Tensions were high on Wednesday night outside the Greek parliament building on Athens' Syntagma Square, which was the center of violent anti-austerity protests in years past.
And while the streets of Athens were largely calm for much of the day, despite thousands marching against austerity measures tied to the country's new bailout agreement, the night took a more violent turn.
As night fell, clashes broke out between protesters waiting to hear the fate of their country's economic future and the police sent to keep them calm.
The authorities responded with tear gas to disperse the crowd, as dozens of men and women, many dressed in black with their faces covered, came into the square wielding sticks and fire extinguishers to fight back.
Police say about 50 protesters were arrested during an hour-long clash outside parliament.
Prior to the clashes, riot police had packed the square as tensions ran high ahead of a planned midnight vote to determine the future of Greece by the country's parliament.
The Greek parliament is scheduled to vote to determine if the country will move forward with a planned bailout agreement that will keep banks will open and fund economic recovery.
But the $92 billion bailout agreement comes at a cost. It means Greece's parliament must accept a deal that would raise its retirement age, institute tax hikes and commit $55 billion worth of government assets to pay off debt and finance the banks.
Μάντεψε τη χρονιά A video posted by @alexveryk on Jul 15, 2015 at 12:04pm PDT
#Grèce Camion de la tv privée Ant1 (AntEna) en flammes. #Athènes #15jgr #Agreekment pic @dromografos pic.twitter.com/0nKhRXzHk4— Olivier Drot (@OlivierDrot) July 15, 2015
This was taken right after I ran away screaming like a baby. #Syntagma the first molotovs from tonight pic.twitter.com/vY0UspLX9b— Omaira Gill (@OmairaGill) July 15, 2015
Earlier on Wednesday, more than 10,000 people, many of them supporters of left-wing groups and a Communist-backed trade union, staged a peaceful rally in central Athens. Around 200 young people threw Molotov cocktails and rocks at riot police, set fires in dumpsters on the street and broke the windows of nearby businesses.
Many of the mask-wearing protesters carried wooden bats and pieces of smashed paving stones.
Small group of protesters singing national anthem during clashes #Greece pic.twitter.com/ENbO5G338a— Derek Gatopoulos (@dgatopoulos) July 15, 2015
Gas and stun grenades litter syntagma square pic.twitter.com/gpwD5mzTVZ— Daniel Hawkins (@DanhawkinsDh) July 15, 2015
While the clashes promptly settled, the police allowed the crowd to remain as the debate continued inside the parliament building's walls.
Previous clashes broke really quickly but cops seem not to be ordered to clear out Syntagma (for now) #agreekment pic.twitter.com/V5vWKcAgSq— Joanna P. (@JoannaP___) July 15, 2015
The flare-up stands in stark contrast to the weeks leading up to the major moment, where demonstrations remained relatively calm despite the fact that the fate of the nation was still very much up in the air.
Greeks peacefully went to the polls on July 5 and overwhelmingly voted against a referendum on a creditor's plan to impose more austerity on the country.
Wednesday evening's clashes drew parallels to the summer of 2011, when Athens was gripped by large scale anti-austerity demonstrations in the same location at Syntagma Square. Greek officials and police were widely criticized for the brutal crackdown that followed.
The violence on Wednesday was the worst seen by protesters in the capital since Tsipras's left-wing government was formed six month ago.
[video id=R2Zm84djrPBFR-95yaV_q8xmdgDUmJRk]
Additional reporting from Catarina Martins in Athens. Some information from the Associated Press.