When Apple and Google removed an election app created by jailed Russian opposition leader Aleksei Navalny from their online stores just as the country's three-day parliamentary vote got under way, his associates were dismayed -- and criticized the U.S. tech giants for giving in to the Kremlin's demands.
There was not much Navalny's allies could do about it, however. And the developments showed that in the battle between the trillion-dollar tech companies and the authoritarian leaders of major economies -- especially those willing to resort to extra-legal means -- the latter may have a stronger position, analysts say.
Russia reportedly raised the possibility of criminal charges against the tech giants' local employees. Given that critics say President Vladimir Putin's government uses trumped-up charges to sideline opponents such as Navalny, that would be a prospect it would be hard to take lightly.
"I don't think they have a lot of choice," Adam Segal, director of the Digital and Cyberspace Policy program at the Council on Foreign Relations in New York, told RFE/RL. "Unless they're willing to give up the Russia market -- which I don't think they are -- I don't think they have a lot of leverage on their own."
Be that as it may, Internet freedom advocates say the companies must fight as hard as they can because authoritarian regimes around the world are watching what happens in places like Russia.
"While companies are understandably concerned for their in-country staff, they also have a responsibility to respect rights," Deborah Brown, a senior researcher and digital rights advocate at Human Rights Watch, wrote in an article published on September 21.
"We definitely don't want tech companies to capitulate in these cases and this decision [by Apple and Google] is concerning," Grant Baker, a research associate focusing on technology and democracy at Washington-based Freedom House, told RFE/RL.
However, Baker says the companies are in a "tough position" because they have to look out for the safety of their employees while also trying to fulfill their obligation to uphold freedom of expression.
And Segal said that because of the divide in the United States over the role of big tech, companies may not be receiving the vocal support they might have in the past in standoffs with authoritarian regimes. "Pushback from the U.S. government...is pretty unlikely these days," he said.
Neither Apple nor Google immediately responded to e-mails and phone calls from RFE/RL seeking comment.
When contacted by RFE/RL, the U.S. State Department declined to comment on the decision by the tech giants, limiting itself to saying that all people have the right to speak freely and that societies "are strengthened, not threatened, by expressions of opinion and dissent, including through the Internet."
For weeks before the September 17-19 voting for the State Duma, Russia's lower house of parliament and a key lever of power for Putin, Moscow had pressured the U.S. companies to remove the app on the grounds that it was promoting the activities of an extremist organization banned in Russia.
Russia in June declared Navalny's Anti-Corruption Foundation and other organizations he founded "extremist" groups, outlawing them in what rights activists said was a baseless and politically motivated attempt to destroy his national network and blunt his challenge ahead of the elections.
His own political movement gutted by the state, Navalny called on his supporters to vote for candidates running against the ruling United Russia party. The Smart Voting app informed citizens which candidate in a particular district had the best chances of defeating the Kremlin favorite.
The goal was to chip away, race by race, at United Russia's chances of holding on to its two-thirds majority in the Duma, which the party needs to pass constitutional amendments without support from other deputies in the 450-seat chamber.
WATCH: How Navalny's 'Smart Voting' Works
The two tech giants defied Russia's request until the first day of the elections. They may have caved when Russia reportedly raised the prospect of opening criminal cases against local staff.
The New York Times reported that Russian authorities named specific individuals at Google who would face prosecution if the app was not deleted, citing a person whom it did not name but said was familiar with the tech company's decision. News agency AFP quoted an unidentified source it said was familiar with Apple's situation as saying that its employees faced "threats of arrest."
Vladimir Dzhabarov, a member of Russia's upper house of parliament who is also an officer with the Federal Security Service, Russia's main domestic security agency, asserted the day before the start of the vote that Apple and Google were committing "specific crimes" and that individuals "contributing to their parent companies' evasion" of Russian law "will be punished."
Analysts say Russia has several factors in its favor in its fight against social-media and tech companies: the size and spending power of its population, a competitive domestic tech industry, and disagreements within and between democracies over how to regulate the industry.
Russia is the world's ninth-largest country by population and 11th by economic output. Moreover, its citizens are active Internet users, with 87 million Russians surfing the web every day.
That makes the country an important market for U.S. tech firms like Apple, Google, Facebook, and Twitter.
Russia is the fifth-largest market for Facebook's photo-sharing app, Instagram.
At the same time, Russia has been tightening the screws on the Internet and social media in particular over the past decade as more citizens turn to online sources for news, loosening the Kremlin's control over the dissemination of information.
In July, Putin signed a bill requiring foreign tech companies with more than 500,000 Russian users to set up a representative office in Russia, a move that may sound benign but would give the authorities the ability to hold local company employees liable for decisions the government doesn't like.
"If you have a representative office, the pressure is already there," Baker said.
Russia is by no means alone, or even first, to take that step. Turkey, Indonesia, and India -- whose governments, like Russia's, have all grown more authoritarian in recent years -- have passed legislation requiring tech companies to have local representative offices.
Brown, of Human Rights Watch, wrote that "the spate of 'hostage-taking' laws being adopted in several countries that require companies appoint in-country representatives may mean a wave of corporate-assisted censorship is on the horizon."
India, the world's biggest untapped technology market, earlier this year threatened to jail local Twitter executives if they refused to follow government orders to take down content it deemed dangerous.
In a vivid sign of the economic consideration that can come into play when dealing with government control of the Internet, a Facebook executive in India last year sought to block efforts to apply the social-media company's hate-speech rules to some Hindu nationalist politicians and groups over concern it would hurt their business prospects in the country.
Whether U.S. tech giants give in to government demands "usually comes down to the size of the market, and the willingness of companies to stand up and perhaps threaten to leave," Segal said.
Another key element in the decision-making process is the dependence of the country on their technology platforms, he said.
Here, Russia has an advantage over countries like Turkey, India, and Indonesia. Russia's domestic social-media, e-commerce, and search companies are competitive at home with the U.S. giants, giving the Kremlin more leverage.
And that edge may be growing as Putin's government tosses money at building up its domestic industry, such as RuTube, the country's answer to Google's YouTube, the platform successfully used by Navalny to disseminate his exposes on corruption at the highest levels of the Russian government.
Andrei Soldatov, a journalist who specializes in Russian technology, says global platforms like YouTube are becoming replaceable, sapping their strength in their battle with the Kremlin.
"You might have billions of users, but if the local government decides to attack your company very few of them will do anything about it," Soldatov said in an opinion article in The Moscow Times on September 20.
The international debate over how to regulate social-media companies, and deep divisions on the issue in the United States, serve as wind to Russia’s back in its struggle against the tech giants, analysts said.
"Liberal democracies are having debates these days about what type of material they keep up, what types of material they take down, what's legal, what's illegal," Segal said, adding that Russia can cherry-pick to defend its actions.
Turkey, a NATO member, has been aggressive in its attempts to censor social media. Ankara has accounted for 27 percent of all legal demands to remove or withhold content on Twitter, surpassing Russia at 20 percent, according to data published on the tech company’s website.
India, sometimes referred to as the world's largest democracy, accounts for 6 percent of all legal demands posed to Twitter while the United States is less than 1 percent.
Baker said that what he called the U.S. government's "laissez faire" approach to technology regulation over the years has enabled other countries -- both democracies and authoritarian states -- to put forth their own models. He believes Washington should take a more active role in building a regulatory framework.
"Democratic countries need to take the lead in this," he said, adding that building a transparent regulatory framework for tech companies would not stop every violation by governments, but "it would probably contribute to a safer and more open Internet."