Scotland conceded soft goals either side of the break to slip to a friendly defeat against Turkey in Diyarbakir.
It was a just third loss in 16 for Steve Clarke's side, who looked shaky defensively in the first meeting of these nations in 62 years.
Ozan Kabak got between two defenders to head in a free-kick, before Cengiz Under finished a smart break after Stuart Armstrong coughed up possession.
John McGinn gave the Scots hope but his stunning strike was mere consolation.
Indeed, for all that the visitors rallied and might have had a penalty when Lyndon Dykes was wrestled in the box, the Turks could have been out of sight before then.
Ranked five places behind Scotland in 45th spot, they struck the frame of the goal and were denied on several occasions by Craig Gordon on his 700th senior appearance.
One bright spot for the Scots was a debut for Liverpool's 19-year-old right-back Calvin Ramsay, who Clarke opted not to use from the start.
Instead, the head coach went with a tried and trusted line-up perhaps in recognition of the test that lay before them. His players wilted under that examination and arguably escaped with a lenient outcome, albeit they did rally as the game wore on.
The intensity of the boisterous home crowd in the first-ever international in Diyarbikar, was matched by the quality of the men in red. It meant a lot and that was reflected on the pitch.
From the outset, Turkey went at Scotland's backline. Captain Hakan Calhanoglu had an early shot parried by Gordon and the Inter Milan playmaker was instrumental, particularly in the first half, with another of his efforts diverted by the goalkeeper's legs.
Scotland hung on and did have a decent chance when Armstrong sent a lovely ball across the six-yard box that just evaded Dykes, but further scares would follow when Andy Robertson diverted an effort over his own bar and Kabak cracked a header off the bar from the consequent corner.
And Kabak would soon break through from another set-piece, rising unchallenged to angle his header from a Calhanoglu delivery across Gordon.
Defensively, Scotland looked ill at ease. They were almost caught out again from a simple diagonal ball but Gordon thwarted Samet Akaydin, so it felt almost like a relief that they reached the break just one behind.
That status didn't last long, though. Armstrong might have slipped in Robertson when in possession on the edge of the Turkey box but was robbed and Under raced away before jabbing a sublime finish through Scott McKenna's legs and away from Gordon.
The game looked gone, but from nowhere McGinn burst forward, rode a challenge and thumped an excellent strike into the far corner. It was his 15th international goal - tied with James McFadden - and suddenly Scotland looked reborn.
Clarke's side had a double penalty shout waved away when Dykes and McKenna appeared to be manhandled while trying to meet a deep delivery and Hendry connected with another ball at the back post but was off target.
Substitute Ryan Christie came close, too, but his angled shot after an excellent move flew over.
Player of the match - Hakan Calhanoglu
Hakan Calhanoglu was an absolute stand-out for Turkey for the opening hourPositives and negative in testing experience - analysis
The positives lie in the resilience shown by Clarke's men after being second best for long spells. They hung in, got the goal and significantly improved. The fact the noise in this arena dampened down told its own story.
However, concerns will persist as Turkey were unfortunate not to have been long out of sight before Scotland's defiant response.
In the long run, the experience may stand them in good stead with European championship qualification next on the agenda.
What they said
Scotland head coach Steve Clarke: "I thought at times we coped quite well, at other times not quite so well. We probably gave up too many chances in the first-half, a lot of them from our own slackness, maybe the mentality of a friendly.
"But it should be mentioned that it is a long trip. We decided to do it in quite a short time-span. We only had 20-25 minutes of tactical work on the pitch yesterday in front of everyone who wanted to watch it. So we can make some excuses from that but I don't want to make too many.
"There were some things that we tried on the pitch, organisation and set-play wise that worked and some that didn't. We have to go away, analyse what we did and hopefully be much better next year."
Scotland goalscorer John McGinn: "We were good at times. It was a testing environment and the conditions were extremely difficult but it sets us up for the Euro 2024 campaign which is going to be tough.
"Certainly in the first half we didn't really stand-up to it to well but the last 30 minutes we showed glimpses of what we are capable of. I think we did enough to get a draw so there are positives to take. When the real stuff comes in March we will learn from tonight."
Line-ups
Turkey
Formation 3-4-2-1
23Çakir
15Kabak4Söyüncü22Özkacar
2Çelik6Kökçü10Çalhanoglu20Kadioglu
17Ünder8Kahveci
9Tosun
23Çakir15Kabak4Söyüncü22Özkacar2ÇelikBooked at 54mins6KökçüSubstituted forÖzcanat 45'minutes10ÇalhanogluSubstituted forTürüçat 69'minutesBooked at 82mins20KadiogluSubstituted forElmaliat 34'minutes17ÜnderSubstituted forYüksekat 81'minutes8KahveciSubstituted forAktürkogluat 81'minutes9TosunSubstituted forÜnalat 69'minutesSubstitutes
1Bayindir3Akaydin5Özcan7Aktürkoglu11Sinik12Alemdar13Elmali14Özcan16Ünal18Yüksek19Bozok21Türüç24Bulut25Güler26SanuçScotland
Formation 3-4-2-1
1Gordon
13Hendry5Hanley6Tierney
19Fraser4McTominay14Gilmour3Robertson
17S Armstrong7McGinn
9Dykes
1Gordon13Hendry5HanleySubstituted forMcKennaat 45'minutes6Tierney19FraserSubstituted forRamsayat 45'minutes4McTominayBooked at 25minsSubstituted forFergusonat 79'minutes14GilmourSubstituted forJackat 67'minutes3RobertsonBooked at 54mins17S ArmstrongSubstituted forChristieat 67'minutes7McGinn9DykesSubstituted forBrownat 79'minutesSubstitutes
10Ferguson11Christie12Kelly15McKenna16Porteous18Brown20Jack21McCrorie22RamsayLive Text
Match ends, Turkey 2, Scotland 1.
Second Half ends, Turkey 2, Scotland 1.
Corner, Scotland. Conceded by Çaglar Söyüncü.
Deniz Türüç (Turkey) wins a free kick on the left wing.
Foul by Ryan Christie (Scotland).
Corner, Turkey. Conceded by Kieran Tierney.
Attempt blocked. Deniz Türüç (Turkey) left footed shot from the centre of the box is blocked. Assisted by Kerem Aktürkoglu.
Attempt blocked. John McGinn (Scotland) left footed shot from outside the box is blocked.
Foul by Deniz Türüç (Turkey).
Kieran Tierney (Scotland) wins a free kick in the defensive half.
Foul by Enes Ünal (Turkey).
Scott McKenna (Scotland) wins a free kick in the defensive half.
Attempt missed. Ryan Christie (Scotland) right footed shot from the right side of the box is too high. Assisted by John McGinn with a through ball.
Offside, Turkey. Ugurcan Çakir tries a through ball, but Kerem Aktürkoglu is caught offside.
Deniz Türüç (Turkey) is shown the yellow card.
Foul by Deniz Türüç (Turkey).
Kieran Tierney (Scotland) wins a free kick in the defensive half.
Substitution, Turkey. Ismail Yüksek replaces Cengiz Ünder.
Substitution, Turkey. Kerem Aktürkoglu replaces Irfan Can Kahveci.
Foul by Irfan Can Kahveci (Turkey).