The Primeira Liga outfit come into this game with a 3-1 advantage, having dominated the away leg despite going 1-0 down early in the game.
In the first leg of this tie, Estoril took a surprising lead through Andre Vidigal, before the game turned in the favour of the Primeira Liga outfit in the second half as Darwin Nunez netted goals either side of a Haris Seferovic finish to give As Aguias a two-goal lead.
However, their recent form has been much less convincing, winning just one of the five games since that cup victory.
Before that, As Aguias took on Arsenal in the second leg of their Europa League round-of-32 tie, after they had drawn 1-1 in the first leg.
Jesus's men led 2-1 on the night as Diogo Goncalves and Rafa Silva both scored to overturn a Pierre-Emerick Aubameyang opener, but second-half goals from Kieran Tierney and Aubameyang turned the game back around, sending the Gunners through.
As a result of their recent inconsistent form, the 37-time Primeira Liga champions have dropped to fourth in the top flight, sitting 13 points behind league leaders Sporting Lisbon, having won just two of their last eight matches in the league.
That means that Jesus will be even more determined to advance to the final, as the Portuguese cup could be the only piece of silverware that the side from Lisbon can lift this season, having dropped out of contention in other competitions.
However, they take on an Estoril team who will be desperate to give a good account of themselves against one of Portugal's biggest clubs.
Bruno Pinheiro's side currently sit one point clear at the top of the Segunda Division, as they look to win promotion back to the top flight after two consecutive seasons of narrowly missing out.
It is hard to argue that they do not deserve to sit at the summit of the table either, as Estoril boast both the best attacking and defensive records in the league this campaign, with no side conceding as few as the 15 they have shipped, or scoring as many as their 36 from 22 league games.
Since the first-leg defeat, Estoril have returned to winning ways by recording three consecutive league victories.
Pinheiro's men have already defeated top-flight opposition on this cup run, firstly beating Rio Ave 2-1 away from home in the round of 16.
After that, they secured a dramatic victory over Maritimo, having trailed 1-0 until the 10th minute of added time when Joao Gamboa netted a late equaliser from the penalty spot, before extra-time goals from Jean Thierry Lazare Amani and Harramiz sealed their spot in the final four.
However, Thursday's game presents a tougher challenge as they take on Portugal's most decorated side, who will be looking to go one step closer to lifting their 27th Taca de Portugal title.
Benfica Taca de Portugal form: WWWWW
Benfica form (all competitions): WDDDLW
Estoril Praia Taca de Portugal form: WWWWWL
Estoril Praia form (all competitions): LLLWWW
Jan Vertonghen is expected to be absent for this game, having missed Benfica's win over Rio Ave with a thigh injury.
He could be joined on the sidelines by Darwin Nunez, who starred in the first leg with two goals, after he also missed the last game through injury.
In Vertonghen's absence, January signing Lucas Verissimo impressed at the back, keeping a clean sheet in his Primeira Liga debut following his move from Santos.
Experienced defender Andre Almeida also remains out for this clash, as he continues his recovery from a ligament rupture.
Jesus is expected to rotate his squad, with Luca Waldschmidt potentially being rested after he recently came back from an injury, while Pedrinho, Pizzi and Gabriel Pires could all come into the side in midfield.
Andre Vidigal will be hoping to repeat what happened in the first leg of the tie, when he netted an early goal for Estoril.
He will be joined in attack by Abdul-Aziz Yakubu, who has netted seven Segunda Liga goals this campaign.
Benfica possible starting lineup:
Leite; Goncalves, Verissimo, Jardel, Grimaldo; Pedrinho, Pizzi, Pires, Everton; Seferovic, Silva
Estoril Praia possible starting lineup:
Figueira; Soria, Basto, Gomes, Joaozinho; Crespo, Gamboa, Rosier; Vidigal, Yakubu, Harramiz
We say: Benfica 3-1 Estoril Praia
While the second-tier outfit will come into this game with plenty of courage, we expect a similar scoreline in this second leg as Jesus's side take Estoril apart thanks to their superior quality.
The visitors will be forced to attack as they look to claw their way back into the game, which could leave them open for counters led by the clinical Seferovic, resulting in another win for Benfica.