The Vest-Day Checklist
Seven things worth doing every time RSUs vest — and the one that costs the most when skipped.
Most people find out a vest happened when a deposit shows up, or when their broker emails. By then the decisions that mattered have already been made by default.
This is the manual version of a routine that takes about fifteen minutes per vest. Work it once and the next one gets faster.
Scope: US-based employees with restricted stock units (RSUs). Stock options (ISOs/NSOs) work differently and aren't covered here.
Before the vest
1. Know the date — before it arrives
Vests land on a schedule, not when you notice them. Pull your grant letter and write down the next vest date and share count.
Two things people miss: the cliff (nothing vests until you cross it, then a large chunk lands at once), and refresher grants, which stack their own schedules on top of your original one. Three grants means three schedules running at the same time.
This is exactly what Cliffvest's vest-day alerts do — the app keeps the calendar so you don't have to reconstruct it from PDFs.
2. Estimate the after-tax number
An RSU vest is ordinary income on the day it vests, valued at that day's share price. Your employer usually withholds by holding back a portion of the shares.
Here's the part that surprises people. Employers commonly withhold federal tax on this kind of income at a flat supplemental rate of 22% (for aggregate supplemental wages up to $1M in a year). If your actual marginal rate is higher, you are under-withheld — and nothing tells you until you file.
Worked example — illustrative numbers
100 shares vest at $80 → $8,000 of ordinary income.
- Withheld at 22% supplemental: $1,760
- Actually owed, at a 32% marginal rate: $2,560
- Gap: $800 — before state tax, which may be withheld at its own flat rate.
Four vests that size in a year is roughly a $3,200 shortfall waiting at filing time.
Knowing the gap early is the whole point. It's the difference between a planned set-aside and an April surprise.
3. Check your trading window
"I'll just sell at vest" only works if you're allowed to. Blackout periods, open-window calendars, and preclearance requirements are set by your company, not your broker.
If you're subject to them, check the window before the vest date. Some people in this position use a 10b5-1 plan to schedule sales in advance; whether that fits your situation is a conversation for your company's counsel or your advisor.
On and after the vest
4. Verify what actually recorded
Log into your equity portal and confirm three things against your own note from step 1: the share count that vested, the price used, and the shares withheld for taxes.
Errors here are uncommon but not rare, and they're far easier to correct in the same month than a year later.
5. Make the sell-or-hold call deliberately
The most useful thing to understand: you owe the tax either way. The income was triggered at vest. Holding the shares doesn't defer that bill — it just adds market risk on top of it.
That reframes the decision. Vested RSUs are cash that happens to be sitting in your employer's stock. So the honest question is:
If someone handed you $8,000 in cash today, would you buy your company's stock with all of it?
If the answer is no, holding is a decision worth making on purpose rather than by inertia. Some considerations people weigh:
- Concentration. Your salary, your benefits, and often your next promotion already depend on this company. Equity stacks more of your net worth onto that same outcome.
- What happens next. Anything you gain or lose after the vest date is a capital gain or loss, measured from the vest-day price — a separate event from the ordinary income you already booked.
There's no universally correct answer, and this guide isn't recommending one. The point is to choose, and to know why.
6. If you hold, set aside the shortfall
If step 2 showed a gap, move that amount somewhere you won't spend it. Some people adjust W-4 withholding to catch up over the year; others make quarterly estimated payments. Both have rules worth checking with a CPA — underpayment can carry penalties even when you settle up in April.
7. Log it — this one pays you back at sale time
Record the vest date, share count, price at vest, shares withheld, and net shares kept.
Here's why it matters. Your cost basis in vested shares is the price at vest — the amount you already paid ordinary income tax on. Broker 1099-B forms have historically reported a basis of $0 or left it blank for equity-comp shares. If that goes unnoticed, you pay tax a second time on income you already paid tax on.
A record you made on vest day is what prevents that. It takes two minutes now and can be genuinely difficult to reconstruct three years later.
Running it without the spreadsheet
That's the checklist. It works, and plenty of people run it by hand.
Cliffvest is the same routine, automated: your vesting calendar in one place, alerts before each vest day, after-tax value estimated for your actual bracket, and sell-vs-hold context when the date arrives. Manual entry, no brokerage logins, all data stays on your device. It is coming to Google Play.