Putin's meeting with the CSTO security alliance went south when an ally repeatedly snubbed him.
Armenia's PM refused to sign a joint document and distanced himself from Putin in a group photo.
It adds to Putin's isolation after other nations cut ties over the invasion of Ukraine.
Russia's president was snubbed three times by his supposed ally on Thursday when he met with some of his country's closest partners at an international summit.
Vladimir Putin met with leaders from the Collective Security Treaty Organization (CSTO), a Russian-dominated alliance of post-Soviet nations.
But the supposedly friendly forum proved hard going for Putin, who was slighted multiple times by the prime minister of Armenia in protest at its ongoing conflict with Azerbaijan.
Nikol Pashinyan used his speech at the start of the summit — held in Yerevan, Armenia's capital — to criticize the effectiveness of the alliance, where Russia is by far the most powerful member.
Its other members are Armenia, Belarus, Kazakhstan, Kyrgyzstan, and Tajikistan. Azerbaijan is not part of the group.
Pashinyan accused the alliance of failing to help Armenia in its ongoing conflict with Azerbaijan, Reuters reported. Armenia tried to invoke the CSTO's collective-defense provision earlier in the year, but was unsuccessful.
Pashinyan said that "Right up to today we have not managed to reach a decision on a CSTO response to Azerbaijan's aggression against Armenia."
"These facts do grave harm to the image of the CSTO both inside our country and outside its borders," he said.
Pashinyan later refused to sign a draft declaration from the summit, arguing that it did too little to oppose Azerbaijan, according to a report by Turkey's state-funded Andalou Agency.
As the CSTO's central and most powerful member, both criticisms were directed in particular at Putin.
Pashinyan compounded his criticism when the country leaders lined up for a photo, standing conspicuously far from Putin to leave a notable gap between the two leaders.
Pashinyan and Putin were photographed together at other stages of the meeting, including shaking hands multiple times, and the Kremlin said the two leaders had a "separate meeting" after the summit.
Putin has become increasingly isolated in the world stage over Russia's invasion of Ukraine. Many world leaders rejecting him entirely and he has found himself in awkward interactions with a number of others.
India's prime minister criticized the Ukraine invasion directly to Putin in September, and he told Puitn he wanted the war to end as soon as possible.
Putin also conceded in September that China, a close partner of Russia, has "questions and concerns" about its actions in Ukraine.
The president of Tajikistan, a big ally of Russia, appeared to berate Putin to his face at an October summit, where he said Russia was not respecting his country.
Putin also did not go to the G20 earlier this month and he did not address it virtually. He instead sent his foreign minister.
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