Youths have repeatedly broken into the historic building on Corbelly Hill for months, sparking callouts to the police and firefighters.
After being blocked out of the ground floor, yobs have been going to great lengths to force their way back into the 138-year-old building.
Dumfries fire service station commander Andy Wilson said this week: “The people who are intent on causing damage, they are now bringing ladders up to circumvent the ground floor measures and try to gain access to the first floor above.”
The issue was raised by North West Dumfries Councillor Graham Bell at Nithsdale Area Committee on Wednesday.
Concerned there may be a fire risk, he said: “We’ve had a lot of issues at the old convent recently. Anti-social behaviour has been going on since October, break-ins to the building, knocking down of barriers etc.
“This could be escalating to quite a serious problem.”
Responding, station commander Wilson said: “The convent is something that’s totally on the radar. The community action team have visited that location on numerous occasions and we’re constantly in dialogue with the owners of the premises, and also the community police.
“The measures being put in place by ourselves or the police, they keep being circumvented by the people who are intent on getting in.”
He added: “We do try to keep on top of it, but there’s only so much you can do. We can’t be a 24/7 presence in these premises.”
The Buildings At Risk Register For Scotland has been notified of trouble at the building. Its website states: “Vandalism within the site is reported to have taken place.”
The building opened in 1884 after nuns came from Arras in France to set up a convent and school. It was known as Benedictine Convent until the school closed in 1982. The convent shut seven years later.
The site was used as a location for The Magdalene Sisters movie in 2002, directed by Peter Mullan.
The 44,832 sq ft, Category B-listed building was put up for sale in 2008 with an asking price of £2.5 million. The last known owner was property developer Bertie McNeilly, from Ballymena in Northern Ireland.
At the time, the building was being marketed as having various potential uses, from a residential-led mixed use development, hotel and leisure or even a wedding venue, subject to the necessary consent.