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Newsletters
- Insights: Financial Planning For Stock Options & RSUs (Oct. 26, 2021)
- Additions & Updates at myStockOptions.com: 3rd Quarter 2021
- ESPPs: myStockOptions Newsletter No. 85 (Sept. 2021)
- Alert: Financial Planning For RSUs & Stock Options (July 20, 2021)
- Additions & Updates at myStockOptions.com: 2nd Quarter 2021
- Restricted Stock & RSUs: myStockOptions Newsletter No. 84 (June 2021)
- Alert: Prevent Costly Tax Mistakes (Apr. 20, 2021)
- Additions & Updates at myStockOptions.com: 1st Quarter 2021
- Tax-Return Reporting For Stock Compensation And Company Shares: myStockOptions.com Newsletter No. 83 (March 2021)
- Alert: Tax Season 2021, Option Exercise Strategies, On-Demand Webinars, & More
- Additions & Updates at myStockOptions.com: 4th Quarter 2020
- Year-End Planning 2020: myStockOptions Newsletter No. 82
- Alert: Planning For Grants Of Restricted Stock, RSUs, & Performance Shares (Sept. 23, 2020)
- Restricted Stock, RSUs, Performance Shares: myStockOptions Newsletter No. 81 (Sept. 2020)
- Alert: Equity Comp Financial Planning In Pandemic Times
- Additions & Updates at myStockOptions.com: 2nd Quarter 2020
- Equity Comp Financial Planning In Pandemic Times: myStockOptions Newsletter No. 80 (June 2020)
- Alert: Equity Comp Survival Guide For Pandemic Times(Apr. 23, 2020)
- Additions & Updates at myStockOptions.com: 1st Quarter 2020
- Tax-Return Reporting For Stock Compensation And Company Shares: myStockOptions.com Newsletter No. 79 (March 2020)
- Tax-Return Alert: Changes In Reporting Rules & Forms (Jan. 22, 2020)
- Additions & Updates at myStockOptions.com: 4th Quarter 2019
- Year-End Planning Ideas & Strategies: myStockOptions.com Newsletter No. 78 (Dec. 2019)
- Alert: Year-End Planning 2019, NQSOs vs. ISOs, Pre-IPO Advice, And More (Oct. 22, 2019)
- Additions & Updates at myStockOptions.com: 3rd Quarter 2019
- Employee Stock Purchase Plans: myStockOptions.com Newsletter No. 77 (Sept. 2019)
- Alert: Additions & Updates at myStockOptions (July 10, 2019)
- Additions & Updates at myStockOptions.com: 2nd Quarter 2019
- Restricted Stock, RSUs, And Performance Shares: myStockOptions.com Newsletter No. 76 (June 2019)
- Alert: Financial Planning After Tax Season (April 24, 2019)
- Additions & Updates at myStockOptions.com: 1st Quarter 2019
- Tax-Return Reporting For Stock Compensation And Company Shares: myStockOptions.com Newsletter No. 75 (March 2019)
- Tax Return Alert: Changes In Reporting Rules & Forms (January 23, 2019)
- Additions & Updates at myStockOptions.com: 4th Quarter 2018
- Year-End Planning For Stock Compensation & Company Shares: myStockOptions.com Newsletter No. 74 (Dec. 2018)
- Alert: Content Updates & Year-End Planning 2018 at myStockOptions
- Additions & Updates at myStockOptions.com: 3rd Quarter 2018
- Employee Stock Purchase Plans: myStockOptions.com Newsletter No. 73 (Sept. 2018)
- Alert: Key Additions & Updates At myStockOptions (July 18, 2018)
- Additions & Updates at myStockOptions.com: 2nd Quarter 2018
- Restricted Stock & RSUs: myStockOptions.com Newsletter No. 72 (June 2018)
- Tax Reform: Key Additions & Updates At myStockOptions (April 25, 2018)
- Additions & Updates at myStockOptions.com: 1st Quarter 2018
- Tax-Return Reporting For Stock Compensation And Company Shares: myStockOptions.com Newsletter No. 71 (March 2018)
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Articles and FAQs
Basics
- Stock Options 101: The Essentials
- Restricted Stock 101: Five Essentials Of Restricted Stock & RSUs
- ESPPs 101: Key Dates And Terms You Must Know
- Stock Options & RSUs: 5 Costly Mistakes To Avoid
- Stock Options Made Simple: Comparing NQSOs & ISOs
- VIDEO! Restricted Stock & RSUs (Part 1): Key Aspects To Know
- VIDEO! Employee Stock Purchase Plans (ESPPs): Core Concepts & Benefits
- VIDEO! Employee Stock Options: Core Aspects To Know
- Stock Option Fundamentals (Part 1): Know Your Goals And Terms
- How To Avoid The Most Common Stock Option Mistakes (Part 1)
- How To Avoid The Most Common Stock Option Mistakes (Part 2)
- Stock Option Terms: What You Can Expect
- How Does Your Stock Plan Compare? Survey Data Has Answers (Part 1)
- How Does Your Stock Plan Compare? Survey Data Has Answers (Part 2)
- Video included! What are the top 10 questions I should ask about my stock grants?
- What is an employee stock option?
- What is restricted stock? Does it differ from restricted securities?
- What advantages do restricted stock and RSUs have over stock options? How do the two grant types compare?
- What types of equity compensation do companies offer?
- In brief, how do nonqualified stock options and incentive stock options differ?
- What are restricted stock and restricted stock units (RSUs), and how do they differ?
- Why do companies shift from granting stock options to granting restricted stock units, and then sometimes back again to granting at least some stock options?
- What is an employee stock purchase plan? What are the key facts to know?
- How does an ESPP differ from a stock option plan?
- Are all stock options taxed the same?
- What is the difference between restricted stock and performance shares or units?
- What are stock appreciation rights?
- Do you have a brief overview of the tax treatment for stock options, restricted stock, RSUs, and ESPPs?
- How do stock options, ESPPs, and restricted stock differ from the company stock fund or contribution offered under my 401(k) plan?
- UPDATES! Why do companies grant stock options, restricted stock, and other equity awards? Do surveys show that employees really value them?
- How many people have or are eligible for stock options, restricted stock/RSUs, or ESPPs?
- How do I use public resources to research a company's stock compensation practices, the grants it is making, and the holdings of its executives?
- Can limited liability companies use stock options or make other stock grants?
- Can some types of companies not offer stock options or other forms of equity compensation to their employees?
- Why doesn't my employer offer me equity compensation?
- Are there any limitations on my company's discretion in granting stock options and/or restricted stock?
- Are stock options, restricted stock, and ESPPs subject to ERISA requirements and regulations?
- Are stock plans affected by the Supreme Court's decisions on marriage equality?
- What is a stock plan?
- What are the important documents I need to understand a stock plan? What are some examples of plans?
- Are different types of stock options granted by employers?
- What do surveys report about equity compensation granted by multinational companies to employees outside the United States?
- When did stock option expensing become mandatory? How does this affect and change my stock grants?
- Am I entitled to voting rights or any stock dividends paid to shareholders before I exercise?
- Will I receive a copy of my company's annual report?
- What is a nonqualified stock option?
- What is an incentive stock option?
- What are the different types of employee stock purchase plans? What are their features?
- How does a Section 423 ESPP work?
- What is a vesting schedule?
- What is capital gain and capital loss? What are the tax rates on capital gains?
- What methods may be used to exercise an option?
- Other than paying the exercise price, what else must I do to exercise a stock option?
- When and how is the income at exercise taxed?
- What is the standard stock option term? Do options ever expire?
- Once my in-the-money options vest, are they mine forever?
- How does a compensatory stock option differ from a publicly traded stock option listed in a newspaper's business section?
- How does a stock option offered to an employee differ from a stock warrant acquired by an investor?
- What is "common stock"?
- What is "preferred stock"?
- I have little cash. Will I still be able to take advantage of my company's stock options?
- What is the SEC?
- Stock Option Fundamentals (Part 3): Income Taxes And Withholding
- How To Report Sales Of Company Stock On Your Tax Return
- What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- 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?
- What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return?
- Do I need to sell my shares at exercise?
- UPDATES! My restricted stock/RSUs will vest soon. Should I sell the shares at vesting or hold them?
- How do I sell shares that I acquired through a stock option exercise, restricted stock vesting, or ESPP?
- Why does my company appoint several brokerage firms or transfer agents for me to use when I exercise my options, or for the deposit of my restricted stock and ESPP stock?
- Must I use a company-approved broker initially or to sell shares?
- How will my broker know which shares to sell? Should I identify them in some way?
- What are the different types of sell orders I can place with my option exercise?
- Why did the brokerage firm that my company requires me to use for option exercises hold the sales proceeds and stock in my account and not send me a check?
- Who pays the brokerage sales commission?
- Form 8949 and Sch. D diagrams Is the brokerage commission taxed and reported separately on my tax return?
- How is capital gain calculated?
- What happens if I have a capital gain from one sale of company stock and a capital loss from another sale of company stock or another security?
- When do I receive the sales proceeds, and how will I know the amount?
- If my company or a third party buys my employee stock options for cash, how is this taxed?
- What is a wash sale?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- Do I always get a Form 1099-B for a same-day-sale cashless exercise? Are there exceptions, and if so how do I report the sale on my tax return?
- If my company requires me to have a foreign bank or brokerage account because of the stock plan, what do I need to know about the FBAR and FATCA reporting rules?
- What are blackout periods and window periods?
- How do blackout periods affect my ability to sell shares?
- Can I sell my company stock through a blind trust, or another type of trust, as a defense against insider trading?
- Can proceeds from stock options be garnished to pay a creditor, an ex-spouse, or a tax authority?
- VOLATILITY SPECIAL! Stockbrokers' Secrets: Equity Compensation Strategies For Volatile Markets
- Stomach Volatility In Your Company's Stock Without Losing Your Mind
- What To Do With Your Just-Vested Shares After Your Company's Stock Price Drops
- 7 Things To Know When You Sell Company Stock To Raise Cash
- How Employee Stock Purchase Plans Offer Special Benefits In Down And Volatile Markets
- Preventing Irrational Decisions About Selling Company Stock Or Exercising Options
- Manage Your Expectations To Avoid The Option Blues
- Better Late Than Never: Stock Option Strategy For The Market Upturn
- Reframing Your Stock Option Exercise Strategy In Volatile Markets
- Equity Compensation Strategies For Down And Rising Markets
- What are underwater stock options? Why shouldn't I exercise them?
- Can restricted stock and performance shares go underwater?
- Can my ESPP go underwater or be affected in other ways by falling or volatile stock prices?
- What approaches do companies apply to underwater stock options?
- How have the stock-market volatility and economic fluctuations of recent years changed stock grant practices?
- I have underwater options. Will I get a tax loss when I exercise them?
- I have underwater stock options that are about to expire unexercised. Can I write these off as some type of loss on my tax return?
- What is an options exchange?
- What factors should I consider in accepting an option exchange, and what is the process?
- What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?
- What impact can a stock option exchange have on employees who are tax residents outside the US?
- If my company offers me options in exchange for underwater options, or reprices them, will there be any tax impact on me?
- My company will let me exchange my underwater options for restricted stock. What is the tax impact?
- I have both in-the-money and underwater options. If I exercise them all and immediately sell the stock, can I offset the gains with the losses on the underwater options?
- Can the exercise price of outstanding stock options ever be raised or lowered? Can the options be repriced?
- If my company or a third party buys my employee stock options for cash, how is this taxed?
- In an acquisition, what happens to my underwater stock options?
- If my company cancels my underwater stock options, will they still count against the $100,000 ISO limit?
- What tax treatment applies if I exercise vested pre-IPO options that now cost more to exercise than they are worth?
- In a divorce case, how do you argue that underwater stock options have value?
- At death, the value of options is included in the gross estate for estate tax purposes. But what happens if the stock's value drops below the exercise price and the options expire unexercised?
NQSOs
- 12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs
- Living And Working In Multiple States: Challenges For Mobile Employees In The USA
- VIDEO! Employee Stock Option Taxes: What You Need To Know
- NQSOs: Tax-Return Tips And Traps
- How To Report Sales Of Company Stock On Your Tax Return
- Get The Cost Basis Right To Avoid Overpaying Tax On Stock Sales: Understand IRS Forms 1099-B And 8949 For Tax Returns
- Tax Strategies With Stock Options, Restricted Stock, And Deferred Compensation
- VIDEO! Tax-Return Reporting Of Company Stock Sales: How To Avoid Overpaying Taxes
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 1): Nonqualified Stock Options
- Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs
- Are there financial-planning strategies for NQSOs?
- After I exercise NQSOs, will I need to make estimated tax payments?
- W-2 diagram What will my W-2 show after I exercise nonqualified stock options?
- May I have my employer withhold more taxes upon my exercise of an NQSO than the minimum required amount?
- What is backup withholding? How do I prevent it or recover it?
- How does a non-US resident reclaim US backup withholding?
- How is fair market value determined for W-2 reporting of NQSO taxable income at exercise and for tax withholding?
- I have already maxed out on Social Security tax this year from stock compensation income at my prior company. Why did my new employer withhold Social Security tax?
- UPDATES! Do NQSO tax withholding and reporting differ if I am an independent contractor, consultant, or outside director rather than an employee?
- What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- 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?
- In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP?
- How do I report the income that results from the exercise of a nonqualified stock option on my federal income-tax return?
- What are the biggest mistakes related to stock options I can make on my tax return, and how can I avoid them?
- 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 do I report a sale of shares in an NQSO sell-to-cover exercise?
- 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?
- I received a notice (CP2000) from the IRS stating that, according to last year's tax return, I owe money for the cashless exercise of my stock options. I thought I paid all the taxes through withholding at exercise. How do I respond?
- I just sold stock that I acquired from option exercises and restricted stock vesting a few years ago. How do I rediscover the cost basis for my tax return?
- 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?
- In what ways can I pay my taxes if I don't have the money to pay them with my tax return?
- UPDATES! 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?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
- What happens if I sell the shares for less than the fair market value on the date of exercise of the NQSO?
- The spread on my NQSO exercise is reported on my W-2 as ordinary income. Can I use my stock-trading losses to offset this income?
- Are there any stock option or restricted stock strategies for using capital-loss carry-forwards?
- What happens if I have a capital gain from one sale of company stock and a capital loss from another sale of company stock or another security?
- Do I receive any tax benefits if a capital loss is generated by my sale of NQSO shares?
- I have both in-the-money and underwater options. If I exercise them all and immediately sell the stock, can I offset the gains with the losses on the underwater options?
- Do I have a tax loss if my NQSOs expire without being exercised?
- Both dividends and long-term capital gains are now taxed at the same rate. Can I net my dividends from my company stock against capital loss from the sale of company stock or another security?
- How will my broker know which shares to sell? Should I identify them in some way?
- When I take an international assignment, will taxes on my stock compensation be equalized?
- My company's stock price has dropped since I exercised my NQSOs. Is there anything I can do to reduce the taxes I owed on the spread at the time of exercise?
- Can the IRS seize stock options or restricted stock under a tax lien?
- My company backdated more stock options than just those of the senior executives. How does this affect employees like me and the taxation of my stock grants?
- I'm a US citizen living and working outside the United States. Do I pay US taxes on income from stock compensation and stock sales? Can I avoid double taxation?
- What happens with taxes on stock options if I live or work in different states during the period between grant and exercise?
- What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- How do I use stock that I own to exercise an option in a stock swap? What is the tax treatment?
- What tax treatment applies after ISOs are converted to NQSOs?
- With NQSOs, is there any tax risk after exercise if the market price of my stock substantially rises or drops by the time I pay my taxes?
- If I were to sell my stock immediately upon exercise or at vesting, the transaction would violate the insider-trading laws and the laws of short-swing profits under Section 16(b) because I had a purchase within six months of the sale. Would this then delay the date of the tax treatment?
- If I exercise NQSOs and immediately donate the shares to charity, do I still need to pay the taxes on the spread at exercise?
- What are the federal income tax consequences if my estate or beneficiary exercises nonqualified stock options (NQSOs) after my death?
- What are discounted stock options? How are they taxed, and why does Section 409A of the tax code matter?
- Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments?
- Is it possible to defer the gains on an NQSO exercise by having the shares delivered in a later tax year?
- What are some key planning strategies at year-end 2021 for restricted stock, RSUs, and stock options?
ISOs
- Incentive Stock Options: 5 Key Points You Must Know To Make The Most Of ISOs And Avoid Costly Mistakes
- Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 1)
- Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 2)
- Treasury And IRS Regulations For Incentive Stock Options
- Early-Exercise ISOs Complicated By Final IRS Regulations
- Is there a limit to the number or value of ISOs that I may be granted?
- Can ISOs be granted at an exercise price below fair market value?
- When I am no longer with my company (e.g. job loss or disability), do tax-law deadlines dictate when I must exercise an ISO?
- Can independent contractors, consultants, or outside directors be granted ISOs?
- How is the $100,000 limit on ISOs calculated?
- Can the annual limit of $100,000 in exercisable ISOs be adversely affected by any post-grant events, such as job termination or the acceleration of vesting in a merger?
- If my company cancels my underwater stock options, will they still count against the $100,000 ISO limit?
- What other limitations apply to ISOs?
- Can an ISO be divided in a divorce?
- Can ISOs be transferred to a grantor trust?
- Do special rules determine when a leave of absence is a termination of employment for the purposes of ISOs?
- Are the disability rules the same for ISOs?
- ISOs: Tax-Return Tips And Traps
- VIDEO! Employee Stock Option Taxes: What You Need To Know
- ISOs And Wash Sales: A Trap Within A Trap
- IRS Form 3921 For Incentive Stock Options: What You Need To Know, And How It Can Help You Understand ISO Taxation
- 12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs
- How To Report Sales Of Company Stock On Your Tax Return
- Get The Cost Basis Right To Avoid Overpaying Tax On Stock Sales: Understand IRS Forms 1099-B And 8949 For Tax Returns
- Hedging Your ISO Stock
- Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 1)
- Final ISO Regulations Affect Stock Plan Design, Optionholders, And Advisors (Part 2)
- Early-Exercise ISOs Complicated By Final IRS Regulations
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 3): Incentive Stock Options
- VIDEO! Tax-Return Reporting Of Company Stock Sales: How To Avoid Overpaying Taxes
- Stockbrokers' Secrets: Year-End Planning For ISOs
- NEW! Is there an optimal time during the tax year to exercise incentive stock options?
- What tax treatment applies after ISOs are converted to NQSOs?
- What is the tax treatment of ISOs after death?
- What happens with taxes on stock options if I live or work in different states during the period between grant and exercise?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP?
- 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?
- What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return?
- What are the biggest mistakes related to stock options I can make on my tax return, and how can I avoid them?
- 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 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 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 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?
- Form 8949 and Sch. D diagrams After I have met the ISO holding periods, how do I report a sale on my tax return?
- How will my broker know which shares to sell? Should I identify them in some way?
- How do I use stock that I own to exercise an option in a stock swap? What is the tax treatment?
- I just sold stock that I acquired from option exercises and restricted stock vesting a few years ago. How do I rediscover the cost basis for my tax return?
- In what ways can I pay my taxes if I don't have the money to pay them with my tax return?
- Can I use ISO stock to exercise NQSOs? Is this a disqualifying disposition that eliminates the special tax treatment for ISOs?
- When I take an international assignment, will taxes on my stock compensation be equalized?
- The amount of my spread at exercise was not listed on the W-2 that I received from my company, even though I made a disqualifying disposition. Do I report this gain on my tax return, and how will I be taxed?
- Can the IRS seize stock options or restricted stock under a tax lien?
- Even though no withholding is required for ISOs, can I still pay the federal and state taxes when I make a cashless exercise?
- What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?
- 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?
- Both dividends and long-term capital gains are now taxed at the same rate. Can I net my dividends from my company stock against capital loss from the sale of company stock or another security?
- The spread on my cashless ISO exercise is reported on my W-2 as ordinary income. Can I use my stock-trading losses to offset this income?
- Is all the income that results from a disqualifying disposition of ISO shares a short-term capital gain that I can net against my capital losses on my tax return?
- If I were to sell my stock immediately upon exercise or at vesting, the transaction would violate the insider-trading laws and the laws of short-swing profits under Section 16(b) because I had a purchase within six months of the sale. Would this then delay the date of the tax treatment?
- Is writing call options on, or buying put options for, my ISO stock a disqualifying disposition?
- I'm a US citizen living and working outside the United States. Do I pay US taxes on income from stock compensation and stock sales? Can I avoid double taxation?
- What if my company is acquired while I'm trying to meet the one-year holding period for ISO shares but the buyer pays cash for the stock before the holding period is over? Is there any way to avoid a disqualifying disposition?
- Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments?
- 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?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- What are some key planning strategies at year-end 2021 for restricted stock, RSUs, and stock options?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
- My company backdated more stock options than just those of the senior executives. How does this affect employees like me and the taxation of my stock grants?
- 7 ISO Strategies That Can Help Minimize Alternative Minimum Tax
- The Alternative Minimum Tax Sweet Spot: Planning Opportunities
- The ISO Tax Trap And The AMT Credit Myth: What To Do Before Exercise And At Year-End
- Early-Exercise ISOs Complicated By Final IRS Regulations
- ISOs And Wash Sales: A Trap Within A Trap
- 12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs
- ISOs: Tax-Return Tips And Traps
- Stockbrokers' Secrets: Year-End Planning For ISOs
- What ISO strategies can help minimize AMT liability?
- 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?
- Is there a way to determine how many ISOs I can exercise and hold before triggering the AMT?
- I have paid AMT, so do I get an adjustment when I sell the ISO shares to get all the taxes back?
- Are there any AMT strategies when I also have NQSOs?
- After I have paid the AMT on my ISO exercise-and-hold income, what are some mistakes that I must avoid on my tax return?
- My ISO exercise/hold will trigger the AMT. How much would the stock price have to drop for my AMT to exceed my ordinary income tax if I instead sell the shares to avoid the AMT?
- Earlier in the year, I exercised ISOs, held the stock, and had a big spread from the market price that will trigger AMT. But my company's stock price has dropped below my exercise price. Can I eliminate AMT and even claim a tax loss?
- I exercised ISOs early last year. The stock price has dropped, and I want to sell my shares before the one-year anniversary of the exercise date. Is this considered a disqualifying disposition that would cause the spread at exercise not to be a preference item for AMT?
- 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?
- What should I do if I forgot to report the ISO exercise/hold on my tax return but now realize I may owe AMT?
- What is the tax basis of my ISO stock that I use to calculate the sale gain for AMT purposes?
- Are qualified dividends included in the AMT calculation?
- My company's stock price fell significantly after I acquired shares from ISOs, leaving me with a tax bill much larger than my gains. Can I reduce or eliminate the ordinary income or AMT that I owe?
- I can exercise my ISOs early and receive shares that still need to vest. Does my early exercise before vesting affect calculations for the AMT, disqualifying dispositions, or capital gains?
- What is a wash sale?
- How does the wash sale rule apply if I sell ISO stock to avoid AMT and then quickly repurchase the stock at current market prices?
- 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?
- What would happen to my AMT credit at death, or to an AMT credit created by my estate?
- I have a large unused AMT credit. Is there still a refundable AMT credit to help me use it faster?
ESPPs
- The Great Benefits Of Your Company's Employee Stock Purchase Plan
- VIDEO! Employee Stock Purchase Plans (ESPPs): Core Concepts & Benefits
- ESPPs 101: Key Dates And Terms You Must Know
- 6 ESPP Essentials (Part 1): Enrollment, Plan Type, Purchase Timing
- Fundamentals Of Employee Stock Purchase Plans (Part 1): Basic Structure And Terms
- Fundamentals Of Employee Stock Purchase Plans (Part 2): Design Limitations And Enrollment Procedures
- Presentation! Employee Stock Purchase Plans: Qualified And Nonqualified Plans
- Video included! What are the top 10 questions I should ask about my company's employee stock purchase plan?
- What is an employee stock purchase plan? What are the key facts to know?
- What makes a Section 423 ESPP a good deal?
- What are the different types of employee stock purchase plans? What are their features?
- How does an ESPP differ from a stock option plan?
- What are the benefits of participating in an employee stock purchase plan?
- What are the most common eligibility requirements for ESPPs?
- Why do companies offer employee stock purchase plans?
- How does a Section 423 ESPP work?
- UPDATES! How does an ESPP work if it is not a tax-qualified plan? For example, can there be a share match?
- What is an ESPP disqualifying disposition, what can cause it, and why does my company care?
- If I leave the company, what happens to the money that has been deducted from my paycheck to purchase ESPP shares?
- When did ESPP expensing become mandatory, and how have ESPPs changed since then?
- How many employees generally participate in ESPPs?
- Do surveys show how employee stock purchase plans are changing with mandatory expensing and other developments?
- How can I find out whether my company has an employee stock purchase plan, what type it is, and what its basic features are?
- What documents should I read before deciding to participate in my company's ESPP? What is my company required to show me?
- What is the eligible compensation that can be used for calculating the money that is available for the stock purchase?
- How is the fair market value of company common stock determined in an ESPP for calculating the discounted purchase price?
- Under my company's ESPP, do I pay commissions on the purchase of stock or on the sale of that stock?
- What happens to my payroll deductions? What happens if more money has accumulated in my ESPP account than can be used to buy shares?
- Do I get voting rights, dividends, and a stock certificate after an ESPP purchase?
- When can I sell my ESPP shares? Can my company restrict the sale?
- How do I sell shares that I acquired through a stock option exercise, restricted stock vesting, or ESPP?
- Why does my employer require me to give notice of a sale of ISO or ESPP stock?
- How will a stock split affect my ESPP and the shares I purchased just before the split?
- How does a stock split affect brokerage accounts of ESPP participants?
- How does a stock split affect an ESPP enrollment price established just prior to the split?
- What happens to my ESPP when my company is acquired?
- In an acquisition, what happens to money that has been waiting to purchase shares in my ESPP?
- 10 Financial-Planning Rules Every ESPP Participant Should Know
- How Employee Stock Purchase Plans Offer Special Benefits In Down And Volatile Markets
- 6 ESPP Essentials (Part 2): Holding Periods, Tax Treatment, Major Corporate Or Personal Events
- Employee Stock Purchase Plans And Your Financial Planning (Part 1)
- ESPP Choices: Flip Or Hold? (Part 1)
- ESPP Choices: Flip Or Hold? (Part 2)
- Employee Stock Purchase Plans And Your Financial Planning (Part 2)
- 2021 Year-End Strategies For Employee Stock Purchase Plans
- What are the top 10 financial-planning rules for employee stock purchase plans?
- Video included! What are the top 10 questions I should ask about my company's employee stock purchase plan?
- Can my ESPP go underwater or be affected in other ways by falling or volatile stock prices?
- Will I receive information statements from my company about ESPP purchases or option exercises? Will I receive Form 3922 or Form 3921?
- When did ESPP expensing become mandatory, and how have ESPPs changed since then?
- Do surveys show how employee stock purchase plans are changing with mandatory expensing and other developments?
- My company's 12-month offering period contains two six-month purchase periods. If I enroll after the start, at the beginning of the second purchase period, what is my lookback offering price?
- In a down market, why does my ESPP automatically withdraw and re-enroll me in a new offering period?
- How will my broker know which shares to sell? Should I identify them in some way?
- How does the company know I've sold my shares?
- How common is it for an ESPP to have a mandatory holding period or transfer restriction for purchased stock?
- Can I name a beneficiary for my stock options, ESPPs, stock appreciation rights, or restricted stock?
- If I die, what will happen to my ESPP participation and the holding period rules?
- Does participating in an ESPP affect my ability to contribute to a 401(k) plan or IRA?
- Can my company use the IPO price as its ESPP's grant-date price?
- Can a purchase of shares through an ESPP ever be considered insider trading?
- Are there any securities-law restrictions on my sale of ESPP stock?
- Do blackout or lockdown periods exist for stock plans? Are there periods during which you can't exercise options or buy stock in an ESPP?
- Can a senior executive or board member participate in an ESPP?
- I am an officer in my company and want to participate in our ESPP. Do Section 16 reporting and liability for short-swing profits raise any special concerns with an ESPP?
- 12 Tax-Return Mistakes To Avoid With Stock Options And ESPPs
- ESPP Choices: Flip Or Hold? (Part 2)
- Fundamentals Of Employee Stock Purchase Plans (Part 4): Down Markets And Other Tax Topics
- Employee Stock Purchase Plans And Your Financial Planning (Part 1)
- IRS Form 3922 For ESPPs: What You Need To Know, And How It Can Help You Understand ESPP Taxation
- How To Report Sales Of Company Stock On Your Tax Return
- Get The Cost Basis Right To Avoid Overpaying Tax On Stock Sales: Understand IRS Forms 1099-B And 8949 For Tax Returns
- VIDEO! Tax-Return Reporting Of Company Stock Sales: How To Avoid Overpaying Taxes
- 2021 Year-End Strategies For Employee Stock Purchase Plans
- 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?
- If I don't meet the ESPP holding periods, how will I be taxed when I sell the stock? Do you have examples?
- When I sell ESPP shares, how will I be taxed if I have met the holding-period requirements for tax-qualified ESPPs?
- If my company eliminates the lookback in its tax-qualified ESPP or does not have a lookback, what is the tax treatment?
- My company has a basic ESPP without a discount but also without commissions on purchase. Is the unpaid commission considered taxable compensation?
- Can I ever have ordinary income but no actual gain on sales of ESPP stock?
- 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?
- 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 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 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?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP?
- 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?
- What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return?
- What if my company is acquired while I am trying to meet the one-year holding period for ESPP shares but the buyer pays cash for the stock before the holding period is over? Is there any way to avoid a disqualifying disposition?
- What is the tax treatment of my ESPP stock in an acquisition?
- 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?
- If I gift stock that has met the holding periods for Section 423 ESPPs, what is the tax treatment?
- If I donate stock that has met the holding periods for Section 423 ESPPs, what is the tax treatment?
- Can my ESPP go underwater or be affected in other ways by falling or volatile stock prices?
- What is a wash sale?
- What is the tax treatment of ESPP shares at death?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
Restricted Stock
- The Great Benefits Of Restricted Stock And Restricted Stock Units (RSUs)
- VIDEO! Restricted Stock & RSUs (Part 1): Key Aspects To Know
- NEW! Restricted Stock, Restricted Stock Units, Restricted Securities: How To Tell Them Apart And Avoid Confusion
- Restricted Stock 101: Five Essentials Of Restricted Stock & RSUs
- Restricted Stock & RSU Fundamentals: What You Need To Know (Part 1)
- Presentation! Restricted Stock And RSUs: Core Concepts, Vesting, And Taxation
- Video included! What are the top 10 questions I should ask about my grant of restricted stock or RSUs?
- UPDATES! My restricted stock/RSUs will vest soon. What must I do and decide?
- Can restricted stock and performance shares go underwater?
- What is restricted stock? Does it differ from restricted securities?
- Does this website's content on restricted stock also apply to restricted stock units (RSUs)?
- Why do many companies grant restricted stock and RSUs instead of stock options?
- What advantages do restricted stock and RSUs have over stock options? How do the two grant types compare?
- What are restricted stock and restricted stock units (RSUs), and how do they differ?
- Why do companies shift from granting stock options to granting restricted stock units, and then sometimes back again to granting at least some stock options?
- Which do companies grant more often: restricted stock or restricted stock units (RSUs)?
- Do I receive dividends on unvested restricted stock and have voting rights?
- What is the process of granting equity awards?
- Are stock option and restricted stock grants negotiable? What terms are negotiable at hire?
- What guidelines do employers use to determine how many stock options or restricted shares to grant?
- My company granted me stock options and restricted stock under its 2016 plan. Why wasn't my grant under a plan of the current year?
- What does a stock grant agreement look like, and what terms does it cover? Where can I find samples?
- Does a grant of restricted stock or performance shares have an expiration date, as stock options do?
- Do I need to buy the restricted stock from my company or exercise something to get it?
- How do I calculate the value of my restricted stock?
- How does a stock split affect my restricted stock grant?
- Can I reinvest my restricted stock dividends in more company stock instead of taking cash income now?
- Do I get to hold the stock itself with a restricted stock grant?
- What is a vesting schedule?
- Are there different types of time-based vesting schedules? Which are most common?
- What is a typical vesting schedule? Do you have any data on vesting schedules and their design?
- What service counts toward vesting?
- Do I forfeit my restricted stock if I leave the company before vesting?
- Can my company fire me or reduce the size of my grant just before the vesting of my stock options or restricted stock/RSUs?
- If my company declares bankruptcy, do I have any special rights in my restricted stock or RSUs?
- My stock will be "released" or "delivered" at vesting. What does that mean?
- What is a lapse election, and why do I need to make it before the restricted stock or restricted stock units vest?
- Once my restricted stock vests, is it mine forever?
- How do I sell shares that I acquired through a stock option exercise, restricted stock vesting, or ESPP?
- 10 Financial-Planning Rules For Restricted Stock And RSUs
- So Your Company Granted You RSUs. Now What? 3 Planning Tips From Top Financial Advisors
- Stockbrokers' Secrets: Restricted Stock And Performance Shares
- Restricted Stock: Tax, Financial, Estate, And Retirement Planning (Part 1)
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 2): Restricted Stock
- Restricted Stock: Tax, Financial, Estate, And Retirement Planning (Part 2)
- Restricted Stock Versus Stock Options: Making A Rational Choice (Part 1)
- Restricted Stock Versus Stock Options: Making A Rational Choice (Part 2)
- Decisions At Vesting With Restricted Stock (Part 2): Hold Or Fold?
- Presentation! Restricted Stock And RSUs: How To Have Effective Employee Education And Communications
- Presentation! Restricted Stock, Performance Shares, And Trends In Equity Compensation: What Financial Advisors Need To Know
- 7 Year-End Strategies For Restricted Stock, RSUs, And Performance Shares In 2021
- Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs
- UPDATES! My restricted stock/RSUs will vest soon. Should I sell the shares at vesting or hold them?
- What would happen to my unvested restricted stock or RSUs if I were to die or become disabled before the vesting date?
- Can you calculate whether it is better to be granted stock options or restricted stock/RSUs?
- Why do companies grant fewer restricted stock shares (or units) than stock options? Are there any trends in the ratios of shares for options?
- What do surveys and examples reveal about the effects of stock market trends, expensing, and other developments on equity compensation?
- Does my company take an earnings charge on its income statement for my restricted stock grant? Does it matter if my vesting is performance-based?
- What is the difference between variable and fixed restricted stock grant guidelines?
- What is the difference between restricted stock and performance shares or units?
- 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?
- What do surveys report about equity compensation granted by multinational companies to employees outside the United States?
- Can stock compensation affect my other employee benefits, such as 401(k) deferral contributions?
- Any data on vesting schedules for restricted stock and RSUs?
- What is a post-vest holding period?
- If my restricted stock vests on a holiday or a weekend, is its value based on the stock price on the day before or the day after the vesting date?
- What happens to my stock grants if I become temporarily disabled?
- After I retire, will my company let my stock options or restricted stock continue to vest, or will it accelerate the vesting?
- Is the original vesting schedule ever accelerated by reaching performance milestones or special goals?
- What is an example of a performance goal that triggers or accelerates vesting?
- What could happen to my restricted stock in an acquisition of my company?
- How do change-in-control and trigger provisions in stock plans work to accelerate vesting?
- If my company is bought for stock of the acquirer, will I be able to purchase the same number of shares in the buyer as I am allowed to with my current options and restricted stock?
- Can I transfer or pledge restricted stock before vesting?
- When I am still working at my company, can it rescind, cancel, or reduce the size of my grant before vesting instead of firing me?
- Can grants of restricted stock or RSUs have noncompete provisions?
- Can options or restricted stock be granted to my IRA instead of to me?
- Can my company require me to retain a certain amount of company stock from a stock option exercise or a restricted stock grant?
- If my company requires me to have a foreign bank or brokerage account because of the stock plan, what do I need to know about the FBAR and FATCA reporting rules?
- How does a dividend affect the value of stock options, restricted stock, and restricted stock units?
- Does receiving dividend payments on my restricted stock before it vests mean I automatically get the stock even if I leave the company before vesting?
- Can I use restricted stock in a stock swap to exercise my options?
- If my restricted stock vests during a blackout period or when I know secret stock-price-moving information, can I be charged with insider trading?
- When and how do senior executives file Form 4 for restricted stock, restricted stock units, and performance shares?
- I am a senior executive and plan to sell enough restricted stock at vesting to cover the taxes I will owe. Is this sale still subject to the short-swing profit rules under Section 16?
- When did stock option expensing become mandatory? How does this affect and change my stock grants?
- Restricted Stock Units Made Simple (Part 1): Understanding The Core Concepts
- Sell Or Hold RSU Shares At Vesting? 3 Approaches To Consider
- VIDEO! Restricted Stock & RSUs (Part 1): Key Aspects To Know
- Financial Planning With Restricted Stock Units: 3 Key Questions
- Restricted Stock 101: Five Essentials Of Restricted Stock & RSUs
- How To Defer Taxes On Restricted Stock Units
- What To Do With Your Just-Vested Shares After Your Company's Stock Price Drops
- Restricted Stock Units Made Simple (Part 2): Taxation
- VIDEO! Restricted Stock & RSUs (Part 2): Taxes & Key Decisions After Tax Reform
- Restricted Stock Units After An Acquisition: Know What Could Happen
- Stockbrokers' Secrets: Restricted Stock And Performance Shares
- Video included! What are the top 10 questions I should ask about my grant of restricted stock or RSUs?
- What are restricted stock and restricted stock units (RSUs), and how do they differ?
- Does this website's content on restricted stock also apply to restricted stock units (RSUs)?
- What is the difference between restricted stock and performance shares or units?
- Video included! When and how is a grant of restricted stock or RSUs taxed?
- Do I get dividends with restricted stock units? How are they taxed?
- Why do many companies grant restricted stock and RSUs instead of stock options?
- Which do companies grant more often: restricted stock or restricted stock units (RSUs)?
- How do companies decide whether to grant restricted stock or RSUs? What are the features that matter to them?
- Why do companies shift from granting stock options to granting restricted stock units, and then sometimes back again to granting at least some stock options?
- With restricted stock units and performance shares, can I defer the delivery of the shares at vesting? How is this taxed?
- My stock will be "released" or "delivered" at vesting. What does that mean?
- W-2 diagram What will my W-2 show after the vesting of restricted stock units?
- 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 shares from restricted stock units (RSUs) on my federal income-tax return?
- Video included! How does the taxation of restricted stock and restricted stock units differ?
- What is a lapse election, and why do I need to make it before the restricted stock or restricted stock units vest?
- I am eligible for vesting acceleration at retirement but have not actually retired, so why has my restricted stock been taxed? Is the treatment different for RSUs?
- Is the payout of restricted stock units ever delayed when vesting is accelerated?
- If my company declares bankruptcy, do I have any special rights in my restricted stock or RSUs?
- When does my capital gains holding period begin for grants of restricted stock and restricted stock units (RSUs)?
- With restricted stock units (RSUs), can I make a Section 83(b) election to be taxed at grant instead of share delivery?
- Can my company convert restricted stock into restricted stock units?
- As a director, can I elect to take part of my retainer as deferred stock units?
- When and how do senior executives file Form 4 for restricted stock, restricted stock units, and performance shares?
- 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?
- Performance Shares (Part 1): The Basics
- From Apple To Uber: 5 Key Features Of Performance Share Grants
- Performance Shares (Part 2): Grant Structure, Expiration, And Job Events
- Performance Shares (Part 3): Taxation And M&A
- Stockbrokers' Secrets: Restricted Stock And Performance Shares
- Presentation! Performance Shares: Taxes And Communications
- Video included! What are the top 10 questions I should ask about my company's performance share plan?
- What is the difference between restricted stock and performance shares or units?
- How is my performance share grant taxed, and how are taxes withheld?
- Does this website's content on performance shares also apply to performance share units or performance-vesting RSUs?
- How soon after the end of the performance period do I receive the shares?
- Can restricted stock and performance shares go underwater?
- What would happen to my performance share grant if I were to lose my job, retire, become disabled, or die?
- 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?
- W-2 diagram What will my W-2 show after the vesting of performance shares?
- Form 8949 and Sch. D diagrams How do I report a sale of performance shares or PSUs on my federal income-tax return?
- What is a post-vest holding period?
- Is the original vesting schedule ever accelerated by reaching performance milestones or special goals?
- Does a grant of restricted stock or performance shares have an expiration date, as stock options do?
- Do I get dividends with performance share awards? How are they taxed?
- With restricted stock units and performance shares, can I defer the delivery of the shares at vesting? How is this taxed?
- What would happen to my performance shares in an acquisition of my company?
- What do surveys report about equity compensation granted by multinational companies to employees outside the United States?
- How common are premium, performance-based, and indexed stock options?
- UPDATES! Can my option grant have premium exercise prices or vesting that is based on performance or stock-price targets? Are there examples of this?
- When and how do senior executives file Form 4 for restricted stock, restricted stock units, and performance shares?
- 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?
- Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments?
- Does my company take an earnings charge on its income statement for my restricted stock grant? Does it matter if my vesting is performance-based?
- Restricted Stock & RSUs: 10 Mistakes To Avoid On Your Tax Return
- Restricted Stock: Tax, Financial, Estate, And Retirement Planning (Part 2)
- Decisions At Grant With Restricted Stock (Part 3): Analyze Your Alternatives
- Living And Working In Multiple States: Challenges For Mobile Employees In The USA
- Get The Cost Basis Right To Avoid Overpaying Tax On Stock Sales: Understand IRS Forms 1099-B And 8949 For Tax Returns
- How To Report Sales Of Company Stock On Your Tax Return
- VIDEO! Tax-Return Reporting Of Company Stock Sales: How To Avoid Overpaying Taxes
- 7 Year-End Strategies For Restricted Stock, RSUs, And Performance Shares In 2021
- Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs
- When my restricted stock or RSUs vest, will I need to make estimated tax payments?
- Will my income from restricted stock vesting be netted against my short-term capital losses from this year (or those that were carried forward from last year)?
- What are the biggest mistakes with restricted stock or RSUs that I can make on my tax return, and how can I avoid them?
- The value of my restricted stock has fallen since vesting. If I sell my shares at year-end, do I get a credit for the income tax I paid at vesting, or do I net the loss against capital gains?
- Are there any strategies for paying estimated taxes on income from stock options and restricted stock?
- How will my broker know which shares to sell? Should I identify them in some way?
- My company is granting restricted stock, and the share price is lower than I think it will be in a few years. Any tax-planning ideas?
- What are some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- 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 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?
- 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?
- What if the wrong cost basis is reported on my 1099-B? How do I report the right cost basis on Form 8949 of my tax return?
- I just sold stock that I acquired from option exercises and restricted stock vesting a few years ago. How do I rediscover the cost basis for my tax return?
- UPDATES! 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?
- In what ways can I pay my taxes if I don't have the money to pay them with my tax return?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP?
- I received a notice (CP2000) from the IRS stating that, according to last year's tax return, I owe money for the sale of my restricted stock when it vested. I thought I paid all the taxes through withholding at vesting. How do I respond?
- Can the IRS seize stock options or restricted stock under a tax lien?
- What is a lapse election, and why do I need to make it before the restricted stock or restricted stock units vest?
- Should I set up a Rule 10b5-1 trading plan to cover the stock I will sell or surrender to pay withholding taxes when my restricted stock vests?
- When I take an international assignment, will taxes on my stock compensation be equalized?
- What is the tax treatment of my restricted stock in an acquisition?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- 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?
- I have already maxed out on Social Security tax this year from stock compensation income at my prior company. Why did my new employer withhold Social Security tax?
- How soon after my restricted stock vests must the IRS receive my withholding taxes?
- May I have my employer withhold more taxes upon the vesting of my restricted stock than the minimum required amount?
- UPDATES! What happens with taxes on restricted stock or RSUs if I live or work in different states during the period between grant and vesting?
- I'm a US citizen living and working outside the United States. Do I pay US taxes on income from stock compensation and stock sales? Can I avoid double taxation?
- I'm no longer an employee, so why is there withholding on my restricted stock vesting?
- If I leave my company to become a consultant, retire, or take another job, will taxes be withheld from my equity grants as they were when I was an employee? What if I live in another state when I receive the income?
- I have started receiving Social Security retirement payments. If I exercise stock options or my restricted stock vests, must I still pay Social Security tax on the income? Can this cause my Social Security payments to be taxed too?
- Can stock option, restricted stock, or ESPP income alone qualify me to establish an IRA?
- I am eligible for vesting acceleration at retirement but have not actually retired, so why has my restricted stock been taxed? Is the treatment different for RSUs?
- The value of my restricted stock at vesting is reported on my W-2 as ordinary income. Can I use my stock-trading losses to offset this income?
- Is the vesting of my restricted stock a wash sale?
- How are shares of company stock that I received from prior option exercises or restricted stock vesting valued for federal estate-tax purposes after my death? Is there a step-up in the basis of the stock?
- Upon my death, the vesting of my restricted stock would accelerate. How would the value be taxed as part of my estate?
- When someone dies with a restricted stock grant, do tax withholding and reporting apply if the vesting is accelerated or allowed to continue?
- What are the federal income tax consequences if my estate or beneficiary sells stock that I received from a prior option exercise or from restricted stock vesting?
- Does the accelerated vesting of my stock options, restricted stock, and/or performance shares in a change of control or termination have any tax impact on me, such as for ISOs and golden parachute payments?
- If my restricted stock vests during a blackout period, or if the stock sale on the vest date would trigger Section 16 short-swing profit liability, is the tax treatment delayed until a later date?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
- What are some key planning strategies at year-end 2021 for restricted stock, RSUs, and stock options?
SARs
- Stock Appreciation Rights 101 (Part 2)
- Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs
- How are stock appreciation rights taxed?
- When I exercise my stock appreciation rights (SARs), will the amount of tax withheld cover the amount of tax that I must pay when I file my tax return?
- If I exercise stock appreciation rights (SARs), will I need to make estimated tax payments?
- I just sold stock that I acquired from option exercises and restricted stock vesting a few years ago. How do I rediscover the cost basis for my tax return?
- W-2 diagram What will my W-2 show after I exercise stock appreciation rights?
- 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?
- 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 some major issues to be aware of when reporting stock sales on my tax return? Why have these issues arisen?
- What tax statement will I receive from my broker after a sale of company stock? What key facts should I know about it?
- In the cost basis I use to report sales of company stock on my tax return, what part comprises the W-2 income from stock compensation or an ESPP?
- 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?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?
- For NQSOs or SARs exercised on the last business day of 2021, or for restricted stock that vests on that day, is the income taxable in 2021 or 2022?
- I'm no longer an employee, so why is there withholding on my NQSO or SARs exercise?
- What are the federal tax-withholding rates on stock compensation? Can my company use a different rate?
- Too much Social Security tax was withheld. How do I recover the excess amount?
- If I leave my company to become a consultant, retire, or take another job, will taxes be withheld from my equity grants as they were when I was an employee? What if I live in another state when I receive the income?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
- What are some key planning strategies at year-end 2021 for restricted stock, RSUs, and stock options?
Financial Planning
- So Your Company Granted You RSUs. Now What? 3 Planning Tips From Top Financial Advisors
- How To Defer Or Pay No Capital Gains Tax On Company Stock Sales: 6 Ways Under The Tax Code
- When To Wait, Hold, Or Sell: A Wealth Manager Reveals His Wisdom On Stock Option Exercise Strategy (Part 1)
- The Tao Of Stock Options: Exercise Strategies From Stock Option Gurus
- Restricted Stock And Stock Options: Financial Planning After Your Tax Return Is Filed (Part 1)
- Restricted Stock And Stock Options: Financial Planning After Your Tax Return Is Filed (Part 2)
- A Least-Regret Analysis For Equity Compensation: Maximizing Value While Minimizing Risk
- How To Develop A Stock Option Exercise Strategy To Reach Your Financial Goals (Part 1)
- Reframing Your Stock Option Exercise Strategy In Volatile Markets
- Strategic Planning With Roth IRAs And Stock Compensation (Part 2): A Case Study
- Better Late Than Never: Stock Option Strategy For The Market Upturn
- Equity Compensation Strategies For Down And Rising Markets
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 2): Restricted Stock
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 1): Nonqualified Stock Options
- How Tax Rate Changes Impact Your Stock Grant Strategies (Part 3): Incentive Stock Options
- When To Wait, Hold, Or Sell: A Wealth Manager Reveals His Wisdom On Stock Option Exercise Strategy (Part 2)
- How To Develop A Stock Option Exercise Strategy To Reach Your Financial Goals (Part 2): Understand Risk Versus Return
- Options For Your Options: Generating Income From Your Vested Employee Stock Options Without Exercising
- Stock Option Valuation And Your Exercise Strategy
- Presentation! Restricted Stock, Performance Shares, And Trends In Equity Compensation: What Financial Advisors Need To Know
- My company is granting restricted stock, and the share price is lower than I think it will be in a few years. Any tax-planning ideas?
- UPDATES! I have vested stock options. What should I do: exercise and hold, exercise and immediately sell, or wait to exercise?
- What are price and time targets for stock option exercises and sales of company stock?
- How do I compare waiting to exercise my options at the end of their term against exercising now to put the current option spread into a diversified investment?
- Can you calculate whether it is better to be granted stock options or restricted stock/RSUs?
- With stock options, what do the terms "intrinsic value" and "time value" mean? How do these concepts apply to financial planning?
- Should I make a Section 83(b) election for my restricted stock grant?
- My company pays a good dividend. Should I exercise my NQSOs and hold the stock instead of just waiting to exercise near the end of the option term?
- Are there any stock option or restricted stock strategies for using capital-loss carry-forwards?
- What is a concentrated stock position, and what can I do to protect myself and get cash for other purposes?
- Is there a way to defer taxation when I sell company stock?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- Are there any strategies for paying estimated taxes on income from stock options and restricted stock?
- What ISO strategies can help minimize AMT liability?
- 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?
- UPDATES! What is a Rule 10b5-1 trading plan?
- Next year I may be in a higher tax bracket. I am thinking about exercising my nonqualified stock options before then to accelerate income into this year. What issues do I need to think about?
- If I sell stock this year, I can avoid higher taxes next year, including the 3.8% Medicare surtax on capital gains. What issues should I consider when I harvest my capital gains?
- The Equity Compensation Planning Dilemma For Corporate Executives
- Strategies For Hedging Concentrated Stock Positions (Part 1)
- Hedging Your Employee Stock Options (Part 1)
- NEW! Estate Tax Planning For Large Company Stock Holdings: Four Tips For Using Record-High Lifetime Exemptions
- International Equity Awards And Company Stock: The Confusing World Of IRS Reporting For Overseas Assets And Income
- Taking An Overseas Assignment: Stock Compensation For Internationally Mobile Employees (Part 1)
- Living And Working In Multiple States: Challenges For Mobile Employees In The USA
- A Least-Regret Analysis For Equity Compensation: Maximizing Value While Minimizing Risk
- Taking An Overseas Assignment: Stock Compensation For Internationally Mobile Employees (Part 2)
- 10 Compliance Concerns That Executives Must Understand To Prevent SEC, IRS, And Corporate Problems (Part 2)
- The Alternative Minimum Tax Sweet Spot: Planning Opportunities
- Tax Strategies With Stock Options, Restricted Stock, And Deferred Compensation
- Foreign Executives Transferring To The United States: Tax-Planning Strategies For Equity Compensation
- Options For Your Options: Generating Income From Your Vested Employee Stock Options Without Exercising
- Hedging Your Employee Stock Options (Part 2)
- Hedging Your Employee Stock Options (Part 3)
- Strategies For Hedging Concentrated Stock Positions (Part 2)
- Strategies For Hedging Concentrated Stock Positions (Part 3)
- Converting Your Stock Option Spread Into Nonqualified Deferred Compensation
- Hedging Your ISO Stock
- Techniques To Defer Or Eliminate Taxes On The Sale Of Your Company's Shares (Part 1): QSB Stock
- Techniques To Defer Or Eliminate Taxes On The Sale Of Your Company's Shares (Part 2): SSBICs
- The Highest-Paid CEOs
- IRS Guide To Auditing Techniques For Stock-Based Compensation
- IRS Nonqualified Deferred Compensation Audit Techniques Guide
- What is a concentrated stock position, and what can I do to protect myself and get cash for other purposes?
- Can my company set ownership guidelines for company stock? Any survey data about their use?
- UPDATES! Has the likelihood of a tax audit increased for people with equity compensation?
- How did the 2018 tax reforms affect stock compensation?
- If my company requires me to have a foreign bank or brokerage account because of the stock plan, what do I need to know about the FBAR and FATCA reporting rules?
- I work and live in the United States but have non-immigrant alien status (L1 visa). My stock options vested when I worked in my home country. I plan to exercise the options while living in the US. Will I have to pay taxes to the IRS and/or the US state where I live?
- What is backup withholding? How do I prevent it or recover it?
- How does a non-US resident reclaim US backup withholding?
- Can my company require me to retain a certain amount of company stock from a stock option exercise or a restricted stock grant?
- UPDATES! Do companies grant stock options or restricted stock to directors? Any survey data on director grants?
- With stock options, what do the terms "intrinsic value" and "time value" mean? How do these concepts apply to financial planning?
- When I take an international assignment, will taxes on my stock compensation be equalized?
- What are the risks of borrowing money from my company to exercise options, purchase restricted stock, or pay the related taxes?
- What are margin loans? Can company stock be used as collateral?
- UPDATES! What is a Rule 10b5-1 trading plan?
- Can I put NQSOs or company stock into a charitable remainder trust or a grantor-retained annuity trust?
- Can stock options and restricted stock be transferred or gifted to people or charities after I get them?
- How does a clawback work to take away gains from my equity compensation?
- How common are clawback provisions? Any survey data about their use?
- What is the tax impact of having a clawback in my grant? What if my company claws back the gains?
- How do I use public resources to research a company's stock compensation practices, the grants it is making, and the holdings of its executives?
- Are my stock grants affected by the rules of deferred compensation under IRC Section 409A?
- Can I use my vested employee stock options as collateral for selling call options on my company stock?
- What is restricted stock? Does it differ from restricted securities?
- I want to automatically exercise options and sell stock to pay a regular bill, such as college tuition. How do I set up a prearranged selling plan so it doesn't violate insider-trading laws and company blackout rules?
- Are senior executives and directors banned from trading company stock during a 401(k) blackout period?
- Can I sell my company stock through a blind trust, or another type of trust, as a defense against insider trading?
- If I enter into a hedging transaction in my company stock, as a senior executive do I need to report this to the SEC on Form 4? Can I be banned from hedging?
- If I hedge my company stock (for example, by selling calls on it), will the dividends get the favorable tax rate for qualified dividends?
- Is writing call options on, or buying put options for, my ISO stock a disqualifying disposition?
- 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?
- What is a "reload" or "restoration" option? How common are they in stock plans?
- Is it possible to defer the gains on an NQSO exercise by having the shares delivered in a later tax year?
- Can my company lend me money to buy its stock, exercise an option grant, or pay taxes on restricted stock at vesting? Can it later cancel or modify that debt?
- Do federal securities laws impose any reporting requirements on a public company's officers, directors, and significant stockholders?
- If I must disgorge short-swing profits under Section 16(b), do I still have to pay tax on those profits? Do I get a tax deduction for the disgorgement?
- If I am no longer an officer or director of a public company, do I still need to meet the requirements of Rule 144 to sell my company stock?
- Can I sell my options to a family trust or a family partnership to defer taxes? Are there other strategies to defer the gain on nonqualified stock options other than the deferred delivery of the shares?
- My company's stock price has substantially dropped. As an executive, I want to buy the stock on the open market to show confidence to investors and analysts. Do I still need to worry about insider trading and liability for short-swing profits under Section 16?
- As a director, can I elect to take part of my retainer as deferred stock units?
- Does the US impose an exit tax on citizens who leave the country and give up their citizenship?
- 12 Ideas For 2021 Year-End Planning With Stock Compensation (Part 1)
- 7 Year-End Strategies For Restricted Stock, RSUs, And Performance Shares In 2021
- 2021 Year-End Strategies For Employee Stock Purchase Plans
- Leading Advisors Reveal Year-End Strategies For Equity Comp And Company Stock
- 12 Ideas For Year-End Planning With Stock Compensation (Part 2)
- Stockbrokers' Secrets: Year-End Planning For NQSOs, Restricted Stock, And RSUs
- Stockbrokers' Secrets: Year-End Planning For ISOs
- Making Donations Of Company Stock
- The ISO Tax Trap And The AMT Credit Myth: What To Do Before Exercise And At Year-End
- Presentation! Year-End Tax And Financial Planning: What Employees And Their Advisors Should Know
- Post-Election Year-End Planning: What Financial Advisors And Tax Pros Are Advising Clients About Uncertain Tax Changes
- What should be on my year-end checklist of items to review, know, and consider about my stock compensation?
- What are some key planning strategies at year-end 2021 for restricted stock, RSUs, and stock options?
- For NQSOs or SARs exercised on the last business day of 2021, or for restricted stock that vests on that day, is the income taxable in 2021 or 2022?
- How do the 2018 tax reforms continue to affect year-end planning?
- If I sell stock this year, I can avoid higher taxes next year, including the 3.8% Medicare surtax on capital gains. What issues should I consider when I harvest my capital gains?
- Next year I may be in a higher tax bracket. I am thinking about exercising my nonqualified stock options before then to accelerate income into this year. What issues do I need to think about?
- At the end of the year, should I exercise my in-the-money options and sell the stock to take advantage of netting the gains against my short-term capital losses from this year (or those that were carried forward from last year)?
- The value of my restricted stock has fallen since vesting. If I sell my shares at year-end, do I get a credit for the income tax I paid at vesting, or do I net the loss against capital gains?
- Is there a way to determine how many ISOs I can exercise and hold before triggering the AMT?
- 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?
- My ISO exercise/hold will trigger the AMT. How much would the stock price have to drop for my AMT to exceed my ordinary income tax if I instead sell the shares to avoid the AMT?
- Earlier in the year, I exercised ISOs, held the stock, and had a big spread from the market price that will trigger AMT. But my company's stock price has dropped below my exercise price. Can I eliminate AMT and even claim a tax loss?
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
- Negotiating And Structuring Your Stock Compensation (Part 3): Equity Rights And Severance When You Terminate Employment
- Watch For Noncompetes And Other Restrictive Covenants In Stock Grant Agreements
- Stock Option Terms: What You Can Expect
- Video included! When I leave my job, what are the top 10 questions I should ask about my stock options, restricted stock/RSUs, or ESPP participation?
- What happens if I terminate my employment before an option grant is fully vested?
- Do I forfeit my restricted stock if I leave the company before vesting?
- Does the reason for my leave of absence, sabbatical, or furlough affect vesting?
- If I leave the company, what happens to the money that has been deducted from my paycheck to purchase ESPP shares?
- I am leaving my job. Is my company required to tell me how many vested options I have, how long I can exercise them after I leave, or when they expire?
- I am planning to leave my job. Do stock options or restricted stock/RSUs stop vesting when I give notice or on the actual date of termination?
- My company recently went through layoffs. What rights do involuntarily terminated employees have in their stock options, and what may my company do?
- Can my company fire me or reduce the size of my grant just before the vesting of my stock options or restricted stock/RSUs?
- I'm no longer an employee, so why is there withholding on my NQSO or SARs exercise?
- I'm no longer an employee, so why is there withholding on my restricted stock vesting?
- Can the terms of my severance accelerate vesting or give me a longer period to exercise my options?
- How much time do I have for exercising vested stock options after my employment ends?
- If I lose my job but I am then rehired, can unvested stock options or restricted stock/RSUs be reinstated, or can the exercise period of my vested options be extended to the end of the original term?
- What are the most common periods after termination during which stock options can be exercised? Does the reason (e.g. disability, early retirement) matter?
- If my employment agreement gives me longer after termination to exercise my stock options than the stock plan and grant agreement do, which controls?
- What is the tax impact on me if my company modifies outstanding stock options or SARs, such as by extending the option term?
- My company is selling or spinning off the division where I work. I will no longer work for that company but will keep the same job under the new corporate owner. What will happen to options and restricted stock in the divestiture?
- Does the reason for my termination affect vesting?
- What happens to the vesting of my grant if I switch from full-time to part-time work?
- According to surveys, how are unvested stock options most commonly treated upon various types of termination?
- After I leave the company, can I still violate insider-trading or Section 16 rules by exercising options or selling company stock?
- Does the severance-pay period extend the clock for post-termination exercise?
- When I am still working at my company, can it rescind, cancel, or reduce the size of my grant before vesting instead of firing me?
- Does receiving dividend payments on my restricted stock before it vests mean I automatically get the stock even if I leave the company before vesting?
- If I remain with the company for the duration of the vesting schedule, is there any way I can lose the benefit of my option?
- When I am no longer with my company (e.g. job loss or disability), do tax-law deadlines dictate when I must exercise an ISO?
- Do special rules determine when a leave of absence is a termination of employment for the purposes of ISOs?
- My company allows me to exercise my ISOs more than 90 days after I leave my job. What is the tax treatment at exercise?
- Must I still file Form 4 for my company stock purchases and sales after I leave the company, or if I want to indicate that I am no longer an insider? Do the rules for matching short-swing profits still apply?
- Negotiating And Structuring Your Stock Compensation (Part 2): Privately Held Companies
- Can consultants or independent contractors be granted stock options or company stock? How common is this practice?
- UPDATES! Do companies grant stock options or restricted stock to directors? Any survey data on director grants?
- Are there any rules of thumb for how many options or shares of stock that consultants should receive on a project?
- What happens to my stock options if I switch from employee to consultant status?
- What are the special issues with options and restricted stock granted to consultants that I need to consider in negotiating my agreement with the company?
- UPDATES! Do NQSO tax withholding and reporting differ if I am an independent contractor, consultant, or outside director rather than an employee?
- UPDATES! 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?
- Can independent contractors, consultants, or outside directors be granted ISOs?
- Do the terms in option grant agreements to consultants differ from the terms in employee grant agreements?
- Are consultant stock options subject to vesting schedules?
- How does the vesting of stock options for consultants and contractors differ from the vesting of grants to employees?
- How do I know whether I am still "consulting" or "rendering services" for purposes of vesting and exercisability of options?
- When my consulting project ends, what should I do to ensure that I get my options or stock? How do I prevent losing my options?
- The company I did consulting for will either go public or be acquired. What should I do to protect my options or stock?
- UPDATES! Do securities laws and regulations place restrictions on stock options or shares granted to consultants and on their freedom to sell the stock?
- If I leave my company to become a consultant, retire, or take another job, will taxes be withheld from my equity grants as they were when I was an employee? What if I live in another state when I receive the income?
- Can a consultant use the proceeds from an NQSO exercise or restricted stock vesting to fund a Keogh or SEP?
- Do advisory-board members usually receive stock options? Does this bear disadvantages for companies?
- I am a consultant. If I have stock options or restricted stock units in a pre-IPO company, do I have the right to receive financial statements or shareholder reports?
- Can a private company contractually restrict my ability to resell my shares, or do the securities laws limit my ability to resell them?
- Is the date for determining taxes delayed if the stock I receive is not registered with the SEC and I cannot immediately sell it?
Life Events
- Retirement Planning With Stock Options And RSUs (Part 1: Pre-Retirement)
- Your Retirement Plan: How To Integrate Stock Compensation
- Maximize Your Social Security Benefits With Stock Compensation
- Stockbrokers' Secrets: Retirement Planning With Stock Compensation (Part 1)
- The Great Drawdown: How To Optimize Stock-Based Compensation For Retirement Planning
- Living And Working In Multiple States: Challenges For Mobile Employees In The USA
- Using Behavioral Finance To Shape Planning For Stock Compensation
- Retirement Planning With Your Stock Options And Other Stock Compensation (Part 2: Retirement Year)
- Retirement Planning With Your Stock Options And Other Stock Compensation (Part 3: Post-Retirement Planning)
- A Holistic Approach To Managing Equity Compensation And Setting Goals
- What are the top 10 questions related to retirement planning that I should ask about my stock options, restricted stock/RSUs, or ESPP participation?
- After I retire, will my company let my stock options or restricted stock continue to vest, or will it accelerate the vesting?
- I retired and moved states. When I exercise my options and my restricted stock vests, will I be taxed by the state where I worked or by my new state?
- Do stock option plans treat early retirement differently from ordinary retirement?
- I am eligible for vesting acceleration at retirement but have not actually retired, so why has my restricted stock been taxed? Is the treatment different for RSUs?
- What are the most common periods after termination during which stock options can be exercised? Does the reason (e.g. disability, early retirement) matter?
- If I leave my company to retire, will I have a longer period to exercise my vested options than I would if I left to take another job?
- My post-retirement exercise period is longer than the remaining term of my stock options. Which term applies after I retire?
- What would happen to my performance share grant if I were to lose my job, retire, become disabled, or die?
- If I no longer work for my company because I retire, become a consultant, or leave to work for another company, will the procedure for exercising my options change?
- If I leave my company to become a consultant, retire, or take another job, will taxes be withheld from my equity grants as they were when I was an employee? What if I live in another state when I receive the income?
- Does my stock option exercise or restricted stock/RSU vesting affect the annual earnings limit of Social Security and reduce my benefits?
- When should I start taking Social Security benefits? What role can stock compensation play in my decision?
- I have started receiving Social Security retirement payments. If I exercise stock options or my restricted stock vests, must I still pay Social Security tax on the income? Can this cause my Social Security payments to be taxed too?
- Strategic Planning With Roth IRAs And Stock Compensation (Part 1)
- Stockbrokers' Secrets: Retirement Planning With Stock Compensation (Part 2)
- Retirement Planning With Your Stock Options And Other Stock Compensation (Part 3: Post-Retirement Planning)
- Strategic Planning With Roth IRAs And Stock Compensation (Part 2): A Case Study
- ESPP Choices: Flip Or Hold? (Part 2)
- How do stock grants affect Roth IRA contributions and conversions?
- How do stock options, ESPPs, and restricted stock differ from the company stock fund or contribution offered under my 401(k) plan?
- Can stock compensation affect my other employee benefits, such as 401(k) deferral contributions?
- What are the top 10 questions related to retirement planning that I should ask about my stock options, restricted stock/RSUs, or ESPP participation?
- Can I use company stock or cash in my 401(k) plan to exercise my stock options?
- Can I use cash in my IRA account to exercise my options?
- Can options or restricted stock be granted to my IRA instead of to me?
- Can I sell my company stock to my IRA for cash or contribute my company stock to it?
- Can stock option, restricted stock, or ESPP income alone qualify me to establish an IRA?
- Are stock options, restricted stock, and ESPPs subject to ERISA requirements and regulations?
- Does income from stock options affect my payments under disability policies or pension plans?
- What is an employee stock ownership plan?
- Does participating in an ESPP affect my ability to contribute to a 401(k) plan or IRA?
- Can a consultant use the proceeds from an NQSO exercise or restricted stock vesting to fund a Keogh or SEP?
- Can I commit insider trading by buying or selling company stock in my 401(k) when I know important, confidential information?
- Are senior executives and directors banned from trading company stock during a 401(k) blackout period?
- Divorce: What Happens To My Stock Options? (Part 1)
- Divorce: What Happens To My Stock Options? (Part 2)
- Divorce: What Happens To My Stock Options? (Part 3)
- Divorce, Taxation, And Stock Options Can Make Strange Bedfellows
- Nonqualified Deferred Compensation In Divorce
- Is my spouse entitled to part of my stock options, restricted stock, and other equity grants upon our divorce?
- How are stock options and restricted stock valued in divorce?
- How is restricted stock handled in divorce? Who pays taxes when restricted stock or vested company shares are transferred in a divorce settlement?
- How are stock options treated in a community property state?
- How are stock options treated in non-community-property states?
- Are stock plans affected by the Supreme Court's decisions on marriage equality?
- In a divorce agreement, how is my ESPP treated? Is transferring to my former spouse ESPP stock that has not met the holding period a disqualifying disposition?
- Do I pay any taxes when stock options are transferred to my former spouse as a part of my divorce settlement?
- After stock options are transferred to my former spouse in divorce, who pays the taxes at exercise? How does my company withhold and report the taxes?
- Instead of transferring stock options to my ex-spouse in the divorce property settlement, can I assign the economic benefits of her/his portion with the right to designate exercise?
- How does a court determine whether my soon-to-be-former spouse should receive any part of my stock grant?
- When are stock options and other equity awards deemed to be acquired for purposes of division in a divorce proceeding?
- If I receive stock options or restricted stock/RSUs after my spouse and I separate but before the divorce is finalized, are those grants subject to division in the divorce proceedings?
- How do the terms of my employer's plan or my grant agreement affect whether my spouse can be awarded any of my stock options or restricted stock in a divorce?
- What is a qualified domestic relations order (QDRO), and how can it be used to divide stock options and restricted stock in divorce settlements?
- Does it matter whether the stock options or other equity awards were granted for past service or for future service?
- With options and restricted stock/RSUs, how do courts decide which grants are marital property? How do they divide grants that are?
- How are ISOs usually handled in divorce?
- In a divorce case, how do you argue that underwater stock options have value?
- Does my spouse also need to accept my stock grant?
- How do I obtain details of my estranged spouse's stock grants for negotiating our divorce agreement?
- How are stock options valued when I give my spouse money or other property instead of transferring the options?
- Are stock grants considered in determining child support and alimony payments?
- Can an ISO be divided in a divorce?
- In a divorce agreement, I am transferring to my former spouse ISO stock that has not met the holding period requirement. Is this a disqualifying disposition?
- Can proceeds from stock options be garnished to pay a creditor, an ex-spouse, or a tax authority?
- In personal bankruptcy, can stock options be attached by creditors?
- Disability And Death: What Happens To Stock Options, Restricted Stock/RSUs, And ESPP Participation?
- What happens to my stock grants if I become temporarily disabled?
- What happens to my stock options if I become permanently disabled?
- What would happen to my unvested restricted stock or RSUs if I were to die or become disabled before the vesting date?
- What would happen to my performance share grant if I were to lose my job, retire, become disabled, or die?
- How is permanent disability usually defined?
- When I am no longer with my company (e.g. job loss or disability), do tax-law deadlines dictate when I must exercise an ISO?
- Are the disability rules the same for ISOs?
- Does income from stock options affect my payments under disability policies or pension plans?
- UPDATES! Does vesting continue while I am on a leave of absence, sabbatical, or furlough?
- Does the reason for my leave of absence, sabbatical, or furlough affect vesting?
- Does maternity leave stop my vesting?
- What are the most common periods after termination during which stock options can be exercised? Does the reason (e.g. disability, early retirement) matter?
- Do special rules determine when a leave of absence is a termination of employment for the purposes of ISOs?
- Disability And Death: What Happens To Stock Options, Restricted Stock/RSUs, And ESPP Participation?
- Stock Options After Death: Learn Before It's Too Late (Part 1)
- Stock Options After Death: Learn Before It's Too Late (Part 2)
- What would happen to my unvested restricted stock or RSUs if I were to die or become disabled before the vesting date?
- What would happen to my vested stock options if I were to die before exercising them?
- Would my death automatically accelerate the vesting of my stock grants?
- What are common periods that stock plans allow for exercising stock options upon death?
- What are the most common periods after termination during which stock options can be exercised? Does the reason (e.g. disability, early retirement) matter?
- Does the post-death exercise period begin to run on the day after my death or only when my administrator, executor, or heir has authority to exercise the options?
- Can I name a beneficiary for my stock options, ESPPs, stock appreciation rights, or restricted stock?
- After my death, what happens to any company shares that I own?
- If I die, what will happen to my ESPP participation and the holding period rules?
- What would happen to my performance share grant if I were to lose my job, retire, become disabled, or die?
- Once my in-the-money options vest, are they mine forever?
M&A
SEC Law
- 10 Compliance Concerns That Executives Must Understand To Prevent SEC, IRS, And Corporate Problems (Part 1): Company Stock Trades
- The Equity Compensation Planning Dilemma For Corporate Executives
- What is insider trading? Do you have to be an insider or executive to commit it?
- What is restricted stock? Does it differ from restricted securities?
- Are sales of shares by executives and directors of a public company subject to any securities-law restrictions?
- What is an affiliate, and why does affiliate status affect the ability to resell company stock?
- My company's stock is now essentially worthless because of securities fraud by senior executives. Can I claim a casualty or theft loss on my tax return?
- What is the SEC?
- Can the SEC, the Treasury, or my company take away stock option gains, restricted stock, and performance shares after accounting fraud has occurred?
- How do I use public resources to research a company's stock compensation practices, the grants it is making, and the holdings of its executives?
- What are Forms 3, 4, and 5? When are these insider reports filed with the SEC?
- What are the rules for resales of securities not registered with the SEC? What requirements must affiliates (e.g. executives and directors) always follow to sell their stock to the public under Rule 144?
- What are blackout periods and window periods?
- Do blackout or lockdown periods exist for stock plans? Are there periods during which you can't exercise options or buy stock in an ESPP?
- Are senior executives and directors banned from trading company stock during a 401(k) blackout period?
- If I gift my company stock to a grantor-retained annuity trust (GRAT), do the securities laws still apply?
- Is the date for determining taxes delayed if the stock I receive is not registered with the SEC and I cannot immediately sell it?
- My company backdated more stock options than just those of the senior executives. How does this affect employees like me and the taxation of my stock grants?
- I am an affiliate. I plan to exercise my options and sell the shares. What forms do I file with the SEC, and when?
- If I am an "affiliate" of my company, how difficult is it to register my stock for resale to the public?
- Do federal securities laws impose any reporting requirements on a public company's officers, directors, and significant stockholders?
- Before senior executives and directors exercise options or sell company stock, does the company require advance notice?
- Insider Trading: How To Stay Out Of Trouble
- Prevent A Martha Stewart Moment: Insider Trading In Company Stock
- How Executives And Directors Can Avoid SEC Troubles Before Trading Their Company Stock (Part 1)
- Presentation! Insider-Trading Prevention
- What is insider trading? Do you have to be an insider or executive to commit it?
- What is insider tipping?
- Why are insider trading and tipping illegal?
- How do civil and criminal insider-trading cases differ?
- What are the civil penalties for insider trading?
- What are the criminal penalties for insider trading?
- Will the SEC really investigate and prosecute small insider-trading violations?
- Can I receive a bounty for providing information about someone who has committed insider trading?
- How do the SEC and the stock exchanges detect insider trading? Aren't stock-trading records confidential?
- Do the rules of insider trading and tipping apply only in business contexts? Do they also apply to what I tell friends and family?
- Does it matter whether the person who violates the insider-trading laws lives outside the US?
- After I leave the company, can I still violate insider-trading or Section 16 rules by exercising options or selling company stock?
- Do Rule 144, Section 16, and the insider-trading rules apply to gifts and donations of company stock by senior executives or directors?
- My company's stock price has substantially dropped. As an executive, I want to buy the stock on the open market to show confidence to investors and analysts. Do I still need to worry about insider trading and liability for short-swing profits under Section 16?
- What if at the time of sale I possessed inside information that did not affect my decision to sell? For example, what if I decided months before to exercise and sell stock when the stock price reached a certain point?
- With insider trading, do I need to be caught in the act to be investigated or prosecuted?
- Is lying during an SEC investigation a crime?
- Can a grant of stock options be an insider-trading violation?
- Can the exercise of stock options be an insider-trading violation?
- Can a purchase of shares through an ESPP ever be considered insider trading?
- If I know something important about our company or another one, when can I use that information to trade? Does the window period always tell me when?
- What are blackout periods and window periods?
- How do blackout periods affect my ability to sell shares?
- How do blackout periods affect stock option exercises and the tax treatment?
- If my restricted stock vests during a blackout period or when I know secret stock-price-moving information, can I be charged with insider trading?
- Can I commit insider trading by buying or selling company stock in my 401(k) when I know important, confidential information?
- Does insider trading include buying stock in a supplier or a customer of my company and not in my own company?
- Can an insider-trading violation bar me from serving as an officer or director?
- Can I sell my company stock through a blind trust, or another type of trust, as a defense against insider trading?
- How Executives And Directors Can Avoid SEC Troubles Before Trading Their Company Stock (Part 2)
- 10 Compliance Concerns That Executives Must Understand To Prevent SEC, IRS, And Corporate Problems (Part 1): Company Stock Trades
- What are Forms 3, 4, and 5? When are these insider reports filed with the SEC?
- When and how do senior executives file Form 4 for restricted stock, restricted stock units, and performance shares?
- Where are Forms 3, 4, and 5 filed?
- If I make a mistake in Form 3, Form 4, or Form 5, how do I amend the filing?
- Will my company help me prepare and file Forms 3, 4, and 5?
- Is the information filed on Forms 3, 4, and 5 confidential?
- When I sell stock under a Rule 10b5-1 plan, do I report the sale differently on Form 4?
- What is the penalty for the failure to file Form 3, 4, or 5? What if the filing is merely late?
- Can I exercise stock options or sell company stock not included in my initial filing of ownership on Form 3?
- Must I still file Form 4 for my company stock purchases and sales after I leave the company, or if I want to indicate that I am no longer an insider? Do the rules for matching short-swing profits still apply?
- What is short-swing profits liability, and how does it affect my stock options and restricted stock?
- What are acceptable methods of avoiding short-swing profits liability?
- If I must disgorge short-swing profits under Section 16(b), do I still have to pay tax on those profits? Do I get a tax deduction for the disgorgement?
- My company's stock price has substantially dropped. As an executive, I want to buy the stock on the open market to show confidence to investors and analysts. Do I still need to worry about insider trading and liability for short-swing profits under Section 16?
- If I gift my company stock to a grantor-retained annuity trust (GRAT), do the securities laws still apply?
- Do senior executives or directors need to make personal SEC filings, such as Forms 4 and 5, for nonqualified deferred compensation plan participation or distributions?
- After I leave the company, can I still violate insider-trading or Section 16 rules by exercising options or selling company stock?
- If I enter into a hedging transaction in my company stock, as a senior executive do I need to report this to the SEC on Form 4? Can I be banned from hedging?
- I am a senior executive and plan to sell enough restricted stock at vesting to cover the taxes I will owe. Is this sale still subject to the short-swing profit rules under Section 16?
- If I were to sell my stock immediately upon exercise or at vesting, the transaction would violate the insider-trading laws and the laws of short-swing profits under Section 16(b) because I had a purchase within six months of the sale. Would this then delay the date of the tax treatment?
- If my restricted stock vests during a blackout period, or if the stock sale on the vest date would trigger Section 16 short-swing profit liability, is the tax treatment delayed until a later date?
- Do Rule 144, Section 16, and the insider-trading rules apply to gifts and donations of company stock by senior executives or directors?
- Can I donate shares and then immediately buy the same number of shares on the open market?
- I am an officer in my company and want to participate in our ESPP. Do Section 16 reporting and liability for short-swing profits raise any special concerns with an ESPP?
- Are there any special securities law issues and filing requirements with stock appreciation rights (SARs) for senior executives and directors?
Pre-IPO
- Stock Options & RSUs From Startup To IPO Or M&A: Top Financial Advisors Cover 5 Key Topics
- Understanding The Risks In Your Pre-IPO Stock Options (Part 1)
- NEW! Financing Stock Option Exercises In A Private Company
- Negotiating And Structuring Your Stock Compensation (Part 2): Privately Held Companies
- Flex Your Negotiating Clout: What You Should Know Before You Negotiate Your Stock Compensation Package
- Private Company Stock Options And RSUs: 10 Facts To Know About The New Tax-Deferral Opportunity
- NEW! Restricted Stock, Restricted Stock Units, Restricted Securities: How To Tell Them Apart And Avoid Confusion
- Drafting An Equity Incentive Plan For A Private Company: Issues Your Company Considers
- LLCs And Equity Incentive Plans (Part 1): Making Sense Of Your Equity Interests
- LLCs And Equity Incentive Plans (Part 2): Income Tax Consequences Of LLC Equity Grants
- Stock Grant Sizes In Pre-IPO Tech Companies
- Google Options Make Masseuse A Multimillionaire
- Video included! What are the top 10 questions I should ask about equity awards I receive at a private company?
- How do I value options and stock in a private company?
- How do stock grants in private companies differ from those in publicly traded companies?
- How do private companies create liquidity for employees' options and stock, other than going public or getting acquired?
- NEW! How does tax withholding work for private company stock compensation?
- Why doesn't my employer offer me equity compensation?
- In a private company, can restricted stock and stock option grants fully vest with a double trigger only when the company goes public or gets acquired? How is this taxed?
- Has there been a tax-law change for stock options and restricted stock units (RSUs) in private companies?
- Any survey data on stock grants in private companies?
- How does a private company decide on the size of a stock grant? Any data on grant sizes?
- How do pre-IPO and other private companies determine exercise prices?
- Why would a private company grant RSUs and not stock options?
- Can a private company contractually restrict my ability to resell my shares, or do the securities laws limit my ability to resell them?
- Is the tax treatment different if I work for a pre-IPO company? For example, are taxes delayed at exercise until the stock is registered with the SEC?
- Is the date for determining taxes delayed if the stock I receive is not registered with the SEC and I cannot immediately sell it?
- What are restricted securities? Do they differ from restricted stock?
- Are stock option and restricted stock grants negotiable? What terms are negotiable at hire?
- How much will my options be worth in the future?
- Can consultants or independent contractors be granted stock options or company stock? How common is this practice?
- A private equity firm is buying my company. What will happen to my stock options and restricted stock?
- What is a buyback? Is my employer required to buy back my shares when I leave the company?
- I have founder's stock that has become subject to forfeiture and transfer restrictions required by new investors. Does my stock become taxable to me, or do I need to make a Section 83(b) election?
- My employer is an S-corporation. Can I still be granted stock options?
- Our company is a partnership. Are stock options available?
- Can limited liability companies use stock options or make other stock grants?
- What is a phantom stock plan?
- How is fair market value (FMV) determined for setting my exercise price? What are common company practices?
- Does the IRS have any rules on setting exercise prices?
- Can I have the exercise price of a new stock option grant lowered or backdated? What is the controversy over backdating?
- Can my company lend me money to buy its stock, exercise an option grant, or pay taxes on restricted stock at vesting? Can it later cancel or modify that debt?
- Are there any rules of thumb for how many options or shares of stock that consultants should receive on a project?
- My friends at public companies do cashless exercises of their stock options. Can I do this with stock options at my pre-IPO company?
- I am a consultant. If I have stock options or restricted stock units in a pre-IPO company, do I have the right to receive financial statements or shareholder reports?
- What tax treatment applies if I exercise vested pre-IPO options that now cost more to exercise than they are worth?
- Why is my private-company employer requiring me to make representations about securities-law compliance before I exercise my options?
- Why is my private-company employer making me sign a "stockholders' agreement" before I exercise my stock options?
- Why is dilution important to me? How do stock grants affect it?
- Can I protect myself from dilution and liquidity preferences in my pre-IPO company? Why does this matter?
- I am getting stock options in an early-stage pre-IPO company. How much dilution can I expect when the company raises more private financing?
- I purchased my ISO shares in a pre-IPO company that went bankrupt without going public. Do I owe AMT? I still have not received a stock certificate proving I have shares, nor do I expect I will ever be sent one.
- I exercised options in a pre-IPO company that went out of business. Can I reclaim the taxes I paid at exercise or write off the money I paid for the worthless stock?
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