New boss Stephen Glass got his Aberdeen tenure off to to the perfect start with a dramatic shoot-out win over Livingston.
It was the end of an era when Derek McInnes left Pittodrie after eight years and the Scottish Cup clash gave Glass the chance to put down a marker.
Lions' striker Jay Emmanuel-Thomas opened the scoring before an inch-perfect volley from Niall McGinn took the game into extra-time.
Things livened moments into the added 30 minutes as Emmanuel-Thomas netted from the penalty spot, but 90 seconds later Florian Kamberi netted his first Aberdeen goal.
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The deadlock was broken in the Granite City as Scott Pittman found Emmanuel-Thomas and he thumped the low drive past substitute goalkeeper Gary Woods after 37 minutes.
Despite a disappointing end to the second half, Glass seemed to have rallied his players during the break. Dean Campbell's dangerous free-kick was met by the head of Lewis Ferguson, but it was straight at Max Stryjek.
David Matindale's men were happy to sit in and soak up pressure, but looked to threaten on the counter attack. Allan Forrest created an opening with a blistering run down the right, but his drilled ball across goal was smothered by debuting Woods.
Glass' side would get themselves back in the game thanks to a moment of magic from McGinn. The Dons hit the visitors on the counter and the ball fell to the Northern Irishman on the edge of the box, who curled it into the top corner of the top left net after 77 minutes.
With the game in extra-time, referee Colin Steven controversially pointed to the spot as Emmanuel-Thomas went down under pressure from Dean Campbell. The towering striker stepped up to convert the spot-kick.
Moments later the Dons dragged themselves level as a neat McGinn pass found sub Kamberi to tap the ball into the net with a deft touch.
That forced the game to go into penalties, and Aberdeen's perfect penalties coupled with Jason Holt smashing the crossbar was enough to see the hosts through.
Aberdeen haven't lifted the trophy since 1990, but can Glass end the drought this year as they prepare to face Dundee United in the next round?
Glass era in focus
It's the kind of game Stephen Glass will have to get used to as Aberdeen boss.
A well-drilled and physical Livingston side that arrive at Pittodrie to sit back and hit on the counter attack.
Given the Lions top six Premiership finish it was never going to be an easy start for Glass, but with a focus on adding to the Dons trophy cabinet it's a positive start for the boss.
It's hard to judge what the major strengths and weaknesses of way the former Atlanta United 2 boss set-up in his first game in the dugout after just two training sessions, but up to the 75 minute mark it was eerily similar to the end of the Derek McInnes era.
However, the moment of magic McGinn gave his rein a jump start going into the final 10 minutes, and Kamberi's strike was a neat finish, Aberdeen managed to increase the tempo.
The addition of Callum Hendry as a partnership with Kamberi seemed to give the side the vital boost, and it will be interesting to see if the front two is now the preferred system going forward.
Finding attacking solutions?
With Allan Russell coming in to work with the strikers it's clear the former England coach will have work to do.
Fraser Hornby was preferred in the starting XI over Florian Kamberi, after the former Rangers and Hibs star was hooked at the break in his last appearance.
However, the Scotland under-21 cap only managed one shot on target and struggled to act as the focal point for the hosts.
He was replaced by Kamberi who suffered similar frustrations before he was joined in a top two by sub Callum Hendry.
Kamberi then got his first goal for the club which would strengthen the case for a new strike partnership when they return to Premiership action.
Since the departure of Sam Cosgrove it's been a problem position and Russell will hope he is starting to find the solution.
Lewis a loss
The captain was forced off after a collision with Livingston defender Jon Guthrie in the first half.
Despite replacement Woods not being at fault for the two goals, the skipper has been one of the most consistent goalkeepers in the Premiership in his five years at Pittodrie.
If the knock to the ribs was as serious as it looked immediately, Glass faces a real headache in a key position just one game into his tenure.