Getting Ready for Tax Season - What to Watch for and What to Do Now

To make filing smooth and avoid surprises, here’s a quick head‑up on near‑term deadlines and some steps to get your documents ready.

Upcoming Tax Deadlines (next few months)

By Jan 15 Final estimated tax payment (prior year), if required.

By Jan 31 W‑2 and most 1099 statements are due to recipients; many tax forms begin arriving.

By Mar 15 Partnerships & S‑Corps file or extend.

By Apr 15 Individuals & C‑Corps file or extend: IRA/HSA contribution deadline for the prior year.

News

Form 1099‑DA (digital assets). New this season for 2025 activity. Brokers will furnish payee statements in mid‑February of the following year

Vehicle loan interest statements. New for vehicles purchased in 2025. Lenders must provide statements showing 2025 interest paid. For 2025 there’s transition relief: these may arrive around mid‑February and could be delivered via your online portal/monthly or annual statement.

What to do now

List your income sources so you know exactly which forms to expect. W‑2 (wages); 1099‑NEC/1099‑MISC (contract work/other income); 1099‑K (payment apps/marketplaces); 1099‑DA (digital assets); 1099‑INT/1099‑DIV (banks/brokers); 1099‑B or consolidated brokerage statements; SSA‑1099 (Social Security); 1099‑G (unemployment/state refunds); K‑1s (partnership/S‑corporation/trust/estate); rent income summaries.

Retirement & health accounts - contributions and distributions. Gather IRA/HSA contribution amounts. Save Forms 5498 and 1099‑SA/1099‑R for any distributions/rollovers.

Education & family items. 1098‑T (tuition) plus related expenses; student loan interest 1098‑E; child/dependent care statements (provider name, EIN/SSN, address, amounts).

Health coverage forms. If you used the Marketplace, you must have Form 1095‑A. Keep any 1095‑B/1095‑C you receive.

Crypto and stock sales. Export gain/loss reports for all platforms; include cost basis.

Foreign items (if any). Interest/dividends/rent from abroad; foreign pensions; account balances for potential FBAR/Form 8938 filings; any foreign taxes paid.

Life changes in 2025: make sure you have supporting documents. Marriage/divorce; new dependents; name/address changes; buying/selling a home (keep closing disclosures and 1099‑S); new businesses/rentals/investment accounts.

Know when to file vs. wait. Don’t file until you’ve received all expected statements. Filing with missing info often leads to IRS notices and amended returns.

For small business owners

Books & year‑end: Reconcile bank/credit cards through year‑end; verify and record loan balances and interest; review A/R & A/P; inventory counts; list new fixed assets and any disposals; mileage and home‑office details.

Tax planning now: Consider timing of income/expenses, equipment purchases, bonuses, retirement plan contributions, and S‑Corp reasonable compensation before 12/31.

Contractors: Prepare to file 1099‑NEC by Jan 31. Collect fresh W‑9s from contractors (the IRS updated Form W‑9; use the current version).

The earlier you start preparing for your tax return, the smoother and faster the process will be!