Tim Cook, chief executive of Apple, attends the second day of the annual Allen & Company Sun Valley Conference on July 12 in Sun Valley, Idaho. (Drew Angerer/Getty Images)

Last December, when the chieftains of some of the largest and most influential technology companies agreed to meet at Trump Tower in New York with then president-elect Donald Trump, some suggested the business titans had little to gain and everything to lose.

Following the tech summit, however, Apple chief executive Tim Cook defended his choice to attend, and to sit alongside the new president after an especially divisive election. “Personally, I’ve never found being on the sideline a successful place to be,” Cook said in a Q&A with Apple employees. “The way that you influence these issues is to be in the arena. So whether it’s in this country, or the European Union, or in China or South America, we engage. And we engage when we agree and we engage when we disagree. I think it’s very important to do that because you don’t change things by just yelling. You change things by showing everyone why your way is the best.”

But in the months since that meeting, it's not clear whether Cook's diplomatic approach to the Trump administration has produced any change. Over vocal objections from the tech industry, Apple included, Trump followed through with his decision to impose a travel ban on visitors from several Muslim-majority countries. And on Wednesday, the president endorsed a bill in the Senate aimed at slashing legal immigration levels, profoundly changing immigration policies that have been in place for decades. Even after a personal call from Cook, Trump also withdrew the United States from the Paris climate agreement, an abrupt move that prompted Tesla's Elon Musk and Disney's Bob Iger to resign from the president's economic advisory council.

Beyond issues here at home, Cook's propensity to engage and his desire to “be in the arena,” has led him to take a similar, conciliatory approach in China.

During an earnings call Tuesday evening, Cook defended the company's decision to remove virtual private network applications (VPNs) from the Chinese App Store this weekend, following heightened enforcement from Beijing to restrict such tools. In China, people can use VPNs to get around the government's “Great Firewall” by making it appear like they are browsing the Web from another country. Rather than pull out of China — one of Apple's biggest markets, with more iPhone owners than exist in the United States — Cook argued that adhering to the restrictions would better serve the company and the Chinese people. And he said he hopes the censorship rules will loosen over time.

But experts say the opposite is more likely to happen: Governments around the world are amplifying their efforts to censor speech, not ease restrictions. And Apple's ability to exert influence over Chinese policy is also in doubt, especially as Beijing seeks to prop up its own domestic tech industry to supplant American platforms and reduce the Asian nation's reliance on foreign businesses.

“The Chinese have not been convinced that an open Internet is good for them,” said Adam Segal, the director of the Digital and Cyberspace Policy Program at the Council on Foreign Relations. “There is no case I can think of where tech companies have convinced the Chinese to change their mind on censorship.”

As with Google and Facebook, which have been banned in the country, Segal said the common refrain among American technology companies is to hold out hope that China will liberalize its policies, opening a wider space for U.S. firms to operate and expand. “You could make the argument that perhaps Apple is differently positioned — it is a product that Chinese users have embraced,” he said. “But the longer-term trends have certainly been more censorship.”

Others point to Apple's economic entanglement in the country.

“Apple is not just participating in the consumer market in China, it also manufactures a significant portion of its products in China. So this is a really extraordinarily difficult circumstance that Apple finds itself in,” said Chris Calabrese, the vice president for policy at the Center for Democracy & Technology, a Washington-based advocacy group that champions free speech and human rights.

Apple could make the monumental choice to leave the country, but Calabrese doubts that taking a dramatic stand in that way would actually bolster freedom of expression in China. “It’s not clear to me that another actor would step forward and would do a better job of providing services like VPNs than Apple,” he said.

Still, Cook's support for free expression could resonate with Apple users in the country, perhaps leading Chinese officials to adopt policies backed by citizens, said Ryan Hass, a fellow at the Center for East Asia Policy Studies at the Brookings Institution. The tension between intense censorship and economic growth could also resolve itself in Apple's favor, he said. But for now, the desire for government control is so strong, Beijing will probably be immune to public pressure. “Apple is playing the long game,” he said.