Port Vale have signed midfielder Robin Hulbert until the end of the season but talks to keep on-loan central defender Clayton Fortune have broken down.
Fortune is available on a free transfer from Leyton Orient but the Valiants can't match his wages at the London club.
Vale had hoped that Orient would help bridge the gap by paying Fortune a settlement on the remaining 18 months of his contract but they have so far failed to reach an agreement.
The 24-year-old is currently set to return to Brisbane Road when his loan deal expires after Saturday's home game with Bradford.
"Orient want to let Clayton go and he wants to come here, so hopefully this isn't dead," Vale manager Martin Foyle told The Sentinel.
"But things can be out of your hands with loan players."
Meanwhile, as well as Hulbert penning a new six-month deal at Vale Park, Foyle has reached an agreement with on-loan midfielder Ross Gardner for the rest of the season.
Gardner has left Nottingham Forest by mutual consent.
"Ross has agreed a deal with Forest now and will hopefully sign for us on Monday after a successful loan spell with us," Foyle told the club's website.
"Robin Hulbert has also signed a contract until the end of the season so we now have more options in midfield, which can only be a good thing for the club."