Pompey have been plagued with injuries across the back-line this season with captain Clark Robertson and Paul Downing facing lengthy spells on the sidelines.
This has seen the former Lincoln boss adapt to his personnel crisis by shoehorning midfielders and full-backs into a back-three.
And the Blues have suffered dearly as a consequence by conceding 11 goals in their last five league games.
However, it may not be as easy at it appears to bring new faces into the club with the January window notoriously difficult to operate in.
As a result, Cowley may have to look for a short-term fix by looking towards the free agents, or at those whose current deals are set to expire.
Click through the list to see who could arrive on the south coast on a free transfer or for a cut-price deal.
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1. Free agents
There are a number of players without clubs who Danny Cowley could look to sign in January. Picture: Robin Jones Photo: Robin Jones
2. Adrian Mariappa - Former club: Bristol City
The Watford legend was last plying his trade for Bristol City in the Championship, but has been without a club since the summer. Mariappa would know doubt provide experience and knowhow in League One and at 35-years-old, still has plenty give - especially on a short-term deal. (Photo by Marc Atkins/Getty Images) Photo: Marc Atkins
3. Martin Crainie - Former club: Luton Town
Former Portsmouth defender Martin Crainie was playing Premier League football as little as four years ago for Huddersfield Town. Since then, he's played in the Championship l for Middlesbrough and then Luton Town. He made a total of 23 appearances in the second tier for the Hatters last season, but wasn't offered a new contract in July. Picture: (MIKE CLARKE/AFP via Getty Images) Photo: MIKE CLARKE
4. Jason Shackell - Former club: Lincoln City
Jason Shackell is by far the most experienced player on this list, but has been without a club since 2020. Blues boss Danny Cowley signed him for Lincoln and could be tempted to reunite with the former Burnley defender. (Photo by Pete Norton/Getty Images) Photo: Pete Norton