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shadow AI ·
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Shadow AI: the AI use the company never authorised

A Vercel employee clicked "allow all" on an AI tool the company never bought, and that is the way the attacker came in. Shadow AI has two doors, what gets pasted into a chat and what gets connected to company accounts, and almost nobody looks at the second.

ACCESS REQUEST CORPORATE ACCOUNT REQUESTED BY AI Office Suite ALLOW ALL WRITE EMAILS ON YOUR BEHALF CREATE DOCUMENTS ON YOUR BEHALF AND EVERY OTHER ONE ASKED CONTRACT WITH THE COMPANY NONE ACCESS REQUEST CORPORATE ACCOUNT REQUESTED BY AI Office Suite ALLOW ALL WRITE EMAILS CREATE DOCUMENTS AND ALL THE OTHERS CONTRACT NONE
Rafael Yashiki CapuaCOO & Co-Founder, Jump
reference document
last revised
↓

START OF DOCUMENT
15 sections · about 27 min read · 7 cases verified against primary sources

IN ONE MINUTE

  1. THE THESISShadow AI comes in through two doors, and almost nobody watches the second.The first is what gets pasted into a chat. The second is what gets connected to company accounts, and it is the one Vercel was breached through.

  2. WHY NOWIn IBM's 2026 study, among organisations with a breach, the share of incidents involving shadow AI rose from 20% to 43% in a year (section 00).

  3. THE RISKIn Google Workspace, unless someone changed the setting, any employee can grant that access alone, and what was already granted stays valid (section 02).

  4. IN BRAZILUnder the guidance of the ANPD, Brazil's data protection authority, the company answers for what an employee connects (section 05).

  5. THIS WEEKOpen the list of third-party apps with access in Google Workspace and in Entra ID, and check the consent setting in both (section 10).

  6. FOR THE BOARDHow many grants to AI tools have already been made with company accounts, and who can list them today?

// 00

Nobody at Vercel bought the tool

the thesis of this edition

In April 2026, Vercel published a security bulletin saying that an outsider had got into its internal systems and read environment variables belonging to a subset of its customers. In the sentence on the origin, Vercel wrote "The incident originated with a compromise of Context.ai, a third-party AI tool used by a Vercel employee."

Context.ai, in its own statement, added the detail that matters. "Vercel is not a Context customer." An employee had signed up for a consumer AI product using their corporate Google Workspace account and, according to Context, accepted every permission the tool asked for. When Context was breached, the authorisation that employee had given became the way into Vercel.

The company was opened by a click on "allow", in a tool that never went through procurement or security.

This is a case of shadow AI, the name the market gives to AI used at work without the company having approved it. It is the person who gets the report done in ChatGPT on a personal account, installs an extension that summarises meetings or hooks an assistant up to their corporate email, because it is quicker than asking IT. The intention is almost always good. The company simply does not know it exists, and so it decides nothing about what passes through it.

Shadow AI comes in through two doors. The first is what the person pastes into the chat, such as code, a spreadsheet or meeting minutes. The second is what they connect to the company's accounts, such as a browser extension, an app that asks for access to email and drive, an agent that starts acting on their behalf. The first door is the one the public debate knows, the one that shows up in internal policy and in training. Almost nobody inventories the second, and that is the door the Vercel case came through.

This edition gives both the same weight. No source I read measures which of them causes more damage, and I will not claim it. With primary sources, something else can be shown. The second door is granted with less ceremony, stays open for longer and almost never makes it onto the list of whoever looks after security.

The most recent figure on the subject comes from IBM's annual study of data breaches, published on 29 July 2026. Among the 602 organisations studied, all with a confirmed breach in the period, the share of incidents involving shadow AI rose from 20% to 43% in one year. In the 2026 report, IBM describes shadow AI as the case "where workers use unapproved AI". IBM itself changed the way it describes that denominator from one edition to the next, so I quote the figure the way it wrote it. Reading it as "43% of companies" would be wrong.

// 01

What shadow AI is, and what connecting means

without this, the rest of the edition makes no sense

The name comes from shadow IT, which is what we called, fifteen years ago, the spreadsheet in a personal Dropbox and the system bought on a manager's credit card.

The difference is that the spreadsheet in Dropbox just sat there. An AI tool reads, writes and, more and more, does things on behalf of whoever connected it. That changes what "using an unapproved tool" means.

The first door, what gets pasted

This is the form everyone already pictures. The person opens an AI chat, pastes in a piece of code, a customer spreadsheet or a meeting transcript, and asks for help. The content leaves the company and goes to a vendor's server.

What defines the risk of this door is the account's contract. The same tool, with the same screen, runs under two different contracts, and the person picks which one applies at the moment they sign up. The table below summarises what the OpenAI and Anthropic pages say.

CONSUMER ACCOUNTCOMMERCIAL CONTRACT
Training on what you writeOpenAI may train, unless you switch it off. Anthropic trains if the setting is on.OpenAI does not train by default. Anthropic barred by the commercial terms.
Switching training off solves itNot entirely. With both, giving feedback on an answer can send the whole conversation to training.Training is already excluded by the contract.
How long it is keptAnthropic five years with training on, 30 days without. OpenAI Free, Plus and Pro fell under the preservation order in the NYT case, in force until 26.09.2025. What was kept from April to September 2025 is still kept.OpenAI on Enterprise and Edu, the company controls it, and the NYT order did not reach them. Team, now Business, fell under it. Anthropic not verified for this edition.
Account created with the company emailOpenAI may tell the employer the account exists. Anthropic may link the account to the organisation's account.The account already belongs to the company.
Who picks which appliesThe person, at sign-up.The company, in the contract.

Sources: OpenAI, training and privacy pages (30.04.2026) and statement on the NYT case (05.06.2025, updated 22.10.2025); Anthropic, consumer terms (28.08.2025), privacy policy (in force since 08.07.2026) and commercial terms.

Paying does not change this. Plus, Pro and Max are consumer plans. And even the commercial contract comes in degrees. OpenAI's Team, now called ChatGPT Business, is a business plan and does not train on content by default, but it fell under the preservation order in the New York Times case, which left out only Enterprise, Edu and the API with zero retention.

The second door, what gets connected

Through this door, what the person hands over is access to the accounts. Almost every modern AI tool offers "sign in with Google" or "sign in with Microsoft". Along with the login comes a second screen, listing what the tool wants to do. Read your emails, send emails on your behalf, see and edit your files, access your calendar. The person clicks allow, and the tool now has ongoing access to those accounts.

In the previous edition I explained the token as a badge that has no photo, does not expire on its own and is already the authorisation. That badge had been issued to an official integration, installed by the company. Here it is the same badge, and the one who signs off on issuing it is the employee, alone, in thirty seconds, with the corporate account.

The analogy I use is the power of attorney. The permissions screen is a power of attorney you sign for someone you have just met. It gives them the power to act on your behalf, it stays valid when you close the browser, it stays valid when you forget you signed it, and it is kept in the files of whoever received it. If those files are stolen, whoever holds the paper acts as if they were you.

Two variations of the second door

  • The browser extension is an even broader power of attorney. Once installed, it can read what appears on every page the person opens, including the corporate AI chat, the CRM and email. It does not need OAuth for that. It only needs someone to click "add".
  • The agent is the power of attorney that works on its own. When a developer connects an MCP server to their coding assistant, or a manager hooks an agent up to their inbox, whatever is connected has the same permissions as the assistant, and none of them shows up in an asset inventory.

IN ONE LINE

Whoever connects an AI tool to the corporate account hands access to the whole archive, for an indefinite period, to whoever holds the power of attorney.

01
THE QUESTION THAT REMAINS
If someone at your company pasted a customer spreadsheet into an AI chat right now, under which contract would that conversation sit, and would anything on their machine notice?

// 02

The path of the power of attorney

the mechanism, step by step

The two doors follow different paths, and the points where you can intercept sit in different places.

1 · WHAT GETS PASTED person AI chat vendor's server classify on the device, before sending 2 · WHAT GETS CONNECTED person permissions screen token stored at the vendor email, drive and calendar console: who can authorise alone list of grants already made breached vendor 1 · WHAT GETS PASTED person classify before sending AI chat vendor's server 2 · WHAT GETS CONNECTED person console: who can authorise alone permissions screen token stored at the vendor breached list of what was already authorised email, drive and calendar
The two doors. In teal, the points where what goes out can be stopped.

The top track has one point where what goes out can be intercepted, which is the person's machine, at the moment of sending. The bottom track has two, and both sit outside the machine. One is the setting that defines whether the person can sign the power of attorney alone. The other is the list of what has already been signed.

What most surprises administrators is the factory default. In Google Workspace, the option that controls unconfigured third-party apps comes set to "Allow users to access any third-party apps (default)". At Microsoft, the default changed in 2025. Entra ID switched to a policy managed by Microsoft itself, which applies to new tenants and to those that had never touched the setting. Under it, users can consent on their own to almost everything except reading email, calendar, chat and all files, which now require an administrator. Anyone who had previously chosen to let users consent to any app stays that way. At Google, unless someone has changed the setting, any employee can grant an AI tool the access the Vercel case showed. At Microsoft, the vendor itself has already closed part of that door, and the question becomes whether your tenant ended up with the new default or with an old choice.

Microsoft adds a detail that holds for both worlds. Changing the consent setting "only affect[s] future consent operations". What has already been granted stays valid until someone revokes it.

WHAT IS NOT KNOWN

Neither company published the exact list of scopes the Vercel employee granted. Context describes the grant as "allow all" on "all requested Google Workspace permissions", and says they existed for "writing emails or creating documents on the grantee's behalf". What else it asked for is not written anywhere I have found.

// 03

Seven cases, two doors

each one for what it actually was

The cases below were chosen because they have a primary source. Each one carries its type, because a real compromise, a coordinated disclosure, a proof of concept and an operational failure are different things, and I insist on not mixing them.

what the cases really were

  • 4real compromise
  • 1coordinated disclosure
  • 1operational failure
  • 1proof of concept

The second door, what gets connected

REAL COMPROMISE

Vercel and Context.ai, March and April 2026

The central case of this edition, confirmed by both companies, each in its own statement, with dated updates. Vercel investigated with Mandiant, and Context with CrowdStrike. The inside story is in the next section.

REAL COMPROMISE

Disney and the fake image generator, 2024

According to the plea agreement filed on 1 May 2025 in the federal court for the Central District of California, a Disney employee downloaded from GitHub, between April and May 2024, a program that "purported to be computer software that could be used to create A.I.-generated art". It was malware. The attacker gained access to the victim's personal computer, "including an online account where M.V. stored login credentials and passwords for M.V.'s personal and work accounts", and with that downloaded about 1.1 terabytes from "thousands of Disney Slack channels".

The machine was personal and the vector was malware, with no OAuth involved. The case is here because it shows what comes along when someone installs an AI tool in the same place where their work credentials live.

REAL COMPROMISE

postmark-mcp, September 2025

A package published on npm with the same name as the official MCP server of Postmark, an email delivery service. Whoever installed it handed it the company's sending key. Koi Security documented that version 1.0.16 began adding a hidden copy to an address belonging to the author on every email the agent sent. Postmark stated the same day that it "had absolutely nothing to do with this package". Nobody has measured how many companies were hit.

REAL COMPROMISE

Urban VPN and related extensions, July to December 2025

Koi Security documented, on 15 December 2025, that a free VPN extension and three others from the same publisher, with more than 8 million installations combined on Chrome and Edge, began capturing from July everything the user typed and received on eight AI platforms listed by Koi, among them ChatGPT, Claude, Gemini and Copilot. The collection ran with the VPN switched on or off. It is the second door capturing what passes through the first, because what the person pasted into the chat also left through the extension.

COORDINATED DISCLOSURE

ShadowLeak, September 2025

Radware showed that an email with hidden instructions could lead ChatGPT, connected to Gmail in deep research mode, to gather data from other emails and send it out, leaving from OpenAI's servers and not from the company's network. OpenAI fixed it. It is here because connecting Gmail is exactly the move an employee makes to "let the AI help with email".

PROOF OF CONCEPT

GitHub MCP, May 2025

Invariant Labs showed, in demonstration repositories, that an agent connected to GitHub with a token that reaches private repositories could be led, by a malicious issue in a public repository, to publish data from the private ones. The authors themselves say that "this is not a flaw in the GitHub MCP server code itself". The problem is the size of the access given to the agent.

The first door, what gets pasted

OPERATIONAL FAILURE

Samsung, March 2023

The most cited case of all. According to Economist Korea, which published first, on 30 March 2023, there were three episodes in less than twenty days after the semiconductor division allowed ChatGPT. Two pieces of code pasted in to find bugs and to optimise, and the transcript of a meeting pasted in to produce the minutes. Nobody broke into anything. Employees sent internal content to an external service, within a use the division itself had allowed. Samsung never published anything about the case, and what circulates about it contains errors that are covered in section 11.

// 04

How it happened on the inside

the Vercel case, with the time each company published

I picture the scene like this, and it is my imagination. Someone needs a presentation for tomorrow, finds a tool that builds it with agents, clicks "sign in with Google" and, on the next screen, "allow all", because it is the button that lets them carry on. Thirty seconds.

Two companies published, and each tells the part it saw. The times below are the ones they recorded themselves, in Pacific time, and dates without a time are as the sources give them.

Jun
2025
Context launches the AI Office Suite, a "self-serve consumer-targeted" product for building presentations, documents and spreadsheets with agents. One of its features allowed "AI agents to perform actions across their external applications".
before
Mar 2026
A Vercel employee signs up for the product with their corporate Google Workspace account and, according to Context, grants "allow all" on every permission requested.
Mar
2026
Context identifies and stops unauthorised access to its AWS environment, hires CrowdStrike, notifies "a customer we identified as impacted" and shuts down the consumer product. The tokens were stolen while the environment was still live.
by
Apr 2026
On a date neither company disclosed, using one of the stolen tokens, the attacker takes over the employee's Google Workspace account, from there reaches their Vercel account, gets into a company environment and starts to enumerate and decrypt environment variables belonging to customers that were not marked as sensitive.
19 Apr
11:04
Vercel publishes the identifier of Context's OAuth app as an indicator of compromise and asks every Google Workspace administrator to search for it.
19 Apr
18:01
Vercel publishes the origin of the attack. Context publishes its statement the same day.
20 Apr
17:32
Vercel confirms that none of the npm packages it publishes were altered.
21 Apr
09:00
Context adds to its statement the passage on what the granted permissions were for.
22 and 23
Apr
Vercel widens the investigation and finds "a small number of additional accounts" compromised.
by 7
May
Context's statement goes offline. In a capture from 7 May, the address already returns 404, and the text survives only in an archived copy.

Two details I would not let slide

The first is the sentence in which Vercel describes Context. "A small, third-party AI tool whose Google Workspace OAuth app was the subject of a broader compromise, potentially affecting its hundreds of users across many organizations." Hundreds of users, across many organisations. Vercel was the one that found out and published. From the sources, there is no way to know how many of the others know, even today, that they had someone connected to Context.

The second is the path the warning took. Context detected and stopped the intrusion in March. It knew it had been breached, hired forensics and notified the customer it identified. But it only learned that tokens from users of the consumer product had been used against Vercel "based on information provided by Vercel". Context warned those who were customers. Vercel was not one, and only entered the story because it found out on its own.

Sources: Vercel, Vercel April 2026 security incident, bulletin of updated through ; Context, Security Incident Response Statement, , updated on , offline since May 2026 and read in an archived copy.

// 05

What was taken is bigger than it looks

one person's access reached the credentials of many companies

Vercel says that "non-sensitive" environment variables were read, and that sounds small. But Vercel itself, in its recommendations, describes what usually lives in them. "API keys, tokens, database credentials, signing keys." These are the credentials Vercel's customers use so that their applications can talk to databases, to payment providers, to other services.

It is the same chain as in the previous edition, from a different starting point. A token led to an account, the account led to an environment, and the environment held other people's tokens. What began as a power of attorney signed by one person ended in the credentials of companies that had never heard of Context.

The access that remains after the use ends

Material Security published a report in June 2026 on OAuth authorisations in corporate Google Workspace environments. The sample is small and the publisher sells the solution, but the numbers give the size of the residue.

22,332applications with access granted

47.2%unused for 90 days, authorisation intactrecently used

1,064applications with no active user

463with sensitive access, such as all of Gmail or Drivenon-sensitive access

Material Security, The Access You Forgot You Granted, 23.06.2026. 21 Google Workspace environments belonging to the vendor's own customers, and the vendor sells the solution. Read it as an order of magnitude.

On the first group, Material writes that "in every one of these cases, the OAuth authorization is still intact".

Under Brazilian law, the company is answerable

The guide from the ANPD, Brazil's data protection authority, on processing agents is explicit. Employees are neither controllers nor processors, because they "act under the directive authority of the processing agent", and the company "assumes responsibility for the acts performed by its agents and representatives". When an employee connects a tool the company never contracted to the email account that holds customer data, the processing is the company's.

Here comes a reading of my own, one the ANPD has never made. Resolution CD/ANPD No. 19/2024 defines transfer as the operation by which an agent "transmits, shares or makes available access to personal data to another processing agent". An OAuth authorisation given to a vendor abroad is, in the most literal form possible, making access available. No document from the National Data Protection Authority has applied this definition to AI tools used by employees, and I would hear a lawyer before treating it as settled.

Recognition of the problem already appears in a document from the agency itself. The ANPD's Radar Tecnológico No. 3, on generative AI, which presents itself as a technical study and not as an institutional position, writes that shifting responsibility to the user "does not seem to be sufficient". The text deals with prompts and attachments. Connectors and agents do not yet appear in any Brazilian primary source I have found.

APPLY IT AT HOME

Every corporate Google Workspace or Microsoft 365 account that holds customers' personal data is, potentially, an account from which someone has already signed a power of attorney to an AI tool. Who is answerable is already clear in the law. What almost no company can say is how many powers of attorney have been signed.

// 06

Nobody noticed on their own

the uncomfortable part

Vercel has a security team, publishes timestamped bulletins and worked with Mandiant on the investigation. I do not think it was careless. The second door is hard to see for four reasons that add up.

  1. Consent goes past nobody. The tool was not bought, so it never went through procurement, legal or vendor assessment. Context was not a Vercel vendor.
  2. The access looks legitimate. Whoever uses the stolen token presents a valid authorisation, granted by the account owner. No wrong-password or login-from-another-country alarm goes off. The second factor protects the moment of login, and here the login had happened earlier, on the day of sign-up.
  3. Notification follows the contract. When a vendor is breached, it notifies its customers. An employee using a consumer account is not a business customer, and their company is on no list at all. In the Vercel case the sequence ran the other way, and it was the victim that notified the vendor.
  4. The first door has a name, the second does not. Among the organisations IBM studied in 2026 that had some AI governance policy, only 29% run regular audits looking for unsanctioned AI, against 34% the year before. The requirement for IT approval to deploy AI fell from 45% to 38%.

Okta's May 2026 survey points the same way. Among workers who use AI, 52% said they had used some tool without IT approval, and only 6% gave not knowing they needed approval as the reason. The reasons cited most were others. Using their own account was easier (80%), the team already used it (78%), approval was too slow (57%).

THE MOST HONEST LINE IN THE CASE

Context wrote that the permissions granted existed so that agents could "perform Google Workspace actions such as writing emails or creating documents on the grantee's behalf". That was what the employee wanted from the tool. When Context was breached, that same permission started working for the attacker.

// 07

The pattern that repeats

putting the three editions together

Side by side, the three editions show a sequence I have not seen anyone write down.

  1. 01

    The instruction

    who handed it overthe agent's owner, by connecting tools to it
    the attacker usedan instruction written where the agent would read it
    what holdswell-maintained conventional controls and an architecture that separates instruction from data
  2. 02

    The vendor's badge

    who handed it overthe company, by installing a vendor's integration
    the attacker usedthe integration's token, stolen from the vendor
    what holdsIP restriction and minimum scope on the connected app
  3. 03

    The badge handed out by the employee

    who handed it overone employee, alone, on the permissions screen
    the attacker usedthe token of a vendor the company never hired
    what holdstaking away the employee's power to authorise alone

What the third edition adds is where the authority comes from. In the first two, someone in the company decided to connect the agent, whether a product team or a CRM administrator. Here the decision was one person's, alone, and the company only learned of it after the incident.

This takes apart a common defence

In almost every company I know, the answer to shadow AI is a written policy and a list of approved tools. Those two things cover the first door, where the act is visible and the person knows they are sending something. At the second, the act looks harmless. The screen says "sign in with Google", the person signs in, and the power of attorney comes with it.

In 2025 the Google Threat Intelligence Group documented a campaign, attributed to UNC6040, in which employees were talked by phone into authorising "a malicious connected app" in Salesforce. GTIG's conclusion holds here too, swapping the platform's name. "In all observed cases, attackers relied on manipulating end users, not exploiting any vulnerability inherent to Salesforce." That was social engineering. At Vercel, from what both companies describe, nobody had to talk anybody into anything, and the employee signed up on their own.

THE SYNTHESIS

In edition 02 I wrote that an agent's security depends less on what it thinks and more on what it can sign. In this one, the question moves one step back and becomes who, in your company, can sign for it.

// 08

The question nobody could answer

and what third-party numbers say about it

When Vercel published the identifier of the Context app, it asked every Google Workspace administrator to check "for usage of this app immediately". To meet that request in minutes, a company needs to be able to answer three things. Which AI tools have delegated access to the company's accounts today. Who granted each one, and when. With what scope.

VENDOR NUMBERS

This edition has no measurement of its own. What exists are numbers from vendors that sell detection, measured among their own customers, who already care about the subject. They give an order of magnitude. None of them supports saying "X% of companies".

17
AI apps with OAuth access to Workspace or 365, in the average organisation among Push Security's customers, in one week of April 2026
>15%
of users with an unauthorised AI extension in the average company, according to Verizon's 2026 breach report, built on data from dozens of partners, browser security vendors among them
58%
of AI extensions request high or critical permissions in LayerX's base, where 20.63% of users had at least one AI extension

Push itself warns that the number of grants is higher, because it counts each product only once. "The total number of individual consent grants across users is larger."

And the first door is still open. The same Verizon report says 67% of users access AI services with non-corporate accounts on company devices, and that the type of data most often sent to external models, across a base of 858,440 data loss prevention events, was source code.

02
THE QUESTION THAT REMAINS
If the administrator of your Google Workspace or your Microsoft 365 opened the list of apps with access to your accounts today, how many AI ones would they find, and for how many could they say who authorised them?

// 09

What holds

sorted by level of assurance, across both doors

It is worth separating what prevents the act from what only limits the damage afterwards.

LEVEL 1

Deterministic and verifiable

does not depend on anyone paying attention

Taking away the employee's power to sign alone

In Google Workspace, under Security, Access and data control, API controls, the setting for unconfigured third-party apps can move from "Allow users to access any third-party apps" to "Allow users to access third-party apps that only request basic info needed for Sign in with Google" or to "Don't allow users to access any third-party apps". At Microsoft, in Entra ID, Enterprise applications, Consent and permissions, user consent can be switched off, limited to apps from verified publishers and low-impact permissions, or left on the Microsoft-managed policy, which already blocks email, calendar and files. Both platforms have a flow for the employee to request approval of an app they cannot authorise alone, and it is that flow that turns an individual power of attorney into a company decision.

With that setting active, the employee's sign-up to Context would have stopped at the permissions screen, or would have become an approval request. This is my inference. Neither company says how Vercel's tenant was configured.

Restricting high-risk services

Google Workspace lets you mark Gmail and Drive as restricted services. The documentation says that, when you do, "any previously installed apps that you haven't trusted stop working and tokens are revoked". It is the only control on this list that also cleans up the past.

Extension allowlist

Chrome and Edge can, through enterprise policy, block every extension that is not on an approved list. It is an identifier comparison, which assesses neither intent nor behaviour.

Classification on the machine, before sending

For the first door, the strongest control is the one that looks at the text at the moment it is about to leave, with a deterministic rule (ID numbers with check digits, key patterns, entropy), and masks or blocks it before it reaches the vendor.

Business account instead of consumer account

Offering the tool people already use, under a business contract, swaps the training and retention clause without changing the screen the person sees. In Okta's survey, 80% of those who used AI without approval said it was because using their own account was easier.

Variables marked as secret

The environment variables Vercel says were decrypted were the ones not marked as sensitive. In its bulletin, Vercel itself recommended using the feature, so that values "are protected from being read in the future". Since August 2026 the option is called Secret, and variables marked as sensitive have moved to that type.

LEVEL 2

Strong, but only works if someone looks

the assurance depends on configuration and on people

Periodic review of the list of apps with access

The Google console lists the "accessed apps", the third-party applications that have already accessed company data, with the scopes each one requested. Entra has the review of permissions granted to enterprise applications. The information exists in both. What is usually missing is someone with a set date to open the list.

Revocation when the employee leaves

Material states that the standard suspension of an account "does not revoke third-party OAuth grants". Google's documentation says otherwise, that suspending "resets the user's sign-in cookies and OAuth tokens", and other vendors say the authorisations come back if the account is reactivated. I have not tested which holds in practice. Either way, the offboarding checklist should include revoking grants, and almost none does.

Alert on a new grant with broad scope

An unknown app receiving full access to someone's Gmail is an event worth an alert. A badly calibrated rule turns into noise nobody reads.

LEVEL 3

Does not hold this

and it is where most of the trust is placed

Written policy and a list of approved tools

In Okta's survey, only 6% of those who used AI without approval cited not knowing they needed approval. Not knowing the rule barely shows up among the reasons, and the written policy did not change the act.

Banning it

Samsung restricted generative AI on company devices and networks in May 2023. Banning it on the corporate network does not reach the personal phone or the personal account, and pushes use to where the company sees even less. Here I am giving an opinion, with no data to back it.

Multi-factor authentication

It protects the login. The power of attorney is issued after the login and works without it.

Awareness training

It teaches people to recognise phishing. From what the sources describe, the Vercel employee was not deceived by anyone and simply signed up to a tool.

03
THE QUESTION THAT REMAINS
In your company, can an employee today, alone, give an AI tool full access to their own corporate email?

// 10

Checklist for decision-makers

ordered from highest to lowest return

This week

  1. Open the list of third-party apps with access in the Google Workspace console and in Entra ID, and look for the OAuth app identifier Vercel published. If the list does not exist ready-made, or nobody knows where it is, that is the most important finding of the exercise.
  2. Check the user consent setting in both environments. In Google, the factory default lets anyone sign the power of attorney. At Microsoft, check whether the tenant is on the Microsoft-managed policy or on an old choice that allows everything.
  3. Mark as secret every environment variable and every secret the platform allows.

This quarter

  1. Switch consent to prior approval, with a request flow that answers in days, not weeks. In Okta's survey, 57% of those who used AI without approval blamed the slowness of the process. If approval takes longer than the shortcut, the shortcut wins.
  2. Offer, under a business contract, the tool people already use on their own. The list of which ones they are is, for the most part, in the apps with access you opened this week.
  3. Put revocation of OAuth grants into the offboarding checklist.
  4. Adopt an extension allowlist in the corporate browser, starting with the teams that handle customer data.
  5. Put local classification before sending on the machines that access personal data, for the first door.

In the contract

  1. With an AI vendor, require in writing the commitment not to train on the company's content and the retention period, as they appear in the OpenAI and Anthropic business terms.
  2. Require incident notification that also reaches your company's users on accounts linked to your domain, not only the contracting account. OpenAI and Anthropic already provide for linking, or informing the organisation of, accounts created with a corporate email. Ask for that to apply to incidents too.
  3. For every approved app, ask for the list of scopes and the justification for each one before authorising.

// 11

Where we differ from what circulates

seven corrections, each with the source that supports it

The Context statement changed, and then went offline

The first version of the Context statement, quoted by The Hacker News on 20 April 2026, said that "Vercel's internal OAuth configurations appear to have allowed this action to grant these broad permissions in Vercel's enterprise Google Workspace". The 21 April version no longer had that sentence. Since May the whole statement has been offline, and both versions survive only as archived copies. Anyone quoting the sentence needs to say that Context itself withdrew it.

What is said about Context that neither company says

That the Context breach began with an infostealer called Lumma, that the way in was a Chrome extension, that the attacker asked for US$ 2 million. All three claims come from threat intelligence firms or an attacker forum, and none of them appears in the Vercel or Context statements.

Samsung, in three corrections

There was no leak in the sense of theft. Employees sent content to a service the division had allowed. "OpenAI trained on Samsung's code" does not hold up. The internal memo, as Economist Korea quotes it, is conditional ("if it is learned"), and the phrase "went in as training data" is the magazine's inference. And the May 2023 ban, according to what Samsung told The Korea Herald and AFP, was communicated to the mobile and appliances division, not to the semiconductor division, where the three episodes happened.

Samsung never published a statement on the case. Everything known comes from the press. The memo it confirmed is the one announcing the May ban, and about the March episodes it told Economist Korea that, being an internal matter, it was difficult to confirm.

DeepSeek, January 2025

What Wiz found was an open database with more than a million lines of logs, with chat history and keys inside, not a million conversations. DeepSeek closed the database after being alerted, and it is not known whether anyone besides the researchers accessed it. "Several countries banned DeepSeek" lumps together measures of different kinds. Italy restricted the processing of data under the GDPR, Korea had a voluntary suspension of new downloads, and Australia and Texas banned it on government devices.

None of the four measures bars citizens from using it, and the Italian decision does not mention the exposure Wiz found.

The most repeated numbers

  • circulatedShadow AI adds US$ 670,000 to the cost of a breach.

    the source saysIt is the difference between organisations with high levels and those with low or no levels of shadow AI. The isolated effect of the factor is about US$ 200,000.

    IBM, Cost of a Data Breach 2025
  • circulatedOne in five companies has suffered a breach due to shadow AI.

    the source saysThe 20% is of 600 organisations that had already suffered a breach, not of companies in general.

    IBM, Cost of a Data Breach 2025
  • circulated78% of employees use unauthorised AI.

    the source saysIt is 78% of those who already use AI, and the question is whether the tool is provided by the company, not whether it is prohibited.

    Microsoft and LinkedIn, Work Trend Index 2024
  • circulated11% of employees paste confidential data into ChatGPT.

    the source says11% is the share of pasted content. Employees who pasted sensitive data were 4.7%, among customers of a data loss prevention product.

    Cyberhaven, 2023
  • circulated40% of companies will have a shadow AI incident.

    the source saysIt is a forecast for 2030, not a measurement, and it says more than 40%. The measured figure in the same press release is that, according to 302 security leaders, 69% of organisations suspect or have evidence of prohibited use.

    Gartner, 19.11.2025

A paid account is safe

Plus, Pro and Max are consumer plans, and can train on the content if the setting is switched on. The boundary that matters is between a consumer account and a commercial contract, and even on the commercial side there are degrees. OpenAI's Team, a business plan, was caught by the preservation order in the New York Times lawsuit.

OmniGPT

It circulates as a confirmed leak of 34 million conversations. It is a claim by an attacker on a forum, with samples considered plausible by threat intelligence firms. OmniGPT never confirmed or denied it, as of the latest source I found, from November 2025.

// 12

What I did not verify

stated, so it does not look as if I know more than I do

  • The exact scopes the Vercel employee granted to Context. Neither company published the list.
  • When the employee signed up, and when the token was used against Vercel. The sources give the month in which Context detected the breach and the publication dates, not the date of use.
  • How the Context breach began. There are reports of an infostealer and of a Chrome extension, and none of them is in the companies' statements.
  • The name of the fake tool in the Disney case and the password manager involved. The plea agreement names neither, and nor does the US Department of Justice press release, going by the reproductions I found (the site was blocked). I did not read the sentence.
  • Whether Samsung's code was ever used in training. Nobody has shown it, and OpenAI has not commented on the case.
  • What happens to OAuth authorisations when a Google Workspace account is suspended. Material says they persist, and Google's documentation says the tokens are reset. I did not test it.
  • A Brazilian shadow AI case with data exposure. I searched the courts, the ANPD (Brazil's data protection authority) and company statements, and found none. That does not mean one does not exist.

// 13

What this would require operationally

from here on I talk about what we do at Jump

Three questions came up along the way in this edition, and none of them is about Vercel.

  1. What leaves through your machines, and under which contract, when someone pastes client data into an AI chat.
  2. How many AI tools have delegated access to your company's accounts today, and who authorised each one.
  3. Whether an employee can, on their own, give a tool full access to corporate email.

If you answered all three without needing to ask anyone, skip this section. It will not add anything for you.

If you did not, this is what we deal with at Jump. From here on I talk about our product, separating what exists today from what is on the plan.

Every level 1 control in section 09 already exists, in the Google console, in Entra ID and in browser policy. What a company lacks is someone who knows, before the incident, which powers of attorney were signed, by whom, and what each one can do today.

What RADAR·AI does today

answers 01 Endpoint layer, at the first door. A browser extension and an agent on the machine classify the text right there, with deterministic rules (Brazilian ID numbers such as CPF, CNPJ and CNH, and card numbers, checked by their check digit, secrets by pattern and entropy), and mask or block the submission according to policy, before it leaves. Without verification, nothing leaves. The content does not leave the machine; only the event goes up, with the data type, the rule and the action.

answers 02 Discovery and an inventory with owners. 29 connectors read only metadata across code, cloud, data, AI providers and identity. Whatever shows up goes into an inventory with an owner and a risk level, and a system without an owner goes in as critical. In the identity connectors (Okta, Entra ID and AWS IAM), the platform reads the AI apps registered with the identity provider and the permissions they inherit.

answers 02 Reporting for the board and the regulator, generated from the recorded state, with exportable evidence and no number typed in by hand.

answers 03 Exceptions with an expiry date. Whoever requests an exception does not decide on it, and every exception expires. It is the approval flow from section 09 applied to what the policy blocked.

What is on the plan, stated as a plan

Three items on the product plan answer what this case exposes, and I name them by the names they have there.

ANSWERS 02 · PHASE 2, HIGH PRIORITY

Cross-connector correlation, which brings together into a single asset what identity, cloud, code and the AI provider see separately. In the Vercel case, the identity account, the OAuth authorisation and the environment that held the secrets were three signals in three places.

ANSWERS 01 · PHASE 2, HIGH PRIORITY

AI Gateway Lite, which brokers calls to models and logs usage, without blocking yet, and Brazilian DLP, which detects Brazilian personal data in prompts through the gateway.

ANSWERS 02 · PHASE 3

Network and DNS discovery, to see shadow AI in the traffic, and the full AI Gateway, which blocks, allows or masks calls.

The limit, said out loud

THE SECOND DOOR IS STILL A BLIND SPOT IN THE PRODUCT

The platform has no Google Workspace connector, and Google Workspace was the door in the Vercel case. There, an authorisation like the one the employee gave Context does not show up in our inventory. The platform does not inventory the extensions installed in browsers either. I would rather say this here than let you find out at the end.

Active protection sits on the endpoint. Until the gateway arrives, a model call that does not pass through a machine running the agent is neither seen nor blocked by RADAR·AI.

And RADAR·AI does not claim that an account is personal. The most it records is "outside the corporate tenant", because claiming more would require evidence only the provider has, and claiming without evidence is exactly what I criticise in others.

The one who closes the second door is the Workspace and Entra administrator, in each one's console. We do not carry out that configuration for you and will not suggest that we do. What an inventory changes is the moment you find out it was open.

Certification does not prevent an incident, but it forces you to ask the question firstJump is certified to ISO/IEC 42001, and that is no insurance against an incident. It does not stop someone at Jump itself from clicking "allow all" on a tool nobody approved.What the standard requires is that the question be asked beforehand. A documented purpose for each AI system, a named owner, an impact assessment, vendor control.A tool that comes in through an employee's consent screen skips every one of those steps, and that is why the question of who can authorise on their own needs a written answer.

What we do is answer the three questions at the start of this section.

And do it before a third party answers them for you.

// 14

Primary sources

all read directly; no third-party summary was used as a source

  • Vercel · Vercel April 2026 security incident · , updated through
    vercel.com · vercel.com/changelog
    The origin at Context, the path to the environment variables, the OAuth app identifier, the timing of the updates and the recommendations. The changelog records the replacement of "Sensitive" by the Secret type.
  • Context · Security Incident Response Statement · , updated
    web.archive.org (offline at context.ai since May 2026; archived copy of 21.04.2026)
    The consumer product, the AWS intrusion in March, the "allow all", the sentence "Vercel is not a Context customer" and the stated purpose of the permissions.
  • IBM and Ponemon Institute · Cost of a Data Breach Report 2026 · ; and Cost of a Data Breach Report 2025 ·
    ibm.com
    The 43% of incidents involving shadow AI, the decline in prior approval and in audits, the definition of shadow AI, and the origin of the 2025 figures that circulate in distorted form.
  • Google · Control which apps access Google Workspace data; Control which third-party & internal apps access Google Workspace data; Identify and secure compromised accounts · read on
    support.google.com · support.google.com · support.google.com
    The default setting for third-party apps, the restriction options, the list of apps that have already accessed data, token revocation when services are restricted, and what account suspension does to tokens.
  • Microsoft · Configure how users consent to applications; Manage app consent policies · read on
    learn.microsoft.com · learn.microsoft.com
    The Microsoft-managed policy as the default and the permissions it blocks, the restriction options, the approval workflow and the fact that the change does not reach what has already been granted.
  • Verizon · 2026 Data Breach Investigations Report · 2026
    verizon.com
    Unauthorised AI extensions on more than 15% of users, 67% of access through non-corporate accounts, and source code as the data most often sent to external models.
  • Push Security · Shadow AI: what Push data reveals about the scale of the problem ·
    pushsecurity.com
    The 17 AI apps with OAuth access in the average organisation, and the caveat that it counts products, not grants.
  • Material Security · The Access You Forgot You Granted: Material's OAuth Risk Report ·
    material.security
    Access that persists after use, across 21 Google Workspace environments, and the claim about account suspension.
  • LayerX · Enterprise GenAI Security Report 2025 ·
    layerxsecurity.com
    AI-enabled extensions on 20.63% of users, 58% of them with high or critical permissions.
  • Okta · AI Agents at Work 2026: Securing the agentic enterprise ·
    okta.com
    The 52% of AI users who use it without approval, the 6% who did not know the rule, and the reasons given.
  • OpenAI · How your data is used to improve model performance; Privacy policy, ; How we're responding to The New York Times' data demands, , updated
    help.openai.com · openai.com
    Training on consumer and business accounts, Team (now Business) as a business plan, linking the account to a corporate email address, the scope of the preservation order and its end on 26.09.2025.
  • Anthropic · Updates to Consumer Terms and Privacy Policy, ; Privacy Policy, in force since ; Commercial Terms of Service
    anthropic.com · anthropic.com/legal
    Training on consumer accounts, the prohibition in the commercial terms and linking the account to a corporate email address.
  • US District Court for the Central District of California · United States v. Ryan Mitchell Kramer, plea agreement ·
    courtlistener.com
    The Disney case: the fake AI tool, the work credentials and the 1.1 TB from Slack.
  • Koi Security · First Malicious MCP in the Wild, ; 8 Million Users' AI Conversations Sold for Profit by "Privacy" Extensions,
    web.archive.org · web.archive.org
    The postmark-mcp package and the Urban VPN extensions. Published on koi.ai, which now redirects to Palo Alto Networks, Koi's acquirer; read in archived copies.
  • Postmark · Information Regarding Malicious "postmark-mcp" Package ·
    postmarkapp.com
    The vendor's confirmation that the package was not theirs.
  • Radware · ShadowLeak ·
    radware.com
    The demonstration with ChatGPT connected to Gmail.
  • Invariant Labs · GitHub MCP Exploited: Accessing private repositories via MCP ·
    invariantlabs.ai
    The proof of concept with private repositories and the authors' statement about the server code.
  • Google Threat Intelligence Group · The Cost of a Call: From Voice Phishing to Data Extortion · , updated
    cloud.google.com
    UNC6040 and the employees persuaded to authorise a connected app.
  • Economist Korea · exclusive report on ChatGPT use at Samsung ·
    economist.co.kr
    The origin of the Samsung case: the three incidents, the go-ahead in the semiconductor division and the conditional memo.
  • Wiz Research · Wiz Research Uncovers Exposed DeepSeek Database Leaking Sensitive Information ·
    wiz.io
    The exposed database, what it contained and the coordinated disclosure.
  • ANPD · Guia de agentes de tratamento e do encarregado (versão 2); Resolução CD/ANPD nº 19, ; Radar Tecnológico nº 3,
    gov.br/anpd
    The company's responsibility, the definition of transfer and the acknowledgement of the problem in a technical study by the agency, Brazil's data protection authority.
  • Microsoft and LinkedIn · 2024 Work Trend Index Annual Report ·
    microsoft.com
    The 78% of AI users using tools not provided by their company, and the exact survey question.
  • Cyberhaven · 11% of data employees paste into ChatGPT is confidential · , later updated
    cyberhaven.com
    The origin of the figure that circulates in distorted form.
  • Gartner · Gartner Identifies Critical GenAI Blind Spots That CIOs Must Urgently Address ·
    gartner.com
    The 2030 prediction and the measured figure that accompanies it.

THE SERIES

  1. 01
    The agent cannot tell what it read from what it was told to dopublished 21.09.2026 · five verified cases
  2. 02
    The agent was not tricked. They used its badgepublished 22.09.2026 · non-human identity and the Salesloft Drift case
  3. 03
    Shadow AI: the AI use the company never authorisedyou are here · AI at work, outside what was approved

all editions and who writes them

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> NEXT STEP

Do you know how many AI tools have access to your company's accounts?

That is the question Vercel asked every Google Workspace administrator to answer "immediately". If you do not have that list to hand, or you have it and nobody knows who authorised each item, get in touch. The conversation is usually shorter than the document.

AUTHOR
Rafael Yashiki CapuaCOO & Co-Founder, Jump linkedin.com/in/rafael-yashiki-capua-863812b8
COMPANY
Jumpdata and artificial intelligence
jump.tec.br/governanca-de-ia