Scotland battled to an unconvincing 2-0 win away to minnows San Marino thanks to goals from Kenny McLean and Johnny Russell.
Alex McLeish's side were humiliated 3-0 in Kazakhstan in their Group I opener three days prior and they again struggled to find any rhythm on Sunday, despite facing the lowest ranked team in the world.
McLean's fourth-minute header, his first international strike, put the Tartan Army on track for a morale-boosting win but Scotland toiled at San Marino Stadium.
Russell, however, netted in the second half to ensure Scotland have three points on which they can build when their Euro 2020 qualifying campaign resumes in June.
Scotland opened the scoring with their first meaningful attack when a short corner was taken to Ryan Fraser and his inswinging cross was deftly flicked in by a diving McLean.
Elia Benedettini made a brilliant double save to deny Stuart Armstrong and Adolfo Hirsch wasted a rare San Marino chance by finding the side netting after rounding Scott Bain.
Filippo Berardi went down in the box under Scott McKenna's clumsy challenge but referee Manuel Schuttengruber waved away hopeful San Marino appeals for a penalty.
Home captain Davide Simoncini superbly blocked a Fraser shot but Scotland finally settled any nerves with their second goal in the 74th minute.
With San Marino pushing upfield they got caught short at the back and Russell stayed cool to fire home his first Scotland goal when James Forrest's cross found him in the penalty area.
Substitute Marc McNulty should have added a late third for Scotland but badly miscued his header from a Forrest delivery, summing up his side's glaring issues in front of goal.
What does it mean? McLeish already under pressure
Scotland's Nations League promotion already feels a long time ago with questions being asked about McLeish's suitability to lead the Tartan Army, despite him only being a year into his second spell. Celtic star Forrest had scored all five of Scotland's previous goals but was surprisingly named on the bench and the lack of attacking threat until his second-half introduction was obvious.
Benedettini impresses in San Marino goal
Scotland's inability to rack up a big score was mostly down to the good work of goalkeeper Benedettini, who kept them at bay for long periods after being given no chance with McLean's header. Benedettini's pair of saves from Armstrong in quick succession were from the top drawer.
Returning Robertson fails to show quality
Andy Robertson missed the Kazakhstan debacle due to a dental problem but he could not provide the injection of class expected from one of Scotland's few players of top quality. The Liverpool defender delivered a string of left-wing crosses without finding his targets, while the captain did not show enough leadership to drag Scotland through a stumbling team display.
Key Opta facts
- Scotland have won each of their seven meetings against San Marino in all competitions, scoring 21 times without reply.
- Since a 0-0 draw with Estonia in November 2014, San Marino have lost 29 consecutive games in all competitions by an aggregate score of 122-3.
- Scotland have won 2-0 in each of their four visits to San Marino.
- Kenny McClean's opener for Scotland was their earliest goal in an away game since Darren Fletcher scored after four minutes in a 3-0 win against Slovenia in October 2005.