Where exactly is this in the 2025 version? I'm looking under Reports but don't see Tax Reports as an option. Is it only available after you complete Schedule D or something?

In the 2025 version they moved it slightly. Look under Reports > My Documents > Generated Reports and then you need to click "Create New Report" and select Capital Gains from the dropdown list. It's definitely not intuitive! The report won't be available until you've entered at least some Schedule D information. Once generated, it creates a nice PDF that you can open in Adobe Reader and copy text from. The data comes out pretty clean and just needs a little formatting in Excel.

That sounds incredibly tedious! How long did it take you to manually enter all 43 trades?

Would the VCSP apply in my situation though? I thought that was more for when you misclassified actual employees as contractors, not for when you incorrectly treated yourself as an employee of your own SMLLC?

You're right - I apologize for the confusion. The VCSP is specifically for reclassifying workers from independent contractors to employees, not for your situation with a single-member LLC. In your case, you'll need to work with a tax professional to file amended returns, correcting the classification error by reporting the business income on Schedule C instead of W-2 wages. You should also look into filing Form 8275 (Disclosure Statement) with your amended returns to explain the situation, which can sometimes help avoid accuracy-related penalties.

This is actually good advice. I was able to get a late S-Corp election approved retroactively by explaining that I misunderstood the filing requirements but had been functioning as an S-Corp in practice. Saved me from having to amend multiple years of returns.

That's a really good point. I didn't even think about the delayed earnings potential. Do you have any rough numbers on what that looked like for you financially? Just trying to do my own math here.

In my case, I was making about $85k during my MBA. The role I moved into after graduating paid $112k. So that's roughly $27k per year in lost salary increase, which means delaying graduation by 18 months cost me about $40k in potential earnings. My total tuition was $36k, and by stretching it I saved paying taxes on about $22k (the amount over the $5250 limit across 3.5 years). At my tax bracket that saved me around $6k in taxes. So I essentially lost $34k ($40k in delayed earnings minus $6k tax savings) by stretching the program. Obviously everyone's numbers will be different, but definitely consider the full financial picture, not just the immediate tax hit.

Some companies definitely do this! Mine doesn't call it a "gross-up" but they essentially pay about 40% extra on the amount over $5250 to offset the taxes. Worth asking about.

I actually did ask about this! My company said they don't offer any tax offset or gross-up for education reimbursement. Their policy is pretty rigid - $5250 tax-free per year, anything above that gets taxed, and that's it. I appreciate the suggestion though. Seems like I need to either stretch the program or just accept the tax hit as the cost of finishing faster.

I used Military OneSource for my taxes when I separated last year. They were decent with the basics but struggled with my situation when a contractor paid for my move. They weren't familiar with how to handle the civilian employer reporting it as income while I was still technically on active duty. I ended up needing additional help.

Thanks for mentioning this! I just double-checked and there's nothing in box 12 or 13 either - it's completely empty across all fields. But that's good to know for future reference. Would you still enter it in tax software even if it's completely empty? Seems like extra work for no reason, but I don't want to mess anything up.

If it's completely empty across all fields, then I wouldn't bother entering it in your tax software. It won't have any impact on your tax calculation or filing. Just keep the physical copy (or a digital scan) with your tax records for this year. The IRS recommendation is to keep tax documents for at least three years after filing, which covers the standard audit window. In the extremely unlikely event that any questions come up about it, you'll have documentation showing that it was indeed a zero-dollar W-2 with no reportable information.

Not likely in this case. When companies keep former employees in their payroll system, sometimes their automated W-2 generation just creates forms for everyone in the database regardless of whether they received compensation that year. If it were identity theft, there would typically be income reported on the W-2, as the whole point would be to earn money using someone else's identity. A blank W-2 is almost certainly just a system glitch or administrative error.