Portsmouth's ability to sign Conor Chaplin permanently is dependent on the division they are in, as the club attempts to avoid relegation under John Mousinho. Chaplin, who is currently on loan at Portsmouth from Ipswich Town, is due to become a free agent when his contract expires in late June. It is indicated that Chaplin will leave Ipswich Town permanently when his contract expires. It is thought that Portsmouth could offer him a contract if they avoid relegation.

A decision is needed soon regarding Conor Chaplin's long-term future as his loan spell at Portsmouth approaches its end, especially since he is out of contract at Portman Road in June. Portsmouth fan pundit Miltos Ioannidis claimed that Conor Chaplin's return to Fratton Park has not been successful. Ioannidis believes that there is better value elsewhere in the transfer market and that Portsmouth should focus their priorities on potentially securing other loan players. Ioannidis stated that only a strong run of form in the final months of the season could change that stance, and that unless Chaplin achieves an exceptional form in the last couple of months, it is not something the club should try to complete. It is mentioned that Chaplin is unlikely to be offered a new contract in Suffolk. The possibility is also discussed that, as a free agent, it could be possible to keep him for a relatively low cost if his wage demands are not extortionate.

According to John Mousinho, the deadline for Ipswich Town to recall Conor Chaplin from his loan at Portsmouth expires today. Mousinho also stated that after the initial cut-off point was extended last Friday, conversations with Ipswich Town will occur this afternoon. Furthermore, Mousinho expressed hope that Chaplin will stay at Portsmouth and noted that Chaplin has played nearly every minute of every game during his loan.

Ipswich Town manager Kieran McKenna revealed that the recall option on Conor Chaplin's loan has been extended and now goes into the following week. McKenna said the likelihood is that Conor Chaplin will stay at Portsmouth for the remainder of the season. McKenna also said the clubs have communicated this week and are planning for him to be at Portsmouth for the rest of the season.

Conor Chaplin returned to Portsmouth from Ipswich Town on deadline day, agreeing a deal for the 2025/26 campaign. Ipswich Town retained an option to recall Conor Chaplin in January. John Mousinho stated that he expects Conor Chaplin to spend the rest of the campaign on loan at Portsmouth. Kieran McKenna revealed that no decision had been made regarding the recall. The option was due to expire this week.

Kieran McKenna said no formal talks have yet taken place on whether Conor Chaplin will be recalled from his loan spell at Portsmouth. John Mousinho stated Conor Chaplin would be staying at Fratton Park following a brief conversation at Sunday’s postponed fixture between the clubs. McKenna said he has not been involved in any talks on the matter and that the first conversation would be between him and Conor Chaplin. There is a clause that is active for another week, and the decision will be resolved before the clause's expiration at the end of the following week.

Pompey boss John Mousinho has revealed that Conor Chaplin is expected to stay at Fratton Park.

Ipswich Town manager Kieran McKenna will consider recalling Conor Chaplin from his loan at Portsmouth after the two clubs play on Sunday. Chaplin, who joined the club from his childhood on loan on summer transfer deadline day, has had difficulty scoring goals and will be ineligible for the upcoming match. McKenna confirmed there have been no talks about a recall yet, explaining that assessments on the whole squad, including players out on loan, will happen after the weekend's game. Any potential move is affected by Ipswich having a full 25-man senior squad, which means they would need to remove a player to add another at the start of the January transfer window.