Executive Summary
If my company reprices my ISOs lower, are they still ISOs?
Do I owe tax when I accept an option exchange?
What should I ask before consenting?
When stock drops, underwater options demotivate teams. Companies respond with repricings, exchange offers, or new grants. Each path has securities law, accounting, and tax layers—employees feel the tax layer in April.
See also: down round and 409A, ISO vs NSO, M&A equity.
Why Repricing Is Not “Free”
| Stakeholder | Concern |
|---|---|
| Company | Accounting charge, proxy disclosure, shareholder optics |
| Investors | Dilution and fairness vs new hires |
| Employees | ISO status, new vesting, tax timing |
ISO-Specific Risks
ISOs must satisfy grant, exercise, and holding rules. A modification that is treated as a new grant can:
- Restart holding clocks,
- Trigger $100K ISO limit issues,
- Convert tranches to NSOs if limits are exceeded.
Coordinate with a tax advisor before exercising repriced ISOs.
Exchange Offer Patterns
| Pattern | Sketch |
|---|---|
| Options for fewer options | Lower strike; fewer shares |
| Options for RSUs | Ordinary income at vest |
| Cash buyout of underwater options | Wage income |
Checklist
- Read the offer document and FAQ
- Model same-day sale vs hold if ISO status is unclear
- Compare to new-hire grants for fairness
- Confirm 409A support for new strike
Disclaimer
Educational only—not tax or legal advice. Structures vary by company.
Primary sources
| Source | URL |
|---|---|
| IRC §422 | https://www.law.cornell.edu/uscode/text/26/422 |
| IRC §424 | https://www.law.cornell.edu/uscode/text/26/424 |