Form-by-form filing guides, deadlines, penalties, and the compliance details that trip filers up — written for the people who actually send the forms.
Track1099 is now part of Avalara, which changes the calculus for a lot of filers weighing a Track1099 alternative. Here’s an honest look at who each…
Banks, brokers, mutual funds, and any corporation that pays dividends use Form 1099-DIV to report distributions to shareholders. Here is who files it…
Both file your 1099s electronically with the IRS. The real difference shows up at the edges: how fast you can start, whether you need a TCC, and what…
Form 1099-DA is the first information return built specifically for digital assets. Starting with 2025 sales, custodial brokers must report their cus…
A new kind of tax-advantaged account for children brought a new information return with it. Form 5498-TA is how the trustee or custodian of a “Trump…
Once nonemployee compensation moved to its own form, Form 1099-MISC became the catch-all for the payments that don’t fit anywhere else — rents, royal…
A new deduction for car-loan interest created a new information return to go with it. Form 1098-VLI is how lenders tell the IRS — and the borrower —…
When a payee’s name and TIN don’t match IRS records, you can end up withholding 24% of their payments and mailing formal notices on a strict clock. H…
QuickBooks already knows who you paid and how much. This is how to pull those vendors and amounts out of QuickBooks Online, map them to the right 109…
Form 8809 gets you an automatic 30-day extension to file most information returns with the IRS — but there’s one big exception (1099-NEC), and it nev…
Every common 1099 has two deadlines that don’t always match: the date the recipient copy is due and the date the IRS e-file is due. Here they are for…
The 1099-K reporting threshold has whipsawed for years: a $600 law, an IRS phase-in at $5,000 and then $2,500, and a 2025 law pointing it back toward…
The penalty for filing a 1099 late isn’t one number — it’s a sliding scale that gets steeper the longer you wait, and it can double when you also mis…
There is a new member of the 1099 family aimed squarely at long-term care insurance. Form 1099-LPS reports the premiums a policyholder paid during th…
A name that doesn’t match its TIN is the number-one reason a clean-looking 1099 comes back to bite you — CP2100 notices, B-notices, backup withholdin…
Brokers use Form 1099-B to report what their customers sold and, for covered securities, what it cost them. Here is how proceeds, cost basis, covered…
If your institution paid someone $10 of interest this year, you almost certainly owe them — and the IRS — a Form 1099-INT. Here is the box-by-box bre…
If you paid a contractor, a freelancer, or an unincorporated vendor for work this year, Form 1099-NEC is probably the return you owe them and the IRS…
Filing 1099s with the IRS is only half the job. Depending on where your recipients live, you may owe a copy to the state too — and the states split i…
Information-return filing runs on acronyms, and half of them look alike. This is the plain-language reference — what a TCC is, how an EIN differs fro…
Three IRS-authorized e-file services, three different centers of gravity. TaxBandits is the broad multi-form platform, BoomTax leans into ACA and bul…
A firm doesn’t file one batch of 1099s — it files for dozens of clients on the same deadline, then fields corrections for weeks after. The best 1099…
You filed a 1099, the IRS accepted it, and then you spotted the mistake. What you do next depends entirely on what is wrong — a wrong dollar amount a…
Your 1099-NEC is due the same day your recipients get their copies, and for tax year 2026 that day lands on a weekend — so the real deadline is Monda…
Filing your 1099s with the IRS does not automatically file them with the states. Here is which states accept the Combined Federal/State Filing progra…