Michael Appleton fears he faces another fight to hang on to his star players after the emergency loan window opened today.
For the next seven weeks, Football League clubs are allowed to recruit players on loan.
It is set to spark plenty more business outside of the Premier League as teams seek to strengthen their squads.
For Pompey, it again raises the possibility of rival Championship sides coming in for their players.
Ipswich manager Paul Jewell has already hinted he may return for previous targets Joel Ward and Stephen Henderson.
The Tractor Boys were also among several clubs to have bids knocked back for Jason Pearce on transfer deadline day.
During the emergency loan window, clubs can agree to take a player on loan and then sign him permanently in the summer, a fund-raising route which could appeal to cash-strapped Pompey.
And Appleton is aware he has another battle to negotiate as he looks to keep his best players at Fratton Park.
After last night’s 1-0 loss at Birmingham, the Pompey boss said: ‘You are going to be just as concerned as January with the opening of the loan window.
‘I would imagine – I don’t know but I would imagine – there were plenty of people there last night having their eye on a few of our players.
‘You would expect that because people know the situation we are in.
‘From our point of view, we will try to be guarded in terms of me keeping the players concentrated on what they’re doing rather than worrying about what other clubs are interested in them and whether they are going to end up elsewhere.
‘The way we have to look at it is, until someone comes in with offers for our players, then we’re just going to work every day with the 17 players I’ve got at the minute.
‘Ipswich might come back in but if that is the case, we just have to use a contingency plan in terms of having players ready to get on loan from other football clubs.
‘If we do lose three players, surely the Football League aren’t going to allow us have 12 or 13 players in our squad?’
One such loan target remains George Thorne.
Yet Appleton has been informed the West Bromwich Albion midfielder cannot return to the Blues until a player leaves Fratton.
That is despite Ryan Williams’ transfer deadline day departure to Fulham.
Appleton added: ‘George is a player we would love to have back and would have loved to have had back over the past six weeks or so.
‘But as far as I am aware, we are still in a position where unless we lose a player we can’t bring anyone in.
‘The likelihood of George coming back to Portsmouth is going to rely on someone leaving us – but we can’t afford anyone to leave us.
‘We will see but it is a Catch 22 situation.’