With a transfer ban expected to prevent Real Madrid from registering any new players for the next two windows, the club have been busy trying to tie down their current stars to long-term contracts.
Toni Kroos and Luka Modric's new deals have already been announced while Cristiano Ronaldo and Gareth Bale are also set to extend their stay at the Bernabeu.
However, it isn't looking quite so straightforward for another one of Zinedine Zidane's star men.
Pepe's current contract at Los Blancos expires at the end of the season and despite brief negotiations between the player's representatives and the club, a deal does not appear to be any closer.
It is believed Madrid's most recent offer was an extension of just 12 months - not the two years Pepe's team are holding out for.
The uncertainty surrounding his future means there is a serious possibility the Portuguese centre-back could sign a pre-contract agreement with another European club in January.
And according to The Sun, Chelsea are one team interested in acquiring his services, a move Pepe is willing to consider.
The Blues were desperate to boost their defensive ranks during the summer but were forced into the last minute purchase of David Luiz after being rebuffed by their preferred targets.
John Terry isn't getting any younger and Gary Cahill has made a shaky start to the season so it isn't much of a surprise to learn Antonio Conte remains keen to improve his defensive options.
Of course, with reports such as these, there is also a very good chance it plays straight into Pepe's hands, who can use Chelsea's interest to negotiate a better deal for himself to stay at Madrid.
But should a new contract fail to materialise before January, it will be interesting to see if the Premier League giants step up their interest in the form of a concrete offer.