I Went Looking for Hidden Money in an AI App. I Found Something Worse.
A Cyprus company that turned out to be innocent, a tidy explanation that fell apart, and one button on a website that undoes Apple's entire content policy from an iPhone.
Part of running Frontier Watch is reading privacy policies almost nobody reads, and providing a score so that you know what the app does with your data, and what level of control you have.
In Janitor AI’s policy, section 7, I found a company that triggered one of my red flags. Payment processing, it said, is handled by “JanitorAI Inc. and its affiliates, including Dulova Investments Limited,” registered at 10-12 Florinis Street in Nicosia, Cyprus.
Cyprus got my attention because for twenty years it’s been the European address of choice for Russian and post-Soviet money via nominee directors and holding companies. So I pulled on that thread for a few hours, looking for a possible Russian connection.
Theory one: the hidden owner
The Cyprus Registrar of Companies keeps a public record of directors, secretaries, and shareholders. Dulova’s record is plain. Incorporated on 12 July 2025. The sole shareholder, holding all 1,000 shares is JanitorAI Inc., a Delaware company.
Dulova’s director is TMF Management Limited, a corporate nominee from a large and entirely legitimate services firm. Ownership ran straight up, one level, to the United States.
I checked the other direction too. No employees. No Russian corporate filings. No Cyrillic-web footprint of any kind. The company behind it, JanitorAI Inc., is a San Francisco startup with an Australian founder and a $3 million seed round from name-brand venture funds.
My Russia connection theory evaporated, but I was still curious about why Janitor AI is using a Cyprus billing company?
Theory two: the payment exile
Janitor AI is an 18+ adult content platform. Uncensored sexual roleplay in the style of dark, sexually-explicit romance novels is the entire pitch. And I confirmed straight from Stripe’s own rulebook that Stripe does not process payments for sexually explicit material. That results in my second theory - Janitor sells what the mainstream payment processors will not touch, gets cut off from the normal rails, and has to build its own: a high-risk processor and an offshore company in Cyprus to take the money.
Then I read Janitor’s own help page. “All payments are securely handled by Stripe.”
Theory two collapses, but now, in addition to the Dulova question, I want to learn why Janitor AI has not been bumped off Stripe for violating its Terms of Service for adult content as well as how it manages to be available for download in Apple’s App Store?
The Federal Loophole
After further investigation, I learned that the U.S. Code that regulates pornography is built around visual depictions. If it’s just text-based, such as erotic fiction, there’s no violation.
Stripe and Apple, however, do prohibit adult-themed companies from using their services.
Unlike federal law, Stripe’s prohibited list does not stop at pictures. It bans “pornography and other mature audience content (including literature, imagery, and other media) designed for the purpose of sexual gratification.” From a digital perspective, “literature” or story-telling is done via text on a chat platform.
Apple’s App Store guidelines (Janitor AI has an iOS app) prohibit “explicit descriptions or displays of sexual organs or activities intended to stimulate erotic rather than aesthetic or emotional feelings.”
So Janitor occupies a strange spot.
While complying with federal law, it violates the written content policy of both companies standing between it and its customers’ money. It runs on Stripe anyway, almost certainly onboarded as an ordinary “AI software subscription,” in quiet breach of a rule Stripe simply has not enforced.
That precariousness, an account that lives against the processor’s own terms until the day it doesn’t, is the best explanation I have for why the merchant (Dulova) is a disposable Cyprus subsidiary and not the US parent (Janitor AI, Inc.). Ring-fence the account that can vanish, and a shutdown takes the subsidiary instead of the company. That’s assuming that Stripe eventually figures out that Janitor AI is in violation of Stripe’s ToS.
Bypassing Apple’s App Store Policy for NSFW Apps
Apple’s anti-NSFW app rule is the same story as Stripe’s, with one difference. I could watch it fail in real time.
Janitor stays in the App Store by shipping the iPhone app with its adult content switched off. That is the version Apple reviews and approves. Janitor’s own help center is candid about it: NSFW is “disabled by default on the mobile application,” while the website “remain[s] completely unchanged.” In other words, Janitor AI provides a clean app for Apple’s developer review, and an unfiltered one for the web.
So I tested how solid that wall is. I created an account. I installed the clean, Apple-approved app on my iPhone. Then I opened Janitor’s website in a browser, clicked a button confirming I was eighteen or over, and switched on a single setting labeled “Enable NSFW on Mobile.” I reopened the app. It was no longer clean. The product Apple reviewed and the product in my hand were now two different things, and the distance between them was one toggle and one unverified click that any 10 year old could do.
That click is the entire age check that supposedly keeps vulnerable children off a very explicit NSFW platform, and the app that Apple rated as safe, immediately becomes unsafe. This is an AI safety issue that demands attention by regulators as well as its users. Guardrails cannot be so easily circumvented or they aren’t guardrails at all.
Q16’s Privacy Watch
I started Q16 with Rachel Grunspan, a retired CIA game designer and futurist, as a Public Benefit Corporation with two missions: independent, public-interest measurement of the trajectory toward advanced AI (Frontier Watch), and monitoring of how the labs building it treat user data (Privacy Watch).
If you visit our dashboard, you can see Privacy scores for 10 U.S. and Chinese AI Models, and 12 consumer AI apps.
How we review a privacy policy
Every Frontier Watch rating runs the same way, and none of it takes a company’s word for it.
Read the binding documents, the privacy policy and terms, including any parent policy an app defers to, and score what they say across six dimensions: training use, retention, jurisdiction, sharing, user control, and transparency. A policy silent on a protection scores low; absent evidence is treated as absent.
Score 0 to 10, by a person, not a model, and tag each score by confidence: contract-backed, policy-based, inferred, or not yet assessed.
For apps, trace the chain to the model provider behind them and score every link. We publish the app’s own score and an Effective score set by the weakest link. Child-safety is scored separately, beside privacy, not blended in.
Verify against primary sources, then keep watching. An aggregator or an AI summary is a lead, not evidence. We re-score when policies change, test the product ourselves when the documents run out, and re-score any evidence-backed dispute within ten business days.
How to support the work of Q16
You can learn more about what we do and how you can support this work by visiting Q16 and then checking out the dashboard. There’s a free version and a membership version, or you can contact us for more information at info@q16pbc.com.
We will have a panel discussion on AI risk and the trajectory towards AGI and Superintelligence at the Whitefish Security Summit in Whitefish, Montana on February 24-26, 2027. Get your tickets today at www.whitefishsecuritysummit.com.