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If the redemption would result in a loss on the stock, it is a capital loss, so the IRS may consider recharacterizing the transaction as essentially equivalent to a dividend to reach its desired result: the less tax-favorable ordinary loss.
Another common type of buy-sell agreement is the stock redemption agreement. This is an agreement between shareholders in a company that states when a shareholder leaves the business, whether it be due to retirement, disability, death, or other reason, the departing members shares will be bought by the company.
Place an entry in the general ledge on the date of the purchase for the redemption. List the date of the transaction; then, on the first line of the listing, write "Treasury Stock" in the column for "Account Title and Description." In the "Debit" column, list the amount paid by the company to redeem the stock.
When a corporation redeems the shares of a shareholder, it is not an income tax-deductible expense of the business. When cash is distributed in exchange for the stock, the business recognizes no gain or loss on the transaction.
Under the normal S corporation distribution rules, the redemption distribution is treated as a nontaxable return of capital to the extent of the adjusted basis of stock, followed by capital gain from the deemed disposition of stock (Sec.