Can I sell my stock early and meet the holding period?

September 21, 2011

Subject:   ISO holding period question
Date:   Tue, 09 Dec 2008
From:   Boris

Dear Mr. Gray,

I obtained shares of my company by exercising an ISO during March 2008. My company is now sold and the closing date will be early in January 2009. The acquiring company will pay a fixed amount per share for the stock effective on the closing date.

This means I probably won’t be able to meet the holding period requirements to avoid a disqualifying disposition.

Is there a way to postpone the receipt of the payment to get the benefit of long-term capital gains?

Can you help?

Many thanks,


Date:   9 Jan 2009

Hello Boris,

No. Even if the payment is postponed, you will merely have an installment sale. It’s questionable whether an installment sale postpones recognition of ordinary income for a disqualified disposition of ISO stock.

It appears you will definitely have a disqualified disposition. However, you might have a minimum tax credit for the alternative minimum tax that is payable relating to the exercise of the ISO during 2008 to offset the 2009 tax.

Good luck!

Mike Gray

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