Investor's Tax Season Checklist

Everything to gather and review before filing taxes if you have investments. Minimize taxes and avoid mistakes.

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Collect all 1099 forms (1099-DIV, 1099-INT, 1099-B, 1099-MISC if applicable)
Brokers mail or email these by mid-February. Check all accounts.
Verify cost basis is correct on 1099-B (especially for ESPPs, RSUs)
Brokers sometimes report incorrect basis. Fix before filing.
Reconcile 1099-DIV: ordinary vs. qualified dividends
Qualified dividends get lower tax rates. Check Box 1a vs. 1b.
Gather IRA/401(k) contribution records and confirm deduction eligibility
Traditional IRA deduction has income limits. Roth has limits too.
Document any Roth conversions or backdoor Roth contributions
Form 8606 for nondeductible IRA contributions and conversions.
Check for wash sales that disallowed losses
Broker 1099-B may or may not report these. Review supplemental statements.
Gather receipts for charitable donations of stock
Deduction = fair market value on donation date. No capital gain.
Confirm HSA contribution limit and whether you're eligible
Triple tax benefit. Max is higher if 55+ or family coverage.
Review estimated taxes and safe harbor amounts
Avoid underpayment penalties. 100%/110% of prior year often safe.
File or extend by deadline (April 15, or next business day)
Extension gives time to file, not to pay. Pay estimated amount by deadline.

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