With the best will in the world, it is the kind of headache the Scotland manager would rather have than not after being deprived of the Arsenal man's services for as long as he's been forced to.
Tierney's last cap came against Switzerland at last summer's Euros, which somehow feels like a lifetime away already - even if it was only nine months or so ago.
In the intervening months, Clarke has recalibrated his side, switching from a five at the back to a four, all in the name of progression and making Scotland a more front- footed, forward thinking force on the international stage.
And yet, here we are back at the start.
In Athens ahead of the first leg of a double-header against Greece that will determine whether Clarke and his players are allowed access to another campaign in the top tier of the Nations League or sent down the divisions to kick about with the also-rans.
And once again, Tierney’s role in it all is the subject of considerable debate.
Does Clarke rip up his brave new template to return to the bespoke formation designed with the sole purpose of squeezing Tierney and Andy Robertson in the same starting XI?
Or does he do the previously unthinkable and leave Celtic's returning prodigal son watching on from a seat on the bench?
The truth is Tierney is as close as they come to being a Rolls Royce of a football player but his history of injuries has rendered him with the reliability of a Morris Minor.
Now he's back fit and firing going into his final months at the Emirates, Clarke has a familiar dilemma on his hands.
This time it feels different and the solution far less certain.
"It's not a headache,” Clarke said, albeit with a touch of a grimace, after arriving in the ancient capital.
"It's a nice problem to have when you have a lot of good players to select from.
"We've also lost a few players in the build-up to the game and we've managed to bring some younger ones in to freshen things up a little bit, so we've had good preparation.
"But, as a coach, you want as many difficult choices as possible.”
Asked directly if he is considering throwing out the tactical blueprint which carried Scotland through the group stage in order to accommodate Tierney in his side, he said: "I'm always thinking of changing things.
"You'll just have to wait until you see the team on the pitch.
"But, listen, it gives us another option. We've spoken about it and hopefully we can come up with the right solutions. The teams been good with a back four. Obviously we changed the whole way we approached the games in the group stage - we went with four at the back and it worked.
"It worked well because we also had an outlet on the right-hand side with the pace of Ben Doak.
"We didn't have the option of putting Kieran into the team, so it has certainly given me a lot to think about.”
It will be fascinating to see what way Clarke twists now a place in League A is about to go on the line over the course of these next four days, with the return to follow at Hampden on Sunday.
He has brought a more youthful looking squad to Athens with teenagers Lennon Miller and James Wilson freshening up his group as well as Ipswich man George Hirst.
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