Liverpool suffered a fresh painful blow in their preparations for the new season, throwing away a 2-0 lead to lose 3-1 to France's Monaco. It was a disappointing echo of their recent chastening defeat to Leeds United, and it laid bare the scale of the task facing new manager Iraola as he sets about rebuilding a side shorn of its legend Mohamed Salah.
The hosts started strongly and in clear control. Isak opened the scoring in the 15th minute, driving a powerful low shot into the net after a superb team move, before Wirtz doubled the lead just before the half-hour mark, bundling home from a scramble inside the six-yard box. A comfortable cushion. Victory looked within reach.
Then came the sudden defensive collapse that has become a worrying feature of Liverpool's recent matches.
A minute before the interval, Golovin pulled one back from the penalty spot, thrashing the ball into the top corner despite Alisson guessing the right way. Half-time: 2-1.
The collapse rolled on after the restart. Monaco levelled just 10 minutes into the second half, Biereth pouncing on the rebound after Mamardashvili had parried his first effort, catching the Brazilian goalkeeper off guard for the equaliser.
Nor did the bleeding of goals stop there. Brunner grabbed the winner for the French side, meeting a corner at the near post and slipping past the English defence with suspicious ease to complete a catastrophic afternoon at Anfield.
For Iraola, still in the earliest days of his project, the defeat lands as a fresh blow. It caps a summer of radical change, with Salah gone and a new coaching staff in place, and it overshadows the two wins earned over Sunderland and Wrexham in their previous friendlies.