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FAQ - Form 5305-SIMPLE

What is the purpose of Form 5305-SIMPLE?
The purpose of Form 5305-SIMPLE is to inform the taxpayer that he or she has a right to claim the income tax deduction for the expenses of purchasing stock of a publicly traded corporation, such as a corporation in the stock market, by filing a Form 5305. There is no obligation under the Internal Revenue Code for the taxpayer to actually perform the purchase. However, the expense deduction may not be denied because the taxpayer did not perform the necessary act. Form 5305-SIMPLE must be filed if an individual purchases more than one share of the corporation, as a result of a sale or exchange. The taxpayer's basis in the shares is equal to the amount of the purchase price, less the aggregate amount deducted in the individual's Form 1120S, Form 5500, Form 8858, Form 8905 or other applicable taxpayer-reported information return. If the taxpayer purchases more than one share of shares within a 12-month period, then the individual must report each sale in a separate individual Form 5305-SIMPLE. The corporation must be a “stock held for speculation,” or “stock held for investment,” such that the corporation will, in fact, be purchased or “held for investment.” Section 1243(a)(3)(B) requires only a “stock held for investment” be disposed of. There is, however, limited relief from the requirements that apply under 14 CFR 600.6910(h) where the purchaser is a nonresident alien employee, a nonresident alien retiree or a nonresident alien individual. See Rev. Run. 2008-12, 2008-1 C.B. 718, available on the IRS website, at. What is the tax deduction for the employee purchase of stock options? Under 14 CFR 600.6926-1(a), the sale of shares of a publicly traded corporation is a purchase for federal income tax purposes. The taxpayer has a right to deduct one-half of the expense of the share purchase. The taxpayer is allowed to deduct any other expenses reasonably incurred. These are any expenses that the taxpayer does not deduct. If the employee buys the shares to sell and is reimbursed by someone else, the employee is not liable for the expense of the share purchase if that person's name appears on Form 5305-SIMPLE. The taxpayer is also allowed a carry back period on the expense deduction. There is a limit on the amount the taxpayer can deduct for each share.
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