Russia has hit Google with a 21.1bn rouble ($373m; £301m) fine for failing to restrict access to "prohibited" material about the war in Ukraine and other content.
Roskomnadzor, the country's communications regulator, said the information included "fake" reports that discredited Russia's military and posts urging people to protest.
It called the US tech giant a "systematic" violator of its laws.
Google did not comment immediately.
The company's local subsidiary declared bankruptcy last month. The move came after Russian authorities seized its local bank account, allowing them to recover 7.2bn roubles that the firm had been ordered to pay for similar reasons last year.
In recent years, Russia has been ramping up pressure on tech firms, accusing them of not moderating their content properly, and interfering in the country's internal affairs.
The efforts to control social media and other news sites have escalated following the invasion of Ukraine in February. The government also passed a law threatening people who spread "fake" information about the war with 15 years in prison.
In March, Google, owned by Alphabet, stopped offering its commercial services in Russia, such as advertising. It has also stepped up its restrictions for news accounts backed by Russia and relocated staff.
However, unlike some other social media sites, such as Facebook, it has not been completely banned in Russia, where many smart phones rely on the company's technology.
In March, Alphabet said the decision to continue offering search, maps and YouTube provided Russians with access to "global information and perspectives".
The fine announced on Monday, which was calculated as a share of the firm's local revenue, marks the biggest penalty ever imposed on a tech company in Russia, according to state media.