Italy will miss their second World Cup in a row after slumping to a shock 1-0 play-off semi-final defeat to North Macedonia.
Aleksandar Trajkovski's low drive in the second minute of stoppage time stunned the European champions in Palermo and set-up a qualifying final with Portugal in Porto on Tuesday for a chance to be in Qatar in November.
Roberto Mancini's side were loudly booed off after a defeat which means Italy will have to wait until at least 2026 to see the national team at a World Cup.
By then it will have been 12 years since the Azzurri's last participation in the world's biggest football tournament after they failed to qualify for the 2018 edition, also crashing out in the play-offs on that occasion.
"It's hard to explain, it's such a huge disappointment," said Giorgio Chiellini.
"We played well but we just failed to score the goal. We've made mistakes since September and we've paid for them. We're distraught."
Italy as predicted dominated the play but as has been the case in recent matches struggled to break down a resolute away side and when presented with chances were not clinical enough to take them.
The hosts should have been ahead on the half-hour mark when Domenico Berardi was gifted the ball on the edge of the area by goalkeeper Stole Dimitrievski.
The Sassuolo winger, who has been in red-hot form this season for his club, took too long to shoot and hit his effort into Dimitrievski's welcoming arms.
It was wave after wave of Italy attack but an initially vibrant crowd began to grow frustrated at their inability to carve out a clear opportunity to score, and it showed in a team which began to look desperate make the breakthrough.
Those fans were on their feet hailing an Italy hero seven minutes before the break, but it was for Alessandro Florenzi stopping Darko Churlinov from giving North Macedonia a shock lead after bursting through into a great scoring position.
Berardi looked Italy's biggest threat and went close three times in the space of five second-half minutes, first hitting a weak shot at Dimitrievski before curling another one just wide seconds later.
And the 27-year-old had his head in his hands in the 58th minute when after beautifully spinning into a shooting opportunity he smashed over with his weaker right foot.
He was frustrated again just after the hour, this time Ezgjan Alioski throwing himself into a fantastic block after Marco Verratti had clipped Berardi through with a typically classy ball.
Giacomo Raspadori then smashed a first-time shot over the bar from the edge of the box and Gianluca Mancini headed a corner over the bar as Italy continued to push without ever managing to break their opponents down.
And just as the match looked to be heading into a tense extra-time Trajkovski popped up to hit a perfect low strike past Gianluigi Donnarumma and cause another earthquake for Italian football.