Cloudflare (NET) NSO Exercise Calculator
Calculator · free · no signup · NETPlan your Cloudflare NSO exercise (federal, state, FICA) and compare sell-vs-hold for long-term capital gains.
Beta · invite-only · AlphaLatitude Inc. · Free Tools
Your grant
Tax inputs
Hold strategy
Best after-tax payout — at year 1
$199,080
Sell + invest wins by $20,783 over Hold 1 yr.
Estimates only. Not financial advice.
Sell + invest
Best payout| Bargain element (sale − strike) | $350,000 |
| Federal | |
| State | |
| Medicare | −$5,075 |
| Additional Medicare | −$3,150 |
| Market gain over 1 yr at 10.0% | $18,573 |
| LTCG on diversified gain (fed + state + NIIT) | −$5,219 |
| Net at year 1 | $199,080 |
Sell every share immediately; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Exercise + hold 1 yr
| Sale proceeds (year 1) | |
| LTCG tax (federal + state + NIIT) | $0 |
| Net at year 1 | $178,297 |
Sold 2,678 shares at exercise to cover strike + tax; 2,322 shares held 1 yr for LTCG.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're exercising as a current employee.
Both columns are stated in year-1 dollars: sell-now proceeds compound at the market return and pay LTCG on the gain at year 1; any cash paid out of pocket on the hold side carries the same opportunity cost.
Net at year N — by hold period
Estimates only. Excludes AMT (NSOs do not trigger AMT), state-AMT, multi-state moves, and disqualifying-disposition edge cases. Not financial advice.
You calculated one NSO decision. The beta plans NSOs alongside RSUs and ISOs in a single multi-year tax plan.
Request beta access →About Cloudflare
Cloudflare (NET) is a public Cloud/SaaS company, incorporated in Delaware and headquartered in San Francisco, CA. IPO'd Sep 13, 2019.
Last close: $230.97 per share (as of 2026-06-16).
Equity grants at Cloudflare typically include non-qualified stock options (NSOs) and restricted stock units (RSUs).
Cloudflare, Inc., is an American technology company headquartered in San Francisco, California, that provides a range of internet services, including content delivery network (CDN) services, cloud cybersecurity, DDoS mitigation, and ICANN-accredited domain registration. The company's services act primarily as a reverse proxy between website visitors and a customer's hosting provider, improving performance and protecting against malicious traffic.
Source: Wikipedia (CC BY-SA 4.0)
Born from Project Honey Pot, the anti-spam research Matthew Prince and Lee Holloway ran from 2004, Cloudflare took shape in 2009 after Prince met Michelle Zatlyn at Harvard Business School. From San Francisco, it routes traffic through a global edge network covering CDN, DNS, DDoS protection, Zero Trust access, R2 object storage, Bot Management, and Workers serverless compute (extended with Workers AI for inference at the edge). Listed on NYSE as NET since September 2019, the company reported 2025 revenue of $2.17 billion, up 30% year-over-year.
Sources: cloudflare.com · en.wikipedia.org · cloudflare.com
Equity comp at Cloudflare
- RSUs use single-trigger vesting: shares become yours as each portion vests on schedule, and the value is taxed as ordinary income at that point. No IPO or acquisition is required.
Researched 2026-05-07.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Cloudflare.
Use this calculator to estimate your Cloudflare (NET) NSO exercise tax (federal, state, FICA), then compare selling now versus holding through the long-term capital gains threshold. Inputs are yours: grant terms, current price, your income, your state.
Example: at Cloudflare (NET)'s last close of $230.97, exercising 5,000 NSOs with a $69.29 strike creates a $808,400 bargain element, taxed as ordinary income on the day you exercise. Combined federal + state + FICA on that bargain typically lands between $218,268 and $363,780 depending on your bracket and state. The calculator above computes the exact figure for your situation and compares selling now vs. holding through the long-term capital-gains threshold.
All Cloudflare tools → · Use the generic NSO Exercise Calculator for any company.
Cloudflare equity questions
- How is a Cloudflare NSO exercise taxed?
- Exercising a non-qualified stock option (NSO) creates ordinary income on the bargain element (the price on the day you exercise minus your strike), subject to federal income tax, state income tax, and FICA. The calculator above computes that tax for your Cloudflare grant and compares selling the shares now against holding past the one-year mark for long-term capital-gains treatment.
- Does Cloudflare grant ISOs, NSOs, or RSUs?
- Equity compensation at Cloudflare typically takes the form of non-qualified stock options (NSOs) and restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Do Cloudflare RSUs use double-trigger vesting?
- No. Cloudflare restricted stock units (RSUs) use single-trigger vesting: each tranche becomes yours as it vests on schedule, taxed as ordinary income at that point, with no liquidity event required.
One piece of the puzzle.
OptionsAhoy plans your Cloudflare equity alongside hedging, vesting, and de-concentration, across bullish, neutral, and bearish market scenarios. Free during beta.