The Constitution of Russia was adopted in 1993, limiting the President of Russia to no more than two consecutive four year terms. Boris Yeltsin was the incumbent president when the constitution came into effect and had already served for over two years. Yelstin was reelected in 1996, but he resigned near the end of his term in 1999, and Prime Minister Vladimir Putin served for the remainder of Yeltsin’s term as acting president. Putin was elected to a full term in 2000 and reelected in 2004.

Putin was not constitutionally permitted to run for reelection in 2008, so he endorsed First Deputy Prime Minister Dmitry Medvedev, who went on to become the next president. The day after Medvedev’s inauguration, he appointed Putin as Prime Minister of Russia. While Putin did not hold the office of president for the following four years, he held de facto control over the country’s executive, extending his tenure beyond what term limits would normally allow.

The Constitution was amended in 2008, expanding the presidential term from four to six years following the 2012 election. Having been removed from the office of the presidency for a term, Putin was constitutionally eligible to run again and was elected president in 2012 and then reelected in 2018. The Constitution was amended in 2020 to reset the number of terms Putin has served, allowing him to circumvent term limits in the 2024 and 2030 elections, enabling him to legally stay in office until 2036.

So I guess he first broke the rules in 2004 if you count his time as acting president, but I think it’s no longer up for debate after 2008.