For what it's worth, your situation screams "the company is not reporting these payments to the IRS." Companies that pay contractors properly don't dodge providing 1099s - it's literally a basic business function. Here's what I think is happening: They're either classifying these payments as something else in their books or they're not recording them properly at all. Either way, it likely means they're trying to reduce their tax liability by not properly documenting contractor payments. As others have said, you MUST report your income regardless. I'd strongly recommend keeping documentation of your attempts to get the 1099 from them. Take screenshots of emails or texts where you're requesting the form. This creates a paper trail showing you were trying to comply properly.

One thing nobody's mentioned - if you've been a contractor making that much ($24k) and haven't been making quarterly estimated tax payments, you might have an underpayment penalty coming. Since no taxes are being withheld, you're supposed to be making those quarterly payments yourself. The good news is you can avoid the penalty if you owe less than $1,000 after accounting for any withholding from other jobs, or if you paid at least 90% of this year's tax or 100% of last year's tax (whichever is smaller). Just something to be aware of when filing!

Just wanted to add - make sure you double-check the numbers on your 1095-A when you get it! Mine had an error last year where they reported the wrong premium amount for two months. The Marketplace had to issue a corrected form, which delayed everything. If anything looks off based on what you remember paying, call and verify before submitting your 8962 to the IRS. Common errors include: - Wrong months of coverage - Incorrect premium amounts - Missing family members on the policy - Wrong SLCSP (second lowest cost silver plan) amount

One thing nobody mentioned yet - if your actual income ended up being significantly higher than what you estimated when you enrolled in your marketplace plan, be prepared that you might have to pay back some or all of your premium tax credit when you file Form 8962. I learned this the hard way last year when I got a big promotion mid-year. My income went up about 35%, which pushed me into a different affordability bracket. Had to repay about $1,800 of the premium tax credits I'd received. Just a heads up so you're not shocked when you do the calculations.

Here's what I'd do in your situation - file the extension ASAP, then file all your back tax returns first before filing 2024. I had to do this last year. File Form 4868 for the extension. Then gather up your documents for the prior years and file those returns. Even if you made very little, you should still file. For the years with stock losses, those can actually help you if documented properly since you can carry forward capital losses. Once your prior years are filed, THEN file your 2024 return and request a payment plan. The IRS is usually pretty reasonable if you're making an effort to comply. You can set up a plan online for up to 72 months.

Let me save you some stress - file the extension but don't panic about an audit. The IRS is primarily focused on high-income taxpayers right now, not freelancers who owe $13k. The audit rate for self-employed people making under $100k is extremely low, like less than 0.4%. Just make sure you report all your Upwork income (they issue 1099s that the IRS gets copies of). Filing an extension is totally normal too - millions of people do it every year. As long as you're not hiding income or claiming crazy deductions, your audit risk is minimal.

Have you considered calling the brokerage firm where the shares were transferred from? Sometimes they maintain historical basis information even when it doesn't transfer correctly during a gift. I was able to get basis info for some gifted Microsoft shares by contacting the original brokerage, and they had records going back to 1998.

Just a heads up - don't forget to check if your grandfather ever received dividend reinvestments on these shares. Each reinvestment would have its own cost basis and holding period, so selling all the shares at once could actually be multiple transactions from a tax perspective. Makes the paperwork more complicated but could help establish at least some basis.

I know you specifically asked about fully online solutions, but I wanted to mention that many desktop tax software providers are moving toward hybrid models. For example, I use Drake Tax which has a desktop component but also offers several cloud features: - SecureFilePro for client document exchange and signatures - Web-based client organizers - Online client portals for document sharing - Mobile app for document capture This combination gives me most of the benefits of an online system while retaining the power and reliability of desktop software. The desktop application handles the complex calculations and form generation, while the cloud components handle client interaction and document management.

Has anyone looked into Canopy recently? Last I heard they were developing a full tax preparation module to complement their practice management software. Their practice management system is already fully cloud-based and quite good.