Almost 500 workers have lost their jobs with immediate effect after a Yorkshire printing firm went bust.
Nearly all of the company's 512 staff have been made redundant and sent home. The three companies are all part of the YM Group.
Darren Rushworth, regional officer for the union Unite, called the redundancies "disgraceful".
He said: "YM Group has behaved disgracefully it repeatedly promised workers would be paid and even encouraged them to undertake over time, in recent days."
FRP Advisory, a restructuring firm, has been appointed as administrators.
Phil Pierce, a partner at FRP Advisory, said: "This has been an incredibly challenging period for the printing sector and York Mailing, YM Chantry and Pindar are no longer able to continue trading.
"Regrettably, the insolvency has led to redundancies at what we know will be an extremely difficult time. We will work with staff to access redundancy support."
In a statement, administrators added that this had happened after a period of rising costs and a "significant period of challenging trading that had been exacerbated by the impact of the pandemic".
Mike Greene, Scarborough Borough Council chief executive, said: “The closure of Pindar, a company with a long and illustrious history of employment in Scarborough, is a huge blow for the town. It is devastating for all those who worked there and have sadly lost their jobs this week.
“In the coming days, weeks and months, our economic development team will work with partners to support those who have been made redundant by offering advice and connecting people to other organisations that will be able to help them through these difficult times.“