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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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Strategic Planning With Roth IRAs And Stock Compensation (Part 1)This is premium content

Sue Stevens
Could the Roth IRA be your greatest opportunity for accumulating tax-free growth? Well, as with most strategic-planning issues, it all depends. Part 1 of this two-part article series looks at the rules and factors to consider in a Roth IRA conversion.

Strategic Planning With Roth IRAs And Stock Compensation (Part 2): A Case StudyThis is premium content

Sue Stevens
Weighing a Roth IRA conversion is complicated enough, but the complexity can explode when you add in stock option exercises or the vesting of restricted stock. Let's take a look at how this can work in real life through a case study.

Retirement Planning With Your Stock Options And Other Stock Compensation (Part 3: Post-Retirement Planning)This is premium content

Carol Cantrell
Tax planning for retirees can be more challenging that it was during their working years. You need to constantly monitor any options and company stock holdings as part of your overall portfolio. Part 3 looks at special issues that can arise after you retire, including Social Security; coordinating with required minimum distributions for IRAs and your 401(k); moving to another state; and the gifting of stock.

Stockbrokers' Secrets: Retirement Planning With Stock Compensation (Part 2)This is premium content

John P. Barringer
Podcast included! See stock compensation in the bigger picture of retirement savings and withdrawal plans. This article considers core points specific to 401(k) plans and IRAs.

ESPP Choices: Flip Or Hold? (Part 2)This is premium content

Timothy A. Farmer and Gregory G. Geisler
You can build your employee stock purchase plan into your long-range savings and retirement strategy. This article compares buying company stock at a discount through your ESPP to putting the same money into your 401(k) or another retirement plan.

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How do stock grants affect Roth IRA contributions and conversions?This is premium content

The grant itself has no impact. The compensation income generated from exercise or vesting can affect...

How do stock options, ESPPs, and restricted stock differ from the company stock fund or contribution offered under my 401(k) plan?This is premium content

401(k) plans are a type of broad-based, tax-qualified retirement plan funded by pre-tax contributions, unlike...

Can stock compensation affect my other employee benefits, such as 401(k) contributions?This is premium content

With a few exceptions, the grant, vesting, or exercise of stock options, or the vesting of restricted stock, should not affect your other retirement-plan benefits. One notable exception...

NEW! What are the top 10 questions related to retirement planning that I should ask about my stock options, restricted stock/RSUs, or ESPP participation?

Retirement savings can be significantly boosted by equity compensation. When factoring stock options, restricted stock/RSUs, or ESPPs into your retirement planning, you should know the answers to the following questions...

Can I use company stock or cash in my 401(k) plan to exercise my stock options?This is premium content

You cannot use shares of company stock in your 401(k) plan to exercise options, because...

Can I use cash in my IRA account to exercise my options?This is premium content

You can, but the tax consequences may make this unwise...

Can options or restricted stock be granted to my IRA instead of to me?This is premium content

Perhaps, but this would be unwise, and the shares received at exercise or vesting may not be covered by...

Can I sell my company stock to my IRA for cash or contribute my company stock to it?This is premium content

The sale of property by an owner of an IRA to the IRA is prohibited by the federal tax code...

Can stock option, restricted stock, or ESPP income alone qualify me to establish an IRA?This is premium content

As long as you meet the other requirements, to be eligible to make contributions under the tax rules you must have "compensation income" that is at least equal to...

UPDATES! Are stock options, restricted stock, and ESPPs subject to ERISA requirements and regulations?This is premium content

The Employee Retirement Income Security Act (ERISA), whose regulations on tax-qualified retirement plans include rules for employee benefit plans such as 401(k) plans...

Does income from stock options affect my payments under disability policies or pension plans?This is premium content

It may. Your payments are rooted in your pre-disability or pre-retirement earnings in some way. Courts have addressed this issue...

What is an employee stock ownership plan?

An employee stock ownership plan (ESOP) is a tax-qualified retirement plan designed to invest primarily in the voting stock of the employer. The contribution to the plan, whether company stock or cash used to buy company stock, is immediately...

Does participating in an ESPP affect my ability to contribute to a 401(k) plan or IRA?This is premium content

ESPPs are not tax-qualified retirement plans or profit-sharing plans, so participating in an ESPP has...

Can a consultant use the proceeds from an NQSO exercise or restricted stock vesting to fund a Keogh or SEP?This is premium content

As long as the NQSOs and restricted stock generate ordinary income, you can...

Can I commit insider trading by buying or selling company stock in my 401(k) when I know important, confidential information?This is premium content

Whether you trade your company stock in your regular brokerage account or in...

Are senior executives and directors banned from trading company stock during a 401(k) blackout period?This is premium content

During any 401(k) blackout period, directors and executive officers...

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