Southend United's bid to extend the loan deal of Wolves full-back George Friend has fallen through.
The two clubs had agreed for Friend to stay at Roots Hall for another month at the beginning of last week.
But the Football League have not ratified the deal because the Blues have an outstanding tax bill.
Southend hope to conclude the deal once the bill has been paid and club officials are due to meet this week to resolve the matter.
Friend was travelling to United's game at Carlisle last Saturday when he was told that the deal had fallen through.
It means that Southend are struggling for numbers ahead of Friday's match at home to Gillingham.
Dougie Freedman picked up a groin injury during the 2-1 defeat in Cumbria, but striker James Walker is back from his loan spell at Hereford.
Kevin Betsy and Alex Revell can not be recalled from their loan deals at Wycombe and Swindon respectively.
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