Turkish President Recep Tayyip Erdogan is due to travel to Russia Wednesday to meet with Russian leader Vladimir Putin in Sochi to hash out a range of critical issues, from Syria to Ukraine and anti-missile batteries to natural gas.

Coming days after Erdogan aired his dissatisfaction with NATO ally the United States, suggested that Turkey would acquire a second set of the Russian made S-400 anti-missile system and asserted that US forces should leave Syria, the stage is set for what may have otherwise been a less cordial reception at the Kremlin.

Relations between the fellow autocrats have cooled ever since Russian air force jets bombed Turkish positions in Syria’s northwest province of Idlib in late February 2020, causing the deaths of at least 37 Turkish soldiers and many more Sunni opposition rebels allied with Turkey.

It may be no coincidence that Turkey has since edged even closer to its other large Black Sea neighbor Ukraine, selling it armed drones and backing its demands that Russia return the Crimean peninsula it occupied in 2014 and end the conflict in the Donbass. Erdogan repeated those demands in his speech to the UN General Assembly summit, prompting a flurry of angry commentary in the Russian media.