Coventry are hoping to resurrect their pursuit of Conor Chaplin through a loan deal.
Boss Mark Robins remains keen on the Pompey striker, despite having previously walked away after becoming frustrated with the wait.
The Sky Blues are pushing for the move to be completed today ahead of the 5pm deadline.
However, with it being a potential loan, any agreement has until the end of the month to be sealed, allowing more time for it to be resolved.
Chaplin has made it clear to Pompey he favours the switch as he seeks regular first-team football.
Despite fielding a 4-4-2 against Luton on the opening day of the season, the frustrated 21-year-old was still an unused substitute.
Pompey remain in the market for another striker, while added David Wheeler earlier this week.
Kenny Jackett has been resolute about not letting Chaplin leave until a replacement has been found.
Yet Coventry are now encouraged their long-standing interest in Chaplin could be rewarded with a loan arrangement.
Previously the Sky Blues were willing to pay around £375,000 for the popular striker, who is out of contract in the summer of 2019.