Penrith star Liam Martin is due to meet with club officials about his future on Tuesday, as one of several big-name Panthers off contract at the end of next year.
Martin's management are eyeing off the possibility of going to market on November 1 if an agreement cannot be reached.
The 29-year-old's talks on a long-term extension come at a delicate time, with Penrith also juggling the futures of co-captains Nathan Cleary and Isaah Yeo.
Penrith have traditionally put contract talks to the side in the second half of seasons, with a preference to have most done well in advance.
And while a more experienced playing group had given officials cause to let talks go later, Penrith's coach indicated that window was almost closing.
"Ideally it's probably pretty close to shutting up shop for the year," Cleary said.
"You'd rather not (have it happening now).
"It's the transfer market that we have in our game. I think it's set up for media and commentary, which is fine, if that's what we want as a game.
"We just have to live with it and deal with it the best we can within those parameters.
"I haven't actually made that call (of when to stop it). It's getting that way. But obviously with November 1, if you want to get something done before then, it's a challenge."
Yeo is close to agreeing to a new deal while sidelined with injury, while Penrith remain confident they will be able to keep co-skipper Cleary.
And while Brian To'o's 2028 PNG move has freed up some salary cap space, the picture remains somewhat muddled with three of their biggest names off contract.
Moses Leota is also unsigned beyond the next year but keen to stay, while Casey McLean, Paul Alamoti and Isaiah Papali'i have all recently extended.
"It's a much bigger exercise (this year)," Cleary said.
"Shane Elford our GM has been doing an incredible job behind the scenes trying to balance all the balls in the air."
Cleary was also coy on his future on Monday, insistent he'd not considered replacing the exiting Kevin Walters as Australia's Test coach after finishing at Penrith next year.
He did confirm Penrith would not rest players against Canterbury on Friday night, with a top-two spot and home final still up for grabs.
Cleary was undecided if he would take a similar approach against Wests Tigers next Sunday, which falls just five days from the start of the finals.
Hooker Mitch Kenny will not return from a fractured leg against Canterbury, while Cleary would not say if Blaize Talagi would get the No.6 jersey back with Jack Cogger suspended.
Cogger will miss the first week of finals with his ban, and Jack Cole looms as the other option after playing No.6 a fortnight ago with Talagi dropped to NSW Cup.
"You'd prefer to get a little bit more cohesion there," Cleary admitted.
"But all the boys that have played there have played enough."
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