Liverpool's moves for midfielders Mahmoud Dahoud and Piotr Zielinski are under increasing doubt as their respective clubs refuse to change their stances.
Zielinski was the subject of a £11.75 million bid last month, but the offer was rebuffed by Udinese, who have accepted a similar bid from Napoli that is said to include full-back Juan Camilo Zuniga plus additional instalments.
The 22-year-old, who has spent the last two seasons at Serie A side Empoli where he has blossomed into a fine all-rounded central midfielder, supposedly prefers a move to Anfield but the Reds' hopes of signing him are quickly fading.
Zielinski move now appearing unlikely
According to reports, Zielinski is willing to see out the final two years on his contract before leaving on a free - having rejected the opportunity to agree personal terms with Napoli as he eyes a switch to England.
While it is unknown why Udinese have rejected Liverpool's advances, it's thought that Zielinski repeatedly making clear his intentions to move to Merseyside have angered his employers.
While the chance to send Zuniga straight on loan to Premier League rivals Watford, also owned by the Pozzo family who own Udinese, is understood to be of interest.
Several reports also suggest that Udinese want closer to £15 million from Liverpool, presumably aware of the increased money available after the £5.1 billion TV rights deal kicked in recently.
No progress on Dahoud pursuit
In another blow, the Reds haven't received much encouragement in their pursuit of Dahoud, who Klopp is said to rate highly.
Though they would be willing to pay towards £25 million for the deep-lying Borussia Monchengladbach playmaker, the Bundesliga outfit are unwilling to lose further key players.
The club's sporting director Max Eberl declared earlier in the year that Dahoud is "not for sale" because Gladbach are "a hungry club" who need "every good player."
They finished fourth in the Bundesliga last season, qualifying for the Champions League play-off round, and are reluctant to lose more members of their strong centre - even though the Germany Under-21 international appears keen to leave, courting interest from Borussia Dortmund among a number of other clubs.
The tenacious 20-year-old is one of Klopp's first-choice options to strengthen his midfield, but the German could instead be forced to change his plans.
Allen set for Anfield U-turn?
Should moves for Zielinski and Dahoud remain at a standstill, it is unlikely a departure for Joe Allen would be sanctioned.
The Wales midfielder, who has been an integral part of the side which has reached the Euro 2016 semi-finals, has just one year left on his contract on Merseyside and had appeared to be edging towards the exit.
The Reds had rejected an £8 million bid from Allen's former club, Swansea City, last month as they looked for closer to their £10 million valuation. But that price may have increased given Allen's excellent performances for his country at the Euros.
However, a popular figure in the dressing room and among supporters, Allen could now be set to stay at Liverpool - who are keen to ensure he doesn't leave on the cheap despite having just 12 months left to run on his existing deal.
But unless the impasse between Liverpool and Zielinski and Dahoud changes, it appears Allen will not be allowed to leave the club this summer.
The Reds boss had been keen to do all of his summer business early, with pre-season training underway and their first friendly next Friday, but it appears he may be forced to wait as he looks to make recruitment.