Rich Hughes and John Mousinho are challenged to bolster a side which tops League One heading into the New Year, yet since 2017-18 it has often proven a frustrating window.
There have been some excellent signings, some awful ones and others simply bang average. So here’s a look at 16 of them from the previous six Januarys in League One...
9. James Vaughan - January 2019
Loaned from Wigan in January 2019, much was expected from the much-travelled ex-Everton striker - however, it was a hugely disappointing stay. Of his 11 appearances, just two were starts, while he failed to score to cap a hugely forgettable stay at Fratton Park. At one point, was bafflingly told he could train with Wigan rather than with the club he was on loan at. Came off the bench in the 2019 League One play-off semi-final second leg against Sunderland as Kenny Jackett's men were eliminated. Photo: Joe Pepler
10. Tyler Walker - January 2022
Reunited with former Lincoln boss Danny Cowley in January 2022, with the Coventry striker catapulted into one of Pompey's highest earners. However, the loan was a disaster, with Walker scoring once in 15 appearances amid frustratingly lacklustre displays. Tellingly, he was an unused substitute in the final six matches of the campaign as the Blues finished 10th in League One - when he had been recruited to haul them into the play-offs. Rejoined Lincoln in the summer, but has not played since August through injury. Photo: Jason Brown
11. Harvey White - January 2021
The promising youngster was recruited on loan from Spurs for the remainder of the season, yet would play a bit-part at Fratton Park. White netted the winner at Oxford United on his full debut, yet, of his 22 appearances, just six were starts. Showed some good touches and impressed in parts, but when Danny Cowley arrived as interim head coach he was on the bench for 10 of the last 11 matches. Now playing for Stevenage, who he joined permanently in the summer. Photo: Joe Pepler
12. George Byers - January 2021
It appeared to be something of a coup when Kenny Jackett signed the attacking midfielder on loan from Championship Swansea in January 2021. However, Byers struggled to nail down a regular spot, firstly under Jackett and then interim head coach Danny Cowley. Of his 15 appearances, just five were starts, while he also suffered from a lack of a defined role, operating either as a number 10, central midfielder or left winger. Has since flourished after moving to Sheffield Wednesday permanently in the summer of 2021. Photo: Joe Pepler