Sunderland boss Steve Bruce is growing increasingly frustrated over his bid to bring Argentinian full-back Marcos Angeleri to the Barclays Premier League.
The 27-year-old has been training with his prospective new team-mates on Wearside for several days, but his move from Estudiantes is yet to go through because of an administrative issue which is a growing concern.
Angeleri qualifies for an EU passport through his Italian father and therefore will not need a work permit.
However, the document is yet to be issued and that is a complication Bruce admits he could do without as he attempts to re-shape his squad for the new season.
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 in 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."