| Every vest- review your stock statement and check how much tax got withheld. Then cover the difference to get to a 35% rate- either sell more stock, pay cash, etc. It’s annoying but not very hard. You have the money. |
| You can (and are "obligated" to, or face (tiny) penalties) make quarterly estimated payments, if your withholding is too low, if your total Federal income tax owed is over 10% higher than last year. |
| If you make large charitable donations, the deduction covers the under-withholding. It's a non issue. |