Transactions processed through services such as Cash App or Venmo are not inherently deductible; rather, the deduction applies to the underlying business expense that these payments represent. The method of payment (digital or paper check) does not affect deductibility provided that the expense is ordinary, necessary, and adequately documented. Retain receipts, invoices, or electronic records to substantiate business purposes. Always review current IRS guidance and consult with your tax advisor to verify that the expense qualifies under your particular circumstances.