The Bundesliga giants have already secured personal terms with the 23-year-old German international, who joined Stuttgart on a free transfer just last year and has since impressed with his versatility and goal-scoring prowess.
However, negotiations between the clubs have stalled over Stuttgart's steep valuation, preventing any formal talks from advancing.
Stuttgart CEO Alexander Wehrle has voiced his frustration over the prolonged saga, setting the Supercup kickoff as the absolute deadline for Bayern to make their move.
"It's been six and a half weeks now. At some point, enough is enough," Wehrle told Stuttgarter Nachrichten.
"If you really want to sign the player, you should be capable of finding a solution in that time. We play the Supercup on Saturday. Everything should be settled by kickoff at the latest."
Bayern's latest bid, reportedly around 50 million euros fixed plus five million euros in add-ons and a 10 percent sell-on clause, was swiftly rejected by Stuttgart, who are holding out for at least 65 million euros given Woltemade's contract runs until 2028 and his rising stock.
Despite an earlier claim from Bayern sporting director Max Eberl that "the matter is off the table" due to the negotiation impasse, insiders suggest this could be tactical posturing, with Woltemade remaining Bayern's top target for a central attacking role.
Recent developments have added urgency, as Bayern prepare to offload winger Kingsley Coman to Al-Nassr for around 35 million euros, freeing up funds and squad space.
The club have allocated a special budget for Woltemade's potential arrival, independent of other deals, viewing him as a flexible option who can operate as a striker or second striker.
Alternatives like Chelsea's Christopher Nkunku are also under consideration to bolster depth amid ambitions in the Bundesliga and Champions League.
Stuttgart, meanwhile, remain confident in retaining Woltemade, who has expressed that Bayern would be his only destination if he departs this window.
With the Supercup looming as a high-stakes opener to the season, this transfer tussle could either ignite a last-minute breakthrough or force Bayern to pivot elsewhere in their squad rebuild.
Borussia Dortmund's star striker Serhou Guirassy has reportedly caught the attention of Europe's elite clubs, with his representatives actively exploring options for a potential blockbuster move.
Karl-Heinz Rummenigge has voiced strong concerns over the growing influence of players and their agents in football contract negotiations.
Kingsley Coman, the dynamic French winger, is poised to leave Bayern Munich for Saudi Pro League giants Al-Nassr in a high-profile transfer.
Nigeria and Bayer Leverkusen forward Nathan Tella has reportedly attracted interest from five Premier League clubs during this summer transfer window.
