Do you use the online version or desktop? I've heard the desktop version is better for military situations because it gives you more control, but it's also more expensive.

I use the online version, but I've used both in the past. The desktop version does give you a bit more control and detailed forms, but honestly for most military situations the online version has worked fine for me. The key is to look carefully at whether you really need the "Deluxe" or "Premier" versions they try to upsell you to. Often the lower-tier version will handle everything you need, especially if you don't have complex investments or rental properties. The military-specific items like combat pay exclusion are actually handled in all versions, even the basic one.

Wait, do they offer this for veterans too or only for those who recently separated? I've been out for 3 years now and didn't know about this.

I'm using Schwab actually. They did send a supplemental document showing the cost basis, but it's not formatted in a way that makes it easy to match up with the 1099-B transactions. There are different dates and lot numbers that don't seem to correspond exactly to what's on the 1099. Did you have to do any manual matching or calculations with yours?

Ah Schwab can be tricky with RSUs. Their supplemental document requires some manual work unfortunately. The lot numbers on the supplemental document should correspond to specific grant dates, not necessarily the sale dates on your 1099-B. You'll need to match each sale on your 1099-B with the appropriate lot(s) on the supplemental document. Look for matching quantities and dates that are close together. Sometimes a single sale on the 1099-B might include shares from multiple lots on the supplemental document, which means you'll need to calculate a weighted average cost basis for that transaction.

Not all RSUs have shares withheld for taxes. Some companies give you the full shares and expect you to pay the taxes separately. The OP should check their vesting statements to confirm whether shares were withheld or not before making adjustments.

Thank you for bringing this up! I didn't even think about quarterly payments. How do I figure out how much to pay each quarter? Can I just divide my expected tax by 4? And do I need to make quarterly payments for both the income tax AND the self-employment tax portion?

You can use Form 1040-ES to calculate your estimated tax payments. It's not always as simple as dividing by 4, especially if your income isn't steady throughout the year, but that's a reasonable starting point if your freelance income is fairly consistent. Yes, your quarterly payments should cover both the income tax and self-employment tax. The IRS doesn't distinguish between them for estimated payments - they just want the total tax paid throughout the year. Another option is to increase your W-2 withholding by submitting a new W-4 to your employer, which can sometimes be easier than managing separate quarterly payments.

This is great advice. I've been freelancing for years and I automatically transfer 30% of every payment I receive into a separate "tax savings" account. It's actually been more than I needed most years, which means I get a little bonus after filing!

Thanks for the tip! I'm definitely going to start doing this. I have a few more freelance projects lined up and I hadn't been setting anything aside. Is that 25-30% a good rule of thumb even for smaller amounts like mine? I'm worried since my regular job already puts me in a higher tax bracket.

I used IRS Free File with FreeTaxUSA last year with both W-2 and 1099 income. It worked pretty well and handled my Schedule C without issues. The federal filing was completely free, and I only paid like $15 for state filing. Way cheaper than TurboTax which wanted to charge me $120+ for self-employment income.

Oh no, I definitely haven't made any quarterly payments. I had no idea I needed to do that. How bad are these penalties usually? Is there any way to avoid them at this point?

Unfortunately, there's no way to completely avoid the penalties now for 2023 since those quarterly payments should have been made throughout last year (typically due in April, June, September, and January). The penalty is basically interest on the amount you should have paid. For perspective, the penalty rate is currently around 8% annually, so if you should have been paying roughly $3,000 each quarter ($12,000 total for the year), the penalty might be around $500-800 depending on how late each payment was. Not catastrophic, but definitely an unnecessary expense.

If I use a bank's EIN I found online and it's wrong, will I get in trouble with the IRS? I'm in a similar situation.

If you make a good faith effort to get the correct information and document your attempts, you won't get in trouble. The IRS understands these situations happen. If you're using an EIN you found through legitimate research and have documented that the bank refused to provide the correct information, you should be fine. The worst that would happen is the IRS might send a notice about the mismatch, at which point you can explain the situation and provide evidence of your attempts to get the correct information.

DON'T DO THIS! I tried that once and got a CP2000 notice from the IRS about unreported income. They couldn't match the 1099-R to my return because of the missing/incorrect TIN. Ended up having to file an amended return and pay interest.