Liverpool's transfer window has continued to veer downhill after reports that Romeo Lavia has opted for a move to Chelsea over the Reds.
He follows on from Moises Caicedo, who was officially confirmed as a Chelsea player on Monday after telling former club Brighton that he wanted to join them, despite Liverpool having a £111 million bid accepted.
Lavia is set to make the same decision, according to The Athletic's David Ornstein, despite Liverpool having pursued the midfielder throughout the summer.
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It now leaves the Reds scrambling to find a new defensive midfielder, with Fabinho having left for Al Ittihad in a £40 million deal earlier this summer.
They have been linked with Crystal Palace's Cheick Doucoure, Fulham's Joao Palhinha and PSV's Ibrahim Sangare, among others.
New sporting director Schmadtke, who joined the club earlier this summer, sealed deals for Alexis Mac Allister and Dominik Szoboszlai - but he may need to be busy across the remainder of the window.
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Here are three 'red flags' that have already emerged during the current window.
Schmadtke's short-term contract
Schmadtke has signed a one-year contract as the Reds sporting director - but has confirmed that he has a break clause which will allow him to leave at the end of August if both parties agree.
He told Sky Sports Germany: "We're waiting until the end of August. We signed an annual contract, but have the opportunity to ask each other in August, are we both still sure or not?
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"If someone isn't sure, then we shake hands and I might get a ticket if I want to stop by."
Should the 59-year-old leave early, it would require Liverpool to find a fourth sporting director in as many years - creating more uncertainty at Anfield.
Caicedo deal
According to reports, Schmadtke did not take the lead on the attempted deal to bring Moises Caicedo to Brighton.
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Instead, it was chief executive Billy Hogan that took charge of the ultimately failed negotiations, with the midfielder eventually joining Chelsea.
There is a concern among fans that the change in leader for that deal could signal a lack of organisation when it comes to Liverpool's transfer strategy.
'Operating in Ibiza'
According to The Athletic, Schmadtke 'mostly operates out of his villa in Ibiza' - but has been pictured at the Liverpool training ground.
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The German is involved in any negotiations, it is claimed, although there have again been some concerns expressed among supporters that he is reportedly not based more often in England.
Featured Image Credit: GettyTopics: Jurgen Klopp, Liverpool, Premier League, Transfers, Romeo Lavia, Moises Caicedo