The striker returned to Ipswich at the end of last term following a Blues season-long loan in which he scored seven goals in 44 appearances.
Primarily the former AFC Wimbledon man was used off the bench by both Danny Cowley and his replacement John Mousinho as he struggled to find a way past Colby Bishop.
Subsequently, Pompey were not interested in making the arrangement permanent, despite Pigott establishing himself as a popular dressing room figure.
Now he has left Championship newcomers Ipswich by mutual consent in order to complete a move to Leyton Orient on a two-year deal.
In the process, the 29-year-old becomes their seventh signing of the summer, following Max Sanders, Ethan Galbraith, Dan Agyei, Sam Howes, Idris El Mizouni and Sol Brynn.
And the Pompey reunion will be swift, with Mousinho’s men scheduled to travel to Brisbane Road in their second league game of the forthcoming campaign (August 12).
‘He’s great with his back to goal and a really clever footballer. In terms of goals, he had a wonderful spell at Wimbledon which got him a great move to Ipswich and subsequently a loan at Portsmouth.
‘He can play centre forward, but he can also play wide, so his versatility is something that could be really important for us.
I think he needs to find a home and someone who trusts him to get back to his goalscoring form, but he offers an awful lot of qualities.
He can score headers, tap-ins and free-kicks, he’s technically a really good player and we think his qualities will really help us this season.’
Although Pigott started alongside Bishop in the opening two league games of last season, that proved to be a false dawn.
With Cowley and Mousinho preferring one central striker, Bishop was inevitably the favoured choice, with the Ipswich loanee on the bench.
There were actually a flurry of appearances as a number 10 operating behind the 24-goal forward towards the end of the campaign.
However, that was wrecked when Pigott was shown a straight red card in a 3-1 victory at Accrington in March, during which he scored, and was suspended for three matches.
His final goal arrived in April, and once more against Accrington, when he came off the bench to grab the winner in a 1-0 Fratton Park victory.
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