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

WEBINARS
In-depth expertise and insights, made easy to understand and entertaining by myStockOptions staff and other experts

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, the United Kingdom, and several other countries

GLOSSARY
Recent additions include CP59 Notice and SPAC

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 2021! The myStockOptions Tax Center

Tax Season 2021: 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

Get Cost Basis Right To Avoid Overpaying Tax On Stock Sales: Understand IRS Forms 1099-B And 8949 For Tax Returns

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 2021 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 are capital gains and capital losses? What are the capital gains tax rates?

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

What should I do if I forgot to report the ISO exercise/hold on my tax return but now realize I may owe AMT?

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?

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Financial Planning

Making Donations Of Company Stock

Making Gifts Of Company Stock

I have vested stock options. What should I do: exercise and hold, exercise and immediately sell, or wait to exercise?

What is the tax treatment for gifts of company stock?

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

Does the US impose an exit tax on citizens who leave the country and give up their citizenship?

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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ARTICLES, FAQs, AND VIDEOS

Basics

What do surveys and examples reveal about the effects of stock market trends, expensing, and other developments on equity compensation?

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?

Can restricted stock and performance shares go underwater?

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Restricted Stock, RSUs, And Performance Shares

NEW! Restricted Stock, Restricted Stock Units, Restricted Securities: How To Tell Them Apart And Avoid Confusion

Do restricted stock/RSU tax withholding and reporting differ if I am an independent contractor, a consultant, or an outside director rather than an employee?

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 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?

Can restricted stock and performance shares go underwater?

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?

Can my option grant have premium exercise prices or vesting that is based on performance or stock-price targets? Are there examples of this?

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?

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Employee Stock Purchase Plans (ESPPs)

Will I receive information statements from my company about ESPP purchases or option exercises? Will I receive Form 3922 or Form 3921?

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?

Who is eligible to participate in an ESPP? Can anybody, such as part-time workers or employees outside the US, be excluded from participation?

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

What is a reset or automatic rollover provision in an ESPP?

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

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NQSOs

Do NQSO tax withholding and reporting differ if I am an independent contractor, consultant, or outside director rather than an employee?

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?

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ISOs & AMT

NEW! Is there an optimal time during the tax year to exercise incentive stock options?

Will I receive information statements from my company about ESPP purchases or option exercises? Will I receive Form 3922 or Form 3921?

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

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?

What should I do if I forgot to report the ISO exercise/hold on my tax return but now realize I may owe AMT?

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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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Job Events

Negotiating And Structuring Your Stock Compensation (Part 2): Privately Held Companies

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Life Events

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

Retirement Planning With Stock Options And RSUs (Part 1: Pre-Retirement)

How do stock grants affect Roth IRA contributions and conversions?

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SEC Law & Rule 10b5-1 Trading Plans

Insider Trading: How To Stay Out Of Trouble

How To Use Rule 10b5-1 Trading Plans To Sell Company Stock (Part 1)

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

What is a Rule 10b5-1 trading plan?

How widely used are Rule 10b5-1 trading plans? Is survey data about their use available?

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

Do securities laws and regulations place restrictions on stock options or shares granted to consultants and on their freedom to sell the stock?

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M&A

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

Can an acquisition of my company accelerate the vesting of my stock options?

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Pre-IPO

NEW! How could my startup's equity compensation change as the company grows, both before and after an IPO?

Your Company Is Going Public: How Your Stock Compensation May Change

Negotiating And Structuring Your Stock Compensation (Part 2): Privately Held Companies

Are there ways around a lockup?

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

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WEBINARS

Webinar: Stock Compensation Bootcamp for Financial Advisors

Register now for this lively educational event on April 29 (2pm–3:40pm ET, 11am–12:40pm PT).

In just 100 minutes, learn what you need to know about stock options, restricted stock, RSUs, and ESPPs to best serve clients, build wealth, and prevent costly mistakes. Whether you are new to stock comp or want to sharpen your knowledge, our bootcamp webinar for advisors provides practical information and insights to maximize your success.

A detailed agenda of the topics to be covered is available at the registration page.

Preventing Tax-Return Errors For Stock Comp And Stock Sales (75 minutes)
Watch on demand at your convenience this lively educational webinar on tax-return topics for stock comp. Tax-return reporting has changed yet again for the 2021 tax season, which brings more risk than ever for expensive mistakes with tax returns involving stock compensation, including cost-basis reporting for stock sales. Understand the rules of tax-return reporting for stock options, restricted stock/RSUs, ESPPs, and sales of company shares. Learn how to avoid the common mistakes that can lead to overpaying taxes or unwanted IRS attention.

Financial Planning For Stock Compensation During The Pandemic (75 minutes)
After wild swings in the stock markets, financial planning for stock comp continues to be tested by volatility, economic uncertainty, and corporate layoffs. It is important for financial advisors to re-evaluate planning approaches for the novel circumstances of Covid-19 and its impacts. In this webinar, available on demand, a discussion by a panel of expert advisors provides insights into how companies are changing their stock grants, including approaches to underwater stock options, and what this means for financial planning.

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PODCASTS

NEW:

Basics Of Financial Planning With Stock Compensation And Company Shares

The Great Drawdown: How To Optimize Stock-Based Compensation For Retirement Planning

Divorce: What Happens To My Stock Compensation?

Compliance Concerns That Executives Must Understand To Prevent SEC, IRS, And Corporate Problems

Stock Option Terms: What You Can Expect

Restricted Stock Units After An Acquisition: Know What Could Happen

How The 2018 Tax Reforms Continue To Affect Stock Compensation And Financial Planning

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

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GLOSSARY

NEW:

CP59 Notice
Form 8960
SPAC

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


GLOBAL TAX GUIDE This is premium content

UPDATES:

Canada
France
Luxembourg
United Kingdom

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ASK THE EXPERTS

NEW:

I have incentive stock options. I have heard that a sound strategy for ISOs is to exercise them at the start of the year. Why could that be a good move?

When I exercised my stock options and my restricted stock units vested, the shares did not show up in my brokerage account that day. By the time they did appear, a few days later, my company's stock price had fallen because of market volatility. However, for my taxable income and the withholding calculation, the company used the stock price on the date of exercise and vesting. Why don't the delay and the price drop affect those taxes?

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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's new for the 2021 tax-return season?

UPDATES! What are the 2021 adjustments to the IRS limits for qualified retirement plans that affect nonqualified deferred compensation?

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! Impact Of The SECURE Act On NQDC Plans And Retirement Distribution Elections

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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