Vladimir Putin, the Russian president, arrived in Germany to protests over his human rights and democracy record and a warning from German Chancellor Angela Merkel that Russia needed an active civil society to flourish.
Protesters carried Syrian flags while others wore devil masks, waving images of Putin dressed in a prisoner's striped uniform. "Stop political terror", read one banner.
Putin's visit to Germany and the Netherlands, Moscow's biggest trade partners in Europe, was supposed to focus on trade.
However, the trip has been overshadowed by a wave of state inspections of foreign-funded non-governmental organisations (NGOs) in Russia, much criticised abroad.
Angela Merkel, the German chancellor, said in her address at the opening of an industrial fair spotlighting Russian business that Russia was propped by its raw material deposits and huge investment in infrastructure but Germany could help it in its aims to innovate and diversify.
"We believe this can happen most successfully when there is an active civil society," she said.
"We must intensify these discussions, develop our ideas, and we must give the NGOs, who we know as a motor for innovation, a good chance in Russia," she added to strong applause.
Germany and the Netherlands need Russia for energy and as a market for exports ranging from Volkswagen Touaregs to tulips.
But the two nations are uneasy about the influence Russia's oil and gas give it and about Putin's treatment of opponents and activists in his new Kremlin term.
Merkel had come under pressure at home to voice her concerns to Putin, not only on the inspections of NGOs, but also on their differences over Syria's civil war and Russian criticism of the German-orchestrated financial bailout of Cyprus.
Her talks with Putin would include "controversial subjects" she told reporters on the sidelines of the fair.
In his address to the trade fair Putin focused on Russia's economic strength, noting, "despite global disarray and the global financial crisis, our country has continued to develop positively".
In an earlier interview with German broadcaster ARD, Putin had dismissed criticism of the NGO inspections and said they would not cast a shadow over the visit, echoing his repeated rejection of Western worries about his domestic policies.
Putin - a former Soviet KGB officer who was stationed in East Germany, where Merkel grew up - has accused Western states of using NGOs to spy on Russia and influence politics.
He said in the interview that Russians have a right to know which NGOs are foreign-funded "and for what purposes".
He sent warmer signals on economic issues, expressing confidence in the euro and toning down criticism of the Cyprus bailout by saying he hoped more money would flow into Russia as a result.