And offering pay-per-play terms has emerged as a potential solution.
While Jacobs’ quality cannot be doubted, concerns remain over his Blues injury record during two seasons on the south coast.
The former Wigan man has started just 17 League One matches since his September 2020 arrival.
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Primarily, that figure has been driven by a number of injury issues which continue to blight his availability.
Nonetheless, the 30-year-old remains an attacking talent hugely appreciated by his manager as well as the Fratton faithful.
Pompey possess an option on Jacobs’ contract which expires this summer – yet Cowley is mulling over an alternative offer.
He told The News: ‘Michael had a really good run of form, then picked up that innocuous injury.
‘To remain at Fratton Park, he needs to stay injury-free and find that form again because he is a top League One player.
‘There is an option on his contract and we’ve really enjoyed Michael, he gives the team a different quality that we don’t quite possess in our other attacking players.
‘However, his time at Pompey has been fragmented because of injury – and that’s the truth.
‘If we can find a performance-related contract that works for him and for us then that would be ideal.
‘Could that happen? I think anything’s possible, where there’s a will, there’s a way.
‘We are going to be a small squad and know the budget, so we must try to maximise it and utilise it to get the very best value.
‘You can maximise it in different ways. For instance, you can take an injury-prone player on less money in a contract and keep him fit and available.
‘There are many different ways to maximise your budget.’
Jacobs was recently sidelined by a knee issue for seven matches, before returning as a substitute in the goalless draw against Wycombe.
On Tuesday night at Bolton, he was granted only his fifth League One start of a season which has seen him tally six goals in 25 games.
Overall, he has featured 47 times and netted eight goals for Pompey following his free transfer arrival, after previously seeing service in the Championship with Wigan.
And he is pencilled in to retain his place for Saturday’s trip to Cheltenham.
Cowley added: ‘Michael’s had some niggles and a couple of serious ones, it has been stop-start it’s fair to say.
‘To be fair to him, his availability has been pretty good this year and we underused him, which you can argue was our fault.
‘He plays in a very similar position to Ronan. Ronan actually gravitates into his space, no matter where you play him on the pitch.
‘That’s where Michael wants to play – and crucially he keeps the ball.’