I paid tax on the perquisite when my stock option shares were allotted. What is my cost when I sell them, and what changes if the company buys them back?
On a sale, s.49(2AA) makes the cost of acquisition the fair market value that was taken into account for s.17(2)(vi) - the perquisite you have already been taxed on - and the section is short enough to quote. On a buy-back on or after 1 October 2024 that cost does you no good: the whole consideration is a deemed dividend under s.2(22)(f) and is taxed as income, not as a gain, so there is no computation for the cost to enter. It comes back only as a capital loss.
The provision the library previously stated without quoting is s.49(2AA), and it reads: "Where the capital gain arises from the transfer of specified security or sweat equity shares referred to in sub-clause (vi) of clause (2) of section 17, the cost of acquisition of such security or shares shall be the fair market value which has been taken into account for the purposes of the said sub-clause." That is the whole of it. Three things follow.
First, the cost is not what the employee paid. The exercise price is irrelevant to the cost; what steps into its place is the fair market value used to compute the perquisite, which is the exercise-date value under the valuation rule. Second, the words are "which has been taken into account", not "which ought to have been taken into account". On the face of the section the cost tracks the figure used for the perquisite. There is now a decision on those words. In Rajesh R Hemrajani v. ITO (Int. Tax) [2026] 189 taxmann.com 183 (Mumbai - Trib.), 31 July 2026, the Bench held at paras 5.7 to 5.12 that the provision does not require the fair market value to have been subjected to tax or included in total income at all: 'taken into account' is of wider import and refers to the fair market value determined in accordance with the statutory mechanism in s.17(2)(vi) read with Rule 3, chargeability of the perquisite being governed separately by ss.4, 5 and 9 and by any treaty. To read in a requirement that the perquisite must have been taxed in India would be to supply words the legislature consciously omitted (para 5.9), and the applicability of the sub-section cannot depend on the jurisdiction in which the perquisite was taxed (para 5.12). The officer was directed to recompute the gain adopting the exercise-date fair market value determined under Rule 3(8)(ii) as the cost, instead of the exercise price (para 6). The reasoning ties the cost to the value correctly determined under the mechanism rather than to whatever figure was actually taxed or returned, which suggests that an employer's erroneous perquisite figure does not fix the cost - but that Bench did not have a wrong employer figure before it, so that step goes beyond its facts and should be put as such.
Third, the holding period does not run from the same date as the value. The value is fixed on exercise; the year of charge and the start of the holding period follow allotment. For unlisted shares the long-term line is twenty-four months from allotment, and the library's entry on holding periods after the Finance (No. 2) Act, 2024 carries that.
Now the buy-back, which is where the cost stops working. Sub-clause (f) was inserted in the definition of dividend in s.2(22) by Act No. 15 of 2024 with effect from 1 October 2024, and on the departmental page for s.2 in its Finance (No. 2) Act, 2024 rendering it reads: "any payment by a company on purchase of its own shares from a shareholder in accordance with the provisions of section 68 of the Companies Act, 2013 (18 of 2013);". A payment that is a dividend is income from other sources charged on the gross amount. It is not a transfer computation, so s.49(2AA) has nothing to attach to and the perquisite value already taxed gives no relief against the buy-back money at all.
What the shareholder gets instead is a capital loss, because the consideration on the buy-back is treated as nil and the cost therefore falls out as a loss. The proviso doing that work has now been read. It is a proviso to s.46A and not part of its main limb, and it reads: "Provided that where the shareholder receives any consideration of the nature referred to in sub-clause (f) of clause (22) of section 2 from any company, in respect of any buy-back of shares, that takes place on or after the 1st day of October, 2024, then for the purposes of this section, the value of consideration received by the shareholder shall be deemed to be nil." Its trigger is twofold - the consideration must be of the nature referred to in s.2(22)(f), and the buy-back must take place on or after 1 October 2024 - and because s.46A computes the gain as consideration minus cost, a deemed nil consideration produces a capital loss equal to the cost, which for ESOP shares is the perquisite-taxed fair market value.
That regime has an end date as well as a start date, and it has to be stated with both. The deemed-dividend treatment of a buy-back, and with it the nil-consideration proviso, run from 1 October 2024 to 31 March 2026 only. From 1 April 2026 the successor is s.69 of the Income-tax Act, 2025 as substituted by the Finance Act, 2026, which taxes a buy-back as capital gains again on the ordinary consideration-minus-cost basis, with an additional income-tax on promoters only under s.69(2) at 2 or 10 per cent for short-term holdings and 9.5 or 17.5 per cent for long-term. The Table of Corresponding Sections maps the main limb of s.46A to s.69(1) and its Explanation to s.69(3)(c), and maps the proviso to nothing at all: there is no nil-consideration limb in the 2025 Act. So an employee tendering ESOP shares in a buy-back on or after 1 April 2026 does not get the deemed nil consideration and does not get the capital loss described above. He gets an ordinary capital gain or loss measured against the perquisite-taxed fair market value - which is the one case in which the cost does its ordinary work.
For shares that began life as stock options this is the worst version of the rule. The cost is large - it is the perquisite the employee has already paid tax on, at slab rates, out of salary - and the buy-back converts it into a capital loss that is worth nothing unless the employee can produce capital gains to set it against within the carry-forward window. The employee is taxed twice in economic terms on the same shares: once as salary at allotment, once as dividend on the buy-back, with the cost stranded.
On withholding, the library previously recorded that its sources differed between s.194 and s.194K. The departmental page for s.194 in its 2025 rendering settles it: the sub-clauses of s.2(22) to which the deduction applies are listed as (a) or (b) or (c) or (d) or (e) or (f), with a footnote recording the insertion of the reference to sub-clause (f) by Act No. 15 of 2024 with effect from 1 October 2024. The rate on the page is ten per cent, and the first proviso removes the deduction where an individual shareholder is paid otherwise than in cash and the dividend does not exceed ten thousand rupees in the financial year - which will not help on a buy-back paid in money. So the deduction on a buy-back consideration is a s.194 deduction, and a company certificate quoting anything else should be questioned.
One related decision in this library is Cognizant Technology Solutions India Pvt. Ltd. v. ACIT, where a share repurchase routed through a court-approved scheme was held to be a deemed dividend. It was decided under the pre-October 2024 regime and on the anti-avoidance limbs of s.2(22), so it does not decide anything about sub-clause (f); it is useful only as a reminder that the department has long treated a repurchase of shares as capable of being a distribution.
Two computations turn on this. A return that treats a post-October 2024 buy-back as a capital gain and deducts the perquisite value as cost will be wrong by the whole of the tax, in the taxpayer's favour, and will be corrected. A return that offers the buy-back correctly as a dividend but then forgets to book the capital loss throws away the only thing the shareholder gets in exchange.
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