Question 1

What should I do first with my equity compensation (RSUs, ISOs, NSOs, ESPP)?

Accepted Answer

Use the assessment to identify your equity type, your main tax risks, and the next best calculator to run for your scenario.

Question 2

Which calculator should I use for ISO exercise planning?

Accepted Answer

The assessment routes you to AMT/ISO tools based on whether you’re considering early exercise, same-day sale, or holding shares.

Question 3

How do I prioritize AMT vs capital gains optimization?

Accepted Answer

The assessment highlights the dominant driver (AMT exposure, holding periods, or ordinary income) and suggests what to model next.

Question 4

Do I have a withholding gap on RSU vesting?

Accepted Answer

The assessment can flag common withholding shortfalls and point you to the RSU estimator to quantify estimated taxes.

Question 5

What are the common tax mistakes with ESPP sales?

Accepted Answer

It surfaces double-taxation and qualifying disposition risks and points you to basis-adjustment and holding-period tools.

Question 6

Is this personalized tax advice?

Accepted Answer

No—this is an educational triage tool to help you model scenarios and decide what to ask your tax advisor.

Question 7

How much tax will I owe when my RSUs vest?

Accepted Answer

Estimate total tax on RSU ordinary income and compare it to expected withholding to spot an underpayment risk.

Question 8

Is RSU withholding enough (22% / 37% supplemental rate)?

Accepted Answer

Model your marginal bracket vs standard RSU withholding to see whether you should increase withholding or pay estimated tax.

Question 9

How do state taxes affect RSU vesting?

Accepted Answer

Include a state rate to estimate incremental state liability on vest income (rules vary by state and sourcing).

Question 10

Should I sell RSUs immediately or hold?

Accepted Answer

RSU vesting is ordinary income either way; the difference is capital gains after vest. Use this plus the capital gains tool to compare.

Question 11

How do I estimate quarterly taxes for RSUs?

Accepted Answer

Use the withholding gap estimate as an input to decide whether to make estimated payments (consult your advisor for safe harbor rules).

Question 12

What numbers do I need for an RSU estimate?

Accepted Answer

Vesting value, your income context, and a state—then compare owed vs withheld.

Question 13

How do I avoid double taxation on ESPP shares?

Accepted Answer

Many brokers report an unadjusted basis on Form 1099‑B. This tool helps compute the adjusted basis for Form 8949 reporting.

Question 14

Why is my ESPP cost basis wrong on the 1099-B?

Accepted Answer

Brokers often exclude the compensation element (discount) that is taxed as ordinary income—so you need an adjustment to avoid double tax.

Question 15

What adjustment do I report on Form 8949 for ESPP?

Accepted Answer

You generally adjust basis to reflect ordinary income recognized; the tool guides the numbers and the typical reporting approach.

Question 16

Does qualifying vs disqualifying disposition affect basis adjustment?

Accepted Answer

Yes—the ordinary income component differs. Pair this with the qualifying disposition calculator to model both outcomes.

Question 17

Is ESPP discount taxed as capital gains or ordinary income?

Accepted Answer

It can be ordinary income (and sometimes partly capital gain) depending on disposition type; this tool focuses on correct basis reporting.

Question 18

What inputs do I need to adjust ESPP basis?

Accepted Answer

Purchase price/discount, FMV, sale price, and disposition details—then compute the broker-basis correction.

Question 19

What is the ESPP $25K limit and how is it calculated?

Accepted Answer

For Section 423 ESPPs, the $25K limit is based on the stock’s fair market value at the offering date (not the purchase date).

Question 20

How do I know if my ESPP contributions exceed the $25K limit?

Accepted Answer

Model offering-date FMV, purchase periods, and your payroll deductions to verify compliance.

Question 21

Does a lookback provision change the $25K limit calculation?

Accepted Answer

The limit is still determined using offering-date FMV—lookbacks affect purchase price but not the statutory $25K cap input.

Question 22

What happens if I exceed the ESPP $25K limit?

Accepted Answer

Your plan/administrator typically caps purchases; exceeding can change qualification treatment depending on plan mechanics.

Question 23

How should I optimize ESPP contributions across offering periods?

Accepted Answer

Use the limit check to set a safe payroll deduction level, then use the sale timing tool for after-tax optimization.

Question 24

What inputs do I need for the $25K ESPP tool?

Accepted Answer

Offering date, offering-date FMV, purchase schedule, and your intended contribution rate.

Question 25

Is my ESPP sale a qualifying or disqualifying disposition?

Accepted Answer

Compare your offering date and purchase date to the sale date to check whether statutory holding periods are satisfied.

Question 26

How much tax do I save by waiting for a qualifying disposition?

Accepted Answer

Model both outcomes to estimate the tradeoff between ordinary income and capital gains treatment.

Question 27

What are the ESPP holding period rules?

Accepted Answer

Generally, 2 years from the offering date and 1 year from the purchase date (confirm with your plan and jurisdiction).

Question 28

Does qualifying disposition always mean lower taxes?

Accepted Answer

Not always—price moves and marginal rates can change the result. This tool helps quantify the scenario.

Question 29

How does qualifying disposition affect my cost basis?

Accepted Answer

It changes the ordinary income component; pair with the basis-adjustment calculator for reporting.

Question 30

What dates do I need to evaluate an ESPP disposition?

Accepted Answer

Offering date, purchase date, and sale date (plus FMV/price inputs if modeling taxes).

Question 31

What is the ISO $100K limit?

Accepted Answer

It’s an annual limit (based on grant-date FMV of shares first exercisable in a year) beyond which options are treated as NSOs.

Question 32

How do I calculate if my ISOs exceed the $100K limit?

Accepted Answer

Use vesting schedule, share counts, and grant-date FMV to see which tranches convert to NSOs.

Question 33

What happens when ISOs exceed the $100K limit?

Accepted Answer

The excess portion is generally treated as NSOs (different tax timing and withholding).

Question 34

Does the $100K limit depend on exercise price or FMV?

Accepted Answer

The statutory calculation uses grant-date FMV, not exercise price or current FMV at exercise.

Question 35

How does ISO-to-NSO conversion affect AMT and ordinary income?

Accepted Answer

ISOs can create AMT on exercise; NSOs generally create ordinary income on exercise. Model both with AMT/ISO tools.

Question 36

What inputs do I need for the ISO $100K calculator?

Accepted Answer

Grant-date FMV, vesting schedule, and the number of shares that become exercisable each year.

Question 37

Will exercising ISOs trigger AMT?

Accepted Answer

Estimate AMT exposure based on the ISO spread (FMV − strike), income, and exemption phaseouts.

Question 38

How much AMT will I owe if I exercise ISOs?

Accepted Answer

Model the AMT base and estimate incremental AMT from the exercise spread to understand cash needs.

Question 39

Is it better to exercise ISOs early to reduce AMT?

Accepted Answer

Early exercise can reduce spread, but has risks; use this tool to compare scenarios and timing.

Question 40

How does AMT credit recovery work after ISO AMT?

Accepted Answer

You may recover AMT as a credit in future years depending on your regular tax vs AMT—this tool includes a high-level view.

Tax Calculators

Relocation Tax Planner

AMT

Assessment

Capital gains

ESPP

ISOs

Planning

RSUs