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VPN Red Flags: How to Spot Criminal Adjacency

VPN red flags illustration showing a smug raccoon mascot wearing mirrored sunglasses indoors inside a server room, projecting suspicious confidence and secrecy.
Their commitment to privacy raised several entirely unrelated questions.”


Cybersecurity experts have cautioned internet users to  be aware of VPN red flags after the Russian-based First VPN was shut down following reports that more than two dozen ransomware gangs around the globe had been using it to conceal their activities.

The VPN advisory was issued by the Center for Digital Ambiguity, a nonprofit organization best known for publishing annual reports ranking the nation’s most suspicious browser tabs.

“People deserve clear guidance,” said Trevor Bellamy, 51, a cybersecurity consultant from Arlington, Virginia, whose previous research helped identify the exact moment a software update becomes a hostage situation.

“Many users have no idea whether their VPN is not only protecting their privacy but also quietly serving as the preferred transit lounge for organized cybercrime.”

Bellamy stressed that merely sharing infrastructure with international extortionists does not make a customer a criminal, although he acknowledged it can create “awkward conversational moments and demands for receipts.”

To assist consumers, Bellamy identified the following warning signs that will help them  determine if their VPN is criminal adjacent.

  1. The customer support chatbot refers to you as “Associate.”
  2. The service’s premium tier includes “covert relocation.”
  3. Its privacy policy contains a section titled In the Event of Extradition.
  4. Every server location is listed as “Undisclosed Warehouse.”
  5. The company mascot wears mirrored sunglasses indoors.
  6. Login verification requires answering the question, “Who sent you?”
  7. Technical support responds exclusively through burner phones.
  8. It markets itself on Russian-language cybercrime forums.
  9. The VPN congratulates you for successfully connecting to three continents simultaneously.
  10. The terms of service repeatedly mention international waters.

The Center for Digital Ambiguity’s findings resonated with Marsha Keene, 44, an accountant from Columbus, Ohio, who believes every life problem can be solved with conditional formatting. Keene said she first became concerned when her VPN dashboard displayed a loyalty badge reading Level Four Accomplice.

“I assumed it was gamification,” Keene explained. “Everything online has badges now. Last week my grocery app awarded me Platinum Banana Status.”

Meanwhile, Derek Holloway, 37, a freelance technology reviewer from Portland, Oregon,  received a customer satisfaction survey asking him to rate his recent money-laundering experience on a scale of one to ten.

“Most VPN users are ordinary people,” said Holloway, who subscribes to three newsletters dedicated to reducing digital clutter, all of which arrive daily. “They just want to browse the internet without being tracked by seventeen different advertisers.”

At press time, millions of Americans were reassuring themselves that their VPN was perfectly legitimate because its logo featured a smiling mountain, which has never been associated with criminal activity in any form whatsoever.

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