Middlesbrough are facing a race against time to strengthen their squad before the transfer window slams shut on Thursday afternoon.
Tony Pulis admitted after Saturday's 2-2 draw with Millwall that his current side "aren't good enough to go up" after recently losing some of his star players.
Boro abruptly lost Patrick Bamford and Ben Gibson last week, after the pair left for Leeds and Burnley respectively.
Meanwhile, Adama Traore appears to be on the verge of joining Premier League side Wolves for a reported £20million.
All three players were key members of the side which reached the play-offs last campaign, and even more worryingly for Pulis, attempts to sign replacements appear to have stalled.
Boro looked set to sign Ipswich striker Martyn Waghorn, only for Derby to hijack the deal at the last minute.
The forward scored 16 goals and provided 11 assists for Ipswich in the Championship last season, but has elected to join Frank Lampard's Rams after they matched Boro's offer.
Newcastle winger Matt Ricthie has also been linked with a move to the Riverside and could fill the void left by Traore.
But, with Thursday's 5pm deadline looming, time is quickly running out.
Boro's attempts to sign Bristol City defender Joe Bryan are further down the line, but they face strong competition.
Both Boro and Aston Villa have had bids accepted for the 24-year-old full-back, believed to be in the region of £5million.
It means there will be an air of uncertainty when Boro host Sheffield United tomorrow night.
Pulis is likely to be without striker Rudy Gestede and midfielder Paddy McNair due to injuries, while the futures of Britt Assombalonga and Martin Braithwaite, who spent the second half of last season on loan at Bordeaux, remain unclear.
If Boro fail to get their business done within the next few days, Pulis may be forced to dip into the loan market which is open for EFL clubs until August 31.