OpenAI's ChatGPT Work hands teams two trust boundaries under one name
Simon Willison's teardown finds a cloud container whose outbound domain list appears open by default, plus a desktop build that runs programs on the employee's machine. Those are two provisioning reviews with different threat models.
The Engineer · Build desk

What happened
- Simon Willison's August 30th writeup splits OpenAI's ChatGPT Work, announced July 9th, into a cloud product reached from chatgpt.com and a desktop product that runs programs on the user's own machine.
- His inventory lists seven capabilities Work has that Chat lacks, among them a persistent filesystem shared between sessions, a headless Chrome browser, sub-agent sessions and scheduled prompt automations.
- Work's code execution environment can reach the open internet, whereas the equivalent request from ChatGPT Chat is blocked by that container's proxy.
- Claude's comparable container has allowed restricted internet access since last September, but with an allowlist Willison describes as very short: PyPI, NPM and GitHub clones.
- Both flavours of Work require a subscription of $20 a month or more, so free accounts and $8 Go seats get no access at all.
Why it matters
- exposure Any private repository, token or file a team hands to Work Cloud sits in a session that can also load pages it did not author and open connections to hosts nobody enumerated.
- decision Approving a line item called ChatGPT Work now approves a local file-and-process executor as well, which puts endpoint policy owners in a review they may not know is happening.
- cost Extending the capability to the cheapest seats costs $12 more per person per month, so who gets an internet-capable agent is decided by billing tier rather than by job.
- constraint If Willison's read on billing is right, scheduled automations run by non-developers draw down the same Codex allowance engineers are using.
The browser tool loads arbitrary pages and will execute JavaScript against their DOM [10]. The filesystem persists between sessions [9]. Outbound network is on, and the allowed-domain list, according to Willison, is configurable with a default that appears to be open to all [8]. Put those together and text from a page nobody on your team wrote can reach a session that has durable storage and an unrestricted socket. Each of those features is defensible on its own, which is exactly why the composition is the thing to review.
Anthropic went the other way, with an allowlist short enough that Willison can summarise it in three items [17]. That design buys dependency installation and forecloses talking to a vendor API. Work has the same control with the polarity reversed: name the domains you want, or inherit all of them [8]. If the default is what Willison observed, the config line is the whole conversation, and it is a line somebody has to write before the first useful task.
Work Local is the desktop app that used to be Codex, and it reads files and runs programs on the machine it is installed on [3]. Willison reads it as Codex re-skinned to be less intimidating to people who are not software developers [4]. That is a fair description of the adoption risk, because the population being handed a program runner is the population least likely to hold a model of what a program runner can do. Work Cloud runs in OpenAI's infrastructure and is reached from chatgpt.com or the mobile apps [2]. One name, two boundaries, and the interface presents Work as a tab alternative to Chat rather than as a different capability class [14].
The configuration surface is also bigger than that tab selector suggests. Work exposes GPT-5.6 Sol, Luna and Terra at Light, Medium, High, Extra High, Max and Ultra, plus GPT-5.5 at the first four of those levels [11]. Three models times six levels is eighteen, plus four, so 22 selectable model-and-effort combinations, against the five options Chat offers, with 5.6 Pro running the other way as Chat-only [18][12]. No team is going to bench 22 configurations, so in practice one gets picked and whatever it does becomes the house default.
"Appears" is Willison's word about the egress default [8], and it is measurable in about ten minutes: from inside the container, request a host you control, then read your own access log. Worth repeating on a schedule, too. Willison reports that Chat's container could install packages back in January and cannot now, and that he found this out by trying rather than by reading a changelog [15]. A capability inventory assembled by experiment carries an expiry date the vendor does not publish.
In my context Work Cloud earns the seat, with the allowed-domain list narrowed before anything points at a private repository, and Work Local reviewed the way any other local process executor gets reviewed. OpenAI's own guidance, which says use Chat for an answer or short draft and Work for a task with a clear outcome, will not help anyone make that call; Willison calls it almost entirely useless because he has been doing all of those task types in Chat for years [13].
What to watch
- Documentation or an admin control that states Work Cloud's default egress policy and logs which domains a session actually reached.
- Whether Work Local gains device management and policy hooks separate from Work Cloud, given that one product name currently covers both.
- Whether 5.6 Pro stays exclusive to Chat, which decides if Work is a strict superset of Chat's model access or a sideways trade.
Clarity's read
What the record supports and how the coverage leans. The claims behind it follow.
Reality
- Evidence55
- Adoption
- Insufficient
- Hype gap+10
- Incentives
- Insufficient
- Confidence50
Claim ledger
Ranked by verification strength, evidence, and original report placement.
- [1]
OpenAI announced ChatGPT Work on July 9th, and Simon Willison published his explainer on 30th August 2026, saying OpenAI had been iterating furiously on it since launch.
- [2]
Willison says ChatGPT Work is actually two products: a cloud version accessed via chatgpt.com or the ChatGPT mobile apps, which he calls Work Cloud, and a version tied to the desktop app, which he calls Work Local.
- [3]
Installing the ChatGPT desktop app, the app that used to be called Codex, gives access to a ChatGPT Work that can access files and run programs directly on the user's computer.
- [4]
Willison writes that Work Local feels more like regular Codex re-skinned to be less intimidating to non-software-developers.
- [5]
ChatGPT Work, in both flavours, is available only to subscribers paying $20/month and up; free users and $8/month Go users do not have access.
- [6]
Willison's list of features Work has that Chat lacks: options to use Luna and Terra in place of Sol; a code execution environment with Internet access; a headless Chrome browser; a persistent filesystem shared between sessions; the ability to publish ChatGPT Sites; the ability to run sub-agent sessions with Sol, Luna and Terra; and scheduled prompt automations.
- [7]
Work's code execution environment can talk to the rest of the internet, while ChatGPT Chat cannot: requests to install packages or reach outside websites and APIs are blocked by Chat's container proxy.
- [8]
Work's environment can be configured with a specific list of allowed domains, but Willison writes that the default appears to be open to all.
- [9]
Work includes a persistent filesystem shared between sessions.
- [10]
Work can launch a full headless Chrome instance that loads websites, fills out forms, takes screenshots and runs JavaScript against the DOM of those pages.
- [11]
In Work, the model picker offers GPT-5.6 Sol, Luna or Terra at Light, Medium, High, Extra High, Max or Ultra reasoning levels, plus GPT-5.5 at Light, Medium, High or Extra High.
- [12]
Chat offers a different selection: 5.6 Instant, Medium, High, Extra High and Pro, with 5.6 Pro appearing to be exclusive to Chat and having no equivalent in Work.
- [13]
OpenAI's official guidance is to use Chat for an answer, explanation, brainstorm or short draft, and ChatGPT Work when you want a task completed with a clear outcome such as a brief, deck, analysis, recurring update, workflow or reviewable file; Willison finds that almost entirely useless because he has used regular Chat for all of those categories for years.
- [14]
The interface for accessing Work is a tab selector that presents it as an alternative to Chat.
- [15]
Willison reports that back in January Chat's container gained the ability to install packages but that this no longer seems to work, and adds that he wishes OpenAI had better changelogs.
- [16]
Willison's inventory of Work-only features contains seven entries.
- [17]
Willison writes that Claude's equivalent container has allowed restricted internet access since it launched last September, with a very short domain allowlist covering package installs from PyPI and NPM and repository clones from GitHub.
- [18]
Work exposes 22 selectable model-and-reasoning-level combinations, against 5 options in Chat.
- [19]
Moving a Go subscriber to the cheapest tier that includes ChatGPT Work costs an extra $12 per month per seat.
- [20]
Willison believes ChatGPT Work sessions are billed against the user's Codex allowance while ChatGPT Chat sessions get their own separate allowance, and offers this as a possible explanation for the model availability differences.
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Sources
2 independent publishers whose own reporting we read for this story.
- dev.toChatGPT Work vs Chat: What OpenAI's New Agent Mode Actually Adds, and Whether It Is Safe
1 article · August 31, 2026
- simonwillison.netUnderstanding ChatGPT Work
1 article · August 30, 2026
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