Sporting director Max Eberl struck a confident tone ahead of Bayern's 2-1 German Super Cup win over Borussia Dortmund on Saturday, telling Sat.1: "The talks have begun. Now we're looking to make it happen. Both Harry and we have positioned ourselves very clearly. We'd like to extend."
That confidence sounded firmer a few weeks ago than it does now, with reports in recent days suggesting an extension for the 33-year-old England captain is not the formality it once appeared.
Kane himself struck a more guarded note when speaking to Sky after the match.
"We'll talk this week and next. We'll just have an open discussion. You'll find out when there's something to find out."
According to reports, the two sides differ on several points, including a possible exit clause and matching rights for Kane's former club Tottenham Hotspur, which would allow Spurs to match any serious offer that arrives for the striker.
The central sticking point, however, is understood to be the length of any new deal. The Abendzeitung reports that Bayern want to tie Kane down for a further two years through to 2029, while Kane is said to be holding out for a three-year contract.
A compromise built around a two-year extension with an option for a third season is also reportedly not something Bayern Munich are willing to accept.
Kane joined Bayern from Tottenham in 2023 and has been prolific in Bavaria, though his current deal is set to expire at the end of this season, giving both sides limited time to reach an agreement before speculation over his future intensifies.