Liverpool suffered a third defeat in their last four pre-season games as they were comprehensively beaten by Napoli in Edinburgh.
The Italians were the better, more dynamic side as they cut through a blunt Liverpool during the first period.
Lorenzo Insigne opened the scoring for the Serie A side with a fine finish, which was then added to when Arkadiusz Milik stabbed home.
The Reds beat Carlo Ancelotti's side 5-0 in a Dublin friendly last year, but they were nowhere near that level and fell 3-0 down when Amin Younes tapped in after Simon Mignolet saved from Insigne.
Liverpool improved when their young players came on in the second half, including debutant Harvey Elliott, but ultimately it was a poor display.
Here are the talking points.
1. Cause for concern for Klopp
Any time a team loses a pre-season game it won't be long before those who have that side's sympathies trot out the line about it being "all about fitness", but off the back of the unconvincing displays in America there was certainly enough for Klopp to worry about here.
Of course there is the caveat of not having any of their first-choice front three or goalkeeper, but Liverpool were too often aimless and passive in a game against opposition who should be behind them in terms of fitness.
Klopp's double sessions in the US looked to be taking their toll on a tired team, but the fans who flocked to Murrayfield had to expect Liverpool to be better than this.
The fact that they weren't has to set off mild alarm bells.
2. Unconvincing Oxlade-Chamberlain
One of the knock-on effects of Liverpool being without their fearsome forwards this pre-season has been that Klopp has has to push midfield players further forward if he wants to remain wedded to a 4-3-3, which it seems he does.
You could argue whether that is the right approach - a front two of Divock Origi and Rhian Brewster would be nice to see, for example - and in the German's approach it has been Gini Wijnaldum and Alex Oxlade-Chamberlain who have been asked to push forward.
This looks to be a particularly difficult task for Oxlade-Chamberlain.
Before his injuries the Englishman was developing into a fine central midfield player, and asking him to head out wide again as he continues his recovery from horrendous injury doesn't look to be doing him any favours.
3. Wijnaldum on the move
Wijnaldum looks a little more suited to the new role he is being asked to play, which comes as an extension of his frequent switches in position towards the end of last season.
The Dutchman was excellent off the left in the draw against Sporting Lisbon, but like everyone he struggled for rhythm during the bitty first half.
One attribute he does have are excellent runs from deep though, and he's a more than likely option to start the season from the left in the absence of Sadio Mane.
Liverpool have to hope things go a lot smoother for him when Roberto Firmino and Mohamed Salah are in the side.
4. Napoli stop the full-backs again
One of Liverpool's least effective games of last season was the 1-0 defeat in Naples in the Champions League group stages, when Carlo Ancelotti drilled his side to stop the Reds' flying full-backs Trent Alexander-Arnold and Andy Robertson.
It was arguably the first time a side had developed a plan to specifically stop the pair, who got the better of so many sides in 2018/19.
Ancelotti's side did it again here, putting two men on the pair to pin them back, and as Liverpool's dynamic duo struggled to make an impact, you'd have to wonder if more sides will take similar approaches in the near future.
5. Insigne shows his worth
For the best player on the pitch you needed to look no further than Insigne, who led Liverpool a merry dance for much of the contest.
The 28-year-old is entering his ninth season in Napoli's first-team, and he showcased all of his talents particularly during a dazzling first half.
Once linked with the Reds, you can expect the transfer hype to ramp up.
