A Moscow court has fined Google 7.2bn rubles ($98m; £73m) for repeated failure to delete content deemed illegal in Russia.
Details of the offending content were not specified in the announcement by the court's press service.
This is the first time in Russia that a technology giant has been hit with a fine based on their annual turnover.
Google told AFP news agency that it would study the court ruling before deciding on further steps.
Russian authorities have increased pressure on tech firms this year, accusing them of not moderating their content properly, and interfering in the country's internal affairs.
Hours after the Google verdict was announced, a 2bn rouble fine was handed to Meta, the parent company of Facebook, for similar content-related offences.
The same offense landed Google with fines of 700,000 rubles and 1.5 million rubles in 2019 and 2020, respectively. This time last year, a Russian court found Google guilty of repeatedly failing to delete search results “containing information prohibited in Russia” and fined the company three million rubles (around $41,000).
Google told The Verge in a statement it will "study the court documents when they are available and then decide on next steps".
Earlier this week, Twitter was also fined 3 million rubles ($40,000) for its failure to purge banned content.
According to Roskomnadzor, Facebook and Instagram have failed to remove 2,000 pieces of content and Google failed to purge nearly 2,600 such items.
Russian officials have also asked Google and Apple to remove political opponents' voting apps from their app stores "by threatening to prosecute the companies' locally-based employees", the report said.
President Vladimir Putin has pushed for development of a so-called sovereign internet, which would give the government more control over what its citizens can access.
Critics have accused Russia of using the campaign to clamp down on free speech and online dissent.
The country's media regulator has blocked dozens of websites linked to jailed opposition leader Alexei Navalny, whose campaign groups have been labelled "extremist".
Google and Apple were also forced to remove an app dedicated to Navalny's "Smart Voting" campaign, which gave users advice on tactical voting to unseat Kremlin-aligned politicians.
Websites like LinkedIn and Dailymotion have already been blocked for refusing to co-operate with authorities, and six major providers of Virtual Personal Networks (VPNs) - which help users to conceal their online activities - have been banned.
Earlier this year, Russia also introduced a new law requiring all new smartphones, computers and smart devices sold in the country to be pre-installed with Russian-made software and apps.
The government said the move would help Russian tech firms compete with foreign rivals.
The fine follows legislation signed into law by Putin in July that requires large social media companies that operate in Russia to open an office in the country by January 1 2022 and maintain a physical presence there. Failure to comply with the law could result in restrictions or total bans.
(Only the headline and picture of this report may have been reworked by the Biovolt Technologies staff; the rest of the content is auto-generated from a syndicated feed.)