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What must a shareholder do to ensure capital treatment when repurchasing shares?

  1. Maintain a stake of more than 75% post-repurchase.

  2. Reduce their holding to below 30% after the buyback.

  3. Keep the shares for an additional five years.

  4. Be a part-time employee of the company.

The correct answer is: Reduce their holding to below 30% after the buyback.

To ensure capital treatment when repurchasing shares, a shareholder must typically reduce their holding to below 30% after the buyback. This is significant because, under tax legislation in many jurisdictions, certain thresholds for shareholding can affect the tax treatment of any gains arising from the sale or buyback of shares. A reduction to below a specified percentage typically signals that the shareholder no longer has significant control or influence over the company, thus allowing the transaction to be treated as a capital gain rather than income. By ensuring their shareholding drops below this level, shareholders can benefit from more favorable capital gains tax treatment, reflecting the nature of the investment rather than income from a dividend or other influences associated with significant ownership. Options that reference maintaining or increasing stake percentages, keeping shares for longer durations, or being an employee do not qualify as effective strategies for securing capital treatment under typical regulations surrounding share repurchases. These other strategies may not support the tax definitions and thresholds needed to achieve the desired capital gains treatment.