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ARTICLES, FAQs, VIDEOS, AND QUIZZES
Our core content sections, organized by topic

PODCASTS
Brief, lively audio recordings on important topics in equity compensation, available at myStockOptions.com, Apple App Store, and Google Play Music

GLOBAL TAX GUIDE
Important updates in Canada, Switzerland, and the United Kingdom

GLOSSARY
Recent additions include auto-cancel options and stock-price forfeiture provision

ASK THE EXPERTS
Selected questions from Premium Members of myStockOptions.com

NONQUALIFIED DEFERRED COMPENSATION
The latest additions and updates at our sibling website myNQDC.com.


Try the myStockOptions.com glossary app!
Get it on Google Play

TAX SEASON 2020! The myStockOptions Tax Center

Tax Season 2020: What You Need To Know About New Reporting Rules

Form 8949 and Sch. D diagrams How To Report Sales Of Company Stock On Your Tax Return

Restricted Stock & RSUs: 10 Mistakes To Avoid On Your Tax Return

12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs

ISOs: Tax-Return Tips And Traps

NQSOs: Tax-Return Tips And Traps

IRS Form 3922 For ESPPs: What You Need To Know, And How It Can Help You Understand ESPP Taxation

IRS Form 3921 For Incentive Stock Options: What You Need To Know, And How It Can Help You Understand ISO Taxation

W-2 diagram What will my W-2 show after the vesting of restricted stock units?

W-2 diagram What will my W-2 show after I exercise nonqualified stock options?

W-2 diagram What will my W-2 show after the vesting of performance shares?

W-2 diagram What will my W-2 show after the vesting of restricted stock?

W-2 diagram What will my W-2 show after I exercise incentive stock options?

W-2 diagram What will my W-2 show after I exercise stock appreciation rights?

W-2 diagram How is an NQSO stock-swap exercise reported on my W-2?

W-2 diagram If I make a disqualifying disposition with my ESPP stock, what will appear on my W-2?

W-2 diagram If I sell ESPP shares after the required holding periods, what will appear on my W-2? What if income is missing from the form?

W-2 diagram My company's employee stock purchase plan is not tax-qualified under Section 423 of the Internal Revenue Code. What will my W-2 show after an ESPP purchase?

What do I need to know about the information on IRS Form 3922 for ESPPs?

What do I need to know about the information on IRS Form 3921 for incentive stock options?

What's new for the 2020 tax-return season?

What are the biggest mistakes with restricted stock or RSUs that I can make on my tax return, and how can I avoid them?

What are the biggest mistakes related to stock options I can make on my tax return, and how can I avoid them?

What are the biggest mistakes related to stock appreciation rights (SARs) that I can make on my tax return, and how can I avoid them?

What are the biggest mistakes related to my employee stock purchase plan that I can make on my tax return, and how can I avoid them?

If I file an extension to complete my tax return after the IRS deadline, are there any mistakes I should avoid that involve stock compensation income?

How have IRS Form 1099-B and cost-basis reporting changed for sales of stock acquired from my stock options, restricted stock, or ESPP? What do I need to do differently?

NEW! What is IRS Form W-4 and how does it relate to income from stock compensation?

What is capital gain and capital loss? What are the tax rates on capital gains?

What are the federal tax-withholding rates on stock compensation? Can my company use a different rate?

When my restricted stock or RSUs vest, will I need to make estimated tax payments?

After I exercise NQSOs, will I need to make estimated tax payments?

If I exercise ISOs and hold the stock (triggering AMT for the spread) or sell the stock in a disqualifying disposition, will I need to make estimated tax payments?

If I exercise stock appreciation rights (SARs), will I need to make estimated tax payments?

If I purchase shares in my company's ESPP or sell the stock in a disqualifying disposition, will I need to make estimated tax payments?

Are there any strategies for paying estimated taxes on income from stock options and restricted stock?

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ARTICLES, FAQs, AND VIDEOS

Basics

Stockbrokers' Secrets: Equity Compensation Strategies For Volatile Markets

Stomach Volatility In Your Company's Stock Without Losing Your Mind

Preventing Irrational Decisions About Selling Company Stock Or Exercising Options

Manage Your Expectations To Avoid The Option Blues

Reframing Your Stock Option Exercise Strategy In Volatile Markets

Equity Compensation Strategies For Down And Rising Markets

Does vesting continue while I am on a leave of absence, sabbatical, or furlough?

Does the reason for my leave of absence or sabbatical affect vesting?

What approaches do companies apply to underwater stock options?

Can my ESPP go underwater or be affected in other ways by volatile stock prices?

How have the stock-market volatility and economic fluctuations of recent years changed stock grant practices?

What is the difference between variable and fixed restricted stock grant guidelines?

What is the difference between variable and fixed stock option grant guidelines?

Why do companies grant stock options, restricted stock, and other equity awards? Do surveys show that employees really value them?

Do equity awards really motivate employees?

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Restricted Stock, RSUs, And Performance Shares

W-2 diagram What will my W-2 show after the vesting of restricted stock units?

W-2 diagram What will my W-2 show after the vesting of performance shares?

W-2 diagram What will my W-2 show after the vesting of restricted stock?

Form 8949 and Sch. D diagrams How do I report a sale of restricted stock on my federal income-tax return?

Form 8949 and Sch. D diagrams How do I report a sale of shares from restricted stock units (RSUs) on my federal income-tax return?

Form 8949 and Sch. D diagrams In the tax-return reporting for restricted stock, do I need to report shares that I sold for taxes or that my company used for tax withholding?

Form 8949 and Sch. D diagrams When I hold restricted stock after it vests and later have capital gains on the sale, will I get any credit for the income tax I paid at vesting?

Form 8949 and Sch. D diagrams When restricted stock units vest, my company automatically sells or withholds shares to cover the taxes. Do I need to report these shares on my Form 8949 and Schedule D?

Form 8949 and Sch. D diagrams How do I report a sale of performance shares or PSUs on my federal income-tax return?

What types of company goals are most commonly set for performance shares and units? What do surveys show about the metrics, periods, and other grant features that companies use?

How do I make a timely and complete Section 83(b) election?

Do the restricted stock/RSU tax rules, withholding, and tax-return reporting differ if I am an independent contractor, a consultant, or an outside director and not an employee?

What are the federal tax-withholding rates on stock compensation? Can my company use a different rate?

When my restricted stock or RSUs vest, will I need to make estimated tax payments?

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Employee Stock Purchase Plans (ESPPs)

What do I need to know about the information on IRS Form 3922 for ESPPs?

W-2 diagram If I make a disqualifying disposition with my ESPP stock, what will appear on my W-2?

W-2 diagram If I sell ESPP shares after the required holding periods, what will appear on my W-2? What if income is missing from the form?

W-2 diagram My company's employee stock purchase plan is not tax-qualified under Section 423 of the Internal Revenue Code. What will my W-2 show after an ESPP purchase?

Form 8949 and Sch. D diagrams If I make a disqualifying disposition with my ESPP stock, how do I report the sale on Form 8949 and Schedule D of my tax return?

Form 8949 and Sch. D diagrams If I sell ESPP shares after the required holding periods, how do I report the sale on my Form 8949 and Schedule D?

Form 8949 and Sch. D diagrams My company's ESPP is not tax-qualified under Section 423 of the Internal Revenue Code. How do I report any gain that results from the sale of my ESPP shares on my federal income-tax return?

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NQSOs

What are the federal tax-withholding rates on stock compensation? Can my company use a different rate?

W-2 diagram What will my W-2 show after I exercise nonqualified stock options?

W-2 diagram How is an NQSO stock-swap exercise reported on my W-2?

Form 8949 and Sch. D diagrams How do I report a sale of NQSO shares on my federal income-tax return?

Form 8949 and Sch. D diagrams How are capital gains taxed and reported when I sell my NQSO shares?

Form 8949 and Sch. D diagrams I did a cashless exercise with my nonqualified stock options last year. Since I have no additional gains or losses from the sale, do I still need to report the transaction on Form 8949 and Schedule D of my tax return?

Form 8949 and Sch. D diagrams How do I report a sale of shares in an NQSO sell-to-cover exercise?

Form 8949 and Sch. D diagrams I exercised NQSOs, held the stock, and now have long-term capital gains on the sale. Do I get any "credit" on my tax return for the income tax I paid for the spread at exercise?

Form 8949 and Sch. D diagrams I did cashless exercises/sales of stock options from several grants simultaneously. Do I need to report each sale separately, or can I attach the 1099-B statement from my broker and aggregate them on one line?

Form 8949 and Sch. D diagrams Is the brokerage commission taxed and reported separately on my tax return?

Do the NQSO tax rules, withholding, and tax-return reporting differ if I am an independent contractor, consultant, or outside director and not an employee?

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ISOs & AMT

W-2 diagram What will my W-2 show after I exercise incentive stock options?

Form 8949 and Sch. D diagrams I did a cashless exercise with my incentive stock options. How do I report this on Form 8949 and Schedule D? What about the alternative minimum tax?

Form 8949 and Sch. D diagrams How do I report a sale of shares in an ISO sell-to-cover exercise? Is there ISO-related AMT?

Form 8949 and Sch. D diagrams I exercised my ISOs and sold the ISO stock later in the same year. How is this reported on my tax return when the stock price at sale was higher or lower than at exercise?

Form 8949 and Sch. D diagrams After I have met the ISO holding periods, how do I report a sale on my tax return?

Form 8949 and Sch. D diagrams How am I taxed if I have made a disqualifying disposition (e.g. sale) of ISO shares in a different year than the year I exercised the option? How do I report this?

Form 8949 and Sch. D diagrams When I sell my ISO shares in a disqualifying disposition, will the broker's commission reduce the amount of ordinary income on my W-2 or the amount of gross sales proceeds on my Form 8949 and Schedule D?

How do you calculate the alternative minimum tax?

I know that my ISO exercises will trigger the AMT for me this year or next. Are there planning strategies related to other tax payments and income?

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Stock Appreciation Rights (SARs)

W-2 diagram What will my W-2 show after I exercise stock appreciation rights?

Form 8949 and Sch. D diagrams How do I report sales of shares from stock appreciation rights on my federal income-tax return?

What are the federal tax-withholding rates on stock compensation? Can my company use a different rate?

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Financial Planning

NEW! 7 Things To Know When You Sell Company Stock To Raise Cash

Are there any strategies for paying estimated taxes on income from stock options and restricted stock?

Is my company's tax deduction limited for the value of my restricted stock, restricted stock units, performance shares, or stock options if my compensation exceeds $1 million?

Advisors, Have You Heard About MSO Pro?
Tools to track and model grants for multiple clients, and proactive communications to build relationships. Selected by CPA Wealth Provider Magazine as one of the best new financial-planning products. Click here for more information.

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Job Events

Job Loss And Your Stock Grants (Part 1): Options, Restricted Stock, And ESPPs

Job Loss And Your Stock Grants (Part 2): Changes Of Employment Status, Post-Termination Tax, Severance

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Life Events

Strategic Planning With Roth IRAs And Stock Compensation (Part 1)

Stockbrokers' Secrets: Retirement Planning With Stock Compensation (Part 2)

How do stock grants affect Roth IRA contributions and conversions?

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SEC Law & Rule 10b5-1 Trading Plans

NEW! Insider Trading: How To Stay Out Of Trouble

What is insider trading? Do you have to be an insider or executive to commit it?

What are best practices for Rule 10b5-1 trading plans?

Is it possible to violate insider-trading laws by terminating or modifying my Rule 10b5-1 trading plan?

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M&A

How do change-of-control and trigger provisions in stock plans generally work to accelerate vesting?

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Pre-IPO

In a private company, can restricted stock and stock option grants be structured so that they vest only when the company goes public or gets acquired? How is this taxed?

Can my company use the IPO price as its ESPP's grant-date price?

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PODCASTS

NEW:

Basics Of Financial Planning With Stock Compensation And Company Shares

Your Retirement Plan: How To Integrate Stock Compensation

Our podcasts are available on our website, at iTunes, and at Google Play Music.

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GLOSSARY

NEW:

auto-cancel options
Enrolled Agent
Form 1099-NEC
Form 4852
front-loaded equity
Green Card holder
make-whole grant
negative discretion
nonresident alien (NRA) withholding
stock-price forfeiture provision

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Get it on Google Play


GLOBAL TAX GUIDE This is premium content

UPDATES:

Canada
Switzerland
United Kingdom

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ASK THE EXPERTS

NEW:

This year I will have compensation income on my W-2 from an exercise of nonqualified stock options and the vesting of restricted stock units. Is there any way to offset that increase of compensation income for tax purposes?

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NONQUALIFIED DEFERRED COMPENSATION

A sample of the latest major additions and updates at our separate website myNQDC.com, a comprehensive publication about nonqualified deferred compensation:

UPDATES! What if I have a financial or medical hardship? Can I get a distribution?

UPDATES! What happens if my company refuses to pay my distributions or other conflicts arise?

UPDATES! What are the 2020 adjustments to the IRS limits for qualified retirement plans that affect nonqualified deferred compensation?

UPDATES! What's new for the 2020 tax-return season?

UPDATES! If I file an extension to complete my tax return after the IRS deadline, are there any mistakes I should avoid that involve nonqualified deferred compensation?

NEW! What is IRS Form W-4 and how does it apply to withholding from nonqualified deferred compensation?

NEW! Advantages To Pre-Tax Deferral Of Income After Tax Reform

NEW! Make The Most Of Social Security Benefits With NQDC Distributions

UPDATES! Participant Viewpoint: My Investment And Risk Management Strategies For Nonqualified Deferred Compensation

UPDATES! Tax Reform: Good Or Bad For Pretax Compensation Deferral?

UPDATES! Tax Reform And The Impact On Nonqualified Deferred Compensation Plans

UPDATES! Future Higher Tax Rates Would Not Reduce The Current Appeal Of Nonqualified Plans

UPDATES! What are the most recent tax changes that affect nonqualified deferred compensation?

UPDATES! How do I fit nonqualified deferred compensation into my financial plan?

UPDATES! I plan to move. What if I live in a different state at distribution than the state where I worked? How is the distribution taxed?

UPDATES! Can I put more away with a nonqualified deferred compensation plan than with a 401(k) plan? What are the limits?

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CONTACT AND LICENSING INFORMATION

TO CONTACT THE EDITORS: editors@mystockoptions.com

TO LICENSE OUR CONTENT: sales@mystockoptions.com

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