An in-person approach combined with an aggressive door-to-door canvassing operation has done well for the president in the past, but campaign members reportedly worry about a path to victory fraught with uncertainty.
While Wisconsin has long been viewed as the president's "best option," the Associated Press reported that aides admitted their strategy was shifting.
Though Democratic challenger and former Vice President Joe Biden would best the president if he clinches Arizona -- a state many see as purple -- and Trump loses Wisconsin, Pennsylvania would be enough to eke out another victory.
“With Pennsylvania, I don’t have to make a play, we’ve got Pennsylvania,” President Trump confidently stated during a rally Tuesday night just outside of Pittsburgh.
Recent polling data paints two different pictures over the current state of the race, with some showing competitive contest and others with Biden slightly in the lead.
Pennsylvania is also a priority for Biden, who was born in Scranton. Large cities like Philadelphia usually swing left and Trump previously underperformed in those suburbs.
Since the beginning of the summer, Biden has made eight in-person trips to Pennsylvania, even under a scheduled limited by the COVID-19 pandemic.
If the president is to carry the Keystone State once again, he'll have to hone in on vulnerable areas.
In 2012 GOP nominee Mitt Romney carried the western edge of metro Philadelphia where Trump fell short by 10 percentage points.
The Trump campaign's over 4,000 meet-ups this cycle have drawn more than 38,000 people and the team is also hitting Biden hard in TV ads.
Biden has outspent President Trump by more than 2-to-1 in Pennsylvania from last spring through this month, according to data from market research and consulting firm Kantar/CMAG.
However, both campaigns had allocated similar figures for the six-week stretch till the election. Trump will spend $11.5 million and Biden $10.1 million.
The Associated Press contributed to this report.