Carlisle United boss Paul Simpson has described the club's debt to Purepay Retail Limited as a "stumbling block" in takeover talks.
The Blues are in discussions with American businessman Tom Piatak, who is set to meet fans this month.
But manager Simpson suggested the matter of Carlisle's seven-figure debt to Purepay is far from resolved.
United's £2.7m debt is a legacy of loans made by Philip Day's Edinburgh Woollen Mill, the debt transferred to another company after EWM went into administration during the Covid-19 pandemic.
Simpson said it is the most obvious hurdle to takeover talks - which he said are otherwise progressing well - reaching a positive conclusion.
Asked by BBC Radio Cumbria at his latest press conference if he was aware of an update, Simpson said: "I haven’t heard anything this week. I think there are stumbling blocks.
"And from my understanding, one of the biggest stumbling blocks is obviously Purepay.
"A situation where Philip Day, a local businessman made a brilliant gesture to help the club out when they needed it, unfortunately with circumstances out of his and our control, the debt then gets transferred to somebody else and what was a fantastic gesture has turned into a bit of a poisoned chalice at the moment, because that could be a major stumbling block if we can't get a resolution to that.
"Apart from that I don’t see there being many other things that could be an issue. The club is in the best state for many years and hopefully everything will go smoothly."
Supporters' trust CUOSC recently said things were at a "delicate" stage in repayment negotiations with Purepay.
Florida logistics businessman Piatak and his son, also Tom, attended Carlisle's most recent home game against Exeter City in August.
The News & Star revealed their interest in the Blues early last month and talks are believed to be at an advanced stage.
Although the Piataks have never been formally named by Carlisle, they are widely believed to be the people who will meet supporters at meetings organised by CUOSC later this month in order to discuss their plans.
Tom Piatak snr is yet to respond to the News & Star's invitation to comment.
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