Two players have left Middlesbrough in the last 24 hours, with young striker Luke Williams moving to Scunthorpe United and released winger Emmanuel Ledesma joining Rotherham United on a free transfer.
Meanwhile, popular full-back George Friend has been speaking about the club's aspirations of a return to the Premier League, while there is no new information on a possible return for West Ham midfielder Stewart Downing.
Academy product Williams departs
The sale of 22-year-old Williams may come as a surprise to some, as he has been tipped as a star of the future by many at Boro for a number of years.
Middlesbrough managers past and present have praised the academy product's exceptional talent on the ball, and he has made headlines in the past with stunning goals against Burnley and Oldham Athletic.
However, Boro's youngest debutant in over a century of football at 16 years and 200 days has also been criticised as being far from the finished product in terms of mental maturity and tactical awareness, two attributes prized by former Real Madrid defender Karanka.
Williams scored twice while on loan at Glanford Park last season, one of a number of spells away from Teesside as the forward, dubbed 'Ginger Messi' by sections of the club's support, failed to make an impact on Boro's first team.
He has now put pen to paper on a three-year contract with The Iron, signing for an undisclosed fee. A statement from Boro read that he "departs with all the best wishes" from everyone at the club, where he began his youth career in 2007.
Ledesma signs on at Rotherham
Meanwhile, 27-year-old winger Ledesma has joined Championship rivals Rotherham, having been released by Boro at the end of last season.
The Argentine joined from Walsall in 2012 and made over half a century of league appearances for Boro, but his inconsistent form proved a major stumbling block to any real progress at the club.
Ledesma's form fluctuated between sublime and anonymous during his time at the Riverside Stadium, and he spent last season on loan first with The Millers, then with Brighton and Hove Albion.
Rotherham boss Steve Evans told the club's official site that he had tried to bring Ledesma back to the club on a permanent transfer on numerous occasions after his loan ended last season, but that Boro were reluctant to let him go.
Now, though, Ledesma joins on a free transfer having not been offered an extension to his expiring contract on Teesside, and will link up with his former team-mates for pre-season training.
Friend wants to bounce back from play-off defeat
27-year-old full-back Friend, meanwhile, is confident that the club can bounce back from last season's play-off final defeat to Norwich City as they target a return to the top flight.
Friend has already dismissed speculation linking him with a move away from a club where he has repeatedly stressed his love for the area, with Premier League clubs such as Everton and West Ham having scouted the left-back extensively.
Last season's Fans' Player of the Year, also named in the Football League Championship Team of the Year, admits that his side "didn't deserve to win" having underperformed under the Wembley arch.
However, he went on to praise the "good group" at the club at the moment, including the "manager, squad, and [the] chairman", and spoke of his confidence in building "another great season".
After a "remarkable" year which saw famous matches in the FA Cup and League Cup against Champions League opposition, though, Friend is hoping for "a little less drama" and a little more success at the end of it.
Could Downing return to Teesside?
It has become a well-publicised fact that Middlesbrough would like to bring former favourite Downing back to the club next season, but there has been no new progress reported in the last two weeks.
Boro are battling with top-flight opposition including neighbours Sunderland to acquire his signature and, though a return to his hometown club is thought to be his preference, the financial logistics of the deal are so far proving a difficult hurdle to cross.
The Teessiders are said to be looking at ways to structure a deal which could include a loan spell with a view to buy, chairman Steve Gibson must keep a check on his finances as he looks to improve a number of areas across the squad.
With Williams gone and Patrick Bamford and Jelle Vossen having returned to their parent clubs after loan spells last season, inconsistent Spaniard Kike is Karanka's only senior forward, and the manager knows his front line needs a serious overhaul if Boro are to challenge for the title again next season.