The One Big Beautiful Bill’s tip and overtime deductions are intended to provide tax relief for working class Americans. However, its success will be challenged by interpretive gaps, administrative burdens, and a ticking policy clock. Employers are left to navigate compliance risks, payroll system overhauls, and the possibility of future reversals. Similarly, workers may benefit in the short term by keeping more of their hustle, but the looming 2028 expiration, unclear IRS rules, and state-level decoupling threaten to create significant complexity that may eliminate much of the benefit that the bill intended.