Portsmouth chief executive Peter Storrie has admitted that his club face defeat in their attempts to sign Trinidad and Tobago international Khaleem Hyland.
However, Storrie admitted: "We have always been looking at Hyland, but there are complications with the work permit situation.
"At the moment he fails to satisfy the criteria. He has played in friendly matches, but they have to be competitive, so they do not count.
"It's a shame because he is very much one for the future and a player we are interested in.
"We are not even sure when we will find out the outcome, it's a case of how long is a piece of string.
"The powers that be are still working towards the permit so we will just have to wait and see."
All this must be very frustrating for Hyland, who recently turned down a new contract from San Juan Jabloteh so as to make himself more available for Portsmouth.
Portsmouth have not yet given up hope on being able to sign Khaleem Hyland, even though the Trinidad & Tobago starlet's work permit issues are proving hard to untangle.