Six defeats in a row, questionable fitness levels and fears that an 11-million-dollar government grant for the sport could be squandered have cast a deepening gloom over preparations for the event.
The situation has got so bad that coach Gus Logie, the stylish former West Indies batsman, was almost at the end of his tether after a series of humbling defeats - three against Kenya, two against Canada and one against Holland, all fellow World Cup finalists - on a five-week tour of Africa.
A late win against the Dutch in a one-dayer, a dead match, did little to prevent a backlash.
Worryingly for Bermuda, one of their sternest critics has turned out to be governing body, the International Cricket Council.
Richard Done, the ICC's High Performance Manager, believes the side lack the tight discipline which is the hallmark of the world's leading sides.
"It's generally application of what they've already got," said Done who watched Bermuda on their ill-fated tour.
"There's some talented players there. But I think they don't always give themselves the best opportunity to get their minds right and their bodies right to perform on the field."
The physical fitness of Bermuda's players is also a concern.
Many fear that when they face Asian powerhouses India and Sri Lanka in their opening World Cup group, which also includes Bangladesh, their poor shape will cost them dear.
"Fitness is critical, not just at this level playing one-day internationals, but also playing the longer version of the game," Done told the Royal Gazette in Bermuda.
"You just can't get by without it in the modern game.
"The West Indies, through the 1980s and Australia through the 1990s and the early part of this decade have been outstanding, and I think without doubt they've been the fittest sides in world cricket, and the most athletic and most physical sides playing the game. Of course, they've had great skill levels as well."
Logie has plenty of headaches ahead of the March-April showpiece in the Caribbean.
He has to decide whether or not to keep faith with the majority of the 15 players who went to Africa.
"In the field, we were the slowest team in the competition," said Logie after his rude South African awakening.
He was concerned by nine wicket and seven wicket capitulations suffered at the hands of Canada and the Dutch respectively.
"A lot of excuses can be given. People talk about playing for their places in the World Cup, but if that's the way they're going to play for their places well, I'm sorry, their places will be up for grabs."
Logie, who played 52 Tests and 158 one-dayers for the West Indies from 1983-1991, calmed down after a face-saving late win against the Dutch.
The World Cup rookies will also look to new recruit David Hemp, who skippers English county championship with Glamorgan, for inspiration.
In a drawn four-day Intercontinental Cup match with the Netherlands in South Africa, he smashed an unbeaten 247 in Bermuda's total of 620, smashing the previous mark of 220 set by Kenya's Steve Tikolo.
"Having Hemp here has been a big plus," said Logie.
"The players have been able to watch and appreciate how, as a professional, he prepares and his dedication to getting the best out of himself."