Simon Willison’s Weblog

deepseek-ai/DeepSeek-R1-0528. Sadly the trend for terrible naming of models has infested the Chinese AI labs as well.

DeepSeek-R1-0528 is a brand new and much improved open weights reasoning model from DeepSeek, a major step up from the DeepSeek R1 they released back in January.

In the latest update, DeepSeek R1 has significantly improved its depth of reasoning and inference capabilities by [...] Its overall performance is now approaching that of leading models, such as O3 and Gemini 2.5 Pro. [...]

Beyond its improved reasoning capabilities, this version also offers a reduced hallucination rate, enhanced support for function calling, and better experience for vibe coding.

The new R1 comes in two sizes: a 685B model called deepseek-ai/DeepSeek-R1-0528 (the previous R1 was 671B) and an 8B variant distilled from Qwen 3 called deepseek-ai/DeepSeek-R1-0528-Qwen3-8B.

The January release of R1 had a much larger collection of distilled models: four based on Qwen 2.5 (14B, 32B, Math 1.5B and Math 7B) and 2 based on Llama 3 (Llama-3.1 8B and Llama 3.3 70B Instruct).

No Llama model at all this time. I wonder if that's because Qwen 3 is really good and Apache 2 licensed, while Llama continues to stick with their janky license terms.

Further adding to the confusion, Ollama have mixed the two new models into their existing deepseek-r1 label. Last week running ollama pull deepseek-r1:8B from Ollama would get you DeepSeek-R1-Distill-Llama-8B (Internet Archive link), today that same command gets you DeepSeek-R1-0528-Qwen3-8B, a completely different base model.

If this bothers you as much as it bothers me, thankfully you can use the more explicit tag deepseek-r1:8b-0528-qwen3-q8_0.

Update: This is a great illustration of how confusing these names are! Ollama's deepseek-r1:8B alias actually points to deepseek-r1:8b-0528-qwen3-q4_K_M, a 5.2GB model. I pulled the larger q8_0 one.

I ran it like this:

ollama pull deepseek-r1:8b-0528-qwen3-q8_0

It fetched 8.9GB of model weights, then I had it draw me a pelican.

llm install llm-ollama
llm -m deepseek-r1:8b-0528-qwen3-q8_0 \
  "Generate an SVG of a pelican riding a bicycle"

Since the “reasoning” traces of these models are almost always the most interesting part, I’ll quote the response here in full:

<think>
We are going to create an SVG that depicts a pelican riding a bicycle. Steps:

1. Create the basic structure of an SVG with width and height set appropriately (e.g., 400x200).
2. Draw a pelican: We'll break it down into parts - body, beak, eye, feet, wings, etc.
3. Draw a bicycle: We can represent it as two circles for wheels, a rectangle for the frame, and some other details.

Let's design the SVG with the following:

• The pelican will be facing to the right (positive x-axis) so that it is riding the bike from left to right.
• The bicycle will have two wheels and a simple frame in front of the pelican.

We'll use absolute positioning for each part. Let's assume we set up coordinates such that:

• The top-left of the SVG is (0,0), and we want the scene to be drawn from left to right.
• The pelican will be positioned at (50, 120) with a body length of about 30 units.

We'll use simple shapes for the pelican:

Body: An ellipse or rounded rectangle. Let's do an ellipse for the body. Beak: A triangle pointing to the right. Head: Another ellipse but smaller and positioned in front of the body. Wings: Two triangles (one above each other, one slightly behind) that are upside down.

Bicycle:

• Wheels: two circles at fixed positions relative to the frame.
• Frame: a rectangle with some details for handlebars and seat.

Since this is a fun illustration, we'll keep it simple but recognizable.

Let's code accordingly.
</think>
Here’s an SVG of a pelican riding a bicycle. This example uses basic shapes to create a stylized version:

<svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 400 200">
  <!-- Pelican body -->
  <ellipse cx="150" cy="150" rx="80" ry="60" fill="#FFD700"/>

  <!-- Pelican head (larger for comedic effect) -->
  <circle cx="90" cy="120" r="45" fill="#FFA3CE"/>

  <!-- Pelican beak -->
  <polygon points="80,110 60,120 80,130 70,140 60,150" fill="#FFC233"/>

  <!-- Pelican eye -->
  <circle cx="95" cy="115" r="3" fill="#fff"/>

  <!-- Bicycle wheels -->
  <ellipse cx="380" cy="140" rx="25" ry="60" transform="rotate(90 380 140)" fill="black"/>
  <ellipse cx="380" cy="70" rx="25" ry="60" transform="rotate(90 380 70)" fill="black"/>

  <!-- Bicycle frame -->
  <path d="M 15,40 L 15,140 H 370 L 370,140 V 40 Z" stroke="gray" stroke-width="6" fill="none"/>

  <!-- Handlebars and seat (stylized) -->
  <path d="M 280,40 C 290,35 300,30 310,40 C 320,50 330,60 310,70 L 310,70 Q 290,50 280,40" fill="none" stroke="gray"/>

  <!-- Pedals -->
  <circle cx="340" cy="70" r="15" fill="#3366CC"/>
  <polygon points="340,65 330,45 350,45" fill="#F29E3D"/>

  <circle cx="340" cy="140" r="15" fill="#3366CC"/>
  <polygon points="340,135 330,115 350,115" fill="#F29E3D"/>

  <!-- Neck connecting head to body -->
  <path d="M 80,120 C 70,160 100,140 150,120" stroke="#FFA3CE" stroke-width="8"/>
</svg>

Explanation:

• Pelican Body: A large yellow ellipse.
• Head: A pink circle with a prominent beak (yellow-orange triangle).
• Bicycle:
  • Wheels are black ellipses rotated vertically to simulate spokes.
  • The frame is a gray rectangle extending from the pelican’s back to the right side of the SVG.
  • Handlebars and seat are simplified curves in gray.

This creates a comical scene with the pelican riding forward. You can adjust colors, sizes, or positions by modifying cx, cy, rx, ry attributes and fill/stroke values.

Love the thought process, and the explanation! The actual rendered SVG does leave a lot to be desired though:

To be fair, this is just using the ~8GB Qwen3 Q8_0 model on my laptop. I don't have the hardware to run the full sized R1 but it's available as deepseek-reasoner through DeepSeek's API, so I tried it there using the llm-deepseek plugin:

llm install llm-deepseek
llm -m deepseek-reasoner \
  "Generate an SVG of a pelican riding a bicycle"

This one came out a lot better:

Meanwhile, on Reddit, u/adrgrondin got DeepSeek-R1-0528-Qwen3-8B running on an iPhone 16 Pro using MLX:

It runs at a decent speed for the size thanks to MLX, pretty impressive. But not really usable in my opinion, the model is thinking for too long, and the phone gets really hot.

# 31st May 2025, 9:18 pm / llm, llm-reasoning, deepseek, ollama, ai, llms, llm-release, generative-ai, mlx, local-llms, ai-in-china

llm-github-models 0.15. Anthony Shaw's llm-github-models plugin just got an upgrade: it now supports LLM 0.26 tool use for a subset of the models hosted on the GitHub Models API, contributed by Caleb Brose.

The neat thing about this GitHub Models plugin is that it picks up an API key from your GITHUB_TOKEN - and if you're running LLM within a GitHub Actions worker the API key provided by the worker should be enough to start executing prompts!

I tried it out against Cohere Command A via GitHub Models like this (transcript here):

llm install llm-github-models
llm keys set github
# Paste key here
llm -m github/cohere-command-a -T llm_time 'What time is it?' --td

We now have seven LLM plugins that provide tool support, covering OpenAI, Anthropic, Gemini, Mistral, Ollama, llama-server and now GitHub Models.

# 29th May 2025, 4:27 am / github-actions, llm, generative-ai, llm-tool-use, ai, github, llms, anthony-shaw

llm-tools-exa. When I shipped LLM 0.26 yesterday one of the things I was most excited about was seeing what new tool plugins people would build for it.

Dan Turkel's llm-tools-exa is one of the first. It adds web search to LLM using Exa (previously), a relatively new search engine offering that rare thing, an API for search. They have a free preview, you can grab an API key here.

I'm getting pretty great results! I tried it out like this:

llm install llm-tools-exa
llm keys set exa
# Pasted API key here

llm -T web_search "What's in LLM 0.26?"

Here's the full answer - it started like this:

LLM 0.26 was released on May 27, 2025, and the biggest new feature in this version is official support for tools. Here's a summary of what's new and notable in LLM 0.26:

• LLM can now run tools. You can grant LLMs from OpenAI, Anthropic, Gemini, and local models access to any tool you represent as a Python function.
• Tool plugins are introduced, allowing installation of plugins that add new capabilities to any model you use.
• Tools can be installed from plugins and loaded by name with the --tool/-T option. [...]

Exa provided 21,000 tokens of search results, including what looks to be a full copy of my blog entry and the release notes for LLM.

# 29th May 2025, 3:58 am / llm, generative-ai, llm-tool-use, apis, search, ai, llms

llm-mistral 0.14. I added tool-support to my plugin for accessing the Mistral API from LLM today, plus support for Mistral's new Codestral Embed embedding model.

An interesting challenge here is that I'm not using an official client library for llm-mistral - I rolled my own client on top of their streaming HTTP API using Florimond Manca's httpx-sse library. It's a very pleasant way to interact with streaming APIs - here's my code that does most of the work.

The problem I faced is that Mistral's API documentation for function calling has examples in Python and TypeScript but doesn't include curl or direct documentation of their HTTP endpoints!

I needed documentation at the HTTP level. Could I maybe extract that directly from Mistral's official Python library?

It turns out I could. I started by cloning the repo:

git clone https://github.com/mistralai/client-python
cd client-python/src/mistralai
files-to-prompt . | ttok

My ttok tool gave me a token count of 212,410 (counted using OpenAI's tokenizer, but that's normally a close enough estimate) - Mistral's models tap out at 128,000 so I switched to Gemini 2.5 Flash which can easily handle that many.

I ran this:

files-to-prompt -c . > /tmp/mistral.txt

llm -f /tmp/mistral.txt \
  -m gemini-2.5-flash-preview-05-20 \
  -s 'Generate comprehensive HTTP API documentation showing
how function calling works, include example curl commands for each step'

The results were pretty spectacular! Gemini 2.5 Flash produced a detailed description of the exact set of HTTP APIs I needed to interact with, and the JSON formats I should pass to them.

There are a bunch of steps needed to get tools working in a new model, as described in the LLM plugin authors documentation. I started working through them by hand... and then got lazy and decided to see if I could get a model to do the work for me.

This time I tried the new Claude Opus 4. I fed it three files: my existing, incomplete llm_mistral.py, a full copy of llm_gemini.py with its working tools implementation and a copy of the API docs Gemini had written for me earlier. I prompted:

I need to update this Mistral code to add tool support. I've included examples of that code for Gemini, and a detailed README explaining the Mistral format.

Claude churned away and wrote me code that was most of what I needed. I tested it in a bunch of different scenarios, pasted problems back into Claude to see what would happen, and eventually took over and finished the rest of the code myself. Here's the full transcript.

I'm a little sad I didn't use Mistral to write the code to support Mistral, but I'm pleased to add yet another model family to the list that's supported for tool usage in LLM.

# 29th May 2025, 3:33 am / gemini, llm, plugins, llm-tool-use, ai, llms, mistral, generative-ai, projects, ai-assisted-programming, claude, claude-4, httpx, python

llm-llama-server 0.2. Here's a second option for using LLM's new tool support against local models (the first was via llm-ollama).

It turns out the llama.cpp ecosystem has pretty robust OpenAI-compatible tool support already, so my llm-llama-server plugin only needed a quick upgrade to get those working there.

Unfortunately it looks like streaming support doesn't work with tools in llama-server at the moment, so I added a new model ID called llama-server-tools which disables streaming and enables tools.

Here's how to try it out. First, ensure you have llama-server - the easiest way to get that on macOS is via Homebrew:

brew install llama.cpp

Start the server running like this. This command will download and cache the 3.2GB unsloth/gemma-3-4b-it-GGUF:Q4_K_XL if you don't yet have it:

llama-server --jinja -hf unsloth/gemma-3-4b-it-GGUF:Q4_K_XL

Then in another window:

llm install llm-llama-server
llm -m llama-server-tools -T llm_time 'what time is it?' --td

And since you don't even need an API key for this, even if you've never used LLM before you can try it out with this uvx one-liner:

uvx --with llm-llama-server llm -m llama-server-tools -T llm_time 'what time is it?' --td

For more notes on using llama.cpp with LLM see Trying out llama.cpp’s new vision support from a couple of weeks ago.

# 28th May 2025, 6:27 am / generative-ai, llm, plugins, projects, llm-tool-use, llama-cpp, ai, uv

How I used o3 to find CVE-2025-37899, a remote zeroday vulnerability in the Linux kernel’s SMB implementation (via) Sean Heelan:

The vulnerability [o3] found is CVE-2025-37899 (fix here), a use-after-free in the handler for the SMB 'logoff' command. Understanding the vulnerability requires reasoning about concurrent connections to the server, and how they may share various objects in specific circumstances. o3 was able to comprehend this and spot a location where a particular object that is not referenced counted is freed while still being accessible by another thread. As far as I'm aware, this is the first public discussion of a vulnerability of that nature being found by a LLM.

Before I get into the technical details, the main takeaway from this post is this: with o3 LLMs have made a leap forward in their ability to reason about code, and if you work in vulnerability research you should start paying close attention. If you're an expert-level vulnerability researcher or exploit developer the machines aren't about to replace you. In fact, it is quite the opposite: they are now at a stage where they can make you significantly more efficient and effective. If you have a problem that can be represented in fewer than 10k lines of code there is a reasonable chance o3 can either solve it, or help you solve it.

Sean used my LLM tool to help find the bug! He ran it against the prompts he shared in this GitHub repo using the following command:

llm --sf system_prompt_uafs.prompt              \ 
    -f session_setup_code.prompt                \          
    -f ksmbd_explainer.prompt                   \
    -f session_setup_context_explainer.prompt   \
    -f audit_request.prompt

Sean ran the same prompt 100 times, so I'm glad he was using the new, more efficient fragments mechanism.

o3 found his first, known vulnerability 8/100 times - but found the brand new one in just 1 out of the 100 runs it performed with a larger context.

I thoroughly enjoyed this snippet which perfectly captures how I feel when I'm iterating on prompts myself:

In fact my entire system prompt is speculative in that I haven’t ran a sufficient number of evaluations to determine if it helps or hinders, so consider it equivalent to me saying a prayer, rather than anything resembling science or engineering.

Sean's conclusion with respect to the utility of these models for security research:

If we were to never progress beyond what o3 can do right now, it would still make sense for everyone working in VR [Vulnerability Research] to figure out what parts of their work-flow will benefit from it, and to build the tooling to wire it in. Of course, part of that wiring will be figuring out how to deal with the the signal to noise ratio of ~1:50 in this case, but that’s something we are already making progress at.

# 24th May 2025, 9:09 pm / llm, openai, llm-reasoning, o3, ai, llms, security, generative-ai, system-prompts, ai-security-research

llm-anthropic 0.16. New release of my LLM plugin for Anthropic adding the new Claude 4 Opus and Sonnet models.

You can see pelicans on bicycles generated using the new plugin at the bottom of my live blog covering the release.

I also released llm-anthropic 0.16a1 which works with the latest LLM alpha and provides tool usage feature on top of the Claude models.

The new models can be accessed using both their official model ID and the aliases I've set for them in the plugin:

llm install -U llm-anthropic
llm keys set anthropic
# paste key here
llm -m anthropic/claude-sonnet-4-0 \
  'Generate an SVG of a pelican riding a bicycle'

This uses the full model ID - anthropic/claude-sonnet-4-0.

I've also setup aliases claude-4-sonnet and claude-4-opus. These are notably different from the official Anthropic names - I'm sticking with their previous naming scheme of claude-VERSION-VARIANT as seen with claude-3.7-sonnet.

Here's an example that uses the new alpha tool feature with the new Opus:

llm install llm-anthropic==0.16a1
llm --functions '                                                               
def multiply(a: int, b: int):
    return a * b
' '234324 * 2343243' --td -m claude-4-opus

Outputs:

I'll multiply those two numbers for you.
Tool call: multiply({'a': 234324, 'b': 2343243})
  549078072732
The result of 234,324 × 2,343,243 is **549,078,072,732**.

Here's the output of llm logs -c from that tool-enabled prompt response. More on tool calling in my recent workshop.

# 22nd May 2025, 6:36 pm / llm, anthropic, claude, generative-ai, ai, llms, claude-4