Pompey booked their place in Monday's Emirates FA Cup second round draw with a dramatic win at Ipswich.
It looked like being a simple job for Kenny Jackett's side, as goals from Ronan Curtis and Tom Naylor saw them hold a commanding lead inside 13 minutes.
But Jon Nolan and James Norwood netted to take the tie into extra-time, where Sean Raggett struck to seal a 3-2 victory.