Higher Education Loan Payment and Enhanced Retirement Act of 2019 or the HELPER Act of 2019 This bill permits annual tax and penalty-free withdrawals of up to $5,250 from 401(k) plans for higher education expenses and penalty-free withdrawals from individual retirement accounts (IRAs) for student loan expenses. The bill also excludes from gross income, for income tax purposes, distributions up to $5,250 from employer-sponsored student loan and tuition payment plans. It repeals the limitation on the deduction of interest on student loans and increases from $15,000 to $25,000 (adjusted for inflation) the maximum contribution amounts for certain tax-preferred retirement plans. The bill allows employees an election to treat contributions to a 401(k) plan as Roth contributions (thus exempting withdrawals from such plans from tax at retirement).