A trip to Ipswich was arguably the tie that Pompey most wanted to avoid when the draw was made for the second round of the Papa Johns Trophy.
The Tractor Boys sit second in the League One standings and have a squad that is the envy of most other clubs in the division.
But Danny Cowley is relishing the opportunity to take his side to Portman Road, where a place in the last 16 of the competition is up for grabs.
And he believes it will be an excellent learning opportunity for the younger members of the squad that are likely to feature.
The Blues boss said: “It’s probably the hardest tie possible for us and you just have to look at the depth they have in their squad.
“I had the pleasure of watching their game at Exeter on Saturday and you see their bench, with the athleticism and power they’re able to bring into the team.
“So it’s going to be incredibly tough, but that’s great for our young players and the clear objectives we have for this competition.
"We anticipate facing a strong Ipswich side and whenever you play top teams, it gives you instant feedback."
“We always go out to win – that goes without saying – but there’s also a development aspect and we’ve previously been able to give exposure to the likes of Zak Swanson and Jay Mingi.
“It means that when they’re called upon in the league – as they have been – they’re in a much better place to step up and perform.
“So we will go to Portman Road and try to put a performance together that will be good both in and out of possession.
“We anticipate facing a strong Ipswich side and whenever you play top teams, it gives you instant feedback. This can help the journey that we’re on.
“We can’t experiment too much because we don’t really have the numbers at the moment, but we’ll utilise the squad as best as we can.”
Pompey’s options are hampered by a few injuries, while Joe Pigott is unable to feature against his parent club.
Cowley said: “We certainly have our challenges, but I don’t think we’re the only team with issues in that area.
“It’s for us to find the solutions and we prefer to see the opportunities in these moments because there will be a great chance for young players or those who have been on the periphery.”