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Annotated diagram of Schedule DTax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.


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Donating Your Company Stock To Charities And Private Foundations (Part 1) This is premium content

Joshua Husbands
The celebrated philanthropy of Warren Buffet has prompted much interest in contributing to charities. In this article series, learn about setting up a charitable foundation, donating company stock, and navigating the related issues of taxation and securities law. Part 1 emphasizes private foundations, direct stock gifts to charities and donor-advised funds, and the issues involved in transferring stock options or restricted stock.

Donating Your Company Stock To Charities And Private Foundations (Part 2) This is premium content

Joshua Husbands
The celebrated philanthropy of Warren Buffet has prompted much interest in contributing to charities. In Part 2 of this article series, learn about the taxation and securities law associated with donations of company stock to charities and private foundations.

Gifts: Save On Estate Taxes With Transferable Stock Options This is premium content

Susan Daley
After you die, taxes may be owed on the value of your property. One pillar of estate planning is to transfer assets that are likely to appreciate in value, such as stock options, out of your control long before you die.

Charitable Remainder Trusts (CRTs) And Your Company Stock (Part 1) This is premium content

Christopher Cline
The charitable remainder trust (CRT) is a mainstay of estate planning. Although designed for charitable giving, CRTs can play a role in financial planning for your stock grants.

The Use Of GRATs With Company Stock To Reduce Taxes: Hurry Before The Rules Change This is premium content

Elyse G. Kirschner and Carlyn S. McCaffrey
The grantor-retained annuity trust (GRAT) is one of the best techniques currently available for transferring company stock or other investable assets to family members with little or no estate or gift tax cost. However, legislative changes proposed by the Obama administration would have an adverse impact on this. Learn about the GRAT technique before the tax rules change.

Using The Gift-Tax Exemption Amounts This is premium content

Elyse G. Kirschner and Carlyn S. McCaffrey
You can take advantage of the current gift, estate, and generation-skipping transfer tax regimes. Transfer tax-free large holdings of company stock out of your estate by using gifts and trusts.

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What is the tax deduction for donations of my company stock?

The tax treatment is the same as it is for donations of any stock to a qualified charity. When you have held the stock for more than one year...

What is the tax treatment for gifts of company stock? This is premium content

It's similar to the tax treatment for any gifts of stock. You may make annual gifts to any number of recipient up to the specified annual amount without any tax impact. Financial advisors often tell clients with substantial stock holding to consider making...

Can stock options and restricted stock be transferred or gifted to people or charities after I get them? This is premium content

Most stock plans do not permit this for stock options or restricted stock during your life (i.e. transferable only at death), or they allow it only...

Can I put NQSOs or company stock into a charitable remainder trust or a grantor-retained annuity trust? This is premium content

Your estate-planning opportunities are more effective with company stock than with options. As a general rule, the contribution of the stock options themselves to a CRT is rather...

Can I exercise my stock options, soon thereafter donate the shares to charity, and get a tax deduction for the stock's new higher price? This is premium content

The charitable market-value deduction is limited to the cost of shares that are not held for more than one year...

Can I donate shares and then immediately buy the same number of shares on the open market? This is premium content

Yes. You may donate company stock to the charity and simultaneously...

If I exercise my NQSO and immediately donate the shares to charity, do I still need to pay the taxes on the spread at exercise? This is premium content

Yes. The option exercise and the...

Is the gifting or donation of stock that I acquired from an ISO exercise or ESPP purchase a disqualifying disposition? What is the tax treatment for early sale? This is premium content

A disqualifying disposition occurs if you sell, transfer, exchange, gift, or donate the stock that you acquired without...

If I gift stock that has met the holding periods for Section 423 ESPPs, what is the tax treatment? This is premium content

You can gift shares purchased from a qualified Section 423 ESPP after the holding requirements are satisfied without disqualifying consequences. However, you do not completely escape taxation...

If I donate stock that has met the holding periods for Section 423 ESPPs, what is the tax treatment? This is premium content

You can donate shares purchased from a qualified Section 423 ESPP after the holding requirements are satisfied without the disqualifying consequences of a premature transfer. However...

If I gift or donate stock from an incentive stock option exercise/hold that triggered AMT, do I get an adjustment for it on my AMT return? What happens to my AMT credit? This is premium content

Unlike with a stock sale, gifting ISO stock does not result in an AMT adjustment for the difference...

Do Rule 144, Section 16, and the insider-trading rules apply to gifts and donations of company stock by senior executives or directors? This is premium content

Not surprisingly, anything you do with your company stock as an executive or director raises issues involving the securities laws, potential SEC reporting requirements, and liability risks...

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