard it is to train a useful LLM without using vast amounts of scraped, unlicensed data I've been dreaming of a model like this for a couple of years now. What would a model trained on out-of-copyright text be like to chat with?

Thanks to Trip we can now find out for ourselves!

The model itself is tiny, at least by Large Language Model standards - just 2.05GB on disk. You can try it out using Trip's HuggingFace Spaces demo:

Honestly, it's pretty terrible. Talking with it feels more like chatting with a Markov chain than an LLM - the responses may have a delightfully Victorian flavor to them but it's hard to get a response that usefully answers a question.

The 2022 Chinchilla paper suggests a ratio of 20x the parameter count to training tokens. For a 340m model that would suggest around 7 billion tokens, more than twice the British Library corpus used here. The smallest Qwen 3.5 model is 600m parameters and that model family starts to get interesting at 2b - so my hunch is we would need 4x or more the training data to get something that starts to feel like a useful conversational partner.

But what a fun project!

Running it locally with LLM

I decided to see if I could run the model on my own machine using my LLM framework.

I got Claude Code to do most of the work - here's the transcript.

Trip trained the model using Andrej Karpathy's nanochat, so I cloned that project, pulled the model weights and told Claude to build a Python script to run the model. Once we had that working (which ended up needing some extra details from the Space demo source code) I had Claude read the LLM plugin tutorial and build the rest of the plugin.

llm-mrchatterbox is the result. Install the plugin like this:

llm install llm-mrchatterbox

The first time you run a prompt it will fetch the 2.05GB model file from Hugging Face. Try that like this:

llm -m mrchatterbox "Good day, sir"

Or start an ongoing chat session like this:

llm chat -m mrchatterbox

If you don't have LLM installed you can still get a chat session started from scratch using uvx like this:

uvx --with llm-mrchatterbox llm chat -m mrchatterbox

When you are finished with the model you can delete the cached file using:

llm mrchatterbox delete-model

This is the first time I've had Claude Code build a full LLM model plugin from scratch and it worked really well. I expect I'll be using this method again in the future.

I continue to hope we can get a useful model from entirely public domain data. The fact that Trip was able to get this far using nanochat and 2.93 billion training tokens is a promising start.

Update 31st March 2026: I had missed this when I first published this piece but Trip has his own detailed writeup of the project which goes into much more detail about how he trained the model. Here's how the books were filtered for pre-training:

First, I downloaded the British Library dataset split of all 19th-century books. I filtered those down to books contemporaneous with the reign of Queen Victoria—which, unfortunately, cut out the novels of Jane Austen—and further filtered those down to a set of books with a optical character recognition (OCR) confidence of .65 or above, as listed in the metadata. This left me with 28,035 books, or roughly 2.93 billion tokes for pretraining data.

Getting it to behave like a conversational model was a lot harder. Trip started by trying to train on plays by Oscar Wilde and George Bernard Shaw, but found they didn't provide enough pairs. Then he tried extracting dialogue pairs from the books themselves with poor results. The approach that worked was to have Claude Haiku and GPT-4o-mini generate synthetic conversation pairs for the supervised fine tuning, which solved the problem but sadly I think dilutes the "no training inputs from after 1899" claim from the original model card.

Tags: llm, training-data, ai, local-llms, llms, ai-ethics, claude-code, andrej-karpathy, ai-assisted-programming, generative-ai, hugging-face, uv

Quoting Matt Webb

2026-03-28T12:04:26+00:00

The thing about agentic coding is that agents grind problems into dust. Give an agent a problem and a while loop and - long term - it’ll solve that problem even if it means burning a trillion tokens and re-writing down to the silicon. [...]

But we want AI agents to solve coding problems quickly and in a way that is maintainable and adaptive and composable (benefiting from improvements elsewhere), and where every addition makes the whole stack better.

So at the bottom is really great libraries that encapsulate hard problems, with great interfaces that make the “right” way the easy way for developers building apps with them. Architecture!

While I’m vibing (I call it vibing now, not coding and not vibe coding) while I’m vibing, I am looking at lines of code less than ever before, and thinking about architecture more than ever before.

— Matt Webb, An appreciation for (technical) architecture

Tags: matt-webb, ai, llms, vibe-coding, coding-agents, ai-assisted-programming, generative-ai, agentic-engineering, definitions

Quoting Richard Fontana

2026-03-27T21:11:17+00:00

FWIW, IANDBL, TINLA, etc., I don’t currently see any basis for concluding that chardet 7.0.0 is required to be released under the LGPL. AFAIK no one including Mark Pilgrim has identified persistence of copyrightable expressive material from earlier versions in 7.0.0 nor has anyone articulated some viable alternate theory of license violation. [...]

— Richard Fontana, LGPLv3 co-author, weighing in on the chardet relicensing situation

Tags: open-source, ai-ethics, llms, ai, generative-ai, ai-assisted-programming

Quoting David Abram

2026-03-23T18:56:18+00:00

I have been doing this for years, and the hardest parts of the job were never about typing out code. I have always struggled most with understanding systems, debugging things that made no sense, designing architectures that wouldn't collapse under heavy load, and making decisions that would save months of pain later.

None of these problems can be solved LLMs. They can suggest code, help with boilerplate, sometimes can act as a sounding board. But they don't understand the system, they don't carry context in their "minds", and they certianly don't know why a decision is right or wrong.

And the most importantly, they don't choose. That part is still yours. The real work of software development, the part that makes someone valuable, is knowing what should exist in the first place, and why.

— David Abram, The machine didn't take your craft. You gave it up.

Tags: careers, ai-assisted-programming, generative-ai, ai, llms

Experimenting with Starlette 1.0 with Claude skills

2026-03-22T23:57:44+00:00

Starlette 1.0 is out! This is a really big deal. I think Starlette may be the Python framework with the most usage compared to its relatively low brand recognition because Starlette is the foundation of FastAPI, which has attracted a huge amount of buzz that seems to have overshadowed Starlette itself.

Kim Christie started working on Starlette in 2018 and it quickly became my favorite out of the new breed of Python ASGI frameworks. The only reason I didn't use it as the basis for my own Datasette project was that it didn't yet promise stability, and I was determined to provide a stable API for Datasette's own plugins... albeit I still haven't been brave enough to ship my own 1.0 release (after 26 alphas and counting)!

Then in September 2025 Marcelo Trylesinski announced that Starlette and Uvicorn were transferring to their GitHub account, in recognition of their many years of contributions and to make it easier for them to receive sponsorship against those projects.

The 1.0 version has a few breaking changes compared to the 0.x series, described in the release notes for 1.0.0rc1 that came out in February.

The most notable of these is a change to how code runs on startup and shutdown. Previously that was handled by on_startup and on_shutdown parameters, but the new system uses a neat lifespan mechanism instead based around an async context manager:

@contextlib.asynccontextmanager
async def lifespan(app):
    async with some_async_resource():
        print("Run at startup!")
        yield
        print("Run on shutdown!")

app = Starlette(
    routes=routes,
    lifespan=lifespan
)

If you haven't tried Starlette before it feels to me like an asyncio-native cross between Flask and Django, unsurprising since creator Kim Christie is also responsible for Django REST Framework. Crucially, this means you can write most apps as a single Python file, Flask style.

This makes it really easy for LLMs to spit out a working Starlette app from a single prompt.

There's just one problem there: if 1.0 breaks compatibility with the Starlette code that the models have been trained on, how can we have them generate code that works with 1.0?

I decided to see if I could get this working with a Skill.

Building a Skill with Claude

Regular Claude Chat on claude.ai has skills, and one of those default skills is the skill-creator skill. This means Claude knows how to build its own skills.

So I started a chat session and told it:

Clone Starlette from GitHub - it just had its 1.0 release. Build a skill markdown document for this release which includes code examples of every feature.

I didn't even tell it where to find the repo, Starlette is widely enough known that I expected it could find it on its own.

It ran git clone https://github.com/encode/starlette.git which is actually the old repository name, but GitHub handles redirects automatically so this worked just fine.

The resulting skill document looked very thorough to me... and then I noticed a new button at the top I hadn't seen before labelled "Copy to your skills". So I clicked it:

And now my regular Claude chat has access to that skill!

A task management demo app

I started a new conversation and prompted:

Build a task management app with Starlette, it should have projects and tasks and comments and labels

And Claude did exactly that, producing a simple GitHub Issues clone using Starlette 1.0, a SQLite database (via aiosqlite) and a Jinja2 template.

Claude even tested the app manually like this:

cd /home/claude/taskflow && timeout 5 python -c "
import asyncio
from database import init_db
asyncio.run(init_db())
print('DB initialized successfully')
" 2>&1

pip install httpx --break-system-packages -q \
  && cd /home/claude/taskflow && \
  python -c "
from starlette.testclient import TestClient
from main import app

client = TestClient(app)

r = client.get('/api/stats')
print('Stats:', r.json())

r = client.get('/api/projects')
print('Projects:', len(r.json()), 'found')

r = client.get('/api/tasks')
print('Tasks:', len(r.json()), 'found')

r = client.get('/api/labels')
print('Labels:', len(r.json()), 'found')

r = client.get('/api/tasks/1')
t = r.json()
print(f'Task 1: \"{t[\"title\"]}\" - {len(t[\"comments\"])} comments, {len(t[\"labels\"])} labels')

r = client.post('/api/tasks', json={'title':'Test task','project_id':1,'priority':'high','label_ids':[1,2]})
print('Created task:', r.status_code, r.json()['title'])

r = client.post('/api/comments', json={'task_id':1,'content':'Test comment'})
print('Created comment:', r.status_code)

r = client.get('/')
print('Homepage:', r.status_code, '- length:', len(r.text))

print('\nAll tests passed!')
"

For all of the buzz about Claude Code, it's easy to overlook that Claude itself counts as a coding agent now, fully able to both write and then test the code that it is writing.

Here's what the resulting app looked like. The code is here in my research repository.

Tags: skills, claude, asgi, ai, llms, open-source, coding-agents, ai-assisted-programming, python, generative-ai, agentic-engineering, kim-christie, starlette

My fireside chat about agentic engineering at the Pragmatic Summit

2026-03-14T18:19:38+00:00

I was a speaker last month at the Pragmatic Summit in San Francisco, where I participated in a fireside chat session about Agentic Engineering hosted by Eric Lui from Statsig.

The video is available on YouTube. Here are my highlights from the conversation.

Stages of AI adoption

We started by talking about the different phases a software developer goes through in adopting AI coding tools.

02:45

I feel like there are different stages of AI adoption as a programmer. You start off with you've got ChatGPT and you ask it questions and occasionally it helps you out. And then the big step is when you move to the coding agents that are writing code for you—initially writing bits of code and then there's that moment where the agent writes more code than you do, which is a big moment. And that for me happened only about maybe six months ago.

03:42

The new thing as of what, three weeks ago, is you don't read the code. If anyone saw StrongDM—they had a big thing come out last week where they talked about their software factory and their two principles were nobody writes any code, nobody reads any code, which is clear insanity. That is wildly irresponsible. They're a security company building security software, which is why it's worth paying close attention—like how could this possibly be working?

I talked about StrongDM more in How StrongDM's AI team build serious software without even looking at the code.

Trusting AI output

We discussed the challenge of knowing when to trust the AI's output as opposed to reviewing every line with a fine tooth-comb.