Manager Ronald Koeman needs to know sooner rather than later whether Toby Alderweireld, Ryan Bertrand and Nathaniel Clyne will commit their future to Southampton.
Saints know all too well what can happen when a club their size flourish, having experienced an unparalleled talent drain last summer.
Champions League qualification would surely avoid such a scenario this time around, although Koeman has highlighted the importance of tying down their key assets before the end of the campaign.
Bertrand and Alderweireld have been tremendous since joining on season-long loan deals from Chelsea and Atletico Madrid, respectively, and Saints have the option to make both moves permanent.
"We would like to know fast what the player likes, if there is any possibility to buy that player, and that's in the case of Ryan and Toby," said Koeman.
"Of course, we don't put exactly a deadline on it but we would like to know it soon what the plans are of the players.
"If it is yes and we can do the deal, then fantastic.
"If not, okay, then we need other players or we have to think about, that we have players in the Under-21s who can play in those positions.
"I think that it is important that the club is growing, the team is doing very well and the players are very happy.
"They have got the possibility to play in the case of Ryan and Toby. I think we have good possibilities to sign those players."
It is not just those on loan that Koeman needs to persuade to stay, with several key players approaching the end of their contracts.
The Dutchman has given Jack Cork a week to extend his deal past the end of the season, while he is aware that Jay Rodriguez and Clyne are amongst those out of contract next year.
The former's recovery from a ruptured anterior cruciate ligament lessens the need for that deal to be struck, although getting England right-back Clyne to promptly sign a new contract is key.
Koeman said Southampton are still waiting to hear on the extension offered to Clyne.
"It is a little bit the same as we would like to know what the player is doing because it all influences the plans with what we would like to do.
"They are important players in the club, like in the case of Jack Cork, as well as Toby, Ryan and Clyney.
"We try to do our maximum to keep these players because they are good players and still at a good age to develop.
Koeman said they wouldn't pressure players to decide this month during the transfer window, but that the club needed to know sooner than later.
"In-between the end of the month and April, there is time, but I think it is a little bit of loyalty between player and club.
"Okay, we hope that they will stay, but we respect every decision and we would like to know it."