Sunday Yokubaitis, president of Golden Frog, a company that makes privacy and security software including VyprVPN, said its software, too, had been taken down from the app store. We gladly filed an amicus brief in support of Apple in their backdoor encryption battle with the F.B.I., he said, so we are extremely disappointed that Apple has bowed to pressure from China to remove VPN apps without citing any Chinese law or regulation that makes VPN illegal.

He added, We view access to internet in China as a human rights issue, and I would expect Apple to value human rights over profits.

In a statement, Apple noted that the Chinese government announced this year that all developers offering VPNs needed to obtain a government license. We have been required to remove some VPN apps in China that do not meet the new regulations, the company said. These apps remain available in all other markets where they do business.

This is not the first time that Apple has removed apps at the request of the Chinese government, but it is a new reminder of how deeply beholden the tech giant has become to Beijing at a moment when the leadership has been pushing to tighten its control over the internet.

The removals signal a new push by China to control the internet. In the past, the Great Firewall has used technology to disrupt VPNs, and Beijing has shut down Chinese VPNs and even aimed a huge cyberattack at a well-known foreign site hosting code that circumvented the filters.

But they also mark the first time China has successfully used its influence with a major foreign tech platform, like Apple, to push back against the software makers.

While internet crackdowns often peak every five years, ahead of a key Chinese Communist Party congress, this years efforts cover fresh ground, a likely indication that stricter controls of things like VPNs will persist after the congress this autumn. Earlier this month, China also began a partial block of the Facebook-owned messaging app WhatsApp.

Greater China is Apples largest market outside the United States. That has left the company more vulnerable than almost any other American technology firm to a Chinese campaign to wean itself off foreign technology and tighten control over foreign tech companies operating there.

In response, Apple has made a number of moves to ensure that it stays on Beijings good side. Last year, the company complied with what it said was a request from the Chinese authorities to remove from its China app store news apps created by The New York Times.

This month, the company said it would open its first data center in China to comply with a new law that pushes foreign firms to store more of their data in China.

Apple has operated its app store in China for many years with only the occasional run-in with the government. The VPN crackdown and Beijings move in December to target news sites indicates that Chinas internet regulators have taken a deeper interest, and are exerting more control, over what is available on Apples China app store.

An earlier version of this article misspelled the name of the software produced by Golden Frog. It is VyprVPN, not VyperVPN.

Carolyn Zhang contributed research from Shanghai.

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Apple Removes Apps From China Store That Help Internet Users Evade Censorship - New York Times