Question 1

What are the key year-end tax planning strategies?

Accepted Answer

Key strategies include maximizing retirement contributions (401(k) up to $23,000, IRA up to $7,000), making HSA contributions ($4,150 individual, $8,300 family), charitable donations, tax-loss harvesting to offset gains, and Roth conversions if income is lower this year.

Question 2

What is the December 31 tax deadline?

Accepted Answer

December 31 is the deadline for 401(k) contributions, charitable donations, tax-loss harvesting, and Roth conversions. Missing this deadline means these strategies cannot be applied to the current tax year.

Question 3

Can I make IRA and HSA contributions after December 31?

Accepted Answer

Yes. IRA contributions can be made until April 15 of the following year. HSA contributions also have the April 15 extended deadline. This gives extra time to maximize these tax-advantaged accounts.

Question 4

How does tax-loss harvesting work at year-end?

Accepted Answer

Sell investments at a loss to offset capital gains. Up to $3,000 of excess losses can offset ordinary income annually. Unused losses carry forward indefinitely. Must avoid wash sale rule: wait 31 days before repurchasing same or substantially identical securities.

Question 5

Should I increase withholding if I will owe taxes?

Accepted Answer

Yes. If projected tax owed exceeds $1,000, you may face underpayment penalties. Increase withholding on last paychecks, or make a Q4 estimated tax payment by January 15. Withholding is treated as paid evenly throughout the year regardless of actual timing.

Tax Year-End Planning Calculator

Income & Withholding

Planned Deductions & Credits

Year-End Planning Assessment

Estimated Tax

Expected Refund

Potential Savings

Year-End Action Checklist:

Key Year-End Deadlines

December 31

January 15

April 15