A Canadian man has pleaded guilty to charges related to a 2014 hack attack at Yahoo, which affected 500 million user accounts.
Described by US law officials as a "hacker-for-hire", Karim Baratov admitted hacking web-mail accounts on behalf of the Russian Federal Security Service (FSB).
The number of hacked accounts is disputed.
His lawyers also say he did not know he had been working for Russian agents.
Three other individuals have been charged over the hack but have not been arrested because they live in Russia, which has no extradition treaty with the US.
Prosecutors have said two of them are FSB officers.
According to court documents issued by the Northern District of California's US Attorney's Office, Baratov's role in the hack was to access the individual web-mail accounts of users whose data had been stolen in the Yahoo attack at a number of other internet service providers - such as Google and Yandex - and send those account passwords to one of the Russian agents in exchange for money.
According to the US Department of Justice, he used spear-phishing schemes that would trick victims into entering their account credentials into web pages that he had built to mimic official web-mail provider's sites.
Baratov will be sentenced in February and faces up to 28 years in jail.