The Russian prosecutor general's office on Wednesday declared The Moscow Times, an online newspaper popular among Russia’s expatriate community, as an “undesirable organization.”

The designation comes amid a crackdown on critical news media and the opposition. It means the newspaper must stop any work in Russia and it subjects any Russian who cooperates with the paper to up to five years in prison.

It is a more severe measure than the “foreign agent” designation applied to the news outlet in November, which subjects individuals and organizations to increased financial scrutiny and requires any of their public material to prominently include notice of being declared a foreign agent.

The Moscow Times already moved its editorial operations out of Russia in 2022 after the passage of a law imposing stiff penalties for material regarded as discrediting the Russian military and its war in Ukraine.

It publishes in English and in Russian, but its Russian-language site was blocked in Russia several months after the Ukraine war began.

The publication began in 1992 as a daily print paper distributed for free in restaurants, hotels and other locations popular with expatriates, whose presence in Moscow was soaring after the collapse of the Soviet Union. It later reduced its print edition to weekly, then became online only in 2017.

Russia in recent years has methodically targeted people and organizations critical of the Kremlin, branding many as “foreign agents” and some as “undesirable." Other news outlets declared as undesirable include the independent newspaper Novaya Gazeta, whose editor Dmitry Muratov won a Nobel Peace Prize, and and the online news site Meduza.

Russia also has imprisoned prominent opposition figures including anti-corruption campaigner Alexei Navalny, who was President Vladimir Putin’s most persistent domestic foe, and dissidents Vladimir Kara-Murza and Ilya Yashin.