Is there a deadline when companies MUST send 1099s and other tax documents for filing?

Wait so if my bank still hasn't sent my 1099-INT by feb 10th, are they breaking the rules? Can I report them or something?

Yes, for a 1099-INT specifically, your bank would be past the January 31st deadline at that point. You have a few options if this happens. First, try contacting the bank directly as sometimes there might be an issue with delivery or it might be available online even if you didn't receive a paper copy. If they acknowledge they haven't sent it yet, you can report this to the IRS by calling their general helpline. However, unless this is a widespread issue, it might be faster to just keep pressing the bank. Sometimes just mentioning the IRS deadline can motivate them to get it to you more quickly.

Does it work for complicated situations like if you have rental property income or contract work from multiple sources? I'm always hunting down like 6-7 different documents and it's a nightmare.

I'm suspicious of AI tools handling tax stuff. How does it actually access your previous returns? Do you have to upload everything? Seems risky sharing all that financial info.

It absolutely works for complicated situations with multiple income sources. The system is designed to handle complex tax scenarios including rental income, multiple W-2s, various 1099s, and investment accounts. It creates a personalized document checklist based on your previous filings. Regarding security concerns, you do need to upload or scan your previous returns, but they use bank-level encryption and don't store your documents after analysis. I was hesitant at first too, but the privacy policy was reassuring and they don't share your data with third parties. You can also just enter the document types manually without uploading if you prefer.

How does this even work? The IRS phone lines are notoriously impossible to get through. Is this just paying someone to wait on hold for you or something else?

Sounds like complete BS to me. No way some random service can magically get you through to the IRS when millions of people can't get through. I've tried calling dozens of times. This has to be a scam.

It's not someone waiting on hold for you. They use a system that navigates the IRS phone tree and secures your place in line, then calls you back when it's about to connect with an agent. It basically waits on hold so you don't have to, and it knows exactly which options to select to get to the right department. As for the skepticism, I totally get it. I thought the same thing initially. What convinced me was that they don't actually take any payment until after you're connected with an IRS agent. They're essentially using technology to optimize the calling process. The IRS is understaffed and their phone systems are outdated, so this service found a way to work within that system more efficiently.

But doesn't filing an extension increase your chances of being audited? I've always heard that but not sure if it's just a tax myth.

That's actually a common misconception. Filing an extension doesn't increase your audit risk at all. The IRS has officially stated this multiple times. Extensions are extremely common - millions of taxpayers file them every year. The things that typically trigger audits are reporting discrepancies, unusually large deductions relative to your income, or claiming credits you don't qualify for. A simple time extension is just an administrative matter and doesn't flag your return in any way. So if you're waiting on documents, it's much better to file an extension than to file an incomplete or incorrect return.

You CAN do this, but I'd be super careful. If your estimates are way off, you might face penalties and interest. Better to make conservative estimates (report more income than you think you had) if you go this route. Amending is also a pain and can slightly increase audit risk.