I'm actually using a pretty basic accounting system that doesn't have built-in W2 generation. That's why I'm trying to find a standalone form I can fill out manually. Do you know if any of the free accounting software options include the 4-up W2 printing feature?

Most free accounting software has limited payroll and tax form capabilities. Wave Accounting offers free bookkeeping but their payroll add-on that includes W2 generation costs extra. If you're doing this just for a few employees, there are some lower-cost options like HR Block's small business payroll that includes W2 printing in different formats. For under $50, you could get access to their system just for generating these forms. Some online payroll services also offer one-time W2 generation for small businesses without requiring a full subscription.

Do you need special envelopes if you're just distributing them to employees in person? Or is that only if you're mailing them?

1 Thanks for pointing that out! The check stub does list two separate amounts - the post TEFRA principal (around $125,000) and the post TEFRA policyholder taxable gain (the $48,500). So it sounds like I should just report the $48,500 as taxable income, correct?

11 Yes, exactly right. Only report the $48,500 as taxable income. The $125,000 represents the principal investment (basis) that was already taxed, so you don't pay tax on that part again. The insurance company that properly completed your other 1099-R likely put the $48,500 equivalent in Box 2a and didn't check Box 2b. For this one, they're making you do the math yourself, but the end result should be the same. Just make sure to save that check stub permanently with your tax records!

5 Definitely file an amended return! That's a $63k difference in taxable income - you probably overpaid thousands in taxes. You generally have 3 years from the original filing date to amend and get a refund. Form 1040-X isn't that complicated.

Thanks for this advice! I didn't know about the Taxpayer Assistance Center option. Do I need to bring anything specific to the appointment? And will they be able to tell me if my return was received even if it's not showing up in their system yet?

Bring a copy of your tax return, your certified mail receipt, photo ID, and any other correspondence you've had with the IRS. These in-person representatives can access different systems than the phone reps sometimes can, so they might be able to locate your return in a different status or location. They can also initiate a formal trace on your return using your certified mail information, which is much more effective than trying to do it over the phone. If they can't find it, they can help you submit a replacement return properly marked so it doesn't create issues. The in-person help is seriously underutilized but much more effective.

That's actually a smart idea. What fax number did you use? I didn't even know the IRS accepted faxes for tax returns.

Would doing it that way cause any problems with e-filing? I'd really prefer not to mail in a paper return if possible. Does OLT allow you to attach explanatory statements to e-filed returns?

You're right to be concerned about e-filing. Most software doesn't allow attaching explanatory statements to e-filed returns in the same way you can with paper returns. Your best option with OLT would be to use their "Additional Information" or "Miscellaneous Notes" section if they have one. Enter a detailed explanation there about your HSA contribution calculation, specifically mentioning the catch-up amounts and why they're correct. This gets transmitted with your e-filed return. If OLT doesn't provide that option, you might need to either paper file or use different software that handles HSA catch-up contributions correctly.

This actually worked for me with FreeTaxUSA! I had a similar HSA calculation issue and redistributing the contributions fixed it. Just make sure the actual contributions match what you're reporting - you might need to make adjustments with your HSA provider if the real-world contributions were different.

1 Thanks for mentioning this! I completely forgot about the worksheet that comes with the form. Is it really accurate though? I've heard mixed things.

11 I've found it to be surprisingly accurate for straightforward situations. I have two W-2 jobs with similar pay levels and following the worksheet got me within $200 of breaking even last year. Where it gets less reliable is if you have more complex situations like self-employment income, substantial investment earnings, or major deductions outside the standard deduction. In those cases, the IRS Tax Withholding Estimator or one of the other tools mentioned here would probably work better.

19 This is great advice! I used to try to get it exactly right but would stress when I ended up owing even $100. Now I just aim for a small refund too and it's much less stressful.