Italy's World Cup nightmare has deepened after Gennaro Gattuso's side suffered a crushing 4-1 penalty shootout defeat to Bosnia and Herzegovina in Tuesday's playoff final in Zenica.
The four-time world champions have made unwanted history, becoming the first former winners to miss qualification for three consecutive tournaments.
Following their absence from Russia 2018 and Qatar 2022, the Azzurri's exile from football's showpiece event has extended further.
The match finished level at 1-1 after extra time, but Italy's spot-kick woes proved decisive as Bosnia secured their place at this summer's finals.
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Moise Kean handed Italy the perfect start in the 15th minute, pouncing on a mistake from Bosnia goalkeeper Nikola Vasilj to give his side the lead.
The Azzurri appeared to be cruising towards qualification at that point, with their early dominance suggesting a comfortable passage to the finals.
However, the complexion of the contest shifted dramatically four minutes before half-time when Alessandro Bastoni received his marching orders.
The defender was dismissed for a last-man challenge on Amar Memic, leaving Italy to battle with ten men for the remainder of the tie.
Italy's World Cup nightmare has deepened after Gennaro Gattuso's side suffered a crushing 4-1 penalty shootout defeat to Bosnia and Herzegovina
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That sending-off breathed new life into the home side's hopes.
Bosnia capitalised on their numerical advantage as substitute Haris Tabakovic found the net with eleven minutes remaining, dragging the hosts level and forcing an additional half hour of play.
Neither side could find a winner during extra time, sending the crucial tie to penalties.
Italy's spot-kick misery unfolded as substitutes Pio Esposito and Bryan Cristante both failed to convert from 12 yards.
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Italy have become the first nation to have previously lifted the trophy yet fail to reach three successive tournaments
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Bosnia, meanwhile, showed composure throughout the shootout, replicating their semi-final success against Wales from the spot.
Esmir Bajraktarevic stepped up to strike the decisive penalty, sparking jubilant scenes in Zenica and condemning Italy to yet another World Cup absence.
Italy's remarkable decline since their 2006 triumph over France in that memorable final has been stark and prolonged.
In the two decades since lifting the trophy, the Azzurri have managed just a single World Cup victory.
The World Cup features an expanded format with 48 teams divided into 12 groups of four
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They suffered group stage eliminations in both 2010 and 2014 before their qualification failures began.
Their last successful qualification came in 2014, which coincidentally marked Bosnia's sole previous appearance at the tournament.
For the Bosnians, this victory represents a return to the world stage after an 11-year wait.
Gattuso's men, meanwhile, have been left to contemplate another four years in the wilderness.