It was a night of mixed emotions for Craig Gordon.
The 41-year-old became Scotland's oldest ever international in what was likely his final cap, but also gave away the spot-kick with a clumsy challenge.
His replacement as Scotland's number one was made to work in the first half, with Angus Gunn called into action a couple of time in a slow Scottish start.
The second half was much better. Hoskonen's own goal might have been a touch lucky, but Shankland's headed finish rounded off the type of swaggering move Clarke's side have lacked in recent times.
Injuries prompted late call-ups for Lewis Morgan and Tommy Conway - the latter earning his first cap at Hampden - as fresh faces looked to make their mark in the last outing before the real stuff starts.
But with a huge occasion looming, Scotland were punished for taking their foot off the gas.
The defence went to sleep for Kallman's header, before Gordon was adjudged to been too hasty rushing out of goal, allowing Antman to step up.
Despite the result, Scotland fans made sure to let their team know they have their full support this summer.
Too often they've been left watching tournaments at home. Now, they're off to Germany.