Nothing brings out taxpayer "creativity" quite like pursuing a bigger refund. Every year, millions of Americans scour their bank statements and receipts, asking the age-old question: "Can I deduct this?"

While the federal tax code clearly allows deductions for legitimate expenses, the line between a brilliant tax strategy and an audit waiting to happen can be notoriously thin. From volunteer mileage and medical home upgrades to grandkid gifts, the IRS has seen it all — and has strict rules about what passes muster.

So whether you're a seasoned self-employed pro or just trying to navigate your return on your own, test your knowledge against these five real-world tax scenarios to see if you can spot a legitimate deduction from a tax-court disaster.

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