Inverness experienced a painful lesson on their introduction to European football after falling to a dead-ball goal against the run of play against Romanian side Astra.
Caley Thistle made a polished start to their Europa League second round first leg but lost 1-0 following a 24th-minute strike by Constantin Budescu.
The William Hill Scottish Cup holders created some late chances but could not reward the 5,534 crowd at the Tulloch Caledonian Stadium as they fell to a side which drew at home to Celtic in the group stages last season.
Inverness boss John Hughes sprung a surprise in his team selection by starting former Tranmere goalkeeper Owain Fon Williams, a new signing which he managed to complete under the radar.
But his first meaningful involvement was to palm the ball into the net as he tried to get across to keep out Budescu’s 25-yard free-kick.
Hughes had warned against giving away free-kicks around the penalty area because of the set-piece threat of Budescu, and Ross Draper paid the price for a mistimed sliding challenge on Brazilian winger William.
And the Astra forward showed what the fuss was about as he curled the ball over the wall, which Williams had struggled to get his message to, shouting at them until the last seconds.
It was a harsh blow for Inverness, who also handed debuts to former Cowdenbeath midfielder Nat Wedderburn and Spanish striker Dani Lopez.
They had dominated possession beforehand and came close through Ryan Christie’s 20-yard strike in the 10th minute.
Christie set Aaron Doran up for a shooting chance from similar distance after the half-hour mark but the Irishman hit it straight at the goalkeeper.
Caley Thistle were struggling to regain the control they had when the game was goalless, though, and Williams made a decent stop from another Budescu long-ranger just before the break.
The Welshman almost cost his side 10 minutes into the second half when he dallied on the ball and nearly lost it when pressed, although Danny Devine’s waist-high backpass had done him no favours.
Inverness soon nearly benefited from some suspect goalkeeping when Silviu Lung could only push Doran’s bouncing effort above his horizontal body following an Inverness break, the ball spinning over the bar.
Astra came close to a second goal when Budescu played in William, who placed his shot against the outside of the near post.
Inverness created their best chances in the final 15 minutes but Doran curled wide from a decent position and Lopez saw an angled strike held by Lung after briefly threatening to get in behind the Romanians.
Caley Thistle threw on Richie Foran up front following 16 months out with a knee injury but there was no fairytale comeback for the Irishman.