There were suggestions earlier this summer that Alderweireld has the contractual right to request a £25m release clause be inserted should Spurs trigger an extension, but the club have apparently so far been unwilling to give in to such demands.
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According to the Daily Mail, there remains a 'willingness from player and club to reach an agreement', but the word 'impasse' is also used as it becomes clearer that Spurs may not be prepared to break their infamous wage structure.
Alderweireld is said to be on just £50,000-per-week, relatively little compared to top defenders at other top clubs, and his entourage is looking for a deal that more closely matches Harry Kane and Hugo Lloris, Spurs' highest earners, at around £110,000.
The former Ajax and Atletico Madrid man is well aware he could earn vastly more should he look elsewhere in the Premier League.
He has already seen former teammate Kyle Walker double his salary after moving to Manchester City, while similar has been said of Danny Rose and Eric Dier after they have also been linked with high profile transfers in recent weeks.
That is where the Mail report brings Manchester City in after previous interest.
Pep Guardiola's team are still in the market for a new centre-back, an area where the squad noticeably lacks depth. There has been talk of a bid for former Manchester United player Jonny Evans, but Alderweireld could become a viable option.
The Belgium international has established himself as one of the best centre-backs in the Premier League since initially joining Southampton on loan in 2014 and was snapped up by Spurs, somewhat underhandedly it must be said, for just £11.5m the following summer.