⚠️ Critical Deadlines: Most items must be completed by December 31, 2025. Credit card transactions should post by 12/31, aim to complete by ~12/29. IRA/HSA contributions deadline: April 15, 2026.
Checklist for your taxes, points and miles. Prepared by Chris Hutchins
TAX OPTIMIZATION
STANDARD DEDUCTION vs. ITEMIZING
Determine whether to take the standard deduction or itemize for maximum tax savings.
STATE & LOCAL TAXES (SALT)
The higher 2025 SALT cap may make prepaying certain taxes worthwhile if you itemize.
- Property taxes due in early 2026
- Additional mortgage payments
CHARITABLE GIVING
Year-end is the best time to optimize donations, especially with rule changes coming.
Recommendation: Daffy (← Free $25)
NEW 2025 TAX DEDUCTIONS
Check whether you qualify for newly added deductions before the year closes.
Car Loan Interest
Qualified Tips & Overtime
Senior Deduction (65+)
CAPITAL GAINS & TAX LOSS HARVESTING
Review gains and losses now to reduce taxes and rebalance efficiently.
Tax Loss Harvesting
Gain Harvesting (Low Income Years)
Advanced Strategies
RETIREMENT ACCOUNTS
Last chance to maximize contributions and consider Roth conversions for 2025.
401(k) - Deadline: 12/31
If plan allows after-tax contributions + in-plan Roth conversions
IRA & Roth IRA - Deadline: 4/15/26 (open account by 12/31)
- Contribute to Traditional IRA (non-deductible)
- Rollover to a Roth IRA
- Beware of pro-rata rule with existing Traditional IRA balance
Roth Conversions
Stock Options (ISOs)
HEALTH SAVINGS ACCOUNTS (HSA)
Make sure you’re eligible, contributed correctly, and saved receipts for future tax-free reimbursements.
Must be enrolled in an eligible high-deductible health plan.
FLEXIBLE SPENDING ACCOUNT (FSA) - Deadline: 12/31
Spend remaining funds now to avoid forfeiting unused balances.
HOME ENERGY IMPROVEMENTS
Check whether 2025 upgrades qualify for available federal credits.
Efficiency Improvements
CHILDREN & EDUCATION
Take advantage of year-end opportunities for gifts, 529s, and kids’ savings.
529 Plans - Deadline: 12/31 (for state tax deduction)
Also requires filling out Form 709
Annual Gifting
Kids' Roth IRA
CREDIT CARDS & TRAVEL REWARDS
AIRLINE & HOTEL STATUS
Status resets soon — confirm whether you’re close to a meaningful threshold.
Mileage/Mattress Runs
Use these steps if you're close to earning or maintaining elite status with airlines or hotels.
Recommendation: hotelmattressrun.com
Credit Card Status Bonuses
Some credit cards offer elite-qualifying miles or nights when you meet spending thresholds. These can help you finish status without extra flying or hotel nights. However, some programs have other ways to earn status (e.g., using their shopping portal or buying sustainable aviation fuel credits).
Choice Benefits
If you reached a milestone that unlocks "Choice Benefits," you must select them before year-end, or they disappear.
Other Elite Qualification
Some loyalty programs have other options for adding elite qualification "points". For example Alaska let's you earn extra EQMs by purchasing Sustainable Aviation Fuel.
ANNUAL SPENDING BONUSES
Finish any spending needed to unlock rewards that reset January 1.
Earning Caps Reset 1/1/26
Some cards cap the amount of spending eligible for high bonus multipliers. These caps restart on the 1st of every January.
Free Night Certificates
If you're trying to unlock extra free nights from card spending, these thresholds must be completed by 12/31.
Lounge Guest Access
Some premium cards limit lounge guest access unless you hit a specific annual spend target. If you're close, finishing the spend by year-end carries the benefit into next year.
Premium Perks
A few premium cards unlock special annual perks once you hit certain spend thresholds.
ANNUAL CREDIT CARD CREDITS
Use all credits before they expire at year-end.
AMERICAN EXPRESS
BANK OF AMERICA
CHASE
POINTS & MILES MAINTENANCE
Prevent points from expiring and keep long-held cards active.
Prevent Expiration
- Making small shopping portal purchase
- Buying small number of points
- Redeeming points for charity donation
- Transferring points
Keep Cards Active
Especially important for oldest credit cards (credit history)
DOUBLE/TRIPLE DIP STRATEGY
Opening premium cards in December can unlock multiple years of credits.
- 2025 calendar year credits
- 2026 calendar year credits
- 2027 credits, if you’re able to use them before the window to cancel and get the 2nd annual fee refunded (usually within 30 days of the statement with the annual fee posting)