Sitting at a long table in Russia's Foreign Ministry, Syrian opposition leaders outlined a plan to protect Moscow's interests if the Kremlin agreed to the removal of its longstanding ally, President Bashar al-Assad.
Throughout the meeting last July, one of many since the start of Syria's civil war, Russian officials sat stony-faced. When the Syrians had finished, there was a long silence.
"The Russians listened but never spoke, and when we were done speaking, we were told that Moscow is dedicated to human rights and we were told to get on our way," said Mahmoud al-Hamza, a Moscow-based member of the Free Syrian Army, who was present at several such sessions.
More than two years after the Syrian conflict erupted as part of the "Arab Spring" uprisings, Assad is clinging to power thanks in large part to Russian diplomatic and military support.
Russia and the United States have agreed to bring together the warring sides for a peace conference in the coming weeks. Yet some fellow mediators suspect a Kremlin ploy to keep Assad in power - at least a little longer. On the battlefield, the momentum has swung Assad's way and on Wednesday forces loyal to him retook the strategically important town of Qusair.
Leaked accounts of Moscow's dealings with the opposition, promises to deliver Assad a potentially game-changing missile system and anecdotal evidence that Russians are training Syrian troops have widened the trust deficit between Russia and the West.
"Our biggest fear is being screwed over by the Russians," said one French official, speaking on condition of anonymity.
As on many other occasions, the July meeting between Russian officials and the opposition foundered on the position championed by President Vladimir Putin and Foreign Minister Sergei Lavrov: the Syrian people should decide their country's future for themselves.
Russia says it is motivated by a desire to stop the fighting, not by a wish to maintain military and industrial interests in one of the Kremlin's last Middle East allies.
"Our position at this moment is to stop the bloodshed and pain, and that is the fundamental task of all efforts connected with the resolution of the Syrian crisis," said a Foreign Ministry official, who declined to be named. "We are not selecting candidates for the future transitional government. We are not supporting any forces that will make it up."
Some foreign diplomats and observers say that if past diplomacy is any guide, Moscow will seek to pack the table with members of tame opposition parties that are part of Assad's tightly controlled political system, while exploiting the divisions among his opponents.
"Everything must be done to convince the opposition to sit at the negotiating table without preliminary conditions, having guaranteed full representation to all Syrian opposition groups, including internal opposition," Lavrov said last week.
Moscow has had several rounds of talks with Hassan Abdel Azim and his National Coordination Committee for Democratic Change, which rebels say is little more than a front for Assad. The group's leader outside Syria, Haytham Manna, did not respond to a request for comment.
The Kremlin has also tried to cast Russian-speaking Deputy Prime Minister Qadri Jamil as a member of the opposition. Jamil came to Russia several times last year to work out an oil-for-fuel swap deal.
"It's reached a point where Moscow knows Assad is no longer an option. Russia only wants people who will keep something of the old ties alive," said Free Syrian Army member Hamza.
While insisting it is not supporting Syria's rulers, Russia has sent them advanced radar anti-ship missiles, unfrozen but not yet delivered an order of S-300 anti-aircraft rockets and promised to fulfil a contract for 12 MiG-29MM2 fighter jets.
Syria is one of the last bastions of support for Moscow in the region and Russia does not want to see Assad go the way of ousted Libyan leader Muammar Gaddafi, a long-time partner.
In another show of force in the region, Russia sent a group of four navy ships from its Pacific Fleet last month to the Mediterranean, where they will join a squadron of warships already stationed off the coast of Syria.
Reports of arms shipments and shipping movements, often conflicting and ambiguous, may strengthen Russia's hand in its dealings with the West.
"Everything that is happening around Syria has less to do with promises to Assad personally and more to do with power plays between Russia and the West," said Fyodor Lukyanov, editor of the magazine Russia in Global Affairs. "And for Russia that means keeping things on the diplomatic track."
"Those ships may be carrying elements for the S-300, they may not be. For Russia, the less clarity the better in arguing its position," he said.
The S-300s are unlikely to be delivered before autumn. A source in the arms industry suggested the deal could be speeded up or frozen depending on what the West does.
"Everything at this point can be used as a bargaining chip," Lukyanov said.
Russia also worries about the security blow-back it could face after the Syrian conflict, in which it estimates 200 of its own citizens are fighting on the rebel side.
Russia's southern Muslim territories in Tatarstan, Bashkortostan and the North Caucasus, where Islamist insurgents wage daily violence, are prone to instability. Alexander Bortnikov, the head of Russia's main security agency, has voiced fears that returning fighters could fuel Islamic radicalism.
Russia has a naval base on Syrian soil, and the two countries have long and deep cultural ties. Thousands of Syrians live in Russia - and many Russians are in Syria - as a result of years of educational, business and security ties.
Pro- and anti-Assad Syrians have emigrated to Russia, one of the few countries to give visas to Syrians wanting to put their families and money in a safe place.
Sitting in his Middle Eastern restaurant in a busy Moscow shopping district, Hassan al-Dubaisi, who came to study engineering five years ago, says he has been visited three times by Syrian businessmen of all political stripes looking for help.
"Usually they want to buy a stake in the restaurant or ask for help getting started in Russia, but I don't like partners," he said blowing out smoke from his water pipe.
Dubaisi, who comes from near Dera'a, where the uprising against Assad began, said he donated money to the opposition - 10,000 roubles ($310) - as have many other Syrian emigrants.
Support for the rebels thrived at first in Moscow's Syrian community, which tends to be more secular and better educated than average Syrians. But enthusiasm has waned as the violence has dragged on and the rebels have turned more Islamist.
Dubaisi and other opposition supporters say they face increasing pressure and sometimes violence in Russia for their political views and for joining anti-Assad protests in Moscow.
"The (Syrian) embassy here has already identified me as an opposition supporter and ... I've heard that if I ever go back to Syria, I'm on a list of people to be arrested before I even make it through passport control," he said.
Security ties between Syria and Russia flourished during the Cold War. Russia, the world's second largest arms exporter after the United States, was the first supplier to which Assad's father, Hafez, turned when he gained power in 1971.
Two years later, Moscow equipped an Arab coalition including Syria that launched a surprise attack on Israeli forces in the 1973 Middle East War. When Egypt turned towards Washington and expelled Soviet advisers, Syria remained in Moscow's camp.
Syria became an even more loyal customer after Russia wrote off some 70 percent of Syria's $13.4 billion debt in 2005, a stumbling block that had frozen arms cooperation in the 1990s.
Since then ties have revolved around arms and military cooperation. Syrian sources say crack troops loyal to Assad have been sent to Russia for training. A Russian military source told Interfax that an unspecified number of Syrian officers have been sent to Russia for coaching on a range of air defence systems, but not yet on the S-300. ($1 = 31.9362 Russian roubles)