Steve Cotterill has admitted the final five games of the season will decide Danny Webber’s Pompey future.
The Blues boss is looking to make his mind up whether to offer the returning striker a new deal between now and the end of the campaign.
Webber put a year of injury pain behind him against Coventry on Tuesday night, with his first start since rupturing his anterior cruciate ligament against Spurs a year ago.
The 29-year-old signalled his recovery from that problem with a 75-minute showing up top against the Sky Blues.
That followed on from two cameo appearances in the recent clashes against Reading and Preston.
Webber was given a warm welcome by fans as he got his first start under his belt after going down a long and arduous road of rehabilitation.
Now Cotterill has indicated he has to build on crossing his latest landmark over the final five games of the campaign.
His manager explained he will be looking closely at the player over the coming weeks before deciding what lies ahead for him.
But Cotterill admitted he has been impressed with what he has seen from the former Manchester United hitman.
He said: ‘It’s more about minutes for Danny now to see where we are at the moment for him.
‘It’s a progression for him really. I said a while back if we could get him to be involved with three or four games to go we would have done well to get him to that stage.
‘Sooner or later he had to go into the deep end.
‘I need to find a little bit out about him and what he’s going to be all about because he’s another one who’s contract is up in the air.
‘It is tough when you come back but I have to say he looks sharp, is fresh and is champing at the bit.
‘There had to be a time when he had to go out there whether he’s ready or not.
‘That may help him to get ready for it.
‘I think it’s a big period for Danny now. But let’s see how he does, what we don’t want to do is put pressure on him from the contract situation.
‘The pressure is for him to go and play his football at the moment.’
Cotterill believes it is the work Webber has put into his recovery at Pompey’s Eastleigh training base that is finally paying off for him.
He feels his improvement has also accelerated massively since he stepped up his work and joined in full training three weeks ago.
But there are things that couldn’t be replicated until the striker stepped back into the cut and thrust of the Championship action he is now getting under his belt.
Cotterill said: ‘The training’s important for Danny now. He’s into the third week of training.
‘I spoke to him last week when he came in and said I thought he’d got a really good week’s training under his belt.
‘He’s far better now than what he was two weeks ago.
‘In training the lads can hold back a little bit rather than going through it.
‘On Saturday against Preston, though, he came on and used his quick feet to get himself out of a tight area.
‘One of the lads clouted him a bit and that was quite interesting because that’s also another mark for him to cross.’