Shares at newspaper group Johnston Press have closed down nearly 40% after it revealed it was renegotiating its financial position.
The company said it had failed to sell its Irish titles and was now in danger of breaching banking agreements.
At one point, the share price fell to 18p - less than a quarter of the cover price of the group's Scotsman title.
Johnston cut more than 1,000 jobs last year and is merging The Scotsman and Scotland on Sunday newsrooms.
The company said it was now in discussions over its financial position, and that the talks had so far been constructive.
Johnston was relying on the sale of its Irish titles to strengthen its financial position. It said considerable interest had been shown, but that the board decided not to go ahead because the price was not high enough.
Three parties were thought to be in the running for the papers but their sale was not expected to achieve much more than £35.5m, just 16% of what the company paid to acquire them.
Titles in the estate include the Limerick Leader and the Tipperary Star.
There is now speculation of further job cuts at the group.
It is thought 25 jobs will go as a result of the recent announcement of the plan to merge the Scotsman and Scotland on Sunday newsrooms.
Johnston Press has been particularly hard hit by the economic downturn because it relies on local advertising in the volatile sectors of housing and employment.
The Edinburgh group said advertising revenues had continued to fall in the first 19 weeks of this year, down by 34.4% in the period to 9 May - although the group said the situation was improving.
The group's chief executive John Fry said: "While our market remains fragile, we have seen some stability in advertising revenue over recent weeks."