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I've been watching The Pitt, but it can be a bit much, so I went looking for something a bit lighter, and found 9 to 5 on Amazon Prime. Jane Fonda, Lily Tomlin and Dolly Parton are the stars, and Dolly's famous song with the same name is the theme. It's a perfect slice of the world I grew up in. I get it confused with Working Girl which came out eight years later, with a similar theme -- what if women ran the business world, how much better would that be? Working Girl also had a really good theme song, written and performed by Carly Simon.
OpenAI announced ChatGPT Work on July 9th, and have been furiously iterating on it ever since. It is an extraordinarily confusing and very powerful product. Here's what I've figured out about it so far.
The more interesting version of ChatGPT Work is the one that runs in the cloud. This can be accessed via chatgpt.com or through the ChatGPT mobile apps. Let's call it Work Cloud.
If you install the ChatGPT desktop app - the app that used to be called Codex - you gain access to a thing called ChatGPT Work that can access files and run programs directly on your computer. Let's call that one Work Local. This one feels more like regular Codex re-skinned to be less intimidating to non-software-developers.
(Update: Work Cloud is also available from the ChatGPT desktop app, via a Where should this chat run? dropdown.)
For the rest of this article I'm going to talk exclusively about Work Cloud.
Right now, ChatGPT Work (in both flavors) is available only to $20/month and up subscribers. Free users and $8/month Go users do not have access.
The interface for accessing Work is a tab selector, which presents it as an alternative to Chat:

The obvious question is when should I use Chat, and when should I use Work?
OpenAI's official answer to that question is:
Use Chat when you want an answer, explanation, brainstorm, or short draft. Use ChatGPT Work when you want ChatGPT to complete a task with a clear outcome, such as a brief, deck, analysis, recurring update, workflow, or file you can review and use.
I find that almost entirely useless, because I've been using regular ChatGPT Chat for all of those task categories for years!
The better question then is what features does Work have that are missing from Chat?
After extensive experimentation I think I've mostly figured that out:
In Work, you get the option to pick GPT-5.6 Sol, Luna, or Terra, each with Light, Medium, High, Extra High, Max, or Ultra reasoning levels. You can also pick GPT-5.5 at Light, Medium, High, or Extra High.
These look to be the same models that are available through the OpenAI API.
Chat offers a different selection: 5.6 Instant, Medium, High, Extra High, and Pro (actually Extra High and Pro are only available for $100/month+ subscribers - $20/month subscribers cap out at High). It doesn't explain if those are Luna or Terra or Sol (I'm assuming Sol?). 5.6 Pro appears to be exclusive to Chat, with no equivalent in Work.
My current understanding from using Codex is that Ultra is a special mode that more eagerly delegates to sub-agents.
I believe ChatGPT Work sessions are billed against your Codex allowance, while ChatGPT Chat Sessions get their own, separate allowance. This may help explain the model availability differences.
As a long-time fan of the Code Interpreter pattern - pioneered by OpenAI in 2023 - this is by far the most exciting feature of ChatGPT Work (Cloud) for me.
The code execution environment can now talk to the rest of the internet!
ChatGPT Chat can't do this - if you ask it to install additional software packages or interact with websites or APIs that access will be blocked by the container proxy.
(Weirdly, back in January it grew the ability to install packages, but that doesn't seem to work any more. I wish they had better changelogs!)
Claude's equivalent container has allowed restricted internet access since it launched last September. Claude can install packages from PYPI and NPM and clone repositories from GitHub. But that is about it: the allowlist of domains is very short.
ChatGPT Work allows a whole lot more than that. It can be configured with a specific list of allowed domains, but the default appears to be open to all.
This makes Work an incredibly useful tool. You can have it clone GitHub repositories, install their dependencies, then use them to interact with the rest of the web!
Another killer feature of ChatGPT Work is the browser tool. ChatGPT Work can launch a full Chrome instance, load websites, fill out forms, and take screenshots.

If a site requires sign in the browser can prompt you to take over and enter both passwords and 2FA codes, without round-tripping those credentials through the model itself.
It can even run JavaScript against the DOM of loaded pages. I prompted:
Load simonwillison.net in your browser and extract the headings using JavaScript
ChatGPT Work fired up a browser instance and ran the code:
await tab.playwright.evaluate(() => { return Array.from(document.querySelectorAll("h1,h2,h3,h4,h5,h6"), heading => ({ level: heading.tagName.toLowerCase(), text: heading.innerText.trim().replace(/\s+/g, " "), id: heading.id || null })); });
This feels a lot like my shot-scraper javascript tool, only now I can access it on my phone!
ChatGPT Chat gets a fresh filesystem for each chat session. These cannot be accessed from any other session.
In ChatGPT Work each session gets its own scratch folder - named something like /workspace/scratch/e00a0a017944 - but each of those are persisted across sessions, so you can access files from previous chats. I have 171 folders in /workspace/scratch right now!
As far as I can tell that /workspace volume is mounted to all Work sessions that are currently running - file edits from one can be instantly seen by the others. They don't seem to share the same process space though, and localhost servers running in one can't be accessed from another.
ChatGPT Work has the ability to build and deploy entire websites, using Cloudflare Workers. These can have HTML and JavaScript and can run server-side features too, including stateful features on top of Cloudflare D1 and R2.
Here's a simple site I built with this feature:
london-pelicans-in-her-piety.simonw.chatgpt.site

My prompt was:
Figure out all of the places in London with a pelican in her piety, then turn that into a JSON file and build a ChatGPT sites site about them
(A pelican in her piety is a fascinating piece of medieval Christian imagery - once you know about them you'll find them all over the place.)
These sites default to being private to the user that created them, but you can make them public and (on team plans) share them with other specific individuals.
There's not much to say about this one. ChatGPT Chat can't run sub-agents. ChatGPT Work can. This is very much a power-user feature: if you are running a complex project that can benefit from multiple parallel agents working together, Work can do that.
Another feature that seems to have migrated from regular ChatGPT to ChatGPT Work at some point. You can prompt ChatGPT Work like this:
run a search to see if Waymo have announced a launch date for Half Moon Bay every day at 8am
This will schedule a prompt to run on that frequency. These prompts can decide that nothing interesting has happened, or they can decide to notify you of some new information.
Update: Actually this seems to work in ChatGPT Chat as well.
It's still worth noting here though, as it can be used in conjunction with other ChatGPT Work exclusive features. You can set a scheduled task to update a ChatGPT Site on an hourly basis, for example.
An open question for me right now is how safe all of this stuff is.
My lethal trifecta model warns about the risks inherent in any agent system that combines access to private data with exposure to untrusted content and a way to communicate stolen information back to an attacker.
ChatGPT Work combines all three!
I'd love to hear more from OpenAI about how they protect ChatGPT Work sessions against prompt injection attacks. I expect their answer is the same auto-review mechanism as Codex.
Figuring this all out took way more work than it should have.
I think there are two key problems here:
If the ChatGPT Work documentation included the exact system prompt and tool descriptions used by the agent I wouldn't have needed to write this post.
Shortly after publishing this article I had an idea. I started a fresh Work session and prompted:
Build a site that lists every one of your tools - nearly grouped into categories - and for each one explain what it does. Try to exactly duplicate arguments and tool descriptions where possible. Design aesthetic should be technical docs, minimal flare
Here's the site it built, which includes details of 223 registered tools - though 6 of those are from my own personal MCPs served via datasette-mcp.
I noticed that the only browser-related tool in the list was web.run, which has methods for running searches, opening URLs, and clicking links, but didn't look like the full story in regards to headless browser automation.
This made me suspicious that something was missing, so I told the ChatGPT Work session that built that tools reference site:
Add full copies of every skill to the website (separate pages linked to from the homepage)
It turns out ChatGPT Work uses a lot of skills - 44 in fact!
The control-browser skill explains how the browser works:
Run browser setup code through the Node REPL
jstool. In this environment the callable tool id typically appears asmcp__node_repl__js. [...]The ability to interact directly with the browser is exposed through the
browser-clientruntime via theagent.browsers.*API. Before trying to interact with it, you MUST emit and read the complete documentation returned byawait browser.documentation()in one go.
So I told Work:
Add the full output of await browser.documentation() to the bottom of the /skills/control-browser page
And now you can read that on /skills/control-browser as well.
A few more interesting Skills:
.docx filesimage_gen tool.xlsx, .xls, .csv, .tsv
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I've been watching Season 1 of The Pitt, and as its reviews said, it's great drama, and there are lots of episodes. I like shows like this because they're simulated communities, we come to know the characters, and think about them even when we're not watching. Before too long we'll have AI programming that makes these shows like software, the stories assemble around the characters, and then are generated the same way ChatGPT generates the art we call slop, which will someday not be a pejorative the same way sick and junk aren't negative terms today. So we'll be able to call up new episodes of The Wire or The Sopranos or The Pitt any time we like. We'd be missing the fun of discussing the latest episode with friends, or maybe we'll have bot-invented friends too who will simulate having watched the episode you just watched, which leads us to another masterpiece of entertainment, The Matrix. On the other hand, I've watched The Wire at least five times all the way through, and even though I know what they're about to say in a lot of places, I do forget the sub-plots so at least some of it can be new each time. And btw, finally an episode of Silo that's was surprising that I didn't see coming. I read the books, so I feel like I should watch the show, but until the latest episode I was uninterested in any of the characters. Finally there's a plot to think about!
An absolutely delicious temperate cloud-free day in the Catskills, so I got up from the computer and enjoyed.
Manton wants to know why Marc Benioff chose the name Claudeforce for his brand-merge of Salesforce and Claude. My two cents. Claude is a great name. I think that’s ultimately what he bought. His customers just want to be able to check the box – we’re using AI. Boss is happy. When I was coming up as a young dude in tech, the old saying was “No one ever got fired for buying IBM.” Today, in 2026, it’s Claude in place of IBM. My father worked in marketing at IBM in Armonk, so I heard a lot about their strategies that meant the IBM brand would be kicking ass forever. All things must pass. But in the early days of the PC industry, IBM sure had the power. Kind of like the US going to war with Iran in 2026. In the end IBM wanted to get rid of Microsoft, but Billg had the last laugh.
My WordPress mirror site stopped updating on August 12. It's now updating once again. I'll try to watch it more carefully.
I've updated my feedland page with 13 aggregator and firehose feeds from Bear Blog, Pinboard, Scour, Hacker News and others.
A good way to use these is to put them all in one folder in your reader and filter for keywords based on your interests.
Full list of feeds and link on my blog:
Test post
Link penalties on social media platforms
Although I’ve known for a while that social platforms make posts with links in them less visible, I didn’t know until recently just how much they did it. So, here’s a run down of how much different platforms penalise links and how you can work with it.
(Although the real answer is of course to use platforms that don’t penalise links, sometimes you have to go where people are)
https://paul.jottit.org/link-penalties-on-social-media-platforms
What is the most frustrating thing about RSS?
https://www.reddit.com/r/rss/s/uXhg2u6noX
// #p-mas
not even counting anymore
Kill the algorithm in your head: Let's set up RSS readers and get news we actually want in 2026
https://scour.ing/redirect/https://www.pcgamer.com/software/kill-the-algorithm-in-your-head-lets-set-up-rss-readers-and-get-news-we-actually-want-in-2026?utm_source=rss
// #p-mas #p-bs
aaaand again
an ode to rss feeds
https://raccoongirltalkstotheworld.bearblog.dev/an-ode-to-rss-feeds/
// #p-mas #p-bs