Scotland ran into the formation spoiling they had anticipated in the Serravalle Stadium last night, though responsibility for a frustrating Group Eight match has to be laid equally at the door of Scotland's dearth of ideas as to how to counter it.
Having scored an early goal - a fine solo effort by John Collins - Craig Brown's side seldom looked capable of adding to it before Colin Calderwood headed in Gary McAllister's pass with five minutes remaining.
If the setting was unreal - a municipal park at the foot of the mountain, where the marching band all but outnumbered home supporters - there was almost a start to match.
With 10 minutes gone Massimo Bonini's pass found Marco Mularani goal- side of Alan McLaren, only for the midfielder to drag his shot wide from 15 yards.
Any anxiety Scotland felt was assuaged when they went ahead nine minutes. Collins taking possession deep in his own half, spotted that his strikers were coming back from offside positions and decided to go it alone.
Despite encountering several lunges, including one outside the box that earned Pier Luigi Benedittini a caution, Collins maintained his balance to prod his eighth goal in 24 internationals into an unguarded net.
Scottish relief was almost tangible, for the strategy of cutting crosses back from the byline had scarcely been implemented until then.
Facing the play, the stocky Benedittini and his not-so-thin blue line coped comfortably. A cleverly curled free-kick by Marco Mazza on the half- hour, which forced a fine save from Jim Leighton, underlined the need for a second goal.
All too often the slick approach work of Collins and McAllister was wasted by a final ball which literally played into the keeper's hands.
When a centre by Pat Nevin did clear him in the 35th minute, to be headed back across the six yard area by Tommy Boyd, John McGinlay planted a free header wide.
Even at 35, Bonini showed flashes of the ability that once saw him partner Michel Platini with Juventus. More importantly, he organised and cajoled his amateur colleagues, which ought to have made his withdrawal due to injury a signal for the Scots to press home their advantage in the second half.
Theory and practice can be uneasy bedfellows, however, and the massed Sammarinese tenaciously continued to compress the space in which Scotland strove to play. The next opportunity did not arrive until the hour mark, when Boyd's cross was mis-headed by Mirco Gennari straight to McAllister, lurking near the penalty spot. The captain's instantaneous volley was tipped over by Benedettini, who drives buses for a living.
Boyd's shot then hit the outside of a post, but the 600 Scotland fans had just begin chanting "What a load of rubbish" when Calderwood smoothed their path towards next summer's finals.
SAN MARINO (1-1-3-5-1): Benedettini (AC San Marino); Guerra (AC San Marino); Gobbi (AC Cattolica), Canti; Gennari (both SS Juvenes); Della Valle (SS Secchiano), Manzaroli (AC San Marino), Mazza (SS Grosseto), Bonini (AC San Marino), Mularoni (SS Juvenes); Bacciocchi (SS Santarcangiolese). Substitutes: Matteoni (AC Cattolica) for Bonini, h-t; Gualtieri (Valbruna Gabicce) for Mularoni, 71.
SCOTLAND (3-4-3): Leighton (Hibernian); McLaren (Rangers), Hendry (Blackburn), Calderwood (Tottenham); Jackson (Hibernian), McAllister (Leeds), Collins, Boyd (both Celtic); Shearer (Aberdeen), McGinlay (Bolton), Nevin (Tranmere). Substitutes: Spencer (Chelsea) for Shearer (67), McKinlay (Dundee United) for Nevin, 78.
Referee: L Loizou (Cyprus).