alot of the times the WP does not get granted as it is rushed at the end of the Transfer Window, then you end up like Robert with a player that does not have a Wp...
what you need to do is loan him out, let him play alot of the games and try offering him a new contract...
most of the time the initial WP is turned down for most players... except for players like Neymar and Lucas etc...
Manutd.. it does not matter if you are in or out of the TW, you need to continue offering him contacts... it may be better during the TW as you could be able to sign him without one, then do what I suggested above
One way to get around this annoyance is to use the FM Editor. What I do is pull up countries such as Brazil, Argentina, then on their information page, change their EEC Member status to 1. This has no other effect on the game other than all players from those nations will automatically be eligible to play in Europe.
The hardcore gamers who want this to be as realistic as possible will not like it, but for people who just want to enjoy the game and sign some amazing young foreign players, this trick is ideal.
Might be worth putting in the opening post that some players still won't get work permits after they have done enough time at a feeder club because they haven't learned the language.
I had a Brazillian on loan in Bulgaria and he couldn't apply because he hadn't learned Bulgarian.