I am an employee of a corporation which does not have an Employee Stock Purchase Program. I have an opportunity to buy shares at less than FMV, which is not compensation for services. Would my taxable gain on these shares be recognized when they are sold years later, or at the time of the purchase? There is not a related-party relationship between me and any of the existing owners of the company. It is a C-corp. There would not be a stock option issued.

I am an employee of a corporation which does not have an Employee Stock Purchase Program. I have an opportunity to buy shares at less than FMV, which is not compensation for services. Would my taxable gain on these shares be recognized when they are sold years later, or at the time of the purchase?==>when they are sold years later; You must report the transaction on Sch D / form 8949 with your tax return. The gain or loss you report on Sch D is the difference between your tax basis in the stock and the price at which you sold it. If you own the shares for one year or less, designate the gain or loss as short-term. The gain or loss is short-term if you held the stock for a year or less, and long-term otherwise. Although this designation doesn?t affect how you treat a loss, long-term gains are subject to lower income tax rates than short-term gains. If the sale does result in a loss, you can use it to offset any other capital gains in the current year and claim a deduction for up to $3k on excess losses that remain. Moreover, you can carryover losses to future tax years. Since selling shares of corp stock often requires assistance from brokers and other professionals who charge fees, your calculation of tax basis and your eligibility to claim additional deductions for investment expenses are different.

There is not a related-party relationship between me and any of the existing owners of the company. It is a C-corp. There would not be a stock option issued
========>as mentioned previously.