Sunderland manager Steve Bruce admits he is becoming concerned about the delay in finalising the signing of Argentine full-back Marcos Angeleri.
The Black Cats have agreed a deal to sign Angeleri on a four-year contract from Estudiantes and are waiting for the 27-year-old to be issued with an EU passport.
Angeleri has been training with the Premier League club, but has yet to secure the necessary paperwork to rubberstamp his move to the Stadium of Light.
If Angeleri fails to secure the passport, which he qualifies for through his Italian father, the move will be in doubt as he is unlikely to secure a work permit.
Bruce was expecting to have already wrapped up the signing of the defender and is growing frustrated by the lack of progress being made.
He said: "With Marcos, the big problem when you are trying to sign them, of course, is work permit issues.
"He has got an Italian father and he is waiting for an Italian passport. We were told a month ago it was going to be here within 10 days.
"That's obviously a concern to me because we were told we were going to get it three weeks ago and it's still not here.
"We will look at it and we will have a conversation again with the agents and see where we end up."
Meanwhile, Bruce is confident he has the midfield resources to cope with the departure of Lorik Cana after the Sunderland captain joined Galatasaray.
He added: "The one thing I am gutted about is the injury to (David) Meyler, because he had a wonderful end of the season and had put big pressure on Cana with his performances.
"But with (Cristian) Riveros coming and (Lee) Cattermole and the emergence of Jordan Henderson too, I wasn't really that fussed.
"He had a wonderful start to his career here, but found the Premier League physically very difficult towards the end.
"He walked in on the first morning with his father and said he wanted to go and play nearer his homeland of Albania, and wanted to go to Turkey.
"I am always a believer that if somebody is not happy and wants to go back and be nearer his family - there were issues with his family, who needed visas and couldn't get here from Albania - so we have reluctantly let him go."