The city has garnered a reputation during recent NHL playoff runs for its jubilant, spontaneous celebrations that occasionally deteriorate into rampages highlighted by vandalism, looting and violence.
In the only Canadian city hosting playoff hockey this year and with the team's biggest rivals in town, authorities say they're ready for anything with the series tied 1-1 heading back to Montreal.
Anie Samson, a member of the city's executive committee, said the administration is prepared ahead of Tuesday's Game 3 at the Bell Centre.
"We are concerned about (potential problems), but we are working with the police and we have a plan," said the city councillor in charge of public security. "We are ready and we hope it's going to work."
The city is expected to decide whether it will limit traffic on Ste-Catherine Street on game nights. The downtown core is always ground zero for both the celebration and the carnage.
Montreal's history of Stanley Cup riots is well documented, with the Canadiens' most recent Stanley Cup triumphs in 1986 and 1993 marred by hooliganism. What's more alarming is that in recent years, an early-round victory has been enough to set off rioting.
The worst came in April 2008 after the Canadiens' seventh-game playoff win against the Bruins. It culminated with police cars being burned and downtown businesses being looted.
At least 16 people were arrested and damages to police property was evaluated at $500,000.
The looting played out again in May 2010, with windows smashed amid clashes between rioters and police on Ste-Catherine Street following a defeat of the Pittsburgh Penguins in the second round. There were more than 25 arrests and police were able to track down other vandals and looters using images and videos that were widely circulated on social media. Some citizens even sent police their own images, angry at the acts of mischief.
Montreal police Sgt. Laurent Gingras said he could not go into specific tactics on dealing with potential trouble.
"The message we're sending is that it's OK for you to celebrate, but we're here and we'll keep an eye out," Gingras said in an interview.
Those smashed windows and images of looting are still fresh for some downtown business owners. An association that represents them says there is always some trepidation.
"There's a certain level of worry because we've felt the negative effects during the playoffs," said Andre Poulin, who heads Destination Centre Ville. "But at the same time, we're confident the police will deploy necessary resources to protect our businesses."
Police are a lot better versed in dealing with massive crowds this time around. Student protests that were a near-nightly occurrence in 2012 allowed many officers to get hands-on experience as well as for the brain trust to put tactical theory into practice.
"We've improved the way certain (tactical) groups work (because of 2012) and the officers have all gained a tremendous amount of experience on the ground," said Gingras.
Gingras notes there is better communication — both with the public through Twitter and with businesses through a variety of tools to ensure everyone is prepared. There is also increased efficiency in moving around town, with bicycle units and horse cavalry having been added since 2008.
The plan is evolving, game-by-game, Gingras said.
"We're keeping a close eye, we know when the games are on and we change the plan accordingly," said Gingras. "That will obviously change if the team goes deeper into the playoffs."
Police were on the ready after the Canadiens engineered a four-game first round sweep of the Tampa Bay Lightning. No one was arrested, although one person was cited for excessive use of a car horn.
But the Bruins series brings a different level of intensity. It was in Montreal in March 2011 when a hit to Max Pacioretty by Bruins captain Zdeno Chara led to the city's 911 service being inundated with criminal complaints.
The Canadiens hockey club will keep its focus on the ice.
Team spokesman Donald Beauchamp said the Habs will leave it to the city to follow the situation. During previous incidents, police have said it wasn't Habs fans involved, rather people using the cover of tens of thousands of revellers to cause damage.
"It's not where the problem arises from, it's not people inside the Bell Centre," Beauchamp said from Boston. "It's more of a public situation and in this case, the authorities have taken the matter into their own hands, and very properly."
And at least one Habs legend believes cooler heads will prevail.
Guy Lafleur said he doesn't necessarily think the ingredients are there this time around. But he briefly joked with reporters there might be one thing that could trigger an outpouring: a second straight Canadiens sweep.
"Maybe if the Canadiens win in four," Lafleur said with a laugh, adding quickly he still didn't foresee any problems.
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