Scotland failed to register a shot on target as they fell to a 1-0 friendly defeat against Italy in Malta.
Southampton striker Graziano Pelle notched the only goal early in the second half but Scotland would have been on the end of a heavier defeat if Emmanuele Giaccherini had shown more composure when presented with several clear chances.
Scotland took almost 78 minutes to produce their one and only effort at goal - Matt Ritchie shooting wide from 18 yards.
Italy had not won in four matches but they were a class apart from Gordon Strachan's side in their penultimate warm-up for a European Championship campaign that sees them pitted against the Republic of Ireland, Belgium and Sweden.
Scotland struggled to mount any attacks and Strachan will be looking for improvement when they face Euro 2016 hosts France in Metz on Saturday.
Hearts right-back Callum Paterson made his Scotland debut and Matt Phillips won his fourth cap on his first start since a 5-1 defeat by the United States four years ago.
Skipper Scott Brown was among those who had been rested but Scotland otherwise had a familiar look to their line-up, although Ross McCormack started up front ahead of Steven Fletcher.
McCormack had very little service, though, and the tone was set by the seventh minute when David Marshall produced a brilliant double save. The Cardiff goalkeeper pushed out Antonio Candreva's powerful 30-yard free-kick, which bounced just in front of him, before stopping Giaccherini's follow-up.
Leonardo Bonucci soon came close from long range before Scotland settled into the game with a long spell of possession, although they got deeper as it progressed.
And the respite proved brief as Italy remained on top.
Giaccherini missed another great chance midway through the first half when he blazed over from 16 yards after Candreva had got in behind the left side of Scotland's defence and cut the ball back.
Candreva was off target from three difficult chances and Giaccherini squandered another clear opportunity when he ran on to Daniele De Rossi's pass over the top but flashed a first-time effort high and wide.
Marshall watched several more long-range efforts go wide as Scotland struggled to get out of their own half before the interval.
Paterson, who was nursing a back injury in training, did not reappear after the break as Christophe Berra came on and Russell Martin moved to right-back.
Giaccherini was wrongly flagged offside as he teed up another chance but the inevitable Italian opener finally came in the 57th minute.
Half-time substitute Fletcher trod on the ball and fell over to surrender possession and Italy worked a couple of quick passes around the edge of the box before Pelle curled into the corner from 20 yards.
Italy appeared to ease off after the breakthrough - and a number of substitutions also affected their rhythm - but Scotland could not capitalise.
Some Scotland fans celebrated their first corner in the 70th minute but the referee blew for an Italy free-kick almost immediately after it was taken.
There was some genuine excitement for the travelling support when substitute Steven Naismith worked the ball out to Ritchie on the left edge of the box after Scotland had won the ball deep in the Italy half, but the Bournemouth player shot just wide of the near post.
Scotland had more spells inside the Italian half but could not fashion another chance.
David Marshall 7
Callum Paterson 6
Charlie Mulgrew 6
Russell Martin 6
Grant Hanley 6
Matt Phillips 5
Darren Fletcher 6
James McArthur 6
Ross McCormack 5
Matt Ritchie 7
Ikechi Anya 5
Steven Fletcher 5
Christophe Berra 5
Steven Naismith 6
Oliver Burke 5
Craig Bryson (N/A)
STAR MAN: David Marshall's seventh-minute double save from Antonio Candreva's free-kick and Emanuele Giaccherini's follow-up was enough to earn him the nod as Scotland's man of the match - no one else managed to make an impact of note. Daniele De Rossi impressed in the Italy midfield despite an Achilles problem.
MOMENT OF THE MATCH: Marshall's recovery from his own early save was top class. No one could have expected him to keep out the follow-up. It gave him further cause to keep his spot as Gordon Strachan's number one amid fierce competition from Craig Gordon and Allan McGregor.
VIEW FROM THE BENCH: Strachan wanted a stern test for his players and they certainly got that against an Italian side whose movement and pressing posed plenty of questions. Whether he can come up with any answers is another matter but Scotland have a swift chance to improve when they face France on Saturday.
MOAN OF THE MATCH: It's not often a team fails to register a single shot at goal - on or off target - but Scotland almost managed it. It took 78 minutes for them to carve an opening and Matt Ritchie shot wide. The Scots were always going to be up against it as they faced an Italian squad playing for places in Antonio Conte's final 23-man Euro 2016 pool, but their attacking play was non-existent for most of the game.
WHO'S UP NEXT?
France v Scotland, Saturday, June 4 (friendly)
Italy v Finland, Monday, June 6 (friendly)