Possessing a professional contract at his boyhood club in East Anglia, the 20-year-old graduated from the side's academy to make his senior debut during the 2021-22 term, whilst the Tractor Boys were still plying their trade in League One.
Since then, an American takeover and the arrival of up-and-coming manager Kieran McKenna has turned the fortunes of the Portman Road club around.
The Tractor Boys finished second in League One during the 2022-23 season before repeating the trick a year later in the Championship, earning promotion to the Premier League for the first time since 2000-01.
Looking to avoid an immediate return to the second tier, Ipswich have spent heavily so far in the summer window, forking out in the region of £71.5m on new signings.
Ipswich's Humphreys in talks over Wycombe move?
With a number of new first-team stars arriving at Portman Road over the course of the summer, it appears that Humphreys could be heading towards an exit.
According to Football Insider, the 20-year-old is being prepared for a loan stint at Wycombe for the entirety of the 2024-25 League One campaign.
The report claims that Humphreys has fallen significantly down the pecking order in East Anglia as the club strives to become Premier League regular for years to come.
It is understood are third-tier Wycombe are currently leading the race for the temporary services of the left-back, who has attracted interest from elsewhere across the EFL.
Looking to mount an unlikely promotion push this season, Matt Bloomfield's Chairboys are 19th in the League One standings after failing to earn points against either Wrexham or Birmingham City so far this term.
Humphrey's Ipswich struggles could be over
Whilst he would have cherished being around the place as Ipswich clinched promotion to the Premier League last season, it would have been hard for Humphreys to feel massively part of the club's on-field success.
The academy graduate made just three appearances and a single start in the 2023-24 second-tier campaign, although he did manage an assist during the 2-2 draw versus Birmingham on November 4.
Unsurprisingly, Humphreys found himself firmly behind playmaking-defending Leif Davis in the pecking order, with an shot at top-flight football unlikely for the 20-year-old until he gains experience elsewhere.
Following a 2-0 defeat at Portman Road to Arne Slot's Liverpool on Saturday afternoon, Ipswich will fight for their first points of the campaign when they travel to champions Manchester City on August 24.