An S corporation with no C corporation history pays its sole shareholder's personal credit card bills from the business account, with no plan to repay. How are the payments best treated?
Personal expenses are never deductible by the business (section 262). Paid for the shareholder without a bona fide loan, they are distributions under section 1368, reducing stock basis (tax-free to the extent of basis for an S corporation without E&P), and must be watched for the one-class-of-stock and reasonable compensation rules. Guaranteed payments exist only in partnerships. Source: IRC 262, 1368; Treas. Reg. 1.1361-1(l)(2); Form 1120-S instructions (2025), Schedule M-2. Tax year: 2025 (law as of 31 Dec 2025).
Deducting personal expenses because the business account paid them.
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