For a qualifying disposition of a qualified ESPP with a discount, the discount is always based on the grant date price ($127.71), even if there's no lookback, so the discount is 183 * 15% * $127.71 = 183 * $19.1565 = $3,505.64. This may seem nonsensical (it is) because you paid $68.221 per share based on a share price of $80.26 and would expect the discount to be $12.039 per share, but the above is how the discount is calculated for qualifying dispositions.

Your total gain/(loss) is your sale price minus your actual purchase price, or 183 * ($61.40 - $68.221) = -$1,248.24.

The smaller of the discount ($3,505.64) and capital gain (-$1,248.24) is your ordinary income (OI) on the transaction, with a floor of $0. -$1,248.24 is smaller but <$0, so your OI is $0. The remainder is capital gain/(loss), so -$1,248.24 capital loss.

Do note that in your case, the OI and capital loss would be the same even if you accidentally calculated the discount based on the $80.26 purchase date price, but there are scenarios where doing this would result in incorrect calculations.

Reference for discount calculation in IRS Pub. 525 within Statutory Stock Options, Employee stock purchase plan, Example 9: "If, at the time the option was granted, the option price per share was less than 100% (but not less than 85%) of the FMV of the share, and you dispose of the share after meeting the holding period requirement, or you die while owning the share, you must include in your income as compensation the lesser of:

• The excess of the FMV of the share at the time the option was granted over the option price, or
• The excess of the FMV of the share at the time of the disposition or death over the amount paid for the share under the option.

For this purpose, if the option price wasn't fixed or determinable at the time the option was granted, the option price is figured as if the option had been exercised at the time it was granted. (emphasis mine)

Any excess gain is capital gain. If you have a loss from the sale, it's a capital loss, and you don't have any ordinary income."

Yes, your calculations of the discount and long-term capital loss are correct, and you'll only have a capital loss with no ordinary income, as shown below. However, it's not that your loss is smaller than the discount, but rather, your gain (loss = negative gain) is smaller than the discount amount.

For a qualifying disposition of a qualified ESPP with a discount, the discount is always based on the grant date price ($127.71), even if there's no lookback, so the discount is 183 * 15% * $127.71 = 183 * $19.1565 = $3,505.64. This may seem nonsensical (it is) because you paid $68.221 per share based on a share price of $80.26 and would expect the discount to be $12.039 per share, but the above is how the discount is calculated for qualifying dispositions.

Your total gain/(loss) is your sale price minus your actual purchase price, or 183 * ($61.40 - $68.221) = -$1,248.24.

The smaller of the discount ($3,505.64) and capital gain (-$1,248.24) is your ordinary income (OI) on the transaction, with a floor of $0. -$1,248.24 is smaller but <$0, so your OI is $0. The remainder is capital gain/(loss), so -$1,248.24 capital loss.

Do note that in your case, the OI and capital loss would be the same even if you accidentally calculated the discount based on the $80.26 purchase date price, but there are scenarios where doing this would result in incorrect calculations.

Reference for discount calculation in IRS Pub. 525 within Statutory Stock Options, Employee stock purchase plan, Example 9: "If, at the time the option was granted, the option price per share was less than 100% (but not less than 85%) of the FMV of the share, and you dispose of the share after meeting the holding period requirement, or you die while owning the share, you must include in your income as compensation the lesser of:

• The excess of the FMV of the share at the time the option was granted over the option price, or
• The excess of the FMV of the share at the time of the disposition or death over the amount paid for the share under the option.

For this purpose, if the option price wasn't fixed or determinable at the time the option was granted, the option price is figured as if the option had been exercised at the time it was granted. (emphasis mine)

Any excess gain is capital gain. If you have a loss from the sale, it's a capital loss, and you don't have any ordinary income."

For a qualifying disposition of a qualified ESPP in a declining price situation such as yours, the discount is always based on the grant date price ($127.71), even if there's no lookback, so the discount is 183 * 15% * $127.71 = 183 * $19.1565 = $3,505.64. This may seem nonsensical (it is) because you paid $68.221 per share based on a share price of $80.26 and would expect the discount to be $12.039 per share, but the above is how the discount is calculated for qualifying dispositions.

Your total gain/(loss) is your sale price minus your actual purchase price, or 183 * ($61.40 - $68.221) = -$1,248.24.

The smaller of the discount ($3,505.64) and capital gain (-$1,248.24) is your ordinary income (OI) on the transaction, with a floor of $0. -$1,248.24 is smaller but <$0, so your OI is $0. The remainder is capital gain/(loss), so -$1,248.24 capital loss.

Do note that in your case, the OI and capital loss would be the same even if you accidentally calculated the discount based on the $80.26 purchase date price, but there are scenarios where doing this would result in incorrect calculations.

For a qualifying disposition of a qualified ESPP with a discount, the discount is always based on the grant date price ($127.71), even if there's no lookback, so the discount is 183 * 15% * $127.71 = 183 * $19.1565 = $3,505.64. This may seem nonsensical (it is) because you paid $68.221 per share based on a share price of $80.26 and would expect the discount to be $12.039 per share, but the above is how the discount is calculated for qualifying dispositions.

Your total gain/(loss) is your sale price minus your actual purchase price, or 183 * ($61.40 - $68.221) = -$1,248.24.

The smaller of the discount ($3,505.64) and capital gain (-$1,248.24) is your ordinary income (OI) on the transaction, with a floor of $0. -$1,248.24 is smaller but <$0, so your OI is $0. The remainder is capital gain/(loss), so -$1,248.24 capital loss.

Do note that in your case, the OI and capital loss would be the same even if you accidentally calculated the discount based on the $80.26 purchase date price, but there are scenarios where doing this would result in incorrect calculations.

Reference for discount calculation in IRS Pub. 525 within Statutory Stock Options, Employee stock purchase plan, Example 9: "If, at the time the option was granted, the option price per share was less than 100% (but not less than 85%) of the FMV of the share, and you dispose of the share after meeting the holding period requirement, or you die while owning the share, you must include in your income as compensation the lesser of:

• The excess of the FMV of the share at the time the option was granted over the option price, or
• The excess of the FMV of the share at the time of the disposition or death over the amount paid for the share under the option.

For this purpose, if the option price wasn't fixed or determinable at the time the option was granted, the option price is figured as if the option had been exercised at the time it was granted. (emphasis mine)

Any excess gain is capital gain. If you have a loss from the sale, it's a capital loss, and you don't have any ordinary income."